Visiting The Florida Keys is like visiting the Caribbean, but without needing a passport! We spent 5 days doing a roadtrip through The Florida Keys. Flying into Miami International Airport (MIA), we rented a car and made our way down the 113-mile Overseas Highway, one of the most beautiful drives in the USA. Our first stop was at Key Largo, where we spent a two days to relax, before making our way to Key West for Pride. There’s so much to do and see in The Florida Keys, we picked out the our the top hotels, restaurants, bars, and tours, and put them all in this guide.

Key West is so full of pride, great community, amazing food, and so much to see — we can’t wait to get back for next year’s Pride! Key West Pride is typically held every year the second weekend in June.

Here is the full 5-day itinerary to Key Largo, Key West and The Florida Keys!

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How to Get to the Florida Keys:

• What’s the Best Airport to Fly into For the Florida Keys?

The Florida Keys are located at the South-Eastern most point of the continental United States. The best airport to get to the Florida Keys depends on where you plan on staying. If you are heading to Key Largo and the north eastern keys, fly into Miami International Airport (MIA). If you are planning to begin your trip in Key West and the south western keys, fly into Key West International Airport (EYW).

For the most convenient experience taking the ultimate roadtrip through The Florida Keys, fly into Miami International Airport (MIA), rent a car, and drive south to start your trip in the largest island in the Florida Keys, Key Largo.

• How Long Does it Take to Drive to the Florida Keys from Miami International Airport (MIA)?

There are a couple different routes to drive from Miami International Airport to Key Largo. You can take one of the toll expressways for a fee of about $4.00, or you can avoid the tolls, which will prolong your drive a little longer. Taking a toll road will get you to Key Largo within about an hour and a half with typically mild to moderate traffic. Avoiding the toll roads will take two to two and a half hours to get from Miami International Airport to Key Largo with moderate to high traffic.

• How Long Does it Take to Drive from Miami to Key West?

The Overseas Highway is a 113-mile highway carrying U.S. Route 1 through the Florida Keys to Key West. If you drive non-stop, the total drive from Miami to Key West can take as little as four hours. However, once you leave the Greater Miami area, the Overseas Highway is just a single lane in each direction. If there is slow traffic or an incident on the Overseas Highway, it can significantly delay your roadtrip. Not to mention, there is so much to see and do in Key Largo, Islamorada, Marathon and the other keys. I highly recommended breaking up your trip into two parts: the first half of your vacation staying in Key Largo or Islamorada, and the second half staying in Key West.

The distance between Key Largo and Key West is a gorgeous 98 miles over turquoise waters. If you drive non-stop, you can make it from one city to the other in just over two hours.

Where to Stay, Where to Eat, and What to See in Key Largo and the Florida Keys

Traveling solo for the next couple of days in @thefloridakeys and having a bit of an eat, pray, be gay moment. Days like this don’t come often. Having the chance to travel alone is like taking myself on a date for the first time. I get some space to get to know me a bit better, and I’m feeling pretty grateful for that.

Where to Stay in Key Largo

Stay at the Reefhouse Resort & Marina

The former Key Largo Bay Marriott Beach Resort has been transformed into Reefhouse Resort & Marina, part of the Opal Collection resort portfolio, situated on 17 acres with views over Blackwater Sound. This 153-unit resort offers a variety of accommodations including traditional rooms and two-bedroom suites. Guests can enjoy amenities such as a private beach, marina, and dive shop. Additional features include the By the Bay Spa, a 24-hour fitness center, a pool with Flipper's Bar nearby, and Breezer’s Tiki Bar. Gus' Grille offers all-day dining in a waterfront setting with an outdoor covered patio. The resort provides 50,000 square feet of indoor and private outdoor event space, accommodating gatherings of up to 200 guests. For larger events, the on-site Key Largo Conference Center offers seating for 250 attendees.

