Ultimate 14-Day Hawaii Itinerary: Up to 7 Islands in Two Weeks

14 Day Hawaii Itinerary blog cover image.  Text overlaying a collage of 4 images from Hawaii, including a sunset luau, manta ray, waterfall, and white sand beach

The best 14-day Hawaii itinerary is one that can be customized to match your personal desires. Whether you are someone who never wants to leave the beach, an adventurous island hopper intent on seeing it all, or anyone in between, this guide has you covered!

Here you will learn everything you need to know for crafting your ideal 14-day Hawaii itinerary. This includes the best things to do on every Hawaiian island, where to stay, finding cheap flights, and how to get around.

We have also created the “Ultimate 14-Day Hawaii itinerary” which provides a thorough daily breakdown of how to see all 7 inhabited islands in two weeks.

In addition, you will find other useful resources linked throughout the itinerary, These complete guides will be helpful in better understanding many important topics in planning your Hawaiian vacation.

NEED MORE HELP THAN JUST AN ITINERARY? READ
PLANNING A TRIP TO HAWAII: THE ULTIMATE GUIDE

Disclosure: In order to keep providing you with free content, this post likely contains affiliate links. If you make a booking or purchase through one of these links we earn a small commission at no extra cost to you. So a HUGE thank you to you if you click one of these links 🙂

How many Islands Should I visit in 14 days on Hawaii?

With 14 days in Hawaii, you should try to include at least two islands. However, two weeks in Hawaii is enough to see up to all 7 inhabited islands, if you so desire!

Put simply, those whose priority is vacation over exploration should choose the 2-3 islands that interest them most and spend 5-7 days on each. The restless and active should attempt 4-7 islands with 2-3 days on the major islands and day trips or overnights to some of the sister islands.

How much island hopping you do is a very personal decision. Don’t worry if you are not yet prepared to make that decision; we will walk you through everything you need to know and consider step by step.

Hawaiian Island Hopping Basics

With two weeks in Hawaii, you will likely take at least one inter-island flight. The good news is that flights between the Hawaiian islands are short and affordable.

If you truly want to understand the topic, consult this complete guide to Hawaii island hopping. This is the holy grail of inter-island travel around Hawaii.

Here are the key takeaways for readers who just want the basics:

  • ALWAYS BOOK YOUR ARRIVAL FLIGHT TO HAWAII DIRECT (if possible)!
  • Most 14 day Hawaii itineraries should begin in Oahu.
  • Arrive and depart from different islands to maximize time & minimize cost.
  • Flights between major islands start at $45 and are about 45 minutes long.
  • There are no Hawaii ferry services, except Maui to Lanai.
  • The best order for island hopping all 7 Hawaiian islands will typically be:
    Oahu -> Kauai -> Ni’ihau -> Maui -> Lanai -> Molokai -> Kona

All topics are covered in-depth in our
ULTIMATE GUIDE TO ISLAND HOPPING IN HAWAII

Getting Around the Hawaiian Islands

With just a couple of weeks in Hawaii, you won’t want to rely on public transportation. The options are very limited and time is the most precious resource you’ll have for your holiday. The best options for getting around the islands will either be rental cars or tours that will literally meet you at your door.

Those of you limiting your 14-day Hawaii itineraries to 2-3 islands will certainly be best off renting a car. They are surprisingly inexpensive and provide the freedom to go where you please.

However, those of you attempting the island hopping itinerary through all 7 islands may want to consider a different approach. With 2 days or less on any given island, you don’t want to spend too much time dealing with paperwork and vehicle pick-ups / drop-offs. Instead, you may actually be better off with pick-up tours and using Lyft / Uber when necessary.

If you would prefer to rent a car, you can look into pricing and availability for rentals here. Rental cars are often in high demand, so it’s worth planning ahead to secure a reservation.

If you prefer to have transport sorted out for you, you will find links to pick-up tour operators for all of the recommended activities within their descriptions.

Quick Guide to Each Island

Four Main Islands: Oahu, Maui, Kauai, Big Island


View from the scenic Makapu'u Point on Oahu during two weeks in Hawaii
Oahu is the most iconic Hawaiian island.

Oahu: The Miami of Hawaii

Incredible white sand beaches with the best nightlife and the largest city in Hawaii. Oahu is mostly about resorts and tourist attractions, drawing people who are more about a fun, curated vacation than exploration. It is by far the most visited island in Hawaii.


The Na Pali Coast in Kauai as seen from a boat tour during 14 days in Hawaii
Kauai is best for outdoor adventure.

Kauai: The Denver of Hawaii

Upscale accommodation and romantic restaurants exist, but the island is most known for its incredible natural beauty. Kauai is best for the hikers, adventure seekers, and nature lovers who see Hawaii as a place to explore rather than somewhere to relax.


A kitesurfer enjoys a day in paradise at VOR Beach on the Maui North Shore.
Maui is best for diverse interests.

Maui: The Los Angeles of Hawaii

Beautiful beaches with lots of high-end visitors, but also appealing to people who like to explore by car. Maui is a mix of upscale vacation, self-drive tourism, and chill-on-the-beach enthusiasts. This is the second-most popular island for tourists.


A young female in a swimsuit walks the stunning shoreline of Waipio Black Sand Beach on Big Island north shore, also known as Poiolu Valley Beach.
Big Island is best for slow travel.

Big Island: The Seattle of Hawaii

Slow pace with the friendliest people and a lot of natural beauty to explore, but more effort is required. The Big Island is best for people who value space, seclusion, and budget over manufactured and lavish experiences.


Three Sister Islands: Molokai, Lanai, Ni’ihau


View of the Molokai coast showing rugged green cliffs and a beach tucked into the base of them

Molokai: The Friendly Island

A mini-Kauai, Molokai hosts incredible landscapes that range from towering mountains to sublime beaches. It is the most beautiful of the Hawaiian sister islands, and also the most populated.


The beautiful, tropical Hulopoʻe Beach Park in Sharks Bay is the best beach on the Hawaiian Island of Lanai.

Lanai: The Pineapple Island

Lanai sees more tourists than any of the other sister islands, but few ever get past Shark’s Bay on a half-day trip from Maui. Those who do explore will discover some unique beaches and scenery that guarantee near-total seclusion.


