The 5 Best Islands in the Florida Keys in 2023

The Florida Keys offer a tropical taste of sunshine and island vibes right here in the contiguous United States. It’s a destination that’s just as incredible, but often more practical than traveling to faraway islands.

Made up of more than 1,700 islands in all, 5 island destinations are considered the “main event” in the Keys.

These islands deserve a place on your travel itinerary – and if you need a little convincing, there are plenty of reasons to visit.

Nature lovers will be beside themselves in the Keys, where wildlife refuges, national and state parks, and amazing tropical scenery abound.

Water sports and fishing are huge pastimes in the Keys, with world-class saltwater fishing drawing tons of visitors each year.

A trip to the Keys would be lacking without taking time to snorkel or dive in the waters around the islands, known for stunning shipwrecks and coral reefs that attract marine life large and small.

History buffs will appreciate the storied roots of the islands in the Keys, with time-honored fishing villages and tribal history adding meaning to your trip.

When you visit the Keys, you’ll have a chance to step foot on the southernmost point in the United States in Key West.

An underwater hotel in Key Largo – the Diving Capital of the World – could be the unique accommodation you need to spark a totally immersive, memorable trip here.

While there are 1,700+ islands in this coral cay archipelago, 43 are connected to the highway leading to Key West from Miami. That makes traveling to different islands easy!

If you want to visit some of the smaller, less developed islands off the highway, you can always take a boat to get to your off-the-beaten-path destination. 

You’ll find that there’s every reason in the world to visit the Florida Keys, but knowing which islands offer the best accommodations, activities, and scenery will make planning a lot easier. 

Below, you’ll learn about each island and what makes it unique. See what each island is known for, what you can expect for accommodations, and how long it takes to reach the island from Miami. 

1. Key Largo

A view of palm trees and huts in Key Largo, one of the best islands in the Florida Keys to visit

  • Best for: Diving, snorkeling, parks
  • Accommodations: Plenty of options for all budgets
  • Access: Easy drive from Miami, close to airports

“Key Largo, Montego, baby, why don’t we go?” – Kokomo by The Beach Boys

Key Largo isn’t just the first island you’ll see when you head south from Miami – it’s one of the best islands in the Florida Keys, period. 

With its close proximity to South Florida, Key Largo is a favorite destination for Floridians and out of state travelers seeking the warmth and laid-back vibes of an island getaway that’s not too far from home. 

There’s a national park, 2 state parks, winding creeks, dense stands of tropical hardwood trees, and all the typical island scenery you’re dreaming of with palms, sandy beaches, and never-ending ocean views. 

Oh, and it’s the scuba diving capital of the world. Not the U.S. – the world! Get certified and check out the 510-foot scuttled Navy ship in the Florida Keys National Marine Sanctuary here. 

There are tons of options for accommodations in popular Key Largo ranging from budget-friendly rooms to jaw-dropping beach house rentals and private resorts. 

There’s even an underwater hotel here, where your room has a porthole to view marine life and you’ll scuba dive to get to your room. 

2. Islamorada

Beach view of Islamorada with palm trees blowing in the wind on a clear day to show one of the best islands in the Florida Keys

  • Best for: Fishing, diving, water sports, parks
  • Accommodations: More mid-tier and luxury options
  • Access: Easy drive 2.5 hours from Miami

Islamorada is a less-crowded natural haven in the Keys made up of 6 islands. It’s a laid-back fisher’s paradise, with incredible opportunities for saltwater anglers to land the catch of a lifetime. 

Together, Plantation Key, Windley Key, Upper and Lower Matecumbe Key, Indian Key, and Lignumvitae Key form Islamorada. 

Book time with a fishing guide to cast for snook and bonefish in the saltwater flats around the island or head out to the deep to catch tuna, sailfish, sharks, and more. 

If fishing’s not your thing, diving and snorkeling around the islands of Islamorada is unforgettable. You’ll see shallow coral reefs, shipwrecks, and smaller mini wall reefs to explore. 

On land, you can check out the local marine mammal park for dolphin encounters, museums, shops, and restaurants serving up seafood and favorite dishes. 

There are plenty of options for accommodations here, but not as many budget-friendly options as you’ll find in the more-visited Keys. 

3. Key West

Smathers Beach at sunrise in Key West for a piece covering the best Florida Keys islands to visit

  • Best for: Nightlife, diving, arts and entertainment
  • Accommodations: Plenty of options for all budgets
  • Access: Easy drive just over 4 hours from Miami

Key West is the most popular island in the Keys for tourists and well-known for its party-centric vibe and thriving culture centered around the arts, entertainment, and the LGBTQ+ community.

Key West is where you’ll find the southernmost point in the United States (a great photo opp for travelers) and is actually closer to Cuba than it is to Miami. 

You’ll find all the usual tropical island trappings here – beautiful beaches, including a few with soft white sand, swaying palms, and fun water sports to take part in. 

Diving is excellent off Key West with great opportunities for snorkeling and swimming as well as paddle boarding and fishing. 

