Tours in Key West

Tours will begin at the corridor of the Southernmost District near the Key West Lighthouse and the home of the infamous author Ernest Hemingway. We will proceed through the Southernmost District and continue onto the neighborhood where the historic "Bahama Village" remains. Your experience will be provided by a fifth generation native of Key West and will include the history, folklore and architecture of traditional Key West.

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering hidden gems and local lore along the way . Explore the vast wetlands of Everglades National Park, encountering unique wildlife and ecosystems . Delve into the rich history and biodiversity of Big Cypress National Preserve . Finally, discover the underwater wonders of Biscayne National Park, from coral reefs to mangrove forests . With GPS-triggered narration, offline maps, and expert storytelling, enjoy the freedom to explore at your own pace without the constraints of group tours. Join thousands of travelers who have transformed their Florida road trips into enriching experiences—download now and let the Sunshine State's natural beauty and history captivate you!

Uncover the hidden gems of Cayo Hueso on our intimate walking tour, where you'll experience the city like a local. Explore charming alleyways, discover secret historical sites, and savor authentic local flavors - all while hearing captivating stories only our knowledgeable guides can share. Book your unique adventure today and see Cayo Hueso through a whole new lens!

Slip into Jimmy Buffett and Hemingway’s sandals and see iconic island sights on this self-guided audio tour. Key West’s quirky island lifestyle has attracted larger-than-life characters, including author Ernest Hemingway, singer Jimmy Buffet, and treasure hunter Mel Fisher. On this walking tour, you’ll hear about the legendary people the island has attracted over the years and see where they made history. Your guide is none other than Frank Everhart, the Schooner Wharf Bar’s very own comedic magician, whose tales are as captivating as the history they’re woven from. Frank, with his intimate knowledge and personal anecdotes, will show you the museums, bars and often-overlooked corners where treasure hunters, eccentrics, and unforgettable locals left their mark. You’ll even see Jimmy Buffet’s first home and his Key West recording studio, Shrimpboat Sound Studio.

Located in the historic Key West Bight, discover this state-of-the-art museum with hands-on exhibits, raw footage, unique artifacts, and the only scale model of Fort Jefferson at Dry Tortugas National Park. As you travel through this interactive timeline of Key West history, uncover the history of sponging, turtling, fishing, cigar making, and tourism that put Key West on the map. Touch a genuine silver bar from the Spanish Galleon Nuestra Senora de Atocha that sank full of gold, silver, and emeralds during a hurricane off of Key West in 1522. Get to know Henry Flagler, John D. Rockefeller’s partner in Standard Oil, in the original paymaster’s railway car from the Florida East Coast (FEC) Railway. Inside the Maggie Atwell House, see the only remaining wooden structure built by the FEC, learn about the backbreaking work of building the railroad over the open ocean and the mosquito infested mangrove swamps of the Florida Keys.

Embark on a self-guided audio adventure through Key West's storied Old Town, where the sun-soaked streets echo with the daring tales of pirates, treasure hunters, and fearless 'wreckers'. Led by the eccentric Captain William Shade, the ghost of an 1800s pirate, you'll navigate from Mallory Square to the Key West Shipwreck Museum. Duck into El Meson de Pepe's for rum-fueled revelry (drinks are not included in the price of the tour), explore Capt Tony's Saloon's ghostly history, visit the Oldest House Museum, and dive into Mel Fisher's Maritime Museum for tales of daring underwater heists. Encounter the wild past at Audubon House, and stand before the Custom House where customs agents once tamed the Key West tides. This is no ordinary stroll; it's a spirited awakening of history, where every step reveals the legends that shaped this island city. Best times for the tour are either early mornings or just before sunset, where the temperature can be a bit more pleasant.

Key West is famous as mainland America’s Caribbean resort town. Here, time slows down as the island vibes take over. But, as you’ll soon find out on this walking tour, there’s more to this island than umbrella drinks and warm breezes. On this tour, travel writer and tour guide Gregg Squeglia will share stories of some of the island’s more famous residents and some lesser-known tales that have given Key West its unique place in American culture and history. He'll tell you about Key West’s incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships along the Great Florida Reef to the hilarious creation of the ‘Conch Republic’. You’ll also find out how, soon after its creation, this micro-state declared war on the United States for a full minute. On this self-paced tour, you’ll also visit the island’s major landmarks and lesser-known treasures.

