Planning a Fun and Fabulous Florida Keys Roadtrip

Driving the Overseas Highway from Key Largo down to Key West is an all-American road trip, be it with family, friends, or your romantic partner. This 113-mile trip travels through small tourist towns, over Seven Mile Bridge (a Florida landmark), and past sparkling water in more shades of blue than your average crayon box. It is one of the most scenic drives in Florida and if a Florida Keys roadtrip isn’t on your bucket list, it should be.

Technically you can complete a Florida Keys road trip in a day, as the drive typically takes about five hours without any long stops. However, you should really try to embrace the relaxed attitude of locals (or the “Conchs” as they call the locals in Key West) and take your time.

There are five major regions in the string of islands that make up the Florida Keys. From north to south these are: Key Largo, Islamorada, Marathon, the Lower Keys, and Key West. Each region offers a different vibe and attractions, so it makes sense to explore a few places along the way. Otherwise you might as well just skip the road trip and fly to Key West — but then you miss so much of the good stuff!

Florida Keys Overseas Highway

Getting to the Florida Keys

Getting to the Florida Keys is pretty easy, as you can find direct flights from across the country to either Miami or Fort Lauderdale. From Miami airport to Key Largo takes about an hour, and it is only a little further (1.5 hours) from Fort Lauderdale.

If you are limited in time, you may want to consider driving one way and flying out of the other, just keep in mind that you may incur some additional car rental fees for a one-way drop off.

Where to Stay on a Florida Keys Roadtrip

Note: This post contains affiliate links. If you click a link and make a purchase, I may receive a small commission. My recent trip was hosted by The Florida Keys and Key West, and we received complimentary accommodations, transportation, and some activities. All opinions are my own.

If you only have a long weekend, it makes sense to either hightail it down to Key West for the duration. Or, skip the long drive and stay in the higher Keys like Key Largo or Islamorada. However, if you have four nights or more, consider splitting up your stay.

I recently took a Florida Keys girls’ trip with my podcast partner Kim, and we spent two nights in Key Largo at Baker’s Cay Resort. Located in the southern part of Key Largo, it is a great jumping off spot for exploring the nearby Keys.

Bakers Cay Resort beach

We also had dinner and a spa treatment at the Playa Largo Resort, a Marriott Autograph property, nearby, which had a great pool and waterfront area for families.

On a previous family trip to the Keys, we stayed at Hawk’s Cay Resort on Duck Key, which is a fabulous choice for families and great for venturing into nearby Marathon.

Once you arrive in Key West, you have the option of staying in town, or saving a little money by staying just outside of town on Stock Island. On our girl’s trip, we stayed at the Perry Hotel Key West on Stock Island, a boutique hotel that offers shuttle service to the beach and downtown.

Baker’s Cay Resort Key Largo

Bakers Cay Resort lobby

Baker’s Cay Resort Key Largo is part of the Curio Collection by Hilton. As with many Curio properties, this renovated property maintains the local character. The beautiful public spaces offer many areas to relax and hang out, from swings on the patio to the library and games area off the lobby.

There are two restaurants on property, as well as a beach bar which serves up complimentary champagne at sunset, and a food truck and bar at the pool.

Bakers Cay Resort swings

The rooms at Baker’s Cay have been refreshed, but the building still maintains outdoor corridors. There are two wings of the resort, one fronting Hammock Beach, which is a tiny beach tucked under the mangroves, and the other near sunset beach, which is the main beach featuring the dock and water activities.

You can book all sorts of excursions and water sports from the resort, including wave runners and paddle boarding. Kids also love the challenge of the resort ABC scavenger hunt, with letter scattered throughout the property.

Perry Hotel Key West

Perry Hotel Key West pool

The Perry Hotel is located on Stock Island, an up-and-coming area approximately 20 minutes outside of downtown Key West. This stylish, boutique hotel caters to young families, groups, and couples.

Even though the hotel isn’t in walking distance to downtown, they do offer scooters for rent for $45 a day, or free shuttle service on the hour from mid-morning through evening.

Perry Hotel Key West Lobby

Of course, you can always hang out at the hotel. Rent a cabana around the pool, hang out in a hammock, enjoy an excursion from the marina next door, enjoy oysters at the pool bar, or experience fabulous sea-to-table dining at Matt’s Stock Island Kitchen and Bar.

The rooms are as tastefully decorated as the public spaces, many offering balconies overlooking the pool. The Perry Hotel Key West is a great choice for those looking for smart, affordable luxury who want to stay out of the hustle and bustle of downtown.

Things to do in Key Largo and Islamorada

While you are staying in the Key Largo area, take some time to explore. It is known for its fishing and scuba diving, and nearby Islamorada is one of the cutest small towns in Florida. Other attractions include:

John Pennekamp Coral Reef State Park

The underwater playground of John Pennekamp Coral Reef State Park is a must-visit if you are spending time in Key Largo. This undersea park covers 70 nautical square miles, whose coral reefs can be explored by glass-bottom boat, scuba, or snorkeling expedition. Upland areas offer mangrove swamps, walking trails, picnic tables, swimming, and a visitor center.

Lunch at Mrs. Mac’s Kitchen

Mrs. Mac’s Kitchen is a long-time favorite of locals and tourists, as you can tell from the license plates lining the walls. Try the crab cakes or the conch fritters, just be sure to save room for some key lime pie.

See more suggestions on where to eat in Key Largo!

Robbie’s of Islamorada

Robbie's of Islamorada

Robbie’s Marina is one of the most popular places in the Keys. Most visitors stop here to feed the tarpon fish, purchasing buckets of fish and paying an entrance fee to access the docks. However, there is also a restaurant and bar on site called the Hungry Tarpon. Just make sure you arrive early because the parking lot fills up fast.

