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 sno... More

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More

Fun in the sun when you make it over to Smathers Beachand have the best day with unlimited use of water activities. Go kayaking, paddle boarding, sailing or just seat in your beach chair and umbrella and enjoy the sun. Make sure t... More

We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of time to determine your goals for the day and make them happen. Our guests almost always say that their trip with us was the highlight... 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

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... More

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, ba... More

This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll cruise up the bay side and back down the ocean side (or vice versa). Learn the history of the ... 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. Ta... More

Experience the best of both worlds with our Island Fishing Tour, exclusively offered by Cowboy Cowgirl Sportfishing Charters. Unlike typical fishing charters, this unique excursion combines thrilling fishing action with serene isl... More

Embark on a tantalizing journey through Key West's culinary and cocktail scene with our Bar & Food Crawl by Boat Charter. About Cruise along the picturesque coastline to a selection of outdoor Tiki establishments nestled along th... More

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More

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

OPEN ITINERARY & CUSTOMIZABLE you can create your dream adventure with our Local Charter Captains in Key West. Whether celebrating a special occasion or simply seeking a personalized experience tailored to your interests, combine ... More

Embrace the naturalist lifestyle. Enjoy intimate Freedom and Relaxation naturalist experience through crystal-clear waters, feeling the breeze on your skin without clothing. Exclusive and Private Experience: Our charters are des... More

Rent your own private yacht and savor the beautiful Key West sunset away from the crowds. Do it all on a luxury catamaran reserved just for you! Dolphin watch, jump off of the bows of the boat, sail along the Key West coastline, a... More

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic buildings with unique histories, uncovering tales of colorful figures who... More

Private Offshore Fishing on Sanctuary – 47 ft Hatteras Experience the thrill of offshore fishing in Key West aboard Sanctuary, our 47 ft Hatteras. Led by an expert Captain and mate, we’ll take you to the best deep-sea fishing ... 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

Join us for the best walking tour in Key West! You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old To... More