Embark on an unforgettable journey through the stunning Florida Keys, starting from vibrant Key West aboard the Jeanneau NC 895 Weekender. Experience a unique blend of adventure and relaxation as you explore the archipelago chain. Discover hidden treasures like historic wrecks, serene mangroves, and pristine sandbars, all brimming with natural beauty and biodiversity. Visit iconic destinations like Marathon, Islamorada, and Key Largo, each offering charm and allure.

Embark on a personalized gourmet journey through the lively streets of Key West, where you'll savor a diverse range of street foods from succulent shrimp to iconic Key lime pie. This tour not only satisfies your taste buds but also immerses you in the rich cultural and historical backdrop of each dish. Led by expert guides, you'll uncover the fascinating stories behind the flavors and traditions that define Key West. Perfect for food enthusiasts and history buffs, this unique experience promises an unforgettable blend of culinary delights and cultural exploration.

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and fantastic food. View the beautiful scenery, while experiencing the thrill of a chance to catch species such as Sailfish, Wahoo, Mahi Mahi, Tuna, Snapper, Grouper, King Mackerel, and Shark. Your tour is guided by a licensed Captain in a 30” open fishing style boat with t-top for shade. All the fishing rods and reels, right and left-handed and all the tackle you need, as well as all other necessities including safety equipment. Travelers that have enjoyed our fishing charters also have enjoyed The Turtle Hospital, a tour down Seven Mile Bridge or a beautiful sunset at Sombrero Beach.

Dive into an underwater wonderland with our Reef Snorkel Charter in Key West. Explore the vibrant coral reefs with tropical fish, colorful marine life, and fascinating sea creatures. Our expert guides will lead you to the best snorkeling spots, ensuring an unforgettable experience for beginners and seasoned snorkelers. Feel the exhilaration as you glide through the crystal-clear waters, marveling at the kaleidoscope of colors beneath the surface.

If you want a professional photoshoot, with top photographers, in the most romantic city and beach at sunset?  this is the right place!. Golden Hour, ocean views, old town views, palm trees and more; let us guide you with poses for stunning photos. Our photography style is authentically candid, that reflects a vibrant lifestyle, aiming to inspire others. Let us be your guide, suggesting fantastic poses and activities, like a casual stroll, a dance, etc., to create photos that truly capture the moment.

Step into beautiful Key West, where something exciting awaits. Tara, your scavenger hunt game show host, will curate a unique adventure. Embark on an extraordinary journey with a twist! This is not your typical scavenger hunt; it's a creative & immersive departure from the ordinary. Unleash your inner detective as you delve into the heart of Key West. Engage with friendly locals, discover intriguing tales of this island, & capture the essence in photos, videos & audio files. Young or old, explorer or artist, it's designed to inspire & entertain all who love to discover and create. This is a perfect chance to connect with your teammates in a light-hearted way. Let your imagination run wild, as you team up to unravel the missions. It's a co-creation between you & your interactive host, Key West itself and you, the hunters, making the experience truly unique. Important to note no drinking/bars are involved in this hunt. Celebrate after the hunt!

Experience the best of Key West on our guided walking and boat tour, where you'll delve into the island's rich history and explore its stunning coastline. Begin your journey by strolling through the charming streets, learning about the indigenous peoples, Spanish settlers, and famous residents who shaped the island's identity. Visit iconic landmarks like the Truman Little White House and Hemingway's former home, soaking in their stories and architectural splendor. Then, step aboard our boat to cruise along the crystal-clear waters, where you'll enjoy panoramic views and spot vibrant marine life through the glass bottom. Whether you're captivated by history, mesmerized by nature, or simply seeking adventure, our walking and boat tour offers an immersive and unforgettable Key West experience.

We are Key West's largest boat rental service and have been helping travelers explore our local waterways for over 39 years. Our boats are located at a full service marina with ice, gas, snacks, drinks, beer, fishing equipment, bait and so much more. We are your one stop shop for everything you need to enjoy your time on the water. Our expert staff will guide you through the boat and give directions to local hotspots. Book with Sunset Watersports and see the difference.

