Top Florida Sailing Tours - page 4

Explore Everglades National Park on a thrilling airboat ride through the Everglades. On this half-day adventure, ride under the mangrove tunnels and through marsh grass, and see wildlife such as alligators, turtles, deer, and birds in their natural habitat. After the boat ride, enjoy some free time to explore the various alligator exhibits.

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlights • Biscayne Bay Cruise: Discover iconic Miami scenery from the water • Millionaire’s Bunker: Cruise past the waterfront homes of celebrities like Jeff Bezos, Ivanka Trump, and Tom Brady • Marine Life: Spot dolphins, turtles, and manatees along the way • Sandbar, Snorkeling & Island Stop: Anchor in shallow, warm waters to swim, snorkel, or simply unwind Onboard Experience • Bluetooth sound system — be your own DJ • Water, ice & cooler included • Bring your own food, drinks & decorations • Amenities: fridge, floating mat, bathroom & bedroom • USCG-certified vessel with a licensed captain Fully Customizable — Ideal to: • Bachelorette & Bachelor Parties • Marriage Proposals • Birthdays • Sunset Cruises By DolphinWaterSport with over 1.2k reviews on Google

Set sail into the glorious Gulf of Mexico for a luxurious 2.5-hour Catamaran day sail, aboard the beautiful 42ft. MaineCat Cool Beans. Journey to an exclusive island paradise where you can bask in the sun and take part in some exciting shelling (weather permitting). Relax with pristine views as calming island tunes fill your ears, while sipping on complimentary drinks from comfortable seating—with the choice of basking indoors or outdoors. Create memories with your loved ones on the high seas.

Immerse yourself in some of Florida’s loveliest scenery—and enjoy a relaxing excursion out on the water—with this private sailing tour. Meet your guide in the afternoon in Goodland, hop aboard your stiletto catamaran, and set sail. You’ll tour the Ten Thousand Islands region, known for its lush seascapes, mangrove forests, and wealth of wildlife. Your guide will point out landmarks and highlights as you go.

Smathers Beach is the largest public beach in Key West and one of the best playgrounds of watersports in the Florida Keys. This Key West Beach Pass is the ultimate ticket to fun in the sun. Do more than swim and suntan with access to multiple watersport activities. Kayaks, rafts, tubes, paddle boards, and Hobie Cat sailboats are available. This pass also includes a thrilling parasail ride.

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the wild dolphins that live, feed and breed right along the south side of Key West. Get that yacht feeling with Champagne Service from your professional crew. Tickets are fully refundable if canceled outside of two weeks in advance!

Look for dolphins around Boca Ciega Bay in St. Pete Beach on a cruise in the Tampa Bay Area. Continue into the Gulf of Mexico to visit Shell Key island, a wildlife preserve where you can snorkel, swim, or collect shells on the beach. Depending on the season, you might spot dolphins, manatees, rays, and a variety of seabirds. This family-friendly tour offers both a late morning and afternoon departure, making it easy to suit your schedule.

Escape to Everglades Holiday Park in Fort Lauderdale for a 1-Hour (approx.) Narrated Airboat Tour. This adventure is a great way to experience the unique subtropical ecosystem of the Everglades. Skim across the grassy water at speeds up to 40 miles per hour while looking for alligators, wading birds and an abundance of flora and fauna in their natural habitats.

Bring your own drinks, snacks and bathing suit, and get ready for fun in the Florida sun, on this party boat trip from Fort Lauderdale. Choose between several departure times, make your way to the marina, and hop aboard: See the city from the water’s edge, zip past celebrity-owned mansions and yachts, and stop at a sandbar for swimming. In between, relax, enjoy the soundtrack, and soak up the ambiance.

Cap off your day and see Miami from another perspective—the water—with this leisurely sunset catamaran cruise in Biscayne Bay. Set out to see top Miami landmarks, including South Beach, the Miami skyline, and the Cape Florida Lighthouse on Key Biscayne. Watch the sun set from the catamaran while you sip a complimentary glass of sparkling wine.

Explore St. Augustine’s Bay Front from the water on this private 2-hour cruise aboard a luxury sailing yacht with space for up to six passengers. With a USCG-licensed captain at the helm, sail along the historic bay front. Look for wildlife, including dolphins, and admire the historic sites. Relax onboard, learn about sailing, or even take the helm.

