🏝 Ultimate Key West to Key Largo Road Trip Guide (2024)

Though not on the way to Key Largo, Key West serves as the gateway to Dry Tortugas National Park; a unique park full of natural beauty and history.

Dry Tortugas is famed for its spectacular blue waters, marine life, and coastal fortress at Fort Jefferson.

Getting to this incredible park takes some planning as visitation is limited and it can only be reached by boat or small seaplane. Book your tickets in advance!

Downtown Key West has preserved much of its early architecture and aesthetics, making for a fun stroll around town.

Of course, it is equally popular as a party destination, especially on the world-famous Duval Street.

Duval Street is often compared to Bourbon Street of New Orleans, and even boasts a touch of Nola culture in some of its bars and pubs.

The downtown area is also where you will find the majority of the main tourist attractions in Key West.

Sunset Pier is the premier place to grab an evening cocktail on the colorful dock and watch the sunset over the appropriately named Sunset Key.

You will find this vibrant, buzzing place in the heart of Key West.

Expect a bit of buzz most times of day, but especially in the evenings.

One of the quintessential Florida Keys bucket list activities is to spend an evening at the Sunset Celebration nightly arts festival at Mallory Square Dock.

Local street performers, food vendors, and even psychics attend each night accompanied by thousands of tourists to watch the sun sink into the Gulf of Mexico horizon as an iconic schooner drifts across the scene.

Smather’s Beach is the best beach you will find anywhere from Key West to Key Largo, and is located within a short drive from the airport.

This postcard-perfect beach features pristine white sand, towering palm trees, and clear water.

It is exactly the beach you daydream about when planning your visit to the Florida Keys.

Higgs Memorial Beach Park is a family-friendly and easily accessible beach on the outskirts of Key West.

Full facilities are available and beach access is free. You will have to pay for parking, however.

The Ernest Hemingway Home and Museum is one of the most iconic places in Key West. During the 1930s it was home to the famous writer and was where he wrote 70% of his work.

Today, it is a National Historic Landmark and home to over 60 cats, including many that are famed for having six-toes!

The grounds are beautiful and you can choose to take a guided tour or explore by yourself.

The Key West Lighthouse & Keeper’s Quarters can be seen from the roadside, across from the Ernest Hemingway House.

However, if you’re physically able, it is worth visiting to climb the narrow spiral staircase to the top of the lighthouse and take in the views over the island.

The museum is small but provides an interesting glimpse into the life of the lighthouse keepers.

Built in 1890, the Truman Little White House first served as the naval station’s command headquarters during the Spanish-American War, WWI, and WW2.

It later became the winter home for President Truman and subsequent presidents.

Today, it continues to be a government building, in addition to a museum where you can take a guided tour to learn more.

While it may look historic, the Tropic Cinema was actually only opened in 2004.

It was created with an artistic vision, as stated on the website:

“Tropic Cinema was created to bring quality movies to people who longed for something more than Hollywood blockbusters. Our artistically diverse island community deserved to see amazing independent films, international favorites and cinematic classics — film that appealed to folks who value going beyond the usual.”

The Key West Butterfly Conservancy was surprisingly our absolute favorite thing to do in Key West!

Imagine walking through a magical trail as tranquil music echoes throughout and hundreds of butterflies and colorful birds swirl about… it is truly an enchanting experience.

Definitely include the Butterfly Conservancy on your Key West to Key Largo itinerary!

While the only “experience” in visiting the Southernmost Point in the US is waiting in a long line to say you’ve been there and take a photo, it continues to be perhaps the most popular activity in Key West.

To add a little experience to the wait, grab a Cuban coffee from the nearby cafe to enjoy while in line.

🌅 Pro tip: Visit early morning to avoid waiting in line.

While it may not be the softest sand, Fort Zachary Beach is one of the prettiest beaches in the Florida Keys.

In addition to ample white sand, lush greenery provides plenty of shade making for the perfect picnic destination.

As it is a state park, you will need to pay a small entry fee.

One of the best ways to enjoy the Key West sunshine is by taking to the water.

From adrenaline-filled activities such as jet-skiing and parasailing to more energetic experiences such as kayaking, or a relaxing snorkel or sunset sail… Key West has it all!

If you can’t decide, many tour companies even offer full-day watersport packages so you can try multiple activities.

Just off the coast of Key West lives a resident pod of bottlenose dolphins.

Honest Eco takes visitors on a sustainable dolphin watch tour and snorkel aboard SQUID, the first electric passenger boat in the USA.

But it’s not just the boat and the wildlife that makes this tour special, the staff is truly exceptional. We were swept away by their enthusiasm and passion and learned so much from them.

Sunset Key is a beautiful little island just off of Key West.

It is technically a private island, but visitors can enjoy this special place via a few options.

The one we recommend most highly is by making a reservation for Latitudes Restaurant – this was the most unforgettable meal we enjoyed in all of Florida.

This 7-mile overseas highway connects the westerly keys to the rest, allowing driving access from Key West to Key Largo.

In addition to its transportation services, it is also quite striking to behold, especially from the sky.

The old 7-Mile Bridge can only be accessed by foot, bicycle, or trolley, but the modern one is easily drivable.

Pigeon Key is a small but stunning little island just outside of Marathon. It is only accessible by walking, cycling, or taking the Pigeon Key Trolley 2-miles down the old bridge which stops just after reaching the key.

In addition to being a beautiful place to explore, Pigeon Key offers perhaps the best beachside snorkeling in the Florida Keys.

A tour of the Turtle Hospital in Marathon is a must on your way to Key West. This incredible place rescues and rehabilitates hundreds of endangered turtles every year.

