Key West has so many cultural, culinary, & Aquatic entertainment options? It can take an expert to coordinate transportation, locations, and times all depending on the weather? Luckily, Barefoot Billy has the island’s most experienced Hotel Concierges standing by at Key West’s Top Three Beach Resorts: Casa Marina, Reach Resort, & Marriot Beachside. If there’s a floral delivery, hidden happy hour, or private island picnic in your future? Barefoot Billy’s team has decades of island experience and will always point your party in the right direction.
Popular Listings
The narrow streets and limited parking in Key West makes renting a scooter a great way to explore the Island. Read More
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The best part of exploring a 2 x 4-mile island is our preferred mode of transportation: Bicycle. Cruise around Key West for a day or longer on an adult cruiser. Read More
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Circle the island of Key West in 90 minutes and experience a unique perspective of the Gulf of Mexico and the Atlantic! Read More
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Hang out like the locals! The shallow, clear backcountry waters of the Florida Keys sets us apart from anywhere else in the country. Just a short boat ride will transport you to what feels like a world away! Explore secluded sandbars, shallow reef patches, and tropical wildlife at your own pace during our private charters. Pack up your favorite refreshments and snacks and cruise into Paradise! Read More
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Cruise into a Key West sunset aboard Barefoot Billy’s 45-foot power catamaran, Seabreeze. Our magnificent sunsets are best appreciated from the turquoise waters and will be a highlight of your Key West vacation. Seabreeze provides a spacious setting, never filled to capacity, leaving ample room for you to stretch out and unwind. Read More
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On this family-friendly cruise, we venture out to balmy Backcountry waters to snorkel in Key West's wildlife sanctuary before searching the Gulf of Mexico's backcountry's balmy waters before searching for Key West’s dolphins in the crystal clear waters for our local dolphin pods at play. Read More
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Experience the feeling of walking on water and getting the best view of marine life at the same time with a Paddle Board rental from Barefoot Billy’s. Paddle boarding provides a unique ability to observe both the world on top of the water and the world beneath it. Paddle boarding is easy, fun, and a great way to work off those Key West cocktails. Read More
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Rent a kayak from Barefoot Billy’s and push off right from the beach to begin your journey through some of the most gorgeous scenery and waters in America. Experience what makes kayaking one of Key West’s most popular activities. Barefoot Billy’s kayak rentals include kayak, paddle and personal flotation devices. Read More
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Led by a professionally trained and licensed crew, your Key West fishing adventure starts here! Spend your day on the water and learn the local secrets that have led us to catch record-breaking snappers & groupers! Read More
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Experience your dream fishing trip in Key West with Captain Conch Charters! With Party Boat, Private & Split Charters, the possibilities are endless! Read More
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Our Split Charter here in Key West, FL, is perfect for solo, double, and small groups. Unlike private charters which require you to reserve the entire boat, a Split Charter allows you to save money by sharing the trip with other fishing parties. Read More
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Light tackle fishing & backcountry sandbar trips. Why choose when you can do both! Read More
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On a Key West Florida Fishing Charter we pride ourselves on using first-class equipment and offer a fleet of vessels to accommodate any sort of fishing experience you are looking for. Read More
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