In Key West, the bucket list isn’t a checklist. It’s the pulse of the island. It’s the collection of moments, both planned and stumbled upon, that turn a simple getaway into the kind of story you tell for the rest of your life.

Close to perfect, far from normal, that’s Key West. On this side of the island, the Atlantic takes over the horizon and the day runs on island time. Once you’re here, there are a handful of things you simply have to do, from landmarks and legends just steps away, to a national park seventy miles out at sea, to the living reef just below the surface, to the colors painted across the sky at sunset, to the festivals that turn the streets into a celebration.

Here are ten experiences to add to your 2026 Key West travel bucket list. Use them as your starting point, then let the island surprise you from there.

1. Take a Photo at the Southernmost Point Buoy

There is almost always a line here, but waiting is part of the experience. It’s a shared photo op and a must-have travel memory. The Southernmost Point Buoy, bold black, red, and yellow, sits just 90 miles from Cuba and marks the southernmost point you can reach in the continental United States. It’s one of the most photographed landmarks in Key West.

2026 heads up: The buoy is at a temporary location through late 2026 while the original corner undergoes seawall reconstruction. The full-scale replica is currently at Duval Street Pocket Park (1400 Duval Street). For Southernmost Beach Resort guests, this means it is literally steps away. You get the same iconic photo with the ocean as your backdrop, just at a temporary new address. It is touristy in all the right ways, and you’ll be glad you have the photo to prove you were here.

→ Read more: The Southernmost Point Buoy Update

2. Looks Like We Made It — Mile 0 Marker

Who knew a sign could be so popular and have so much meaning? At the corner of Whitehead and Fleming, a small green and white sign marks the official beginning of U.S. Highway 1, the longest north-south highway in America, stretching more than 2,300 miles all the way to the Canadian border in Maine. This is where it starts—or ends—depending on how you look at it. For road trippers, history buffs, and anyone who has ever driven U.S. 1, standing here is a genuine moment. There is something about reaching Mile 0 that stops people in their tracks, a quiet moment of arrival that says, I made it. The end of the road. Somehow, exactly where you were always meant to end up. Day or night, there is almost always someone here getting the photo. Get yours and add it to your bucket list album.

3. Drive the Overseas Highway

Few drives anywhere in the world feel quite like this one. The Overseas Highway is Florida’s only All-American Road, a title reserved for the most scenic drives in the country. It stretches 113 miles across the Florida Keys, connecting 42 bridges over open water from the mainland all the way to Key West.

It is one of those rare road trips where the drive itself is the destination. The Seven Mile Bridge is the crown jewel, a straight shot across the open ocean that makes you feel like you are flying over the water. Keep an eye out for Fred the Tree as you cross, a scrappy Australian pine that sprouted from the old bridge’s concrete, survives hurricanes, gets all decked out for Christmas, has its own children’s book, and even landed a Hollywood cameo. Only in the Keys.

→ Read more: Iconic Miami to Key West Drive: It’s All About the Journey

4. Meet the Hemingway Cats

There are approximately 60 cats living on the grounds of the Ernest Hemingway Home & Museum on Whitehead Street, and half the people who visit will tell you they came for the cats, not the writer. That’s not an insult to Hemingway; it’s just that the cats have a story too. The cats are polydactyl, most with six toes, descendants of Snow White, a cat given to Hemingway by a sea captain. They have the run of the property, they have names, and they have personalities — and here’s the fun part: every cat is named after a Hollywood legend, a famous athlete, or a cultural icon from Hemingway’s era. Piper Laurie holds court near the fountain. Betty Grable naps in the bedroom. Babe Ruth and Joe DiMaggio tend to stay close to the house. When a new litter is born, the staff submits name ideas and votes — keeping a tradition that Hemingway himself started when he named his own cats after famous friends. The house and gardens are worth the visit on their own — but the cats are what make it unforgettable.

→ Read more: A Local’s Guide to Hemingway’s Home & Cats

5. Snorkel the Only Living Barrier Reef in the U.S.

Just offshore from Key West sits the Florida Reef, the only living coral barrier reef in the continental United States and the third-largest in the world. Home to more than 500 species of tropical fish and dozens of species of stony and soft corals, that alone makes it worth getting in the water. Slip beneath the surface and you’re suddenly surrounded by brain coral and purple sea fans, with clouds of tropical fish flashing past. Imagine a sea turtle gliding by as you take it all in. It’s the kind of experience you’ll be talking about long after you’re back on shore.

