Which Florida Keys Island is Best? Here's A Key-By-Key Guide

The Florida Keys is a Caribbean getaway that feels a little closer to home. Life moves to a gentle but purposeful rhythm, a pace that has beguiled Great American novelists of the past: including Ernest Hemingway himself. The Florida Keys may be more old-school, but amidst all the golf clubs and fishing boats, you can still let loose down south in Key West.

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Sunset at a dock, Key West.

Enjoy a Hemingway Daiquiri in Key West 🍸🪩

If you prefer your vacations to be packed with activities, consider staying in Key West. Bookworms will be intrigued by the Hemingway Home; whereas history buffs should stop by former US President Harry Truman’s Little White House. Although Key West is easy to walk around, taking the Conch tour train at least once will add a charming touch to your sightseeing.

There are a few different beaches to choose from, with Higgs and Smithers being the most popular choices. Many are deterred by the entrance fee to Fort Zach beach ($7 for 2 people in a car), but it is worth the money. The water quality is truly the best in all of Key West, and is deep enough for swimming or snorkelling.

All of the Key islands’ nightlife is contained into the 1.25 mile long Duval Street: nicknamed the ‘Longest Street in the World’. If you can believe it, Duval Street has the highest number of bars per capita than anywhere else in America. Since there are 43 bars in total, attempting a bar crawl here is hardly an easy feat.

Even if you are up for the challenge, we recommend looking into this bite-sized (and liver-friendly) bar crawl tour instead. And if you are stuck on what to order, check out this local guide to Key West’s best cocktails.

Fort Zachary Taylor Historic State Park Beach at sunset.

Get competitive in Key Largo🏌️🤿

They say that when visiting the Keys, you should bring half the clothes and twice the money. Nowhere is that more true than Key Largo: Florida’s golfing getaway. It is a world away from the rowdy rustle of Key West —  but just as expensive.

Instead of spending money on shots and hotspots, Key Largo’s appeal is more physical. Hitting a hole in one at America’s only Caribbean-style golf course is one option, but if that idea sounds dull to you, don't scroll past just yet.

What might be unexpected is that Key Largo is a phenomenal scuba-diving destination. From the astonishing Christ of the Abyss statue to the second largest wreck diving site in the world, the diversity of underwater sights here is almost unbelievable. Not to mention the near heavenly abundance of coral reef which acts as a shining example of the marine conservation efforts made by the sanctuary.

With all this in mind, it is easy to see why resort reservations are snapped up despite the costly price-point. If you are lucky enough to stay here, consider booking a snorkelling tour with Key Largo Scuba Diving.

Birdseye view of Ocean Reef Club, Key Largo.

Move around in Marathon 🚗🛥️

There is no denying that the Key Islands is expensive — especially if you are looking to stay in either Key Largo or Key West. But if you venture outside of these two, there are more budget-friendly options available on the middle islands.

Marathon is about as central as it gets: taking an hour drive in either direction to reach Key Largo or Key West. Set across 13 islands, Marathon is most famous for its wildlife sanctuaries. Animal lovers will adore this destination — from swimming with dolphins in an all-natural setting, to taking an educational tour around the Turtle Hospital.

Resorts are being slowly introduced to Marathon, making now the time to visit this former fishing town. Its beaches are some of the best in the Keys: Sombrero and Coco Plum are particularly gorgeous. Going on a boat tour is a favourable choice, but why not add a little adventure to your vacation by going parasailing?

Fall hook, line, and sinker for Islamorada 🎣⛵

If your dream vacation is nothing more than days spent by the sea, look no further than Islamorada. A village of 6 islands, Islamorada has risen to fame as the world’s sportfishing capital. Whether you are an expert angler or this will be your first catch, you are in good hands.

There is an abundance of fishing opportunities inshore, nearshore and offshore. Whilst the likelihood of catching certain types of fish changes throughout the year, the odds are still quite high. Even absolute beginners have a good chance of catching something, albeit you might need a little more skill to catch a mahi mahi.

(Please keep in mind that it is illegal to keep certain catches in Florida. Check out this Catch and Release guide to find out more.)

Even if fishing is not your thing, travelling through Islamorada by boat is still highly recommended. From sailing to paddleboarding, there is no shortage of ways to explore these tranquil islands.

Islamorada at golden hour.

Escape into nature in Big Pine Key 🦌🚣

Prefer somewhere more low-key? Whilst Big Pine Key still offers a little luxury — including America’s only private island resort — it is more concerned with the great outdoors.

For $10, you can spend the entire day at the Bahia Honda State Park. Other than a store, this beach is mostly quiet — making it a suitable spot for a picnic or a day spent swimming and sunbathing.

We wouldn’t recommend dipping your toes in the Blue Hole though. As the only freshwater location in the entire Keys, this watering hole is a prime spot for observing alligators. It also belongs to the National Key Deer Refuge: a habitat dedicated to protecting the endangered species that are endemic to the region. This sublime attraction encourages visitors to explore the wilderness via 1  of several trails available.

Key Deer photographed in Big Pine Key.
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Kick back and relax with our Island Life series.

Florida Keys — Facts before you go


🇺🇸 English (Official).


💸 US Dollar ($)

When to visit

🌀Hurricane season in the Key islands tends to fall between the middle of June to the end of November.

🧳The high season is from December to March.

☀️April to early June is a good time for cheaper, off-season travel — just keep in mind that it will be hotter than high season weather.

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Hannah Douch
September 15, 2023

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