Ni’ihau: The Forbidden Island

A private island that is most known for its exclusivity and one-of-a-kind precious shells. Ni’ihau was impossible to visit prior to 2021, but now a half-day tour from Kauai allows 3 hours on this mysterious island.


14 Day Hawaii Itinerary for 2-4 Main Islands

For readers who prefer a relaxed pace, you will want to limit your time to 2-3 main islands. This will allow you about 5-7 days on each island, which is really the right amount of time.

All three of the sister islands can be visited on individual day trips as well if you’re playing Hawaii bingo and just want to say you’ve been. Getting to the sister islands is discussed in-depth in the next section.

You probably already know if you’re the kind of person who likes to sit still and soak it in, or stay on the move and see it all. Still, it may help to imagine the two proposed options below for a moment, then peruse the accompanying 5-7 day itineraries for each island to see what feels right for you.

  • Two Islands in 14 Days
    Choose the two that look most appealing to you, or the two that have the cheapest flights, then spend 7 days on each. The most popular choices are Oahu and Maui.
  • Three Islands in 14 Days
    Introduce another island and cut down to 4-5 days on each. The most popular choices are still Oahu and Maui, but adding in Kauai or Big Island as well.

Consult these complete 5-7 day itineraries if you are electing one of these options:
Oahu
MauiKauaiBig Island

Is your idea of the perfect Hawaiian vacation more about adventure and exploration than drinks and relaxation? If so, the option below is the one for you!

  • All 4 Major Islands in 14 Days
    Spend 3-4 days on each major island, skipping the extreme planning and loss of time that comes with including the Hawaiian sister islands. The best order will typically be Oahu to Kauai to Maui to Big Island.

Use the guide below but add 1 extra day to each island to make it a 14-day Hawaii itinerary:
10 Day Hawaii Itinerary for Island Hoppers


ULTIMATE 14 DAY HAWAII ITINERARY: ALL 7 ISLANDS

  • A turtle looks up at Laniakea Beach on the Oahu North Shore in front of clear water and breezy palm trees.
    Stop 1 / 7: Oahu

As discussed, there are a lot of ways to spread two weeks in Hawaii around. The “Ultimate 14-Day Hawaii Itinerary” has been designed specifically as a way to see all 7 inhabited Hawaiian islands in one epic trip.

While the other variations above were flexible, this one is mostly not. The sequence of travel is important in regards to the accessibility, options, and pricing for travel to some of the smaller sister islands.

If you are going to attempt this itinerary, we cannot stress enough how helpful it will be to first read and refer to our Complete Guide to Hawaiian Island Hopping!

In it, you will find a plethora of useful links, information, times, tips, and resources for booking travel around the islands.


Is 14-Days on Hawaii enough to see all 7 islands?

A collage showing photos from the 4 major Hawaiian islands of Oahu, Maui, Kauai, and Big Island for 14-day Hawaii island hopping itineraries.

While it takes a well-planned itinerary, you can easily and enjoyable visit all of the Hawaiian islands in two weeks.

Understand that Ni’ihau can only be visited on a half-day trip from Kauai, Lanai is typically visited as a day trip from Maui, and Molokai is a short flight from Lanai. This still leaves up to 3 days for each of the major islands!

Follow this itinerary for exact guidance on how to arrange your trip. Every island-hop, as well as things to do and where to stay on each island, will be explained in greater detail in the subsequent sections.


Ultimate 14-Day Hawaii Itinerary Daily Breakdown

  • Day 1-3: Oahu
  • Day 4-6: Kauai / Ni’ihau
  • Day 7-9: Maui
  • Day 10: Lanai
  • Day 11: Molokai
  • Day 12-14: Big Island

Booking Flights

A Hawaiian Airlines flight plane taking off in Maui during an island hoppers 14-day Hawaii itinerary.

The following breaks down the order in which you should arrange your flights and ferry with explanations regarding the importance of the order.

  1. Arrival flight to Oahu (HNL).
  2. Departure flight back home from Kona, Big Island.
  3. Inter-island flight from Oahu to Kauai.
  4. Half-day tour to Ni’ihau (helicopter or snorkel) from Kauai.
  5. Inter-island flight from Kauai to Maui.
  6. Ferry ticket from Lahaina Harbor (Maui) to Lanai.
  7. Small plane flight from Lanai to Molokai.
  8. Small plane flight from Molokai to Big Island.

It is recommended to first book your arrival flight to Oahu because non-stop arrival flights prevent possible complications with connecting flights, and Oahu has the most non-stops available. Then, book your departure flight as these will be the most expensive and important.

Don’t worry if something goes wrong with some of the short inter-island flights – there are plenty of options for getting to the Big Island even if you end up having to skip one or two of the islands in between.

From then on, the order of operations is based on the sequence in which you will hop from one island to the next.

Day 1-3: Oahu

Begin your two week trip to Hawaii with the most popular and visited island of Oahu. This island truly has something for everyone, from history to nature to the best beaches in Hawaii, and so much more.

There will be no island hopping from Oahu so you can plan on spending most of your time enjoying the best things there are to do on the island.

We recommend arriving in Honolulu to give you the best chance at a direct flight to Hawaii.

Oahu Overview

  • Nickname: The Gathering Place
  • Where to Stay: Waikiki or Honolulu
  • Number of Days: 3
  • Airports
    • Honolulu (HNL) – Main Airport
    • Kalaeloa (JRF)

Best for: People who prefer resorts and tourist attractions; those that are more about a fun vacation than exploration, as well as beach enthusiasts.

Suggested: PLANNING A TRIP TO OAHU: THE ULTIMATE GUIDE


Where to Stay on Oahu

View of Waikiki Beach in Honolulu and Diamond Head in the background as seen from a high rise hotel.

If you are spending more time on Oahu, you could consider staying in some of the more remote and arguably prettier parts of the island. With only a few days available, however, you will most likely want to stay in the neighborhood of Waikiki, though you may be able to find a good deal elsewhere in Honolulu as well.

While not recommended with such a short time on the island, those who detest crowds and family resorts may want to at least look into the remote and beautiful Oahu North Shore.