Robbie’s also offers all sorts of water excursions, including snorkeling, parasailing, scuba, kayaking, paddle boarding, and fishing charters. We took a snorkeling tour from Robbie’s out to Alligator Reef (don’t worry, there aren’t any alligators, although you may see a nurse shark!) It was pretty choppy on the day we went out, so if you get seasick you may want to inquire about conditions before you board.

Boat Tours

You may also want to consider a glass-bottom boat tour or sunset cruise with Key Largo Princess. The glass bottom boat tour will allow you to see the underwater world of the John Pennekamp Coral Reef State Park and the Key Largo National Marine Sanctuary without going under the water!

Places to Stop on a Florida Keys Road Trip

If you take my advice and spend a couple of nights in Key Largo before heading down to Key West, you will still have quite a drive in front of you. The trip from Key Largo to Key West took us nearly five hours, with a few stops along the way. If you want to break up your trip, check out these options.


Burdine's key lime pie

If you are getting hungry while driving through Marathon, plan to stop for lunch at either Island Fish Co. and Tiki Bar, which is a great spot to catch the sunset too. Or head off the highway to go to Burdine’s Waterfront Marina. Both have a delicious fried key lime pie, but Burdine’s is pretty unique and served chimichanga style.

While you are there, stop and visit the sea turtles at The Turtle Hospital, with rescues, rehabilitates, and releases injured turtles. Just keep in mind that reservations are recommended.

Bahia Honda State Park

Bahia Honda State Park

Even though the Florida Keys aren’t known for its beaches (see this list of the best Florida Beaches), Bahia Honda State Park used to be one of the most beautiful beaches in the country, but it has taken a hit from Hurricane Irma a couple of years ago and is still recovering. Even though some of the beach is currently closed, it is still a scenic spot for a photo opportunity or a beach stop.

Big Pine Key

Just after Bahia Honda State Park, you will enter Big Pine Key. Also hit hard by Hurricane Irma, you can see the impact on many of the trees in the area. Just make sure you drive slowly through this area and keep your eyes peeled for the native key deer.

No Name Pub

Stop for lunch or a drink at the No Name Pub. It sounds like a local joint but despite being off the highway, it isn’t really unknown with the tourists. They are mostly known for their wings, and the dollar bills that hang from the ceiling and walls.

Things to do in Key West

Key West conch train tour

You can easily spend a week enjoying Key West, especially if you enjoy getting out on the water. Be sure to plan to stay at least two or three nights to get a real taste of the Keys. Just watch out you don’t get “Keys disease” and end up moving down there like so many of the people you will meet down there.

In addition to shopping on Duval Street, checking out the Key West Aquarium, stopping at the Butterfly Conservatory, visiting Ernest Hemingway’s house, and getting a photo opp at the Southernmost Point in the Continental United States marker, here are some other fun things to do in Key West. And if you have the time, I’d recommend a day trip to Dry Tortugas National Park.

Sunset Celebration at Mallory Square

Mallory Square sunset celebration

Key West sunsets are famous, as are the Sunset Celebrations at Mallory Square. You will find food carts and all sorts of street performers from fire jugglers to tightrope-walking cats. Just be sure to line up at the water’s edge early to get a prime spot for watching the sunset.

The Sunset Deck at the Margaritaville Key West Hotel is a prime sunset viewing opportunity. If you can’t find a seat there, or if a cruise ship is blocking your view, head over to Sunset Pier and stake out a rail-side table. Of course, the best place to see the sunset would be over at Latitude’s at Sunset Key.

Sunset Catamaran Cruise

Sebago Key West sunset cruise

Don’t miss a sunset while you are in Key West. After enjoying one evening in Mallory Square, get out on the water for an unobstructed view. There are many different types of sunset cruises, from major party boats with live music and disco lights, to smaller catamaran cruises.

We picked a sunset catamaran with Sebago Key West. There was plenty of room to move around the catamaran and the crew was very attentive. The cruise included an open bar of wine and beer, along with four courses of light bites including cheeseburger sliders and key lime tarts.

I would also recommend the two hour sunset cruise with Wild Dolphin Adventures or the sunset and snorkel combo sail with Sunset Sail Key West.

Island Adventure Tour

Fury Key West Island Adventure Tour

Key West has a few beaches, but to experience the Keys, you need to spend time on the water. You can find every type of water activity, but one that we loved was the Island Adventure Eco-tour from Fury Key West.

This half-day tour included breakfast and lunch. It started with a short snorkel time in a coral gardens, where we saw plenty of sponges. Next we headed out to Woman Key for an eco-kayaking tour along the mangroves. We also had plenty of time to hang out on the sandbar and paddle board.

On the way back we even lucked out by spotting a pod of dolphins along the side of the boat. This was such a fun tour, but be sure to bring plenty of reef-safe sunscreen and a good sun hat because the sun is strong out on the water.

Key West Food Tours

Garbo's Grill food truck

If you are a foodie, be sure to sign up for an excursion with Key West Food Tours. They offer a seafood tour, Cuban tour, and cocktail tour. We took a seafood tour with Rose, who was an amazing guide and former chef and he made the tour so interesting.

We sampled food in five different locations and ended our day at a brewery. If you are looking for more meal suggestions, be sure to check out my recommendations on where to eat in Key West.

Find other great Key West excursions and tours with my partner Trip Shock.


Planning a Florida Keys road trip
Tips for planning a FL Keys road trip
Planning a Florida Keys road trip

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Publish Date: August 5, 2019

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