Top Florida Sailing Tours - page 2

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. You’ll see highlights like the Bridge of Lions, Castillo de San Marcos National Monument, and National Shrine of Our Lady of La Leche; can spot wildlife like dolphins; and will learn the stories behind the sights from your captain’s narration.

Swim among coral and tropical fish in Key West's living reef on this snorkeling excursion. Sit back and relax on a custom-built boat, and sail to the reef where a professional crew is on hand to provide snorkeling instruction and guidance. After your swim, enjoy included beer, soft drinks, and water on the boat for your ride back. All snorkeling equipment is provided.

Combine a snorkel session on North America's only living coral reef with a Key West sunset during this catamaran cruise. Listen to lively reggae beats, snorkel using the provided equipment, and watch the sunset with a rum punch in hand.

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.

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.

Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.

See the beauty of Biscayne Bay from a whole new perspective with this sailing adventure. Ride along the coastline in an eco-friendly wind-powered sailing boat, and visit sandbars, mangroves, and islets along the way. If you're lucky—you may even spot dolphins or manatees—which are frequently spotted around the bay.

Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.

Set sail for adventure on this exciting, interactive Pirate Adventure Cruise along Fort Lauderdale’s Intracoastal Waterway. This spirited 1-hour excursion is fun for the whole family. 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 bag of loot to take home. This tour is great for birthday parties, group field trips or just a day of fun on the high seas.

Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.

This cruise along the Gulf Coastline and Bay area offers a great opportunity to photograph local wildlife and scenery. At our onboard bar we have snacks and beverages available for purchase. Enjoy a variety of cocktails, including our signature Privateer Punch! Please note our bar accepts debit/credit card transactions only. As you cruise around the Gulf and Bay areas, you'll have the best chances of finding dolphins, and there's no better place to be than on the water in beautiful Panama City Beach.

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.

Experience the best that Key West has to offer with this combination tour that includes a dolphin watch, snorkeling, and a view of the island’s famous sunset. Spot dolphins in their natural habitat in the Florida Keys National Marine Sanctuary and snorkel in the blue waters surrounding Key West during this family-friendly excursion.

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 unlimited drinks from the full onboard bar.

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.

Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.

Climb aboard a schooner for an afternoon of sailing in Clearwater Beach with this tour. Enjoy sea breezes and admire views of the coastline 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.

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.

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.

Explore the patch reefs, mangrove islands, and waterways of Key West on a 6-hour cruise and snorkeling tour aboard a wooden sailing schooner. Take a hand at the wheel on your way across the Gulf of Mexico, kayak through the mangroves, then snorkel through patch reefs and sponge gardens. This 6-hour tour includes lunch and access to an open bar on the return sail to Key West.

Set sail on the schooner Appledore for a scenic cruise from Key West. Join the crew to raise the sails, take a turn at the wheel, or just soak up views of the gorgeous Florida coast with a cocktail. Choose a time for your sunset sail in the late afternoon or early evening, and then enjoy a selection of drinks during your time on the water.

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.