By taking a tour of the hospital, not only will you get up close to lots of turtles from hatchlings to fully grown adults, but you will also be helping to support their amazing work.

The tours last approximately 1.5 hours and run every half hour from 9am-4pm.

Of the many underwater places to explore, few are as impressive as Florida Keys National Marine Sanctuary.

What lurks below the crystal clear water is a world of colorful, thriving marine life and vegetation.

The only way to experience the Florida Keys National Marine Sanctuary (without your own boat) is via tour!

We went with Horizon Divers and highly recommend them.

John Pennekamp is the first underwater park in the US.

This park is best known for the diving and snorkeling opportunities it provides, the most famous being a visit to “The Christ of the Abyss.”

The beaches at Pennekamp are also the best you’ll find in Key Largo.

The only way to see the Christ of the Abyss is via a snorkel tour.

You can also take a glass-bottom boat tour to witness the beauty of the underwater world without getting wet!

Latitudes promises to be one of the most unique, memorable dinners of your life. That is not hyperbole, it is truly that special.

This Caribbean-inspired restaurant is located on a small, private island known appropriately as Sunset Key. To reach it, you will hop onto a ferry from Key West and take a short ride to a pristine, white sand beach.

Tiki torches and unbeatable sunset views surround beachside seating. Even on a busy night, the tables are arranged so that you forget anyone else is there.

Latitudes is the perfect place for a special occasion and/or to celebrate your final night in Key West. Every detail has been dialed in from the elegant service to the innovative menu; this is one you will not forget!

Downtown Key West is a colorful, vibrant place that really comes alive at night.

For your first night in the area, we recommend a more casual option that lets you see and feel what Key West is all about.

First Flight Brewery is the perfect choice. Leave the collared shirts and heels behind and come as you are for hand-crafted beer and exceptional comfort food in a garden-like setting.

With so many upscale and more elegant meals on the itinerary, we truly appreciated the experience at First Flight. Live music could be enjoyed from the bar adjacent, but provided ample distance for us to chat and enjoy each others’ company.

Matt’s Kitchen was one of our sneaky favorite meals in all of our time in the Keys. We visited on our last night, exhausted from so much sun and food and running around, and could not have been more impressed with everything.

Matt’s is not a fancy place, it is just a great one. It is located on a small harbor in a very quiet region of Stock Island just a short drive from Key West.

Sit by the fireplace and begin your evening with one of their incredible cocktails as the sun goes down. I recommend the Key Lime Pie martini, complete with crust-lined rim and absolutely perfectly flavored.

Pair it with some appetizers ranging from locally sourced and expertly prepared scallops to their signature duck wings. Both exceeded even our high expectations.

We ordered everything from appetizers to desserts and could barely move by the end, but we enjoyed every single bite.

Located on Marathon, on the way to Key Largo from Key West, the beach bar at Isla Bella provides a great option for a lunch stop.

Head to the beach and recharge with a signature island cocktail and a light nosh. The menu is somewhat limited, but will have some good options to tide you over until your dinner in Key West.

Mrs. Mac’s Kitchen is the most popular lunch spot in Key Largo and an absolute local favorite.

This quaint restaurant has been serving the Florida Keys delicious food longer than nearly any other establishment, opening in 1947 as one of the few places to eat in all of the Keys.

Mrs. Mac’s Kitchen is a nearly-perennial winner of local People’s Choice Awards and is a must-visit while staying in Key Largo.

We recommend you end your day by enjoying delicious local cuisine with an unbeatable ocean view at Calusa restaurant at Baker’s Cay Resort.

Calusa serves all the Southern Florida favorites, primarily locally-caught seafood with a Caribbean influence, but they also prepared one of the finest filet mignons we have ever tasted.

Beyond the food, views, and service, what we loved about Calusa was that it felt elegant and upscale without feeling formal or pretentious.

That and the Jerk Prawns… you have to try the jerk prawns!

The Key Largo Conch House is another local favorite and an excellent place to fuel up for the day.

This historic house is one of the oldest in the Keys and has been serving large portions of local fare for over half a century.

Prices are reasonable, portions are ample, and flavor is true.

The “water table dinner” at Sol by the Sea is the perfect way to spend your final night in Key Largo and promises to be one of the most unforgettable meals of your life!

Sol by the Sea restaurant actually arranges a table and service IN the water. Imagine dining while fish swim about and the sun sets magically over the very water you are eating in.

“But what about the food?” you may be asking. Rest assured, they have that covered. Sol by the Sea serves some of the best food you will have anywhere in Florida, specializing in local favorites such as seafood, key lime pie and cocktails, and catch of the day.

Our sunset dinner in the water was one of the most unique dining experiences we have ever experienced. This is definitely one you will not want to miss!

The most important decision you will make when planning your Florida Keys itinerary is deciding where you are going to call home.

We stayed at Parrot Key Hotel and genuinely feel it is one of the best options in Key West for accommodation. Our “room” was more like a house, and the views were just unbelievable.

Among the endless list of features and amenities you can expect, the most notable is their shuttle services to downtown Key West and Smathers Beach (the best beach in the region). This means you can just walk to the front desk and not have to worry about parking and driving in the busy streets of downtown.

Parrot Key also has FOUR pools for their guests, one with a full bar and a small restaurant.

Kona Kai Resort is the best place to stay in the Florida Keys and offers an experience unto itself.

This incredible resort is an all-in-one staycation destination with paddle boarding, dolphin watching, kayaking, and more right from the dock!

Our stay at Kona Kai was one of the most memorable of our extended travel lives. We cannot recommend this place highly enough!