Top Florida Sailing Tours

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.

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.

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.

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.

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.

Spend a few hours sailing Florida’s Atlantic waters with this sunset catamaran cruise launching from Cocoa Beach. Climb aboard this boat and enjoy the views as you sail along the Banana River Lagoon and the Thousand Islands. As the golden glow illuminates the water with a special hue, you might catch a glimpse of dolphins or other wildlife.

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.

Cruise to Shell Island and search for wild dolphins on a catamaran sailing trip from Panama City Beach. The catamaran’s broad, stable deck makes it a comfortable alternative to smaller boats prone to rocking in the waves, and since it’s stocked with paddle boards, snorkeling gear, and a waterslide, it’s the perfect base for playing in the clear water off Shell Island.

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 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.

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.

This Fort Lauderdale private half-day sailing experience is ideal for visitors to the city who want to get out on the water without having to drive a boat themselves. This relaxing experience takes you down the historic Fort Lauderdale New River through the city's Downtown section. Take in the sights as you chat amongst yourselves. The private charter provides you with ice, cups, plates, and cutlery in case you want to bring your own food and drinks to enjoy.

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.

This private Miami boat tour is a great way to explore the local area without the worry of having to navigate and steer the ship. Accompanied by your own private captain, sail out into the Miami waters and around Biscayne Bay with a Bluetooth sound system to play your favorite music, and coolers to store any drinks that you bring with you. Along the way, feel free to ask questions, make route requests, or relax on a floating mat.

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.

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.

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.

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.

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.

Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.

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.

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.

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.