Top Key West Culture

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.

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 the streets of Key West on this guided small-group walking tour. As you wander through Old Town, discover the history and culture of the island, which includes tales of shipwrecks, cigar manufacturing, and treasure hunting. Stop at popular attractions such as the Ernest Hemingway Home and Museum, the Southernmost Point, and Audubon House & Tropical Gardens.

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.

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.

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.

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.

The Key West Museum Culture Pass is an excellent way to explore the rich cultural history of this vibrant city. With the pass, you can access four unique and diverse museums.

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.

Are you brave enough to lock eyes with the world's most haunted object… in the dark? Don't get stuck on a crowded trolly, step behind the velvet rope with us and investigate Key West's greatest mysteries and darkest legends. Located within a museum named one of America’s 10 Most Haunted Destinations, join us at the historic Fort East Martello for an eerie evening centered around the chilling legend of Robert the Doll. This isn't just a story—it's an encounter. Your night begins with a 30-minute guided ghost tour through the shadows of the Civil War-era citadel, where you’ll learn the dark history of the site. Then, settle in for a 30-minute seated experience directly with Robert. We will separate the terrifying facts from the folklore and discuss the latest activity surrounding the doll.

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.

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.

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.

Capture the memories of your holiday in Key West with a private photo shoot with a local professional photographer. Enjoy a unique photo experience and discover some Key West’s most photogenic beaches, along with its hidden gems, and receive 45 fully edited photos within just days of the shoot.

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.

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

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.

Of the 800 islands in the Florida Keys, Key West is one of the most popular. Between its charming old town, lively pubs, and dazzling sunsets from Mallory Square, you’ll have your phone snapping photos of every activity you do. Instead of relying on selfies alone, let a professional photographer help you capture your vacation memories. This private photoshoot will take you to fantastic backdrops in Key West that’ll help create amazing vacation photos that you’ll cherish.

This is your chance to go beyond the ghost stories and become the investigator in a place where the past refuses to rest. Exclusive inside access after hours. More than a ghost tour - its an experience. Tickets benefit local non-profits. Locally owned and operated by the Sloan Family.

Jimmy Buffett has left his mark on Key West since he arrived 50 years ago. If you have a passion for all things Buffett and Margaritaville, this walking tour is the best way to find the locations around Old Key West that inspired his songs. Your guide will also take you to the location of his first gig, some of his favorite watering holes, bars he played in and his recording studio.

Key West is rich in spooky history but you need a local's insight to fill you in. This walking tour is focused on the island city's hauntings and ghost tales. As you visit notable spots such as St. Paul's Episcopal Church and the Audubon House and Tropical Gardens, your guide will shed light on prominent figures and the dark history of Key West.

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 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.