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Anybody seen HBO’s It’s Florida, Man? Yeah, it’s not exactly a selling point for booking a vacation to the Sunshine State, now is it?
But that’s now the story for the whole state, Florida is a top-visited destination for a reason!
TripAdvisor has revealed one of the top destinations in the state, and you’re going to want to add it to your bucket list.
One silly (albeit true-story-based) TV show doesn’t define a whole state — and we all know Florida is the most popular getaway for winter sun.
But where can you feel truly secluded in one of the most sought-after destinations for beach vacations?
One of our favorite getaways here at Travel Off Path feels borderline Caribbean, where Hawaiian shirts and flip-flops are all but obligatory in this vibrant hideaway said to be a 2026 must-visit to unwind in paradise.
Key West is Florida’s top destination for 2026. No other sunny Florida getaway made the cut — not Miami, not Orlando, not even Siesta Key, which is known to be named the top beach in America year after year.
When you think of Key West, you almost picture another country — at the very least an extension of America geographically.
Truth be told, that’s all part of the appeal. No matter if you opt for perhaps the most gorgeous road trip in the U.S. or fly in and snag a window seat to witness the blue dreamscape down below you’ll soon embark, Key West only disappoints when you check your bank account.
That’s why many choose to drive, not only for the beautiful venture ahead, but to save on airfare and splurge on experiences, whether it be nice hotels known to cost a pretty penny or double-digit margaritas, even during Happy Hour — not that any hour in the Keys go unhappy…
Drive or Fly?
The Truth: If you fly, you miss the 7 Mile Bridge. The drive is the vacation. Rent a convertible and blast Jimmy Buffett.
But hey, if there were ever a place to set your watch to 5’o’clock all day, it’s here. The Jimmy Buffett vibes are real and not just cheesy establishments like Senor Frog’s. You can even stay at the Margaritaville Beach House if you want Buffet vibes nonstop!
A visit to Key West, the most popular city of the map-dot cluster of the Florida Keys, is practically a travel sin without stopping at Mallory Square — made famous by many a beachy Jimmy Buffett tune and known for waterfront bars, fiery sunsets, and the most laid-back vibes you’ll find in Florida
Look — we’re not promising tank tops and swimwear are the best attire for a select group of golden-year retirees, but there’s no question anyone can have a fun time in Key West.
Plus, can you blame the older crowd for wanting to live out their sunset years in such a gorgeous locale, where time ticks slower and Happy Hour never seems to end?
Sure beats Bingo Night where I’m from…
But don’t let a few extra wrinkles deprive you of your own blissful escape in Florida’s most far-flung coastal outpost.
Beaches may not quite be up to par as other popular towns, but the vibe is unmatched.
You can enjoy ample excursions, such as deep-sea fishing, close-to-shore snorkeling, kayak tours, and common dolphin sightings and beachside bars blasting your favorite song well after sundown.
TripAdvisor’s #1 Florida pick. Tap a card to plan your escape to the “Conch Republic.”
Not “Just” Florida
The Feel: It feels like another country. Hawaiian shirts and flip-flops are mandatory.
Must Do: Mallory Square at sunset. It’s a travel sin to miss it.
The Best Route
Winter vs. Summer
More than Drinking
Beaches aren’t the main draw here; the water is.
Only 2 emails per month.
As you can imagine, Key West is a year-round destination. For example, this week’s weather report mostly reads low 70s and sunny while others are bundled up shoveling their driveway.
That said, as enticing as winter may be to visit, our vote goes to mid-summer for one simple reason: Key Lime Festival.
What better way to ring in Independence Day than by celebrating America’s birthday with a forkful of Key Lime pie?
The Key Lime Pie Test
If it’s neon green, send it back!
Yes, it may be more crowded than winter but the whole city comes alive with pop-up events and fun street festivities.
Late summer and early fall are the times of year to be weary about given Key West’s fully exposed location in the open sea during ‘Hurricane Season’.
Actual landfall is rare, however, which makes September the most enticing month to visit if festivals aren’t your jam.
You can enjoy the quietest (and often most affordable) time Key West sees in between the popular Key Lime Festival and 10-day Fantasy Fest in October.
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Sam Sears
Sam, our Lead Writer & Journalist based in San Diego has visited 36 countries and written over 1000 articles with a focus on sharing his own travel experiences and shining a light on lesser-known gems.
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