If you’re someone who loves the idea of a tropical beach vacation but you crave something more than just lounging in the sun, The Florida Keys should be your next trip. The Florida Keys are a group of tropical islands off the southern tip of Florida that span 125 miles. The last city in the string of islands is Key West, which also happens to be the southernmost point of The United States. This is the ultimate destination in the US for barefoot luxury. After all, The Florida Keys are as tropical as you can get while staying within the continental U.S. and they’re considered the American Caribbean. In fact, Key West is only about 90 miles from Cuba!

I visited The Florida Keys as a guest of the Florida Keys Tourism Board. I had been to The Keys before on a few occasions and have always loved the area, but I really fell in love on this trip. My trip focused on luxury experiences in The Florida Keys, or as I like to call it “barefoot luxury.” That’s because luxury in The Keys doesn’t mean stuffy. The Keys are one of my favorite domestic travel destinations for a beachy, upscale getaway. There are many new hotels and upscale dining destinations that create a breezy, carefree elegance (my favorite type of luxury!). If luxury travel isn’t your speed, that’s ok! The Keys have something for everyone- the thrill seeker, the beach lounger, the luxury-minded traveler, the partier, the nature lover. My recommendations can be used no matter what vibe you’re looking for in The Florida Keys, but there is a focus on luxury (especially with my hotel picks!).

This post is a comprehensive travel guide to The Florida Keys. I dig into the different areas of The Keys and off-the-beaten-path activities and locations. Read on for my comprehensive travel guide to The Florida Keys!

If you’re looking for a list of the top 10 things to do in The Florida Keys, check out my post on that topic here!

About The Florida Keys

The Florida Keys are a coral archipelago of approximately 1,700 islands that begin 15 miles south of Miami. The island chain is broken into three areas: Upper Keys, Middle Keys and Lower Keys. The biggest islands are Key Largo, Islamorada, Marathon, Big Pine Key, and Key West. Each region has its own personality and offers something different to visitors. I recommend breaking up a trip to The Florida Keys with spending a few nights in each of the regions so you can really get a feel for the variety of The Keys.

Getting to The Florida Keys

Despite feeling like a remote paradise, The Florida Keys are easily accessible. There are two airports directly in the Keys, one in Key West and one in Marathon and other nearby airports include Miami and Ft. Lauderdale. My favorite way to visit the Keys is by flying into Miami, renting a car and driving down the string of islands. This drive is one of the most beautiful, and iconic, road trips in the U.S. The Keys are connected by The Overseas Highway, a 113 mile long road that runs through the islands connected by over 40 bridges. As you drive down this road you’ll see turquoise water on both sides and beautiful tropical vistas. Getting there is definitely part of the fun! Even if you do fly directly into The Keys I recommend renting a car; you would do yourself a disservice by not exploring more than one island.

When to Visit The Florida Keys

The Florida Keys see warm, tropical weather all year long. High season runs from the winter through spring and you’ll find hotel prices on the higher side during this time. Hurricane season is June 1 through November 30, with the peak hurricane months being August- November. This is a great time to experience The Keys with fewer crowds and better prices, but the chance of a storm interrupting your travel plans does exist. My most recent trip to The Keys was in November and it was great- perfect weather and low crowds.

Where to Stay- Middle Keys

The best way to experience The Keys is to break up your trip with overnight stays on different islands. A great combination is staying a few nights in the Upper or Middle Keys and staying the rest of your time in Key West.

Isla Bella Beach Resort in Marathon is my recommendation for a hotel in the Middle Keys. This hotel opened April 2019 and it’s redefining barefoot luxury in The Keys. Often people think of The Keys as a party vacation; a destination that beckons young people looking for a rowdy time. Sure, you can still find that, and you should experience some of the famous bars and nightlife The Keys are known for, but there’s so much more than partying and spring break. Isla Bella is proof that The Keys can accommodate the luxury-minded traveler and that they do elegance well.

Your stay at Isla Bella begins with a winding drive through a forest of palm trees that ends at a striking white building with architecture reminiscent of The Greek Isles. This is reception. Opening the front door to reception, you’re met with sweeping views of the ocean and glasses of champagne.  I couldn’t get over this view, it truly took my breath away! Check out my Florida Keys story highlight on Instagram to see what I’m talking about!

At Isla Bella every guest room has an ocean view and a beautifully furnished terrace. The color scheme is dreamy blues and turquoise that match the waves outside your window. The decor throughout the resort, from the rooms to the pool areas to reception, looks straight out of Pinterest. It’s a beautiful resort, filled with Instagram photo opportunities!

The resort is long and low, with 199 guest rooms spread throughout three floors. The guest rooms are very spacious with huge bathrooms stocked with Molton Brown products. Each hotel section has its own semi-private pool with luxurious lounge chairs and cabanas. Isla Bella also boasts a sandy beach area with loungers and a large main pool with food and beverage service. The hotel’s main restaurant, Il Postino, is located right on the beach and serves fresh seafood and Italian specialties.