Key West is a melting pot of cultures with Cuban, American, and Bahamian roots influencing the food, architecture, and arts and entertainment here.

If you’re here at the right time of year, you can catch the adults-only costumed Fantasy Fest in October. 

Try the world-famous Key Lime pie while you’re here and prepare for the tart and tangy sweetness that bakers off the island struggle to recreate. 

4. Marathon

Sombrero Beach in Marathon shows palm trees and a walkway to the beach on one of the best islands in the Florida Keys

  • Best for: Families, ecotours, fishing, diving
  • Accommodations: Several resorts, hotels, and rentals
  • Access: Easy drive just over 3 hours from Miami

Marathon is actually a 10-mile island chain smack dab in the middle of the Florida Keys. Like Islamorada, it’s a fisher’s paradise but offers more activities and options for families. 

Smaller islands like Vaca Key, Grassy Key, Boot Key, Hog Key, and Fat Deer Key are part of Marathon. You’ll find several resorts, hotels, and vacation rentals to stay in here. 

Families really enjoy trying water sports, from diving and snorkeling to paddle boarding and windsurfing, in Marathon. 

With 8 marinas in Marathon, boaters really enjoy visiting and venturing out to nearby islands to fish, explore, or see the scenery. 

There’s a Turtle Hospital that kids will enjoy touring, a dolphin research center you can take an interactive tour of, and the Crane Point Museum for educational wildlife fun.

Seafood lovers will delight in eating fresh daily catches – or casting out and having a local seafood joint cook up their catch – with delicious local flavors. 

Flyfishing and deep sea fishing are popular around Marathon and if you’re here at the right time, you can check out the Original Marathon Seafood Festival in early March. 

5. Big Pine Key

Calusa Beach in Bahia Honda State Park in Big Pine Key shows that the Lower Keys are one of the best islands in the Keys to visit

  • Best for: Ecotours, diving, natural beauty, fewer crowds
  • Accommodations: Limited to a few resorts and vacation rentals
  • Access: Longer 3.5 hour drive from Miami 

Part of the Lower Keys (along with Summerland Key, Big Torch Key, Little Torch Key, Cudjoe Key, Sugarloaf Key, Big Coppitt Key, Saddlebunch Keys, and Stock Island), Big Pine Key is a traveler’s dream in the Florida Keys.

This is one of the Keys that’s still wild and free, almost totally in its natural state. The National Key Deer Refuge is here, spanning 8,500+ acres and home to tiny dog-sized Key deer and other wildlife. 

The beaches you’ll find here aren’t the typical pristine white sand variety, with the exception of Bahia Honda Beach in the 500-acre state park by the same name.

Dive the 210-foot Adolphus Busch Sr. freighter shipwreck off the coast of Big Pine Key and see the Looe Key protected coral reef just south of the island. 

A bridge connects to No Name Key, where you’ll find hiking trails that wind through the hardwood pine forests with views of the ocean just feet away. 

Be sure to see the Blue Hole, a manmade, abandoned rock quarry now filled with freshwater. When you want to step out of the wilderness, there’s the Big Pine Flea Market and a handful of restaurants to fill you up! 

You won’t find many places to stay directly on Big Pine Key, but there are a few resorts and vacation rentals up for grabs if you can book early enough. 

Things to Consider

Overseas Highway leading to Key West aerial view for a things to consider section on the best islands in the Florida Keys

What else should you consider to have the most enjoyable trip to any of the best islands in the Florida Keys? Here are some tips to keep in mind. 

  • Getting there is easy. You can drive to all of the best islands in the Florida Keys – some just take longer to reach than others. If you won’t be driving, you can take a ferry from Ft. Myers and Marco Island to Key West or fly into the Key West International Airport or on a request-only basis to the Florida Keys Marathon Airport.
  • Visit nearby islands. Since the Overseas Highway connects the main islands of the Keys, it’s a great idea to leave extra time in your trip to head out to nearby islands to see more of the archipelago. You can drive further down the scenic highway, across the 7 Mile Bridge, or take a boat to smaller, uninhabited islands. 
  • Consider your crew. If you’re traveling alone or with adults, your trip itinerary will likely be a bit different from someone traveling with a family and young children. While there are family-friendly activities on most of the islands, kids can be bored with the wilder, less-developed areas and may appreciate the bustling activity on the larger, more popular islands. 
  • Plan your itinerary before you go. Making sure the activities and attractions you want to visit will be open, making any needed reservations, and coming up with options for places to eat and shop is smart before you visit the Florida Keys. Consider the time of year you’re going and check out local calendars to see what’s happening! 
  • Go during the best time of year. You’ll always have a more enjoyable visit when you know the best time to visit the Florida Keys. December through May is generally ideal with 70F-80F temperatures and little rain. June to November is the cheapest period, with the exception of Pride Week in June. For fewer crowds, visit the smaller islands or head to popular areas from March to May or September to November. 

Leave a Reply

Your email address will not be published. Required fields are marked *