Book your private transfer from Key West Int Airport (EYW) to Key West hotels and return. Avoid the hassle of waiting in long taxis or shared shuttle queues and use our private, door-to-door airport transfer. Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination. Our transfers will provide you with such services: meeting with a name plate, door-to-door delivery, no hidden fees, clean cars and professional drivers, which will make your trip more comfortable and safe. We guarantee the quality of the services provided.

Experience the charm of Key West from a unique perspective with our Harbor Cruise. About Set sail from historic seaports and meander through picturesque harbors, where colorful sailboats and historic landmarks line the waterfront. Take in the sights and sounds of this vibrant coastal town as our experienced captain regales you with tales of its storied past. Whether you're enjoying a romantic sunset cruise or a leisurely daytime excursion, our Harbor Cruise offers a front-row seat to the beauty and charm of Key West – a true maritime adventure not to be missed.

This private sunset cruise is the perfect way to enjoy a romantic evening or spend quality time with loved ones in the stunning surroundings of Key West. With everything taken care of, you can sit back, enjoy the views, and make lasting memories. Step aboard our 24’ center console for a private, unforgettable Sunset Cruise in Key West! Perfect for up to six guests, this two-hour adventure offers a relaxing and scenic way to experience the beauty of Key West’s waters as the sun sets over the horizon. Cruise through the tranquil waters of the Key West harbor, enjoying sweeping views of the open sea as the sky transforms with the colors of the sunset. Relax and unwind with your friends or family while a professional captain guides your journey. Bring your own drinks (BYOB) or enjoy the bottled water and soda we provide. Set the perfect mood with your favorite tunes via Bluetooth speakers, and make this a truly special evening on the water.

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll through the narrow, historic streets, you'll hear chilling tales of ghostly encounters, from restless spirits who never left to eerie legends passed down through generations. We’ll pass by the famous haunted landmarks, including the Key West Cemetery, where some say the dead still walk at night, and the eerie corners of Old Town, known for their strange, unexplainable occurrences. With the breeze in your hair and the moonlight casting long shadows, prepare for a spine-tingling ride into the heart of Key West’s most mysterious and supernatural stories. Buckle up, it's going to be a night you won't forget!

Book your Private Transfer from Key West Int Airport (EYW) to Key West Cruise Port. Don't go through all the hassle of waiting in a long taxi or shared shuttle queues and use our private, door-to-door airport/port transfer. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. • Meeting with a Nameplate • We track your Flight • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers

Rent your own private yacht and savor the beautiful Key West waters away from the crowds. Do it all on a luxury catamaran reserved just for you! Snorkel a pristine reef, dolphin watch, jump off of the bows of the boat, sail along the Key West coastline, and enjoy cocktails with friends on your own private yacht! If the big, crowded boats are not for you, we're the perfect option for a more private sail catered specifically to your needs. Our boat is the cleanest you will find, with a spotless bathroom and an electric flush toilet. We are owner-operated so every detail of your sail is important to us. We also allow you to bring your own food and cocktails on the boat to create your own perfect experience. The S/V Liberty is a luxurious 44-ft cat, offering 5 different seating areas, so you can spread out and savor the coastline as we sail by. Bigger groups and longer charter times are available upon request. Let's go sailing!

Set sail for a thrilling morning on the Atlantic with this shorter offshore fishing trip. Departing at 8 AM, you'll head into the deep blue, fishing in depths exceeding 1500 feet. This adventure targets popular species like Mahi Mahi, Tuna, Wahoo, and Sailfish, allowing you to cast your line in some of the best fishing grounds in the state. Plus, if you land a trophy catch, arrangements can be made to have it beautifully mounted for display.

Enjoy the waters of the Florida Keys, don't have experience on the waters around Cudjoe Key? We have separate colored tracks to spots on the water on the 9" GPS.

Embark on an unforgettable private fishing charter in the stunning waters of Key West, guided by an experienced professional captain. Glide through the tranquil, crystal-clear shallows of the Florida Keys, where breathtaking views and abundant marine life set the stage for your adventure. Cast your line at carefully selected fishing hotspots, reel in your own fresh catch, and take advantage of the unique opportunity to have your dinner prepared to perfection at one of the area's renowned local restaurants. This is more than a fishing trip—it's a true taste of the Key West lifestyle!