Best Things to Do in Oahu

Oahu is most well known for its beaches and resorts. However, most people don’t realize just how much else there is to see and do on the island!

With its rich history, both native and colonial, world-class beaches, majestic mountains, lush rainforests, and remote regions all waiting to be discovered, you will definitely wish you had more time to explore no matter how many days you get!

Below are the most popular activities and the best things to do in Oahu.


Go Beach Hopping

With apologies to Maui, you will discover the best beaches in Hawaii on Oahu. When you close your eyes and imagine a postcard-perfect white-sand paradise with swaying palm trees and crystal clear water, you’re likely picturing Oahu!

While Waikiki is the most famous and easiest Oahu beach to get to, some of the best ones are scattered throughout the island.

If you only take one day on your 14 day Hawaii itinerary to enjoy some beach time, save that day for Oahu. In particular, be sure to visit the unspeakably picturesque Lanikai Beach in the Kailua region on the southeast shore.


Visit the Pearl Harbor National Memorial

Aerial view of Pearl Harbor in Oahu Hawaii

With over 2 million visitors each year, the Pearl Harbor National Memorial is the most visited attraction in Hawaii. The memorial is managed by the National Park Service and includes five historic sites that honor the devastating events that occurred here during World War 2 and changed the course of history.

Visits to Pearl Harbor Visitor Center are free and no ticket is required for the museums. The USS Arizona Memorial program does require a ticket, however, the tickets are free.

There is no longer a walk-in first come first serve ticket system. It is, therefore, strongly recommended that advanced reservations are made online at recreation.gov. Half of the tickets are released 3 months ahead of time and the rest are made available at 3pm HST the day before.

Typically we would not recommend booking a tour to visit Pearl Harbor as tickets are free. However, if this is a must-see for you and you’re unable to reserve your free ticket, then a tour may be a good option. By booking a tour, not only is transport taken care of but you are guaranteed entry to Pearl Harbor National Monument and USS Arizona Memorial.


Kualoa Ranch (Jurassic Park)

Kualoa Ranch, famous for being the production site of Jurassic Park, is seen in this photo from Oahu during 14 days on Hawaii.

Often referred to as Jurassic Park or Jurassic Valley, Kualoa Ranch is most famous for being the filming location for Jurassic Park. As you explore the beautiful ranch, it’s hard not to expect a dinosaur to appear!

The spectacular area is a 4000-acre private nature reserve and working cattle ranch, and one of the most popular attractions on Oʻahu. There are numerous tours offered each day at Kualoa Ranch including movie, ATV, e-bike, horseback, sailing, and farm tours. All of the tours typically take you to the same area, the Kaʻaʻawa Valley, and have excellent reviews.

Each of the tours will teach you more about the stories, legends, and past uses of the area as you become immersed in the striking verdant folds of the valley.


Oahu North Shore

A honu sleeps on the shore of Laniakea Beach on the Oahu north shore in Hawaii.
A honu (Hawaiian sea turtle) says aloha from tropical Laniakea Beach on the Oahu North Shore.

The Oahu North Shore has been made famous over the years by surf legends, songs, and even popular cinema such as Forgetting Sarah Marshall. It is also considered a mecca for surfers, particularly during the winter months when huge waves crash on the shore.

Here you’ll find cool laidback vibes, ample food trucks, and picturesque beaches with far fewer people than in the Waikiki and Honolulu region. If you want the tropical aloha vibes of Hawaii without the hustle and bustle of crowded resorts and cities, you may find your Oahu home on one of the many magical beaches to the north.

For the truly adventurous, you can even go on a shark dive to come face to face with wild sharks from the inside of an underwater cage.


Ho’omaluhia Botanical Garden

A girl in a red dress walking up the road at the entrance to Ho’omaluhia Botanical Garden in Oahu on a 14 day Hawaii itinerary.

You don’t need to be interested in flowers or gardening or photography to enjoy Ho’omaluhia Botanical Garden (though it helps)!

While we typically prefer to include naturally occurring beauty over manicured gardens on our Hawaii itineraries, the scenery at Ho’omaluhia is too breathtaking to miss out. With 400 lush acres, it is truly a remarkable place with a seamless blend of native flora with tropical plants from around the world.

It is easy to see how it has become one of the most popular Instagram photo stops on Oahu!

If you want a break from the cities and resorts and high rises, take the H3 out to Ho’omaluhia Botanical Garden and tie it into a trip to some of the amazing south shore beaches of Oahu!


Hike Diamond Head

Looking out over Waikiki from Diamond Head on Oahu after hiking the Diamond Head trail.

Providing a spectacular backdrop for Waikiki, Diamond Head Crater is one of Hawaii’s most iconic sights. For those that enjoy a more active vacation, it is also home to one of Oahu’s best hikes.

From atop the 760ft (230m) summit, you will be rewarded with breathtaking panoramic views, looking out over Koko Head to the east and Honolulu to the west.

However, if adding a hike to your 14 day Hawaii itinerary doesn’t appeal to you, don’t worry – you can still enjoy views of Diamond Head from Waikiki Beach while sipping on a cocktail!

It is worth noting that as of May 12th, 2022 all out-of-state visitors must have an advanced reservation to enter Diamond Head State Monument. More information about reservations and entry fees can be found on the State Parks website.

Additionally, the last entrance for hiking the trail is at 4pm and the gates are locked at 6pm daily, at which time all visitors must have left the park.

Again, while tours are not required to hike Diamond Head, it can remove the hassle of transportation and reservations. You can find Diamond Head hiking tour options here or using the button below.


Climb the Stairway to Heaven?

The Haiku Stairs, aka the Stairway to Heaven, was once the most popular hike in Hawaii. Unfortunately, it was closed down in 1987. Still, visitors continued to do the hike illegally even after a security guard was put into place.

Due to the endless trespassing, the Honolulu City Council voted unanimously in September 2021 to actually remove the stairs. A budget has been set aside, but the trail is still there for now.

We are in no way recommending this hike. We are only including this information as we know many people visiting Oahu have this on their itineraries. There is no legal way to hike the Stairway to Heaven, despite some local guides who may offer a private tour.


More Oahu Travel Guides

Day 4-6: Kauai & Ni’ihau

The second stop on your two week island hopping adventure is on the Garden Isle of Kauai. This is the wettest island by far but most agree that this is what makes it the most beautiful.