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern coast of Key West. When all the sailors in Key West heard there was booty to be had, they'd get in their boats and race each other out to the reef. The first one there could claim the ship's cargo. Today, we celebrate it with the firing of the canon to start the race, and all of the schooners of Key West are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, "wins"!

Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google. Perfect for birthdays, bachelor or bachelorette parties, proposals, anniversaries, or simply a day out with friends & family, this private experience is fully customizable to match your vibe. Cruise through the famous Millionaire’s Row and discover why celebrities, athletes, and entrepreneurs choose Miami Beach as their home, surrounded by stunning waterfront mansions, tropical scenery, and breathtaking skyline views. Connect your phone to our Bluetooth sound system and be your own DJ. Bring your favorite food, drinks & alcohol—we include water, ice & cooler onboard. All boats & captains are fully licensed and certified by the USCG, ensuring a safe, smooth, and worry-free experience from start to finish. An unforgettable Miami experience designed to be remembered long after you leave the boat.

As the oldest continuously occupied colonial settlement in the United States, St. Augustine has a wealth of history within its city limits. See both historical sites and natural landscapes while on this shared sailing cruise. Climb aboard a luxury yacht and sail down the Tolomato River and Matanzas River. This small-group sailing tour passes by the St. Augustine Lighthouse and Bridge of Lions, as well as showcases spectacular sunset views.

See more marine life than you’d be able to if snorkeling from the beach on a day trip to Key West, which includes a catamaran snorkeling cruise. Sail the Florida Keys’ crystal waters with expert guides who offer insight about the surrounding area and hop into the water to spot brilliantly colored coral and tropical marine life. After your swim, head back to shore to explore vibrant Key West.

Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant schooner built for General Patton in the late 1930s. Cruise around the coast with the boat’s crew looking after you the whole time, and even letting you take the wheel if you want to try your hand at boating. Watch the sunset from the ocean before heading back.

Discover the ultimate Dubai experience with this luxurious 7-night package. Stay in a 5-star hotel with daily breakfast and explore the city's iconic attractions, including Gold and Spice Souks, a Burj Khalifa visit (124th floor), and the dazzling Dubai Fountain Show. Indulge in unique experiences like the Sky View Glass Slide, Miracle Garden, Global Village, and a Marina Dhow Cruise with dinner, all while enjoying private transportation throughout your stay.

Set sail along Key West's coast on a relaxing catamaran cruise combining dolphin watching with a front-row view of the island's famous sunset. Glide across the water aboard a spacious sailing catamaran, with wide-open views of the surrounding seascape and opportunities to spot Atlantic bottlenose dolphins along the way. With fresh fruit and water provided, and space to bring your own drinks, this is a laid-back way to spend an evening on the water.

Getting into the holiday spirit usually involves a lot of planning. Ideal for anyone who likes to let someone else handle all the logistics, this family-friendly Christmas cruise in Key West includes epic ocean views, a live band, drinks, and plenty of festive celebrations—all you have to do is show up and take in the scenery.

Marvel over Miami’s sweeping skyline, mansions, and historic buildings from the water during this half-day catamaran excursion. Enjoy a perspective on the city not all visitors get to see—and with a little luck, you'll spot some wildlife beyond the mansions. With trips departing on weekends, most travelers can find the time to fit this catamaran ride into their schedule.

Leave the crowds on land behind and sail into the Gulf of Mexico on board the immaculate Orion’s Child with this small-group sailboat tour. Set off with the husband-and-wife crew and relax on board as you pass shrimp boats and waterfront homes lining the channel. Once in the gulf, the sails are raised and course set for Sanibel lighthouse or Fort Myers Beach. Spot dolphins, sea turtles, and other marine wildlife as you fly across the waves.

Escape the crowds with a Nights of Lights sailing tour aboard a comfortable yacht in St. Augustine. Unlike larger boat tours, this sailing experience offers an intimate, relaxed way to enjoy the city's famous festive light display from the water. Guided by a captain, take in the illuminated waterfront from carefully chosen vantage points for a more luxurious, personal sightseeing experience.

Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West as so many locals do, visiting little known, breathtakingly beautiful spots with small groups of friends while enjoying great food and drinks in a relaxed and casual environment. No structured activities. Do as much or as little as you want. After all, you're on vacation! Step aboard Sebago Cubed, a spacious and luxurious sailing catamaran, for a day of sun, sailing and sangria!