See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour. • Find out how the town nearly went bankrupt before reinventing itself as ‘The Conch Republicâ... More

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwi... More

Our 4-passenger golf cart rentals are the perfect blend of convenience, fun, and flexibility for exploring Key West. With a smaller footprint than larger carts, these vehicles are easy to maneuver through Old Town’s charming s... More

Experience the Thrill of Offshore Fishing in Key West Join us for a 4-hour shared deep-sea fishing adventure aboard a top-tier 6-passenger sportfishing boat(max is 6 on a boat)! This trip is perfect for solo anglers or small group... More

Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate storytellers, you’ll wander through historic Old Town, where every co... More

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

If you’re looking for some of the best fishing that money can buy out of Key West, Florida, you can’t go wrong with Corsair 2 Sportfishing. With over 3 decades of local fishing experience under his belt, Captain Russ McKinley ... More

This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, ... More

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury boat, ensuring a swift and comfortable journey through the stunning turquois... More

Turn your trip into something unforgettable with a Polaris Slingshot rental from Keys Vacation Supply Rentals. This open-air ride lets you feel the ocean breeze, soak in panoramic views, and enjoy the road like never before—all ... More

The USCGC INGHAM was the longest continually serving, most decorated ship in Coast Guard History. Serving in active duty from 1936 to 1988. Only remaining American ship afloat to have fought in the Battle of the Atlantic. Comman... More

Dolphins are widespread in the Florida waters especially Key West as they prefer the warm waters of the tropical ocean. As we visit the Dolphin pod in the Key West Waters don't be surprised to hear their vocals in the form of clic... More

A Sunset Cruise with a Twist aboard the Island Pearl Wrap up your perfect day in the 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 o... More

This snorkeling adventure goes beyond the ordinary by offering crystal-clear waters, vibrant coral reefs, and an incredible variety of marine life—all in a serene, picturesque setting. Unlike standard tours, we prioritize your s... More

At SeaEO Luxury Boat Charters, our meticulous attention to detail, expert captains, and premium vessels set us apart, transforming every trip into your perfect day on the water and why we dominate other charter companies. There is... More

Explore the calm, clear waters between Stock Island and Key West with a 2-hour standup paddleboard rental. Glide over sea grass and through mangrove tunnels as you look for fish, birds, sharks, rays, and manatees. This is a great ... More

Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk. This self-guided adventure immerses you in the rich tapestry of island life where writers like Ernest Hemingway and Tennessee Williams fo... More

Ready for the most beautiful 2 hours of your Florida Keys vacation? Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into the beautiful water of the Florida Keys. Our 2-Hour Sunset Tiki Cruis... More

The Experience: Don't miss your chance to experience a luxury charter in the Florida Keys, versatile enough for any on-water activity you can envision. Whether you're interested in snorkeling, light tackle fishing, sandbar hopping... More