Kauai is also where you will book your trip to the sister island of Ni’ihau from. Known as “The Forbidden Island of Hawaii,” it used to be impossible to step foot on the island without being a member of the Robinson family who owns it. Recently, however, a half-day helicopter tour option has emerged which gives travelers 3 hours on one of the island’s best beaches.

Kauai Overview

  • Nickname: The Garden Isle
  • Where to Stay: Poipu or Princeville
  • Number of Days: 3 on Kauai with a 1/2 day tour to Ni’ihau
  • Airports
    • Lihue (LIH) – Main Airport

Best for: People who see Hawaii as a place to be explored more than have a holiday. It is about adventure and activity, not just sunbathing and cocktails.

Suggested: PLANNING A TRIP TO KAUAI: THE ULTIMATE GUIDE


Getting to Ni’ihau

An aerial view of the entire island of Ni'ihau, known as the "Forbidden Island".

There are only two ways for tourists to see the forbidden island of Ni’ihau. The first is with a half-day helicopter tour that includes a scenic flight and 3 hours on the beach. This is the only way to legally step foot on the private island and there is only one provider.

The second option is still a great one but comes with a caveat. That is, you will boat to and snorkel off the shores of Ni’ihau but are not allowed to step foot onto land. This option involves booking a snorkeling tour that begins at the incredible Na Pali coast and then continues across the channel to the Forbidden Island.

If you are hellbent on seeing all 7 Hawaiian Islands, including one that few people on this planet have ever touched foot on, this will be your biggest challenge. Accordingly, it should probably be the first thing you book.


Where to Stay in Kauai

A young woman on a hammock in front of blue water and palm trees on the beach of Poipu on the south shore of Kauai in Hawaii.

If you plan on taking the helicopter tour or snorkel tour to the Forbidden Island of Ni’ihau, your Kauai itinerary should include accommodation specifically near Poipu. This is because the tour companies offering services to Ni’ihau operate on the south shore of Kauai.

Typically, Princeville on the north shore of Kauai is another popular option that we would recommend. However, for a 3 day visit that includes a trip to Ni’ihau, most of the top sights and tours will be in the southern region.

It may help to read the Where to Stay on Kauai Complete Guide for more information.


Best Things to Do in Kauai

Kauai is the best Hawaiian island for hiking, exploring, and outdoor adventures. This is a place where the true treasures are hidden and require effort, or at the very least, hiring a guide or tour to get you there.

Below are the top things to do on the Garden Isle with limited time; those true bucket-list items. However, there are a ton more to consider. For a full list of all the best options, be sure to have a look at the Best Things to Do In Kauai Complete Guide.


Na Pali Coast Tour

If there is only one thing you do in Kauai, you absolutely must do a tour of the Na Pali Coast. The savage Na Pali coast is one of the most incredible natural marvels you’ll see in your life!

The sheer cliffs that make the coastline so striking are also what makes it so difficult to see. Without a tour by sea or by sky, it is impossible to see much of this impressive landscape. Both are amazing experiences and completely unique.

Regardless of which tour you choose, we recommend booking it for as late in the day as possible! As the Na Pali coast is on the west, the light is best in the late afternoon when the sun is hitting it. Some companies offer sunset and dinner cruises, which is a beautiful time to be on the water!

By Boat

The biggest advantage of a boat tour is that you get a lot more time for your money. For young and active travelers, we highly recommend a raft tour. These smaller boats allow you to explore the coast in a unique way, giving you access to the sea caves and waterfalls that dot the Na Pali Coast. 

If you have younger children or are less interested in a bumpy ride, you will want to consider a catamaran tour of the Na Pali coast for a smoother ride and a higher priority on comfort.

By Sky

Witnessing the Na Pali cliffs from the sky is truly an incredible experience. If you’ve never been on a scenic flight before, it’s also a great excuse to tick it off your bucket list!

The unique birds-eye vantage point allows appreciation for the rugged landscapes in a way you’ll never forget. There are many different tour providers offering scenic flights over the Na Pali coast to choose from.


Waimea Canyon & Koke’e State Park Drive

Referred to as “the Grand Canyon of the Pacific”, Waimea Canyon is one of the largest and most spectacular canyons in the US. Fittingly for the “Rainbow State”, even the color palette of their canyon looks like a rainbow melted into it!

Most of the helicopter tours of the Na Pali coast will also fly over the Waimea Canyon as a bonus. However, it is easy to visit on a self-drive tour if you are renting a car, or with a tour company if not.

If you are driving, continue along Koke’e Road into Koke’e State Park for some amazing views of the Na Pali cliffs. Those who are young and able should include the short Kalepa Ridge Trail hike on their Kauai itinerary on the same day as Waimea Canyon State Park. This is the best hike in Kauai for seeing the Na Pali cliffs by land. However, be sure to read the complete guide to the Kalepa Ridge Trail first as there are some safety and legal considerations you need to understand.


Explore the Wailua Valley

The Wailua Valley region is home to lush rainforest with plenty of jungle to explore by foot, paddle, or tire.

Within this area, you will discover several of the best waterfalls in Kauai (including Secret Falls and Wailua Falls). Additionally, the Wailua River is a popular spot for kayaking.

If adventure is your thing, you can search for Secret Falls by renting a kayak and traveling up the river on your own, or hire a guide to take you there. Of course, some people prefer to just paddle upstream to enjoy the jungle that surrounds them. Either way, this is one of those bucket list Kauai things to do.


Hanalei Bay & Kauai North Shore

Located on the north shore, Hanalei Bay is the most famous and popular region of Kauai. Here you’ll discover golden sand tropical beaches colliding with verdant rainforest, resulting in astounding beauty.

Princeville is the nearest town and the one most people choose to stay in. However, with just a few days on Kauai, we recommend staying in Poipu on the south shore as discussed in the “Where to Stay in Kauai” section above.

Regardless of where you choose to stay, a day trip and even a sunset at Hanalei Bay should definitely be included in your itinerary.

Time, interest, and physical ability permitting, photographer’s in particular should also consider the short walk down to Queen’s Bath. Here, you will find one of the most photogenic volcanic coastlines in The Rainbow State.