6. Celebrate Sunset

Every evening, crowds gather at Mallory Square to watch the sun slowly dip into the ocean, painting a colorful masterpiece across the sky while street performers, artists, and travelers turn it into a nightly celebration. But the secret is that the best sunset is wherever you find yourself at that hour, whether you’re on a sunset cruise, at a restaurant or bar, on the beach with your feet in the sand, or taking a stroll by the Seaport. The ritual is not about the view. It is about stopping long enough to actually see it. Whatever spot you choose, make sure there is at least one Key West evening where you do nothing but watch the sun dip and kiss the ocean good night.

→ Read more: Plan Your Snorkel and Sunset Adventures

(Photo credit: Fury Water Adventures)

7. Explore America’s Most Remote National Park

Imagine a massive 19th-century fortress rising out of turquoise water, 70 miles from the nearest city, surrounded by some of the most pristine coral reef in North America. This is Dry Tortugas National Park. It remains one of the most remote national parks in the country because the only way to reach it is by ferry or seaplane from Key West—a journey that is just as memorable as the destination. (Photo credit: NPS Submerged Resources Center)

What awaits you is Fort Jefferson, the largest brick masonry structure in the Western Hemisphere. Built with more than 16 million bricks, it rises out of the sea with a scale that feels almost impossible for its location. Crystal clear water, rare birds, and sea turtles surround the fort on all sides; with less than 1% of the park being dry ground, the rest is a submerged world waiting to be explored. This is a true bucket-list item that requires planning in advance, but it is a hidden gem you need to experience at least once.

→ Read more: Plan your visit: Dry Tortugas National Park — National Park Service

8. Dive the World-Famous Vandenberg Wreck

The USS Vandenberg is the second-largest vessel in the world ever purposely sunk to become an artificial reef, and even that stat doesn’t fully prepare you for the scale of the experience. Frequently recognized as one of the premier wreck dives on the globe, this former military missile-tracking ship—measuring 524 feet, 10 inches long—was intentionally sunk seven miles off Key West in 2009.

Today, she rests upright on the seafloor in nearly 150 feet of water, with her superstructure rising to within 40 to 45 feet of the surface. Now covered in coral and home to massive Goliath grouper and thousands of tropical fish, “the Vandy” is genuinely extraordinary at every depth. For experienced divers, it isn’t just a wreck; it’s one of the most memorable dives in the Western Hemisphere.

Explore the wreck: The Florida Keys Shipwreck Trail: USNS Vandenberg

9. Join the Great Key Lime Pie Debate

Welcome to one of Key West’s most delicious debates. Who has the best Key Lime Pie? Our signature dessert exists in dozens of variations across the island, and locals will argue passionately about who does it best. The classic is tart and dense with a graham cracker crust, topped with either a swirl of meringue or whipped cream—though some get creative with that too.

One thing everyone agrees on: it should be yellow, not green, served cold, and made with actual Key lime juice. Beyond the slice, you can drink it in a martini or find it infused into savory local dishes. Do your own taste test and let us know who you think has the best in Key West.

For all Key Lime lovers, there’s even a festival. From July 1–5, 2026, the Key Lime Festival is where a little bit of zest and a lot of creative chaos come together to celebrate our signature citrus fruit and its most iconic dessert.

→ Read more: Why Key West is Obsessed with Key Lime

(Photo credit: @theshayspence)

10. Experience a Key West Festival

You don’t just attend a Key West festival, you become part of it. Our island may be small, but it transforms into a global stage for some of the most extraordinary festival experiences you’ll ever have. Whether you’re standing inches from the next Grammy-winning artist at the Key West Songwriters Festival or stepping into the 10-day costume extravaganza of Fantasy Fest, the energy spills into the streets, onto the beaches, through pool parties, and out on the water.

Somewhere along the way, the line between visitor and local disappears. You’re in it, from the moment you arrive until the moment you leave. With festivals happening year-round, you don’t have to leave it to chance. You can plan your trip around the experience. Southernmost Beach Resort is proud to be part of it all as a sponsor and host of onsite events that keep you right in the center of the celebration.

• The Insider Story: Get a look behind Key West’s biggest festivals with Nadene Grossman Orr.
• Plan Your Year: Check out our Key West Festivals 2026: A Planning Guide to the Year’s Top Events.

Southernmost Beach Resort sits at the quiet end of Duval Street, where the island’s most iconic landmarks meet the Atlantic. Whether you’re here for a long weekend or a week, this is your base camp for everything on this list.

Collect the moments that turn into memories you’ll be talking about for a lifetime. There’s no better place to start than right here. #somolife