Top Restaurants in Key Largo

Key Largo Conch House

Hidden behind trees and shrubbery, Key Largo Conch House is an air-conditioned restaurant with outdoor seating, nifty decorations and a menu featuring fresh local seafood and delicious desserts. ​​This iconic eatery celebrates the island's culinary heritage with a menu rich in fresh seafood and traditional Conch recipes. Best known for their conch fritters and irresistable key lime pie.

The Fish House

The Fish House specializes in fresh local seafood including yellowtail snapper, mahi mahi, grouper, Florida lobster and stone crab. Every single dish is prepared with a commitment to quality and local sourcing. The inside of The Fish House resembles that of an old fishing boat’s interior. It’s cozy, it’s casual, and it’s so much fun to visit. The Fish House is one of the last remaining restaurants that actually source their fish freshly and locally daily.

Gus’ Grille at Reefhouse Resort

With views of the sunset over Key Largo Bay, Gus’ Grille provides the perfect atmosphere to linger over a plate of tasty local seafood. I highly recommend choosing from the lobster tail, almond-crusted snapper, and pan-roasted shellfish. I tried the snapper and was blown away by the fresh citrusy flavor. Eating seafood in the Keys makes it difficult to want seafood anywhere else! The fish is just too fresh here. For cocktails, enjoy a classic piña colada or a margarita with juicy key limes.

Morada Bay Beach Café

Located in Islamorada, the Morada Bay Beach Café & Bar is an outdoor Mediterranean bistro café set in the sand. Serving a blend of Caribbean and American cuisines, the atmosphere out on the sand is unmatched. I enjoyed fresh conch ceviche and perfectly grilled yellowtail all while watching the sun set. Most recently the property of Morada Bay Beach Cafe, The Moorings and its sister restaurant, Pierre’s, were filming locations for the Netflix drama series, “Bloodline.” In addition to these properties, “Bloodline” features a number of other Upper Keys locations. The setting is so iconic, that I happened to witness a marriage proposal, all while enjoying my dessert!

Keys Fisheries

This casual island favorite on Marathon Island is home to some of the freshest seafood around. Specialties include the famous Florida Keys lobster Reuben, succulent stone crab claws, and a variety of fish tacos prepared to perfection. If enjoy fish “fresh off the boat”, this is the restaurant to try. Keys Fisheries is well known for its lobster Reuben.

Lazy Days South

Lazy Days South is a beachfront seafood eatery that overlooks the harbor on the south end of Marathon. With deck seating and a cook-your-own-catch option, Lazy Days is a laidback eatery that emulates the chill vibe of the Florida Keys. Dine on the outside patio overlooking the beautiful waters of the Atlantic and enjoy romantic Florida Keys sunsets… or dine indoors in our cozy, yet spacious atmosphere.

Top Tours and Things to See in Key Largo

Go Snorkeling and Scuba Diving with Horizon Divers

Horizon Divers offer a variety of underwater activities, including scuba diving and snorkeling. Known for their expertise and commitment to marine conservation, Blue Star rated Horizon Divers provides a safe and educational underwater experience suitable for all skill levels. From shallow reefs teeming with colorful coral formations to encounters with diverse marine life including sea turtles and rays, every excursion is bound to provide some awe-inspiring sights. The knowledgeable guides at Horizon Divers not only ensure safety but also enhance the journey with insightful commentary on the marine ecosystem and its inhabitants.

During our tour we visited two iconic diving locations including Carysfort Reef and the City of Washington shipwreck, all located within the Upper Keys National Sanctuary. If scuba diving, the trip includes the use of air tanks, weights, and weight belts. 

Taste the Florida Keys Best Beer at Florida Keys Brewing Co.

The Florida Keys Brewing Company has a way with surprising flavor combinations. Brewing up tasty beers in Morada Way’s Arts and Cultural District, the Florida Keys Brewing Co. brewery and taproom infuses their beers with local flavors such as hibiscus, Key limes, and local honey. Try the incredibly popular Iguana Bait Honey Hibiscus Kolsch. The Brewing Company even hosts live music in the evenings in the back patio area, perfect for locals and visitors alike to sip and mingle.