Hike the Na Pali Coast

A hiker on the Kalepa Ridge Trail looking out over the Na Pali cliffs in Kokee State Park Kauai.

Most of the Na Pali coast is inaccessible by land due to the sheer, vertical cliffs. However, there are two trails that provide incredible views to enjoy on foot.

The Kalalau Trail is the most famous and begins at Ke’e Beach on the north shore. We highly recommend this trail for those who have more than two weeks in Hawaii and can take an extra one in Kauai. However, it is unfortunately too long and difficult to prepare for if you only have 3 days on Kauai.

For those who do have more time or prefer to prioritize the hike over other adventures, you can find out more about the hike and permits required on the Hawaii State Park website.

With only 3 precious days in Kauai and so much to see, you should instead consider the Kalepa Ridge Trail. This short hike has some legal and safety considerations that you need to truly consider, but it does fit nicely into a road trip to Waimea Canyon and Koke’e State Park.


More Kauai Travel Guides

You can find plenty more helpful resources for planning your time on Kauai with these popular guides to “The Garden Isle”:

Day 7-9: Maui

The second half of your 14 day visit to Hawaii begins with a flight from Kauai to the island of Maui. This will be a connecting point to the sister island of Lanai, which is clearly visible in the distance from anywhere along the west coast. Lanai is the only Hawaiian island you can visit by ferry.

Maui is the island that provides the best mix of everything. It boasts popular must-see shorelines to secret beaches, and even the otherworldly marvel of Red Sand Beach.

Additionally, it’s home to the world-famous Road to Hana Scenic Drive, charming historic towns, upscale shopping and dining, romantic hotels, and everything you dream of doing on a Hawaiian vacation.

Maui Overview

  • Nickname: The Valley Isle
  • Where to Stay: Kihei or Wailea
  • Number of Days: 3
  • Airports
    • Kahului (OGG) – Main Airport
    • Hana (HNM)
    • Kapalua (JHM)

Best for: People who want a little bit of everything; some lavish, upscale options, nature to explore but mostly by car, famous and secret beaches, something for everyone.

Suggested: PLANNING A TRIP TO MAUI: THE ULTIMATE GUIDE


Where to Stay in Maui

Map of Maui showing the 6 districts in different colors
Kihei and Wailea have incredible beaches and are centrally located for most Maui highlights.

With only a few days on Maui, the best area to stay is certainly going to be Kihei or Wailea. These regions neighbor each other on the western shoreline of South Maui.

Kihei is the most central option and features a wider range of accommodation options such as BnBs, condos, and hotels for most budgets. It is also closer to the restaurants, bars, and many beaches and shops.

Wailea is a bit pricier and further south which will increase drive times. However, it is best for higher-end travelers looking for a bit of luxury, as well as honeymooners and those looking for a romantic getaway.

If you want more information with a full detailed breakdown of where to stay and why, open our Complete Guide on Where to Stay on Maui in another browser.

Still undecided? Find out more:
WHERE TO STAY ON MAUI; BEST AREAS, HOTELS & RESORTS


Best Things to Do in Maui

Along with Oahu, Maui has some of the best beaches in Hawaii. However, while you’ll certainly find some of the softest sands and postcard-worthy shores during your visit, there is so much more to see!

The Road to Hana is one of the most famous scenic drives in the world, the channel between Maui and Lanai is a freeway for migrating whales, and the luaus here are the best in Hawaii, to name a few activities.

Below are some of the absolute can’t miss activities with 3 days on Maui.


Snorkel the Molokini Crater

An aerial view of snorkeling boats at Molokini Crater, Maui

From the southern coast of Maui you can spot a small, unusual shape in the distant ocean. What you are looking at is the extinct volcanic crater of Molokini. The reef surrounding this small island is a protected marine reserve and is considered to be the best snorkel spot in Maui.

As such, it makes for an incredible underwater adventure. You can expect pristine conditions and a reef abundant with life. While snorkeling you can spot manta rays, an array of tropical fish, sharks, and turtles that inhabit the coral reef.

The only way to visit Molokini Crater is by tour. There are a number of tour companies to choose from. Many also include stops at Turtle Town, which as the name suggests is a great place for spotting turtles.


Go Beach Hopping

Maui is perhaps most famous for its beautiful beaches and vibrant sunsets. If you are staying in the Kihei area as recommended, you could walk to literally a dozen beaches in one day. You shouldn’t, but you could!

Learn about all 15 beaches in our
COMPLETE KIHEI BEACHES GUIDE

If you are the adventurous type or just prefer quiet beaches to those with services and amenities, you can discover some incredible secret beaches on Maui where you are all but guaranteed to have the place almost to yourself.

Makena Cove Secret Beach in the Wailea-Makena region just south of Kihei is our personal favorite. If photography is of interest, this one is a can’t miss!


Drive the Road to Hana

The Road to Hana is considered one of the best scenic drives in the entire US and, as such, should absolutely be on your 14 day Hawaii itinerary! It is one of those bucket-list items that demands a place on your schedule.

For those that are comfortable driving, we recommend renting a car to start very early and following this Road to Hana itinerary for a self-guided tour. In it, you can find everything you need to know for planning a day trip and seeing as much as possible, including the otherworldly Red Sand Beach as well as the best 25 stops on the Road to Hana.

The other option which may be easier for most is to simply book a tour. There are some real advantages to this, especially with such a compressed schedule. A tour allows you to see most of the highlights with a guide who can maintain pace and also provides hard-to-get permits for Waianapanapa State Park and the world-famous Holokalani Black Sand Beach.


Whale Watching

From November through May it is whale season in Hawaii, with thousands of humpback whales migrating to Hawaii from Alaska. During this time, the shallow channel between Maui and Lanai off the west coast becomes a whale highway!

You do not need to book a tour for whale watching as you will see plenty right from the beach this time of year. However, you may want to consider one if you want the best chance to get up close and personal with these gentle giants of the ocean.


Explore Haleakala

View from the summit of Haleakala, a must see on a 14 day Hawaii itinerary

One of the most beautiful places to get immersed in the island’s volcanic nature is at Haleakalā National Park. Visiting the summit for sunrise is considered by many to be one of the best things to do on Maui.

