Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike roadside rentals, this tour transports you by boat to the untouched M... More

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

Let us take you on a guided golf cart tour around Key West with a seasoned and sober driver! We will cruise past Jimmy Buffett's studio, Mallory Square, Sloppy Joes and Hog's Breath Saloon just to name a few of the great popular p... More

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch fo... More

On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to 5. An experienced licensed boat captain who knows the waters will lead your tour. Dinghies can go thr... More

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef system after the Great Barrier Reef in Australia, and the Palancar Reef in Mexico and Beli... More

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & Sunset Cruise! This exclusive trip takes you to a beautiful sandbar, where you can l... More

Join me, a true seventh-generation local captain for a personalized Key West adventure on my private boat. Spend the day exploring the stunning turquoise waters and hidden islands of the Florida Keys, with opportunities to snorkel... More

Max 6 people. Explore the waters around Key West. This versatile boat let's you plan your own adventure. Snorkel the reef, explore an offshore island, look for dolphin and other marine life or simply relax on a sandbar with your t... More

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the Lower Keys really well. So there are a few different areas to choose from on... More

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

Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with a drink in hand, explore the local marine sa... More

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring with stops like Fort Zachary Taylor Historic State Park, U.S. Coast Guard Cutt... More

Welcome to Key West Boat & Jet Ski Adventures! Enjoy a fully customizable 6-hour private boat charter exploring Key West’s stunning backcountry. Begin with a scenic cruise past iconic landmarks like Mallory Square and the South... More

Unlike crowded party boats, this is a private Key West sunset cruise reserved exclusively for your group. You’ll enjoy personalized service, spacious seating, and the flexibility to customize your evening — whether you want mu... More

Get ready for an exhilarating adventure on the vibrant waters of Key West with our private deep sea fishing charters. Led by the skilled and experienced Captain, our team is dedicated to making your fishing trip unforgettable. Ree... More

Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Return at 12:00pm and have 4 hours... More

Experience Key West’s waterfront the way locals do—by private boat. This harbor cruise offers a more comfortable experience, complete with narration and flexibility. With a USCG-licensed captain, you’ll glide past historic f... 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

Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat for the USS Roosevelt. Set off on a scenic excursion past Marathon�... More