Visit Sea Turtles with a Tour of the Turtle Hospital

On the front lines of conservation, the Turtle Hospital has been rescuing injured sea turtles and treating them back to health since 1986. Much of the Turtle Hospital’s work is based in educating the public. Because of the delicate nature of revitalizing the sea turtle population, the Turtle Hospital teaches its visitors about what to look for to tell if a sea turtle needs help or assistance. Walk the grounds, get introduced to the resident sea turtles and the hospital's curative programs for loggerhead, green sea turtles, hawksbill and Kemp's Ridley turtles. The hospital is believed to be the world’s only state-licensed veterinary hospital dedicated solely to the treatment of sea turtles and is absolutely worth the visit.

Where to Stay, Where to Eat, and What to See in Key West

Now that we’ve made our way from Key Largo to Key West, it’s time to explore the best restaurants, accommodations, and tours in Key West, Florida.

Where to Stay in Key West

🌈 Stay at Alexander’s Guesthouse

We stayed at Alexander’s LGBTQIA+ Guesthouse, an exclusively LGBTQIA+ clothing optional resort. When we were checking in, there was already a pride pool party underway around the main central pool at the back of the house. Alexander’s Guesthouse is a lovingly restored Key West “conch house” built in 1902 and boasting original pine floors and stately windows. The well-air-conditioned rooms provide the perfect private space to relax, and some include clothing-optional decks overlooking the grounds. This lovely three-story house is located on a quiet, tree-shaded street in the heart of Key West’s Old Town within a close walk of Duval St.

Alexander’s Guest House is the last remaining exclusive LGBTQ+ accommodation in Key West. Other accommodations in the region have either changed to specify for men-only, or open up to “all are welcome,” meaning, not specifically LGBTQ+. @alexanderskw

🌈 Stay at Island House Key West

Island House is where you can find the party. During Key West’s Pride Week in June, Island House hosts daily parties with plenty of attendees ready to swim. Chique furnishings and a large outdoor pool, Island House may make you want to stay in Key West just a little bit longer.

Stay at Eden House

LGBTQ+ friendly Eden House is your home away from home. Located just minutes from Key West’s historic Duval Street, Eden House is at a great location, provides free coffee & water on tap, runs a happy hour daily from 4-5pm, with incredible staff and a lovely pool and jacuzzi to relax in after a long day touring the city.

Top Restaurants in Key West

🌈 Dinner at Azur

Flavor is a thing that Azur does not lack. Perhaps our favorite meal of the entire trip, Azur is LGBTQ+ owned and offers a memorable dining experience featuring Mediterranean specialities. For dinner, try the yellowtail snapper with petite shrimp, diced yellow potatoes, capers, chives and lemon butter. Other must-tries include pulpo, or charred confit octopus, and branzino.

Cuban Coffee Queen

Cuban Coffee Queen is by far the most popular coffee on Key West. Try a café con leche Cuban style, or get something even sweeter with the Cuban chocolate mocha. Cuban Coffee Queen is so popular, that even on the hottest of days you’ll likely see a line extending from it’s order window. With breakfast options and Cuban sandwiches for lunch, the Cuban Coffee Queen is a classic you cannot miss!

Hot Tin Roof

One of the most sought after reservations on the island, Hot Tin Roof’s aesthetic is gorgeously tropical with a perfect view of the sunset over Sunset Key. Hot Tin Roof provides a romantic dining space, perfect for an al fresco experience along its veranda. The menu is extensive with a variety of small plates, including a Manhattan style lobster bisque and duck leg confit. For large plates, try the plantain crusted swordfish or the filet mignon.

Half Shell Raw Bar

Located in the Key West Historic Seaport, the casual Half Shell Raw Bar serves fresh seafood, from fish and chips to its famous Half Shell conch ceviche. Our favorite dishes include the buffalo shrimp, crab-stuffed yellowtail, and the best oysters on the island. As you watch the sun set over the harbor, you’ll see boats making their way back to the docks and large fish idling below just waiting for a shrimp tail to drop. For dessert, try the house-made Key lime pie.

