Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More

Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approac... More

The hop-on hop-off trolley tour of Key West is a fantastic way to explore this historic island. Sit back and relax while your expert tour guide turns back the pages of history to the days of Indians, pirates, wreckers and the Civi... More

What makes Fury’s Live Music Sunset Sail unique is the combination of luxury and a vibrant, immersive experience. Guests embark on a spacious 65-foot catamaran, ensuring comfort and plenty of room to enjoy breathtaking views of ... More

This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters of the Key West National Wildlife Refuge—a remote area... More

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you on an exhilarating, up-close adventure across crystal-clear waters, winding ... More

100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the blueish-green waters. Eco-Tours with Marine Viewing: Our eco-tours ... More

Key West is famous for it's sunsets and it doesn't get any better then on an intimate sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an ... More

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West. Your guide will be talking you through many points of interest around the island. Make sure to keep an ... More

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings that celebrate the island’s unique mix of Cuban, Caribbean, and Floridian influenc... More

Gulfstream Fishing is the longest-running party boat fishing charter in Key West, catching steady loads of reef fish since 1947. Our 58-foot Gulfstream IV carries up to 45 passengers and is inspected twice a year by the U.S. Coast... More

When you arrive in port in Key West, take an independent, hop-on hop-off trolley tour shore excursion for the best way to explore the island. While you’re off your cruise ship, simply sit back and relax while your expert tour gu... More

For the quintessential Key West adventure, don't miss the 'Duval Crawl' pub crawl! Immerse yourself in the island's iconic and buzzing bar culture. Join the original Key West Pub Crawl, a local favorite since 2002. Your ticket inc... More

Key West is famous for stunning sunsets, and this dinner cruise offers the perfect way to enjoy them. Savor breathtaking views as the sky transforms, while indulging in a tropical buffet, live music, and incredible vibes. It’s a... More

This isn’t your average ghost tour. Key West Ghost and Mysteries is a locally owned and operated family business offering a small, intimate experience that lets you hear every story, ask questions, and truly connect with your gu... 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

Experience the Florida Keys like a true Conch! Our 4-hour Backcountry Sandbar Excursion takes you to a stunning location chosen by your captain based on the day's weather and tides. Immerse yourself in the intoxicating beauty of t... More