However, due to its popularity, you will require a reservation for visiting Haleakalā Observatory at sunrise. It is also worth noting that the drive from Kihei to Haleakalā Visitor Center is 1h 25 minutes (45 miles) through winding switchbacks.

If you plan on visiting independently, we recommend exploring the official Haleakala NPS site. You will find everything you need to know about the park, including reservations, hiking information, as well as planners, maps, and important park alerts including closures.

With just 14 days in Hawaii and so much to see, it is worth considering taking the stress out of scoring reservations and driving switchbacks in the dark by booking a tour to Haleakalā. You’ll find that there are several tour options, explore these different tours using the button below.

Pro tip: Pack warm clothes! You will be at 10,023 feet (3,055m) in elevation so it’ll be much cooler than the beach, particularly at sunrise!


Feast at a Sunset Luau

A traditional Hawaiian luau is one thing you should try to include on your 14 day Hawaii itinerary. During a luau, the beauty of Hawaii is showcased through food, traditional dance, and storytelling.

While each island has various luaus available, Maui has the most famous, and most would agree, the best. We thoroughly enjoyed “The Feast at Mokapu” luau at the Andaz Resort but it only takes place two days per week.

However, there’s no need to worry if it’s not available for your days on Maui! There are many other luau options on Maui with excellent reviews. Use the button below to browse other options and see which are available during your visit.


More Maui Travel Guides

Many people consider Maui the best Hawaiian island. We have written an extensive list of additional guides to help you plan your time in Maui, with some of our most popular including:

Day 10: Lanai

Shark's Bay is the most beautiful beach on Lanai visited while island hopping during 14 days in hawaii.

Lanai is the small sister island off the west coast of Maui. It is the least-inhabited of the public islands of Hawaii, which brings with it a truly unique experience.

Discovering Lanai and its intriguing beaches and landscapes is something that few visitors take the time to do. There are some incredible places to snorkel, sunbathe, golf, and explore on the island, whether you choose a day trip to and from Maui or decide to stay overnight.


Getting to Lanai

There are three options for traveling to Lanai from Maui: by ferry, by small plane, or by tour.

The most cost-efficient option is to take the Expeditions Passenger Ferry from Maui to Lanai for just $30. This goes out four times daily and returns just as often.

The fastest option is to take a small plane from the main Maui airport at Kahului (OGG) to Lanai with Mokulele Airlines with flights starting at $48.

Finally, for those that would prefer an arranged tour, this small group Lanai snorkel and landing adventure may be perfect for you. The 6.5 hour adventure will take you to Hulopo’e Bay and you will spend three hours on the island. In addition, time and equipment are provided for an off-shore snorkel.

As the only way to get from Lanai to your next stop (Molokai) is by small plane, taking the ferry is the best option. This also provides a unique sightseeing experience through the channel with a high probability of spotting whales and dolphins.

If you are content with just seeing Lanai from a boat or sky, there are plenty of snorkeling trips that take you just off the shore, or scenic flights that allow you to see it from above. Browse Lanai tours here.


Lanai Day Trip vs Overnight

Aqua water laps the white sand beach, surrounded by red lava rock cliffs at Puu Pehe Bay (Shark's Bay) Lanai

You do not need to stay in Lanai, but it is the option we recommend for this 14-day Hawaii itinerary. Staying overnight will allow you to truly experience the island and the unique things it has to offer. Additionally, staying allows you to catch the morning flight to Molokai to continue your island hopping adventure.

However, it can be expensive to stay on Lanai and accommodation options are beautiful, but limited. If this is outside your budget or just not your preference, you have two more options.

Both options require one of the first ferries to Lanai from Maui at 6:45am or 9:45am and spending half a day there. You can then either catch the last ferry back to Maui that evening and fly to Molokai from Maui (OGG) in the morning, or catch the last flight from Lanai (LNY) to Molokai (MKK) at 5:30pm.

Example 1: Take the 6:45am ferry to Lanai, spend the day there, then fly to Molokai from Lanai.
Example 2: Catch the 9:45am ferry, spend all day on Lanai, take the last ferry to Maui and stay overnight, then fly to Molokai from the Maui airport in the morning.


Where to Stay on Lanai

There are limited options for places to stay on Lanai, with only two hotels to choose from. These hotels include the 5-star Four Seasons Resort Lanai and the 3-star Hotel Lanai. You may also find a few options available on VRBO.


Things to do in Lanai

Aside from enjoying the beautiful beaches and local establishments, there are a few one-of-a-kind destinations that may be worth exploring for adventurous travelers.


Keahiakawelo (Garden of the Gods)

The Garden of the Gods (Keahiakawelo in Hawaiian) is Mars-like landscape in a remote part of the island of Lanai.

The Garden of the Gods (Keahiakawelo in Hawaiian) is an otherworldly landscape in a remote part of the island of Lanai. It is known for the vibrantly-colored earth which looks like one of the many rainbows for which Hawaii is known melted into the soil.

Understand that reaching the Garden of the Gods requires significant effort and 4WD is required.


Shipwreck Beach

Shipwreck Beach is the one of the best photography destinations on Lanai, seen here with Maui in the background.

This is one of the true hidden gems for anyone photographing Hawaii. As the name implies and the photo displays, Shipwreck Beach is named for the rusted remains of a ship that crashed onto the shallow reef at the base of the shore.

Much like Garden of the Gods, reaching Shipwreck Beach requires a long drive down a rough road.


Hulopo’e Bay

The beautiful, tropical Hulopoʻe Beach Park in Sharks Bay is one of the most beautiful beaches visited on a 14 day Hawaii itinerary.

As you step off the boat or ferry from Maui, you will see the white sand beach of Hulopo’e Bay and Marine Reserve. It is the main reason most people visit, offering incredible snorkeling and the nicest beach on Lanai. You will find smaller crowds here than on the beaches of Maui across the water.

If you choose to take a day tour to Lanai, this is the beach you will land at and spend time on.


Shark’s Bay

A long exposure of the ocean dragging on the shore of white sand surrounded by red lava cliffs at Puu Pehe Bay (Shark's Bay) Lanai

Just a short walk from Hulopo’e Bay is the more secluded Shark’s Bay, also known as Puu Pehe Bay. This white sand beach is surrounded by red lava cliffs, creating an impressive and dramatic landscape. While this beach is incredible to look at, swimming is not recommended at Shark’s Bay due to strong currents and a rocky ocean bottom.