Blue Heaven

For brunch, try Blue Heaven. A huge and beautiful back patio setting holds the perfect space for live music while you enjoy brunch classic. Make a reservation or show up early to beat the crowds. I recommend trying the popular Key West Pink Shrimp Benedict. @blueheavenkw

Two Friends Patio

Nestled in the heart of Old Town Key West, Two Friends Patio is a beloved eatery that welcomes you on an open-air patio, perfect for enjoying the island breeze. Known for its fresh seafood dishes and classic American fare, the eatery serves up favorites like Key West pink shrimp, conch fritters, and hearty seafood platters. For meat-eaters, the restaurant also serves some of the island’s best char-grilled steaks and burgers.

🌈 Mangoes Key West

Start any Sunday off right with a hearty Drag Brunch! Mangoes Drag Brunch has been voted in the Top 10 Drag Brunch Shows in the USA by the Miami Herald. Hosting a fabulous Drag show, a live DJ, and bottomless mimosas, every Sunday is one to remember (or forget!) when brunching in Key West. Mangoes is open for lunch and dinner as well, and don’t forget those happy-hour cocktails! Located directly on Duval Street, it’s the perfect place to stop for a bite.

What to See and Do in Key West

🌈 Snorkel and Sandbar Tour with Blu Q Catamaran

Sailing with the Blu Q Catamaran crew is the best way to enjoy the day out on the water. As an LGBTQ+ clothing optional catamaran tour, Blu Q welcomes all adults for snorkel and sandbar tours. Feel free to wear as much or as little clothing as you like and enjoy the company of like-minded people in a safe and welcoming space. Blu Q is Located three blocks North of the intersection at Fleming and Margaret Street – at the Key West Historic Seaport in Old Town – 120 Margaret St.

Butterfly and Nature Conservatory

I’ve never seen so many butterflies in one place! Transport to a tropical rainforest as you enter Key West’s Butterfly Nature Conservatory. There’s an impressive array of flowering plants, as well as hundreds to thousands of butterflies that call this fabulous place home. Learn about butterfly physiology, lifecycle and feeding patterns within their learning center and find a souvenir to take home in the Nature Conservatory’s gift shop!

See the Key West Lighthouse and Keeper’s Quarters

Walk up the 88 steps to the top of the lighthouse to see sweeping views of Key West. The current lighthouse opened in 1848 with a woman as its Keeper; nearly unheard of during the 19th century. The lighthouse and keeper’s quarters now stand as a museum dedicated to Key West’s maritime heritage. Dive into Key West’s history and learn how this lighthouse protected sailors for over a hundred years.

Top Gay Bars and Clubs in Key West

🌈 Aqua

Located on the main drag of Duval Street, Aqua is a fierce and fab bar and club that hosts a variety of great drinks. It’s a great bar to lounge, but can also get quite busy and packed with people ready to dance on the weekends!

🌈 The Birdcage Cabaret

Get tickets to The Birdcage Cabaret and get ready for an epic performance by the beautiful Aquanettes. The Birdcage Cabaret, formerly SideBar, is the pinnacle of Live Drag! Key West’s newest live act features is produced and hosted by the iconic Christopher Peterson. The Aquanettes will dance and sing the night away! This performance is not only hilarious and contains great lip-syncing and comedy, but also some fantastic singing as well. Nothing’s better than seeing the queens belt it out!

The Key Largo and Key West are vibrant, fierce, welcoming cities that are so full of pride! We’ve fallen in love with The Florida Keys and this community. Staying at gorgeous Alexander’s LGBTQIA+ Guesthouse, we’ve had an incredible time at Key West Pride and have met some amazing new friends along the way.

Whether you’re going to the Florida Keys for Pride, a roadtrip, or just a fun visit, we hope this guide has helped and that you have a great trip.

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