Boat Tours in Key West

Sailing, sunset cruises, and catamaran adventures.

Top Boat Tours Listings

  • Fury Water Adventures Dolphin Watch — Come aboard Fury's Key West Dolphin Watch and Snorkel Tour for an aquatic journey to observe the grace and beauty of our resident Key West dolphins. Take our fast powered catamaran on an adventure ... (4.7/5, 211 reviews) | 631 Greene St. Key West, Florida, Key West, FL 33040-6624
  • Western Union Schooner — Schooner Western Union is the official flagship of Key West and the State of Florida. She's one of the oldest working wooden schooners in the United States and on the National Register of Historic ... (4.8/5, 140 reviews) | 202 William St, Key West, FL 33040-6645
  • Seaborn Charters — Seaborn Charters in Key West, Florida. (4.9/5, 125 reviews) | 202 William St Behind Scooner Warf, Key West, FL 33040-6645
  • Good Times Key West — Good Times Key West offers 100% customizable boat trips and private charters. We have a capacity of six guests. And do (almost) what ever you would like. Some poplular activities include island hop... (5/5, 111 reviews) | 1605 N Roosevelt Blvd, Key West, FL 33040-7253
  • Blue Ice Sailing Charters — The BLUE ICE is a beautiful 47' Jeanneau Sailing yacht. She has been based out of Key West doing luxury Day sailing trips since 1998. We offer many options when choosing a key west sailing adventur... (5/5, 103 reviews) | 201 William St, Key West, FL 33040-6679
  • Blue Ocean Yacht Charters — Blue Ocean Yacht Charters in Key West Florida is here to make your yacht rental or yacht charter a vacation to remember. We specialize in affordable overnight and day charters. All our yachts, whet... (4.6/5, 139 reviews) | 7005 Shrimp Rd, Key West, FL 33040
  • Bluesail Yachting — Immerse yourself in the tranquil beauty of the Florida Keys and experience a vacation of a lifetime with TripAdvisor's 3-time Traveler's Choice Award Winner, Bluesail Yachting. Established in 2018,... (5/5, 93 reviews) | 7005 Shrimp Rd, Key West, FL 33040-6053
  • Second Nature Charters — Second Nature Charters in Key West, Florida. (5/5, 92 reviews) | Key West, FL
  • After Hours Yacht — After Hours is Key West's premier yacht available for luxury private charters. Guests are provided personalized service tailored to their specifications, including food and drinks. Your friendly, l... (5/5, 74 reviews) | 202 William St Schooner Wharf, Key West, FL 33040-6645
  • Salty Soul Charters — Explore the waters of Key West the way the locals do. Encounter wildlife and enjoy the peace and serenity as we drive through mangrove trees and up to sandbars. (4.9/5, 80 reviews) | Key West, FL
  • Spencer's Boatyard — Cleanest boats in Key West! From 26' deck boats to 22' center consoles. Local owner with a staff that will help to get you out on the water and find your perfect day out on the beautiful Key West o... (4.6/5, 101 reviews) | 701 Palm Ave, Key West, FL 33040-7031
  • Soul Shine Adventures — At Soul Shine Adventures, you'll experience Key West like a local, from a local. Each of our private charters is fully customizable, so you don't have to commit to just one activity-you can design ... (5/5, 65 reviews) | Key West, FL
  • Southernmost Sailing School — Southernmost Sailing School, located in the heart of Key West, Florida, is a premier sailing institution dedicated to providing top-tier instruction for all sailing enthusiasts of all levels. As an... (5/5, 53 reviews) | 5555 College Rd, Key West, FL 33040-4307
  • Key West Tiki Boat — Welcome to Key West Tiki Boat! (5/5, 50 reviews) | 5130 Overseas Hwy, Key West, FL 33040-4324
  • Dibs On Bottom — Spearfishing, fishing, snorkeling, lobstering, sandbar and sunset trips! Captain Aaron will help you plan your perfect day on the water! Call now to book! (5/5, 49 reviews) | Key West, FL
