Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature ... More

Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests Leave the crowds behind and experience the magic of a Key West sunset from the water on your own private 2-hour cruise aboard a brand-new Manitou lu... More

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your guide will be talking you through many points of interest ar... More

Mel Fisher Maritime Museum is the only fully accredited museum in the Florida Keys. That means this is more than just an exciting adventure story - it is also a nationally recognized research institution!... More

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point out sea birds and various sea-life such as different fish species, shrimp, crab... More

This is the best 1 day combo where you will enjoy the water and land in Key West. Get to Hop On Hop off the conch train, one of Florida's most popular attractions, going to Truval Village: Steps away from the Ernest Hemingway Home... More

1 Traveler is equivalent to reserving the entire boat. (Up to 6 Guests) Explore the vibrant waters of Key West on a fully custom private charter designed for up to 6 guests. Enjoy family-friendly bottom fishing, where all bait an... More

Whether you are visiting Key West for a special occasion, Anniversary, Romantic Getaway, Family Reunion. We can meet you at your Resort or one of Key West beaches to have a personal photo shoot We are at times available for Sunset... More

Sail from Key West Bight aboard Papa’s Cat, a 48-ft catamaran inspired by Hemingway’s island spirit. Dive vibrant reefs, drift over sugar-white sandbars, and sip fresh coconuts as you soak up the sun. With snorkel gear, towels... More

What makes our e-bike rental truly unique is the combination of easy-to-ride electric bikes and a built-in GPS guided tour experience. While most rentals simply give you an e- bike, our e-bikes can guide you through Key West wit... More

This is a private Key West fishing charter focused on accessibility, fun, and variety. Unlike specialized sportfishing trips, Six Fins Patch Reef Fishing offers a welcoming experience for beginners and seasoned anglers alike. With... More

This is the only private charter that focuses exclusively on the Marquesas Keys, offering a rare combination of history, remoteness, and adventure. ✅ Remote islands 30 miles offshore with pristine beaches and clear waters ✅ M... More

Experience a private dolphin safari in Key West, exploring the famous Dolphin Playground where wild dolphins are often seen playing in the wake. Unlike large group tours, this charter is tailored just for your group, with a flexib... More

This is the only private eco boat trip that focuses exclusively on the Key West National Wildlife Refuge in such depth. Rather than hitting common tourist spots, you’ll venture into parts of the Refuge that most tours skip — w... More

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s weather refunds of course. Premium drinks & snacks included! Enjoy a premium sha... More

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key West was discovered and became so rich? Explore Key West’s history, lore, and legends from the ground up with an intimate walking ... More

With your friendly and knowledgeable tour guide, this 4 Hour VIP Tour of the South Keys promises to amaze you. En route, you’ll learn the history, culture, and ecology of the Keys, listen to island music, and enjoy the breathtak... More

Looking for an unforgettable culinary experience? The expert chefs are passionate about sharing the unique flavors of Key West while keeping you entertained. Watch as they bring fresh, local ingredients to life with traditional co... More

Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to Marathon and stop along the way to explore the natural splendor and man-made wonders of the Fl... More