One of the best features of Isla Bella is that you can watch both the sunrise and the sunset from its property. The hotel has a designated “sunrise pier” and a “sunset point” that’s set among a rocky corner of beach filled with palm trees. Isla Bella is a stunning resort and was a highlight of my trip to The Keys. A stay here is an absolute must.

Where to stay- Key West

The Perry Hotel is my hotel recommendation for a hotel in Key West. This stylish, boutique property is not located right in downtown Key West, it’s actually on Stock Island. And that’s not a bad thing. Since it’s a little set back from the action it’s a great spot to unwind and relax. A free shuttle service operates all day and drops hotel guests off right in the center of Key West. You’re a short drive away from the area’s best restaurants, bars and shops.

The Perry Hotel is fresh, modern and has an industrial feel. It’s located on a marina and all rooms have a water view. The amenities at The Perry are great. Along with the free shuttle service, there is a pool that’s right along the marina, fire pits, free WiFi and free onsite parking. The Perry is home to Matt’s Stock Island a beautifully decorated restaurant that serves the freshest seafood. The build-your-own whole roast snapper tacos were my favorite!

What to Do- Upper and Middle Keys

The Florida Keys are one of the most beautiful places in America, and many of the area’s best activities are outside in nature. The Keys are home to the only coral reef in the continental U.S. so snorkeling, diving, fishing and boating are all popular.

If you want to get out on the water Robbie’s of Islamorada is a perfect place to start. Robbie’s is a huge complex located on a marina with souvenir stands, a restaurant called The Hungry Tarpon and a variety of water sport activities.  Snorkeling, fishing and parasailing expeditions are all available at Robbie’s, but hand feeding their world-famous tarpon off the dock is the most popular draw. John Pennekamp is a beautiful Coral Reef State Park in Key Largo where visitors can camp, fish, picnic, rent boats or take excursions like glass bottom boat tours or snorkel trips.

Get to know some of Florida’s famous residents at The Dolphin Research Center in Marathon, an education and research facility where visitors learn about and experience these beautiful animals. Guests are invited to watch narrated behavior sessions and educational presentations with the dolphins. There are also interactive and VIP experiences available, like becoming a trainer for a day. The Turtle Hospital, also located in Marathon, rehabs injured sea turtles, educates the public and works towards environmental legislation. The facility is open to the public through guided educational tours.

Restaurant Recommendations- Upper and Middle Keys

The Keys are home to delicious farm-to-table cuisine and some of the freshest seafood you can find. Restaurant highlights in this area include Angler & Ale a new spot at the Hawks Cay Marina. You can order off their menu or bring your fresh catch to get it cooked. Il Postino at Isla Bella Resort is a not-miss for creative Italian and Neapolitan pizza. For those looking to imbibe, Florida Keys Brewing Company in Islamorada is a must. They use fresh local ingredients like hibiscus, key limes and honey in their brews. The brewery has a big beer garden for families with children to hang out and sample the expansive beer menu.

What to Do- Key West

Key West is jam-packed with things to do. In the historic Old Town section you’ll find the tourist favorite Duval Street, lots of bars, charming cafes, popular restaurants, historic homes and endless activity options. One of the best things to do in Key West is just wander around and explore. Duval Street is home to kitschy t-shirt shops and unique art galleries. This is also where you’ll find Sloppy Joe’s, the notorious watering hole made famous by one of Key West’s most popular former residents, Ernest Hemingway. Hemingway Rum Company is right off Duval and is a great stop to learn more about rum and Hemingway’s connection to the spirit and Key West. A visit to the Hemingway Home and Museum is also a must-do. Here you’ll learn about the author’s storied past and see the resident six-toed cats (all descendants of Hemingway’s pet cat) who call the site home.

If you want to get a better lay of the land of Old Key West, the Conch Tour Train offers a narrated tour of the area’s most historic spots. Thrill seekers can get out on the water with Fury Water Adventures. Their most popular tour is a day that packs in the action with parasailing, jet skiing, kayaking and snorkeling. Danger Charters offers daily sunset sails that are limited to 25 guests. If you’re looking for a big adventure hop a ferry to Dry Tortugas National Park. This is one of the most remote national parks in the country, located 70 miles off the coast of Key West.

Restaurant Recommendations- Key West

Foodies will be in paradise in this land of key lime pie, tropical cocktails and fresh seafood. An absolute must is a visit to Sunset Key, an island 500 yards off the coast of Key West. You’ll arrive by water taxi and find Latitudes one of the best restaurants in all of The Keys, and the epitome of a “barefoot luxury” experience. Latitudes is set on the beach and surrounded with swaying palm trees and tiki torches. It serves elegant Floridian cuisine and a delicious key lime pie. Dinner here is a not-miss and was another highlight of my time in The Keys. Speaking of key lime, another great slice can be found back on the main land at Kermit’s. Banana Cafe is a French bistro with a Caribbean flair that serves up a great breakfast. Don’t miss their banana waffle!

The Florida Keys is a great vacation destination that feels worlds away, yet is close to home. Whether you want to get active on the water, enjoy fine dining, or just lounge in the tropical sun, The Keys offers something for every type of traveler.