  • Argo Navis Sailing Charters — Set sail aboard the SV Argo Navis, a stunning 75-foot luxury catamaran — the last boat built in Key West. Enjoy sunset sails with craft beers, fine wines, charcuterie and chocolates, all while soaking in the sounds of wind and water. Coast Guard certified for up to 91 guests. (4.9/5, 51 reviews) | Historic Seaport, End of Margaret Street, Key West, FL 33040
  • World Sailing Adventures — Join us aboard Makara, our 47-foot catamaran, to enjoy your private sailing charter for a few hours or join us under the stars for a multi-day, offshore adventure among the Florida Keys. Sail with ... (4.6/5, 57 reviews) | 6810 Front St Safe Harbour Marina, Key West, FL 33040-6054
  • Stock Island Charters — Stock Island Charters is a custom private charter company that offers sandbar and sunset tours in and around the waters of Key West. (4.9/5, 44 reviews) | 5950 Peninsular Ave, Key West, FL 33040
  • Hindu Sailing Charters — Sail aboard the historic 1925 Schooner Hindu, a beautifully restored classic vessel offering an authentic sailing experience in Key West. Family-owned and operated, Hindu Charters provides sunset sails, day sails, brunch cruises, and private charters year-round from the Historic Seaport. (4.9/5, 40 reviews) | Key West Bight Marina, End of Margaret Street, Key West, FL 33040
  • Key West Glass Bottom Boats — Key West Glass Bottom Boats in Key West, Florida. (3.5/5, 180 reviews) | 700 Front St, Key West, FL 33040-6689
  • Tails2Sails — Tails2Sails Charters out of Key West, FL offers you the ultimate in light tackle sport fishing. The Boat is a 31Ft Yellowfin Center Console with Twin Suzuki Outboards and excellent sea comfort. All... (5/5, 36 reviews) | 5130 US Highway 1, Key West, FL 33040-4324
  • Sail Away Key West — Welcome to Sail Away Key West, your source for private bareboat or crewed catamaran charters in Key West. Your group's accommodations, snorkel/dive tours, kayaks, paddle boards, are all included in... (4.9/5, 29 reviews) | 7005 Shrimp Rd, Key West, FL 33040-6053
  • Flying Fish Charters — Flying Fish Charters in Key West, Florida. (5/5, 24 reviews) | 1212 Olivia St, Key West, FL 33040-7221
  • Bimini Charters, Private Catamaran Sailboat, Key West, FL — Private sailing catamaran charters. Sail, snorkel, swim, dolphin and sea turtle watch, enjoy a KW sunset, and more! (5/5, 19 reviews) | 6840 Front st, Key West, FL 33040
  • eFoil The Keys — We offer eFoil lessons, tours, and full or half day boat charters from Key West to Key Largo. We use the two top eFoils (Flite and Lift Boards) for all our lessons and run a spacious 26' Twin Vee f... (5/5, 19 reviews) | 1605 N Roosevelt Dr, Key West, FL 33040-7253
  • Key West Cruises — Key West Dinner Sunset Cruise. Cruise the Key West sunset with live music, an open bar and great food. Take in the fabulous sunset on the open air upper deck of our cruising yacht. Come aboard for ... (3.5/5, 65 reviews) | Key West, FL
  • CN-it Adventures — Our trips are tailored to your requests; depending on the weather. We can take you for an eco tour, snorkeling at a shipwreck or coral reef, watch dolphins, feed sharks, have fun fishing, celebrate... (5/5, 17 reviews) | 951 Caroline St, Key West, FL 33040-6720
  • Havana Fleet Luxury Charters — Experience Key West from a luxury yacht with Havana Fleet. Offering customizable charters from 2.5-hour sunset cruises to multi-day adventures to the Dry Tortugas. Professional Coast Guard-certified captains and crew, full-service amenities including water toys, fishing equipment, and optional private chef. (5/5, 16 reviews) | 245 Front Street, Key West, FL 33040
  • Safari Charters Key West — Safari Charters Key West in Key West, Florida. (4.7/5, 19 reviews) | 2319 N Roosevelt Blvd, Key West, FL 33040-3835
  • SeaEO Luxury Boat Charters — SeaEO Luxury Boat Charters is the top luxury charter available for any water activity imaginable. With several years of experience, we focus on providing the right boat, equipment, and people that ... (4.8/5, 17 reviews) | 6000 Peninsular Ave, Key West, FL 33040