Top Florida Sailing Tours

The laid-back waters of the Indian River and the lavish yachts flowing along the Intracoastal Waterway set the stage for this relaxing catamaran cruise launching from Merritt Island. Native wildlife is often spotted while sailing between Cocoa Village and Ponte Vedra Beach, including dolphins, manatees, sea birds, and more. Let your captain sail you smoothly through this ecologically diverse area while you kick back with soda and snacks.

Climb aboard a schooner for an afternoon of sailing in Clearwater Beach with this tour. Enjoy sea breezes and admire views you wouldn't get if you stayed on shore during this scenic cruise. Keep an eye out for wildlife like dolphins and manatees during the sail. Guests are permitted to bring alcoholic beverages on board the schooner. Note that hard soled shoes are not allowed onboard for safety.

Set sail aboard the iconic schooner Suncoast Horizon in the picturesque waters of Treasure Island, Florida, about an hour before sunset for an unforgettable experience. Enjoy smooth sailing, stunning sunsets, and starry skies, with cozy blankets provided in case you want to relax or cuddle on deck. Complimentary sodas and water are available, and a cooler with ice to stash any BYO beverages.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Unwind after a long day aboard a relaxing sunset cruise along Fort Myers Beach. Watch as the sun starts to dip below the horizon and changes the sky from blue to several hues of oranges, reds, and pinks. Relax on the spacious catamaran with a drink in hand and watch as the scenes pass you by.

Step aboard a fun sightseeing cruise in Miami, showcasing beautiful views of Biscayne Bay and the homes of the rich and famous. Enjoy panoramic views of Miami's skyline, the vibrant Port of Miami, secluded Fisher Island, and the sun-kissed shores of Miami Beach, all with bilingual commentary. Witness the opulence of Miami Beach mansions and create lasting memories. Check-in at the Bayride Ticket Kiosk behind Victoria's Secret at Bayside Marketplace.

While in Treasure Island, see the beautiful area without getting caught in the crowds on land. This Treasure Island Sailing Experience lets you go on a small-group cruise around either the Gulf of Mexico or Boca Ciega Bay. You can bring your own drinks as a cooler is provided for cruiser goers to use, or you can enjoy the included soda and bottled water.

Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.

Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.

Watch the sun set and the moon rise off the coast of Key West on this relaxing sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer, and soft drinks are included.

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico offers a great opportunity to relax and leave your worries behind. Listen to tropical music as you enjoy a complimentary beverage on board Panama City Beach’s best sunset cruise! At our on board bar we have snacks and a full liquor bar for additional beverages available for purchase. Enjoy a variety of cocktails, including our signature Privateer Punch! Please note our bar accepts debit/credit card transactions only. Our Sunset Sails offer you an opportunity to see some of our area's greatest sights while enjoying the breezes of the water. Be on a sharp lookout for dolphins as these majestic creatures seem to be more active in the later afternoons.

Set off on a unique pirate-themed boat cruise that travelers of all ages will enjoy. Depart Destin and sail the Emerald Coast while kids and kids at heart enjoy pirate-themed games and entertainment with everything from dancing to sword fighting to a treasure hunt. Adults can join in or relax with alcoholic beverages (to purchase) and enjoy the beautiful scenery.

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature the perfect blend of natural beauty, maritime history, and the thrill of the open sea. Don't forget your camera – this is a photo opportunity you won't want to miss! Book your spot now and get ready to create memories that will last a lifetime.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.

Watch dolphins frolic through coastal waters on this scenic 2-hour sunset sail. Board your comfortable catamaran, and listen to music. Cruise through Grand Lagoon, passing elegant homes and St. Andrews State Park. See pods of dolphins travel together and leap above the water. Take photos and admire incredible sunset views. Don’t miss the chance to participate in games and dance when the boat docks.

Set sail for adventure on this interactive Pirate Adventure Cruise along Fort Lauderdale’s Intracoastal Waterway. Help find the hidden treasure, learn to talk and dress like a pirate with face painting and temporary tattoos and fend off the attacks of rival pirates with onboard water cannons. Kids receive a pirate certificate and a bag of loot to take home. This tour is great for birthday parties, group field trips, or just to have an entertaining experience on the high seas.

This half-day Fort Lauderdale sailing experience is ideal for visitors who want to get out on the water without having to drive a boat themselves. This relaxing, small-group experience takes you down the scenic New River, dubbed the "Venice of America," lined with mangroves and waterfront homes, down to Port Everglades. Take in the sights as you chat amongst yourselves. The charter provides you with ice, cups, plates, and cutlery in case you want to bring your own food and drinks.

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico offers a great opportunity to relax and leave your worries behind. Listen to tropical music as you enjoy a complementary glass of wine, Sangria, cold beer or non-alcoholic beverage on board Panama City Beach’s best sunset cruise! At our on board bar we have snacks and a full liquor bar for additional beverages available for purchase. Enjoy a variety of cocktails, including our signature Footloose Punch! Please note our bar accepts debit/credit card transactions only. Our Sunset Sails offer you an opportunity to see some of our area's greatest sights while enjoying the breezes of the water. Be on a sharp lookout for dolphins as these majestic creatures seem to be more active in the later afternoons.

Spend some time on the water with this half-day sailing charter in Fort Lauderdale. When out to sea, sit back and relax on the boat or jump in for a swim or to snorkel. The boat is equipped with shaded seating areas, a Bluetooth speaker, a freshwater shower, and snorkeling and other water activity equipment. Plus, the captain can instruct you on how to sail yourself.

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.

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.

The Egmont Key National Wildlife Refuge is a serene, secluded island in Tampa Bay that’s popular for hiking and fishing. Go beyond the beauty of St. Pete’s Beaches and visit this island on a relaxing half-day tour. Sail from the St. Pete Pier over to Egmont Key and spend a few hours wandering miles of white sand beaches. Bottled water is available but you can bring your own food and drink to enjoy a quiet island lunch.

Set sail from Key West on a 60-foot catamaran and enjoy the clear blue waters and Atlantic bottlenose dolphin sightings. Afternoons are when dolphins are the most active so you’re sure to see the adorable creatures jumping and swimming around the boat. You’ll also see some Key West landmarks from the water and enjoy the sea breeze.