Top Key West Culture

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

Watch the sun set and the moon rise off the coast of Key West on this relaxing sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer, and soft drinks are included.

Explore the best that Key West has to offer on this narrated tour aboard a miniature train. See Key West’s top attractions and learn about the Conch Republic’s history and residents, including Ernest Hemingway and Harry Truman. Get to know Old Town Key West, from the Front Street Depot to Mallory Square, and learn the stories behind the sights from the live on-board commentary.

Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.

Explore Key West through the eyes of a local on a craft cocktail tour that stops at six off–the–beaten–path establishments for drinks and food tastings, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.

Discover some of Key West’s deepest, darkest secrets on a ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of what is said to be one of the most haunted cities in the US. Travel down the narrow, dark streets of the Old Town at night. The wooden houses still bear the secrets of their former inhabitants. This tour is narrated by an actor playing a gravedigger.

For the aquatic adventure of a lifetime, cruise to North America's only living coral barrier reef. No need to go diving or snorkeling for this great view—see tropical fish, sharks, turtles, colorful coral, and other sea life from the deck of the glass-bottom boat. Opt for an evening departure to enjoy a glass of Champagne as the sun sets into the Gulf of Mexico.

Get ready for fun in the sun—and check off two top experiences in just one trip—on this dolphin-watching and snorkeling tour off the coast of Key West. Departing Key West, look out for dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breezes, and select from a variety of refreshing beverages on board the boat.

Pedal through the charming streets of Old Town Key West on a guided bike tour, perfect for first-timers exploring the island. Along the way, you’ll uncover its rich history and stop at iconic spots like Mallory Square, Mile Marker Zero, and the Southernmost Point Buoy. With morning and afternoon tour options, it’s easy to soak in panoramic ocean views and experience Key West at your own pace.

Explore the best that Key West has to offer on this narrated, hop-on, hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Enjoy free admission to the Sails to Rails Museum for extra sightseeing fun.

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most legendary paranormal figures. Your experience begins with a 30-minute guided ghost tour through the Civil War-era fort, exploring its dark history, unexplained activity and stories gathered over decades. Then you'll spend 30 minutes seated directly with Robert the Doll. Hear the documented history behind the legend, separate fact from folklore, and discover the latest unexplained activity surrounding Robert. USA TODAY has named Fort East Martello one of America's Top 10 Haunted Destinations. This isn't a ghost tour that simply tells you about Robert. You'll enter his fort and meet him after dark.

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local guide, you'll discover how nature, history & community shaped Key West into the unique place it is today. With a small-group setting, you'll enjoy a personal experience filled with stories, insights & local knowledge that most visitors never hear.

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on a 75–90-minute tropical fruit hunting tour. This engaging experience takes you through the grove where you'll learn about its 70+ year journey of restoration and resilience. Depending on the season, guests may even have the chance to pick ripe fruits directly from the trees. The tour includes a scenic walking exploration, followed by a delightful tasting session in an outdoor tasting room featuring prepared exotic fruits. - 75–90-minute tour revealing the history of Grimal Grove - Guided walking tour with opportunities to pick fruit (seasonal) - Outdoor tasting experience with a variety of exotic fruits - Learn about the 70+ years of restoration and resilience at the grove

Get front row seats to a stunning Florida Keys sunset, without the hassle of chartering your own vessel, on this catamaran cruise from Key West. Sip on your choice of wine, sparkling, beer, margaritas, or sangria as you watch the sun go down over the water. As you sail, catch glimpses of the island and marvel at the views from the turquoise water.

Explore the only living coral reef in North America during this snorkeling adventure from Key West. Sail toward the reef on a state-of-the-art catamaran. Receive snorkeling guidance from your crew—ideal for first-time snorkelers. Use of sanitized snorkel gear and reef-safe sunscreen means you don’t need to pack your own, plus cocktails and non-alcoholic drinks are provided after the snorkeling.

Discover an important part of Florida’s history with admission to the Harry S. Truman Little White House. This former naval base compound is now a treasured museum, open to educating the public about its past and present. See where President Truman retreated for rest and relaxation during his term in office. Learn about the notable people who visited, including Thomas Edison and Dwight D. Eisenhower. And listen to the stories told by those historians who not only know what happened here, but when and why.

Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the docks into some of the most colorful neighborhoods in Key West, pausing to sample locally caught pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere.

Exploring the highlights of Key West with a ride on the Conch Train is a great way to get a feel for the area, but it’s smart to book your ticket in advance to avoid sold-out rides. Get a feel for the lay of the land as you pass by top attractions, while listening to live onboard commentary from a professional tour conductor.

Explore the stunning Dry Tortugas National Park with a private boat charter tailored just for you. Departing from Key West, enjoy a full-day offshore adventure that includes visiting historic Fort Jefferson and snorkeling in crystal-clear waters. This exclusive experience allows you to set your own itinerary, ensuring a flexible and customized journey without the crowds. Your adventure is aboard a premium charter vessel, captained by experienced locals familiar with the area, making your visit both enjoyable and memorable. - Private charters provide a customized experience for your group - Full-day exploration of the Dry Tortugas National Park - Snorkeling opportunities at beautiful locations - Flexible itinerary means you choose the pace and activities

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at (6) locations, helping tell Hemingway’s story in Key West & Cuba. Each ticket includes guided entrance into his famed Key West home. Then eat, drink, and explore the island on foot through “Papa’s eyes”, feasting on Cuban cuisine (& 3 boozy beverages) while your knowledgeable local guide impresses with interesting stories & amazing fun facts. The adventure takes you behind the scenes of a 3rd generation family run cigar rolling factory, and into the newly remodeled Social Club at Hemingway Rum Co. for his favorite drink made with his family company’s premium rum. Then finish with a slice of our famous key lime pie! After the tour, you’ll receive a collection of exclusive recipes, recommendations on restaurants, attractions, entertainment, and cultural offerings.

Discover Key West through its most iconic dessert on a small-group walking tour of the Historic Seaport. Sample different styles of key lime pie and a cocktail while a guide shares local history and context. Combining tastings with storytelling, this experience offers a structured, engaging, and delicious way to explore Key West—perfect for first-time visitors and avid foodies alike.

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for upcoming events, digital download of local artists music, and historical overviews of the venues and artists who have left their mark on the island. Learn from a local about the diverse music scene and creative island life that continues to inspire so many.