Day 11: Molokai

View overlooking Halawa Bay in Molokai and the lush greenery surrounding it.

Moloka’i was once a leper colony with a dark history, but has since become a thriving island with more residents than any of the other sister islands. It is also incredibly beautiful, especially from the air, and has earned the nickname “The Friendly Island”.


Getting to Molokai

As of 2022, the only to get to the sister island of Molokai is via Mokulele Airlines. There used to be a ferry option but it was shut down in 2021.

Mokulele offers tourist flights to Molokai (MKK) only from Lanai City (LNY) and Maui airport (OGG). The flight from Lanai to Molokai is non-stop at 8am each day. There are also a handful of 1-stop flights throughout the day that transfer in Maui.

If you decide to stay in Lanai, the best option for time and money is to take the 8am direct flight to Molokai, with rates beginning as low as $39 for a 20 minute flight.

If you decide to only do a day trip to Lanai, you will have to travel to Molokai from the Maui Airport (OGG). Rates begin at $74 and flights are 30 minutes.


Where to Stay on Molokai

You’ll find more options for accommodation on Moloka’i than Lanai. While Molokai is fairly small at just 38 miles long and 10 miles wide, as you will only have an overnight stay on the island, it is best to look for accommodation around Kaunakakai in Central Molokai. This is closest to the airport and is the main settlement on the island, as well as being centrally located for exploring.


Things to Do in Molokai

View of Molokai coastline from a scenic flight over the Hawaiian Island.

The biggest draws to Molokai are the lack of crowds and the unspoiled nature. With that in mind, you won’t find many commercial attractions or tour companies here. Rather, your efforts will be rewarded with breathtaking landscapes, fascinating history and culture, and pure aloha.

Explore Kaunakakai

Take time to explore the historic town of Kaunakakai either on foot or by bike. Here you’ll discover some local shops and eateries, as well as historic sites such as Church Row, the Alii Fishpond, and Kapuaiwa Coconut Grove. The quiet town has changed little in the past century and is a fascinating glimpse into the past.

Kalaupapa National Historic Park Mule Ride

The iconic, rugged north shore of Molokai as seen from Kalaupapa National Historic Park
The iconic rugged north shore of Molokai.
Image: NPS

For the more adventurous, a mule ride to Kalaupapa National Historic Park is truly a unique, thrilling, and humbling experience. Tucked away on the remote and rugged northern coast of Molokai, Kalaupapa is a former fishing village and leprosy colony.

To reach the peninsula, you will ride your mule along the winding 2.9 mile trail descending 1700ft of the tallest sea cliffs in the world, marveling at spectacular views along the way. Once you reach sea level, you will find a beautiful, tranquil, and isolated place.

However, Kalaupapa has a dark and compelling history. Since 1886, the area has been the forcible home for thousands with leprosy that were exiled by King Kamehameha V. During your time here, you will learn of the many incredible stories of human suffering, as well as those of love and courage.

Due to permits being required, it is not possible to visit Kalaupapa National Historic Park without a tour. You can find out more information on the NPS website.

Halawa Valley

The Halawa Valley is home to some of the most breathtaking landscapes in Hawaii. A scenic drive to the valley is an exhilarating experience, with numerous one-lane switchbacks and awe-inspiring views over the coast.

The valley itself can only be explored by a guided hike. The Halawa Valley Cultural Hike takes you through the heart of the valley, considered one of the most sacred sites.  Along the way, you will hear stories and learn about the history of the valley from the men who were born and raised here. Finally, you will arrive at Mo’oula Falls, where you can enjoy lunch and take a refreshing dip.

Beach Hopping

Halawa Bay Beach in Molokai on a 14 day Hawaii itinerary

As Molokai is too far off the beaten path for most Hawaii vacationers, you will be rewarded with miles of unspoiled beauty without the crowds. In fact, it is not uncommon to have an entire beach to yourself.

Here you won’t find any oceanfront resorts with perfectly manicured gardens, instead, you’ll find nature in all its glory, perfect for long beach walks, picnics, and admiring the spectacular landscapes.

The only downside to the beaches on Molokai is that they are typically not as good for swimming or snorkeling. The water visibility is not typically great and there are often strong currents and waves.

Some of the best beaches on Molokai include Halawa Bay, Papohaku Beach, Kapukahehu Beach, and One Ali’i Beach Park.


Day 12-14: Big Island

The 14-day Hawaii itinerary ends in Kona on the Big Island. This young island is home to all manner of volcanic landscapes and marvels and is also arguably the best place to snorkel in Hawaii.

If you have followed the itinerary to include all 7 of the islands, you will be flying into Kona from Moloka’i to complete the list.

If, however, you decided to skip “The Friendly Island” of Molokai and are island hopping from Maui instead, look into flights with Mokulele! They offer the first affordable small plane flights between these two islands that begin at $45, which is the same price as Hawaiian Airlines with a much more memorable experience.

Big Island Overview

  • Nickname: The Big Island
  • Where to Stay: Kona or Waikoloa
  • Number of Days: 3
  • Airports
    • Kona (KOA) – Main Airport
    • Hilo (ITO)

Best for: People who value space, seclusion, and budget over manufactured and lavish experiences with a sense of adventure.

Suggested: PLANNING A TRIP TO BIG ISLAND: THE ULTIMATE GUIDE


Where to Stay on Big Island

A map of the regions of Big Island.

First, understand that “Kona” can refer to the entire west side of the island, a region spanning as far north as Waikoloa, or the town of Kailua-Kona.

For most people, the best area to stay on the Big Island is in Kailua-Kona town. This is near the airport, beautiful beaches, a walkable and charming historic town, and is the most central point to begin your adventures.

The other option worth considering is the resort region of Waikoloa on the Kohala Coast. This tends to be more expensive and is farther away from many of the activities you will likely want to include in your Hawaii itinerary, but the resorts tend to be built on the best beaches. If you are not renting a car, this can be a big advantage.


