Top Florida Sailing Tours

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.

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.

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.

Watch the sun set over Key West from the deck of a traditional schooner on an evening sailing experience with a full open bar. Settle into the rhythm of the water as the crew sails offshore, taking in unobstructed Gulf views while bartenders serve cocktails, wine, and spirits throughout the cruise. Combining classic sailing with an easygoing onboard atmosphere, this is a memorable way to experience Key West at sunset.

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.

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.

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.

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.

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.

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.

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.

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico to watch a breathtaking sunset while sipping your favorite cocktail. Cruises are narrated to point out interesting sights along the way. Dolphin sightings are plentiful and fun for all ages. Pack your favorite drinks and snacks in a cooler, and don't forget to take some pictures! We've been cruising the Naples Waterways since 1991 and are family-owned and operated. Guests are welcome to bring small coolers with their favorite beverages and snacks. Alcohol is permitted. Please note this is not a private boat tour, this is a group tour with others onboard Boarding time is 15 minutes prior to scheduled departure time. Please allow enough time to park and walk down the dock. We leave promptly on time.

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.

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.

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.

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!

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.

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.

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 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.

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.

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.