Top Key West How to Get Around in 2026

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, unwind in a refined and intimate setting away from crowded party boats. Enjoy complimentary beer, wine, champagne, and soft drinks throughout the cruise, with cocktails available for purchase. Savor a selection of hors d’oeuvres including cheese and crackers, fresh vegetables with dip, and shrimp cocktail — perfectly paired with a breathtaking Florida Keys sunset. Watch the sky transform into vibrant shades of orange, pink, and gold as the sun dips below the horizon, creating unforgettable photo opportunities. Perfect for couples, celebrations, or anyone seeking one of the top-rated experiences in Key West. Advance reservations are highly recommended, as this popular sunset sail often sells out.

The 21' Hurricane Sundeck is the perfect blend of comfort, versatility, and performance, making it a top choice for adventurers and families alike. Whether you’re fishing, snorkeling, or cruising, this boat delivers an exceptional experience on the water. Why It Stands Out: Smooth & Safe Ride: Handles well in all conditions for a worry-free outing. Versatile Design: Ideal for fishing trips, family adventures, or group excursions. Premium Features: Includes a Bimini top for shade, live well, rod holders, swim ladder, spacious deck, and comfortable seating. Perfect Size: 21 feet long with capacity for up to 10 passengers—room for everyone without sacrificing maneuverability. Adventure Ready: Great for sandbar hopping, snorkeling, or simply relaxing in style.

Explore the charming streets of historic Key West at your own pace. Enjoy a personalized experience as you visit iconic sites like the Hemingway House, famous for its feline residents, and the stunning views from the Key West Lighthouse. Relax at Smather's Beach and indulge in a unique alligator snack. Capture memories at the 90 Mile to Cuba buoy and discover the Truman White House. With private vehicle transport and flexible itinerary, this tour is perfect for those who value freedom and personal choice. - Private vehicle for a comfortable, no-crowd journey - Tailor your own itinerary to explore Key West's highlights - Visit memorable spots like the Hemingway House and Smather's Beach - Pickup and drop-off at your hotel for convenience

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 while being easy to drive with a standard license. With built-in navigation, premium sound, and flexible rental options, you can explore at your own pace and make every mile part of the adventure. It’s more than just transportation—it’s the highlight of your vacation waiting to be booked.

The 24' Hurricane Sundeck stands out as the ultimate choice for families and groups looking for comfort and versatility on the water. Its spacious design and thoughtful features make every outing enjoyable and stress-free. Why You’ll Love It: Perfect Balance: Combines generous space with easy maneuverability for smooth cruising. Room for Everything: Plenty of space for coolers, gear, and unforgettable memories. Premium Features: Wraparound seating, built-in cooler space, Bimini shade top, stereo system, swim ladder, and a wide deck area for lounging. Ideal for Any Occasion: Great for family outings, sandbar trips, sightseeing, or celebrating with friends. Capacity: Comfortably accommodates up to 12 passengers.

Discover the unparalleled joy of exploring Key West waters aboard this center console! Our fleet boasts the newest, most luxurious vessels, fully equipped with top-tier upgrades for your comfort and convenience. Nestled within our full-service marina, we've proudly served our community for 39 years, earning our reputation as the go-to destination for boat rentals in Key West. Join us and embark on an adventure of a lifetime – where every wave carries the promise of unforgettable memories!

Experience the ultimate adventure aboard our 25' Cobia Center Console with twin engines, designed for power, stability, and comfort. Perfect for fishing trips, sandbar cruising, or exploring offshore waters, this vessel offers unmatched versatility. Highlights A safe, comfortable ride that handles well in all conditions, making it a favorite for those who want flexibility on the water. • Length: 25 feet • Capacity: Up to 9 passengers • Features: T-top shade, live well, rod holders, swim ladder, spacious deck, and premium seating • Best For: Fishing enthusiasts, families wanting versatility, or groups looking for comfort and style

Climb aboard and let the tropical breeze set the tone as we cruise past working marinas, colorful houseboats, and mangrove-lined shores where dolphins often play in our wake. With island tunes flowing and an ice-cold drink in hand, you’ll drift effortlessly into vacation mode. Our first stop: Hogfish Bar & Grill, a local legend tucked into the heart of the docks. Here, fishermen unload their daily catch and the vibe is pure Old Key West. Sink your teeth into their famous fresh hogfish sandwich or sip a cocktail right on the waterfront. Next, we glide over to Bad Boy Taqueria, a fun and funky stop known for bold flavors, creative tacos, and the kind of energy that makes you want to stay all afternoon. Grab a bite, grab a drink, and soak in the local charm. Then it’s off to Hurricane Hole Marina, a favorite for both locals and salty sea captains. With strong drinks, great music, and unbeatable views of the harbor, it’s the perfect place to relax before we head back out on the water.

Escape the crowds and experience the best of Key West on your own terms with the Vitamin Sea Dolphin Safari. Designed for couples, families, or small groups of up to 6 guests, this 4-hour journey offers a perfect mix of adventure, relaxation, and natural beauty — all with your own captain and guide. Cruise through crystal-clear waters, spot playful dolphins in the wild, snorkel above vibrant reefs, and unwind on a remote sandbar that few ever get to see. Whether you're looking for marine life, island serenity, or picture-perfect moments, this tour delivers unforgettable coastal magic.

Enjoy a memorable sunset experience aboard your private charter in Key West. This two-hour cruise takes you through the stunning Man-O-War Harbor, offering breathtaking views of the western horizon and the chance to spot dolphins. Relish in the comfort of the luxurious 32’ Belzona 325, equipped with plush seating and a premium sound system while you toast to another beautiful day. - Depart from Hilton Key West Resort and Marina for a scenic sunset cruise - Capture the elusive Green Flash as you relax on the water - Family-friendly experience, perfect for all ages - Customizable packages available to enhance your adventure

Set sail for adventure with our Tiki Party Boat rental, cruising the breathtaking waters! Whether you're soaking up the sun, spotting local marine life, or enjoying refreshing drinks on deck, our 14-passenger tiki boat is the perfect way to experience paradise. Complete with bar top and chairs, take your party to the sea! Want a stress-free day? Hire a captain and let them handle the navigation while you focus on fun. Book now and turn your day on the water into a true paradise escape!

Create your own adventure: fish, snorkel, paddleboard, or just cruise in style! The newest fleet in town! Our spacious pontoons provide plenty of space and shade while you make your way through our beautiful local waterways! What’s Included: 12 Passenger Pontoon Boat Rental (Children and babies count as passengers) Safe, reliable, and well-maintained equipment Includes a 70qt cooler (purchase ice at check-in) Life vests for all passengers Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+ Optional Add Ons: Paddleboards- A fun and suitable activity for people of all ages and abilities. Lily Pad- This floating foam island allows you to rest, kick-back, tan, run, and play on.

Double Decker Pontoon Boat with slides for up to 14 passenger Rental in sunny Key West, Florida. Want a stress-free day? Hire a captain and let them handle the navigation while you focus on fun. Book now and turn your day on the water into a true paradise escape!

This private eco boat tour focuses on the Key West National Wildlife Refuge and its mangroves, islands, flats, and coastal habitats. Your group can prioritize wildlife viewing, photography, snorkeling, swimming, or relaxed exploration. The flexible itinerary responds to current conditions and refuge protections, giving guests a private and respectful way to experience Key West’s backcountry environment.