Top Florida Sailing Tours

Perfect for those who want to squeeze a lot of sightseeing into a limited amount of time. A fully narrated 90-minute cruise along the New River through Fort Lauderdale will let you soak up such sights as the lavish homes and mega yachts along Millionaire's Row.

Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands in the Key West National Wildlife Refuge. Keep an eye out for dolphins, sea turtles, manta rays and many other wildlife that call the Refuge home. Your captain knows where dolphins are frequently seen and will let you know if he spots any. Upon reaching the mangrove islands, the schooner anchors and your exploration begins. Your day is divided between guided kayaking tours and guided snorkeling tours. The warm, shallow water is calm, sheltered by the uninhabited mangroves, making kayaking a breeze. After your tours, come back aboard and wash off with our fresh water rinse, and relax on deck. Choose from plenty of complimentary cold drinks – frosty cold beer, wine, homemade sangria, chilled sodas and filtered water. This is the best of laid-back island living.

Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the *America 2.0*, a replica of the schooner that won the very first America’s Cup. Relax on decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip drinks from the full onboard bar.

Step aboard an evening cruise for dinner and drinks while you take in views of St Pete Beach. Watch over the landmarks of St Petersburg and fill up on food from the tropical-themed buffet. An open bar means you won't go thirsty while jamming to island music from the onboard DJ and other entertainment.

Make sure you tick off the most important highlights of the Everglades with an experienced guide in the lead when you book this Everglades airboat tour. Race through the River of Grass listening to in-depth commentary on the local environment and wildlife. Plus, round-trip transport from Fort Lauderdale is provided for a stress-free adventure.

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fun in the sun on this sailing, dolphin watch, beach hopping and snorkeling adventure. Sail away through historic Grand Lagoon and see dolphins swimming alongside the Daydreams, then jump in for a shallow-water snorkel experience to see different species of marine life. Relax, feel the warm sea breeze and enjoy complimentary beverages on board! Again, this is charter for up to 6 guests. Price is all inclusive and includes fuel, ice, water, soda, beer, wine and sangria. You are also welcomed to bring your own food and drinks on board.

Discover a new perspective on St. Augustine—and enjoy a relaxing trip out on the water—on this sightseeing boat tour. Pick from multiple start times, head to the marina, and hop aboard. See highlights like the Bridge of Lions, Castillo de San Marcos National Monument, and National Shrine of Our Lady of La Leche, and learn the stories behind the sights from your captain’s narration.

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!

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.

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.

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and a myriad of sea creatures and incredible Birds! The best part is that then you can share what you have learned so we can all help to preserve the beauty of the bay and its precious Wildlife.

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.

Get more out of your time in Florida, and take advantage of the proximity to The Bahamas with this hassle-free round-trip ferry service. The boat has plenty of seating areas, restrooms, and air-conditioning to ensure a comfortable journey, as well as an onboard snack bar. Once you’ve arrived at Bimini Island, enjoy free time to do whatever you wish—explore world class beaches, eat, shop, or take part in watersports.

Enjoy Destin’s waterways without the hassle of arranging your own private boat. This guided cruise offers an exclusive experience for your group, with opportunities to spot dolphins, watch the sunset, and take in the scenic coastline from the water. Relax onboard with thoughtful amenities while your captain handles the navigation.

Cruise along Fort Lauderdale’s historic New River and enjoy a delicious barbecue dinner on this cruise. Board the Jungle Queen Riverboat and see the luxurious mansions and yachts along Millionaire’s Row, stretching from the Bahia Mar Yachting Center to the Intracoastal Waterway. The cruise travels to a tropical isle for an endless dinner offering barbecue ribs, and chicken with all the trimmings. Then experience a laugh-out-loud variety show to cap off an enjoyable and entertaining evening.

This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon: extended time at a shallow-water sandbar, snorkeling in clear backcountry waters, and a sunset on the water. Sailing aboard a historic schooner with a small group, guests enjoy a more personal experience in calm, less crowded areas of the Keys, all while soaking up one of the best afternoons Key West has to offer.

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.

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.

Your 90 minute sunset sail on 41ft, 32 passenger Lazy Daze Catamaran will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. If you are looking to unwind before dinner or a night out on the town, enjoy a romantic sunset sail with Paradise Adventures. Sailing along the Gulf of Mexico is a great opportunity to relax and leave your worries behind. Enjoy your first beverage complimentary, then a full service bar is available for additional beverage and snack purchases. Listen to tropical music and enjoy the Panama City Beach sunset! Sunset sails offer you an opportunity to see some of area’s greatest sights while enjoying the breezes of the water.

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic pose, sit on the sides and dangle your feet in the water; feel like you're surfing or flying up on the bows; or drive a world-class Condor!

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.

Nature lovers and eco-adventurers will love this private, low-key tour. Take a pontoon boat to explore mangrove forests, winding waterways, and mangrove-lined tidal creeks. Enjoy kayaking, or stand-up paddleboarding in a diverse marine ecosystem. A cooler is provided so guests can bring snacks and drinks, which can be savored on a deserted sandbar.

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.