Top Florida Sailing Tours

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.

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.

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.

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.

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.

Set sail from Naples aboard a spacious catamaran that cruises along the Gordon River, Naples Bay, and drops anchor at Keewaydin Island. This half-day cruise takes you to pristine white-sand beaches where you can go swimming and shelling. Hear live commentary about the sights along the way and keep an eye out for dolphins. The catamaran accommodates up to 44 passengers and is suitable for all ages.

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.

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.

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.

If you’re looking to snorkel in Key West, but don’t know where to plan your experience, this Key West snorkeling cruise makes things easy. Just prebook this experience, and enjoy a cruise over to a coral reef area—perfect for snorkeling and spotting tropical fish. Plus, all equipment, as well as lessons, breakfast, showers, and a beer or soda is provided for you.

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.

Set sail from Key West aboard a spacious catamaran for a morning snorkeling cruise combining relaxation and adventure. Glide across the waters where the Gulf of Mexico meets the Atlantic Ocean before stopping at a secluded snorkeling location. Enjoy a gourmet breakfast and unlimited mimosas on board, offering a convenient way to experience Florida’s coastal scenery before the rest of your day begins.

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.

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.

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh less than 275 pounds - IMPORTANT- plan to arrive 45 minutes before departure time for mandatory check in to collect your boarding passes. -Our USCG credentialed Captain & Crew will welcome you on board like an old friend and treat you to a relaxed sailing excursion. -Expect a 5 Star "True Sailing Experience" on our 52' custom steel Schooner sailing vessel. -Our motto is "We SAIL and We SAIL Well"!

End the day relaxing on the Atlantic Ocean with this sunset cruise. Hop aboard a comfortable catamaran for this evening excursion and take in views of the mansions on “Millionaires Row” and the Florida coastline. Then, head out to the Atlantic Ocean and catch the sun set, casting fiery hues of orange and red on the water.

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.

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters of Clearwater Beach. Welcome aboard the ultimate coastal adventure with Fins Up Clearwater! Dive into the crystal-clear waters of Clearwater Beach and let us whisk you away on a journey of discovery and delight. Embark on our exhilarating Sandbar Tours, where you can explore hidden treasures and pristine shores. Glide through the waves on our Dolphin Cruises, witnessing these majestic creatures in their natural habitat. Experience the breathtaking beauty of a Sunset Cruise as the sky paints a masterpiece. Let Fins Up Clearwater be your guide to unforgettable moments and endless wonder along Florida’s stunning coastline.

Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.

Cruise into the sunset on St. Augustine’s sole all-inclusive sunset sail with unlimited beer, wine, and margaritas (non-alcoholic options available) on a luxurious catamaran. As you sip your drink and enjoy complimentary snacks, live music will accompany the colorful setting sun on the water, for an unforgettable night. See the historic city and its landmarks bathed in beautiful colors from the water.

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.