Key West Tours & Activities: Handpicked Adventures

Discover the best sandbar charter in Key West with Salty Bottom Boats! Perfect for bachelor and bachelorette parties, spring breakers, and family gatherings, our Coast Guard-certified boat comfortably hosts groups of up to 36 passengers. Cruise to the sandbars, party to your playlist on our big stereo system, satellite wifi, and enjoy snorkeling, water toys, and dancing under the sun. We can even bring the TV and stream the big game for you! Whether it’s a booze cruise, a football watch-party, or a family day on the water, we’ve got you covered. Book now for the ultimate private Key West sandbar experience!

Explore Key West like a local on Barefoot Billy’s Barefoot I Private Charter. This 26-foot custom tritoon is built for comfort, with shaded seating, twin loungers, and all the gear you need. Visit sandbars, snorkel shallow reefs, and relax in the clear backcountry waters at your own pace.

With prices starting at $750 for up to 6 passengers, you get a fully private, customizable experience. Choose a 4, 6, or 8-hour charter, or go for the $450 sunset harbor cruise. Pack your snacks, bring your drinks, and see why Barefoot Billy’s stands out from the rest. Book now—paradise is waiting!

Why choose between reeling in the catch of the day and relaxing at a pristine sandbar when you can do both? Our combo fishing and sandbar charters are the ultimate Key West experience, designed to give you the best of what the island has to offer. These trips are hard to come by, but we’ve got you covered with expert guides, meticulously maintained boats, and a plan that makes it all possible. For the best experience, book 6-8 hours—trust us, 4 hours just isn’t enough to hit the fish and enjoy the sandbar. Let us guide you to an unforgettable day of adventure and relaxation!

Discover the romance of Key West aboard the iconic Schooner America 2.0. This 2-hour champagne sunset sail offers plush seating, stunning ocean views, and the chance to see dolphins, sea turtles, and the legendary “Green Flash.” With hors d’oeuvres and refreshments served by a friendly crew, this is more than a sunset—it's your story of Key West elegance.

Experience the thrill of Key West’s turquoise waters aboard Schooner America 2.0, the stunning 105-foot replica of the first America's Cup champion. Glide effortlessly under 3,600 square feet of sail while enjoying expert narration, complimentary refreshments, and breathtaking views of iconic landmarks. Whether spotting dolphins or feeling the warm breeze, this 1.5-hour day sail is your ticket to a classic Key West adventure. Book your journey now and make memories to last a lifetime!

Set sail on the legendary Schooner America 2.0 for Key West’s thrilling Wreckers Race! Feel the excitement as schooners race to Sand Key Lighthouse, enjoy a delicious lunch from Old Town Bakery, and toast the adventure with beer, wine, or champagne. History, adventure, and ocean views await—book your spot now!

Embark on a 1.75-hour starlit sailing adventure aboard the breathtaking Schooner America 2.0. Guided by a NASA Solar System Ambassador, you’ll explore the night sky like never before. Relax, sip your favorite drink, and marvel at the cosmos as you sail the tranquil Key West waters. A truly magical evening awaits!

Experience the magic of a 1.5-hour moonlit sail aboard the stunning Schooner America 2.0. Glide silently across Key West’s waters under the glow of the full moon, with twinkling stars above and golden reflections dancing on the waves. Perfect for date nights, quiet reflection, or unforgettable evenings with friends.