Best Things to Do on Big Island

The Big Island is the youngest of the Hawaiian islands and is still being formed as we speak. This perpetual volcanic activity is experienced throughout the entire island, from the lava-rock fields to the black sand beaches, and even an active lava lake within Volcanoes National Park.

The Big Island is also known for having the best snorkeling in all of Hawaii!


Manta Ray Night Snorkel or Dive

Incredible close up night photo of a giant manta ray scraping the bottom of a boat on a Big Island night snorkel during 14 days in Hawaii.

If there is only one thing you do on the Big Island, make sure it is the manta ray night snorkel (or dive if certified). You are guaranteed to see manta rays and it will likely be the most memorable experience you have on your 14 days in Hawaii.

There’s nothing quite like being in the water beneath the stars, watching these gentle creatures gracefully dancing underwater.

Note that you do not even need to know how to swim or snorkel to do this, though it is less intimidating if you are comfortable with both.


Hawaii Volcanoes National Park

Night photo of a lava lake at Volcanoes National Park on Big Island during a 14 day Hawaii itinerary.

Not many people actually get to behold the savage power of mother nature as evocatively as looking into an active caldera with a bubbling molten lava lake.

A trip to Volcanoes NP is special any time of day. However, is even more powerful at night. Seeing the earth glow an otherworldly red as lava bubbles swell and burst while the stars twinkle overhead is something worthy of every bucket list.


Snorkel at Captain Cook Monument

The Big Island is considered the best island for snorkeling in Hawaii, and the best spot on the best island is at Captain James Cook Monument.

While it is technically possible to reach this cove on a self-tour, a long drive and even longer hike are required. The easiest and most enjoyable way to discover the underwater paradise at Captain Cook Monument is to book a morning tour that delivers you to two of the best spots on the island.

You are almost guaranteed to see dolphins from the boat and maybe even from the water, with a high likelihood of spotting some turtles as well. You are 100% promised to see one of the most vibrant coral gardens in the Pacific Ocean and a vast assortment of colorful tropical fish.


Green / Black Sand Beach

The remote south shore region of the Big Island is home to two of the most unusual and best beaches of Hawaii. Unsurprisingly, both owe their unusual colors to their volcanic heritage.

Papakolea Beach, aka Green Sand Beach, is a sheltered cove featuring olive-colored sand contrasting against vibrant blue and green water. The strange color is derived from a rich deposit of the mineral “olivine”. But more than that, Papakolea is home to the softest sand on the entire Big Island.

Just down the road is one of the most famous black sand beaches in Hawaii called Punalu’u Black Sand Beach. This pebbly shoreline is not as comfortable but is amazing to see. It is also a sea turtle sanctuary and you are almost guaranteed to see a resident honu (Hawaiian for sea turtle) on a visit.

Note: The most famous Black Sand Beach in Hawaii is Honokalani Black Sand Beach on the island of Maui.


Beach Hopping in Kona

Hapuna Beach in North Kona from a drone on a Big Island of Hawaii 14 day itinerary.

If you’re planning two weeks in Hawaii, then undoubtedly you will have tropical beaches on your mind! As you may recall, we recommend staying near Kailua-Kona or Waikoloa on the Kona side of the island as these are the two regions with the closest proximity to beautiful beaches.

You can read all about the best beaches in Kona in this complete guide, or just visit the ones closest to your accommodation. The important thing is you take some time to enjoy them, especially on your last days.

EXPLORE THE BEST BEACHES IN KONA


Coffee Tour

Picking coffee beans on a coffee tour during 14 days in Hawaii

Kona coffee has become a world-famous commodity. With its rich volcanic soil and perfect climate, the west coast of Big Island is ideal for coffee growing.

If you are a coffee enthusiast, consider visiting one of the farms to learn more about it and taste it right from the source!


More Big Island of Hawaii Travel Guides

If you would like more help planning your time on the Big Island, you may find some of these other guides to the island useful:


Packing for 14 Days in Hawaii

Printable Hawaii Packing List for 10 days in Hawaii.

If you are attempting the ultimate 14-day Hawaii itinerary, will absolutely want to ensure you fit everything you need into carry-on luggage! Since you will be flying from island to island, the price and time commitment for oversized baggage will mount quickly and become a constant burden.

Nearly every airline has the same size restrictions for carry-on luggage. Buying a full-sized carry-on will actually be cheaper than paying to check bags, not to mention easier to travel with. You can find airline-approved carry-on luggage here.

For help learning what to pack and a printable checklist, consult our ultimate Hawaii Packing List Guide. This printable list covers all of the essentials plus some useful items to consider for your vacation.

Don’t forget anything for your 14 day Hawaii vacation:
ULTIMATE HAWAII PACKING LIST

Traveling to Hawaii in 2022

Turquoise waters and white sand beach surrounded by black lava rock as sen by airplane when traveling to Hawaii
The Big Island adventure begins before you even land!

Hawai‘i is welcoming most travelers again. However, there are some pre-travel requirements for international travelers visiting Hawai‘i.

Domestic Travel to Hawaii

As of March 26, 2022, there are no COVID-related requirements for domestic passengers arriving in Hawai‘i.

You can find current information, advice, and guidelines related to COVID and travel in Hawaii on the Hawaii Covid-19 website here.

International Travel to Hawaii

For those traveling from international destinations with direct flights to Hawaii, you will need to follow federal international requirements. There are no additional State of Hawai‘i requirements.

As of June 12, 2022, international visitors are no longer required to show a negative COVID-19 viral test or documentation of recovery from COVID-19 before they board their flight.  However, the CDC is still requiring proof of vaccination for international visitors to travel to the United States. Requirements are constantly changing so ensure you check the CDC website or within your airline for current guidelines.

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6 thoughts on “Ultimate 14-Day Hawaii Itinerary: Up to 7 Islands in Two Weeks”

  1. Wow, I love this article! I can see that you put so much work into it and I’m dreaming about Hawaii. I would love to spend 2 weeks there and follow this itinerary. Thank you for putting this together!!

    Reply
  2. This is literally the guide of my dreams – so well written and so detailed! Hawaii has been on my list for the longest time and I absolutely can’t wait to visit – saving your post for whenever I do. Snorkelling the Molokini Crater sounds like the first thing I’d do, tbh!

    Reply

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