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Top Key West Sailing Trips
Sunset Sail Cruise in Key West
120 minutes - Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or...Read more
Adults only Champagne Celebration Sunset Cruise from Key West
2 hours Escape to the stunning shallows of Key West on an Adults-Only Champagne Celebration Sunset Cruise, where you can savor Moët & Chandon champagne while admiring the sunset. The tour cost includes house champagne Chandon Brut, 7 varieties of red and white still wines, 3 types of ice-cold beers and a gluten-free Gourmet Cheese Buffet featuring 4...Read more
Small-Group Key West Sunset Sail with Wine
2 hours Sail off into the sunset with an array of international and homegrown wines, brews and hors d'oeuvres. Whether you're looking for a romantic evening or just some time to relax with friends, this cruise will be perfect. Please make sure to arrive 30 minutes before you set sail to check...Read more
Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
2 hours Imagine the ideal Key West sunset as you lounge on the deck of a romantic two-masted schooner. Feel the wind against your hair as the boat sails off into the sunset near America's Southernmost Point. As you admire the view, your captain will show you Mallory Square's Sunset Celebration and Navy Mole, where enormous ships dock.
Treat...Read more
Key West Sunset Sail Aboard Schooner
2 hours Relish in a magnificent two-hour sunset voyage on board a breathtaking modern schooner! Witness the majestic sights of Key West from Schooner America 2.0, the most exquisite schooner around, as you sail past Mallory Square, Sunset Pier, and Sand Key Light Tower and more. While indulging in complimentary libations, savor individually prepared...Read more
Group Sunset Cruise from Duck Key
1 hour 30 minutes - The Solé Watersports Sunset Cruise at Hawks Cay Resort is the only Sunset Cruise in the Duck Key area. It includes cruising along the resort and homes of Duck Key, into open water and over to the uninhabited islands of Tom's Harbor. During the cruise, we'll watch for coastal birds hiding in the mangroves, pods of dolphins, and other sea life...Read more
Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel
6 hours Encompassed by the glistening azure waves of the Gulf of Mexico, beautiful Key West offers kayaking and dolphin watching as an amazing way to enjoy a day in the sun. With Island T’ing, you'll hop on board a large catamaran and set off from the hustle and bustle of Key West. Paddle through serene mangrove islands located within the Key West...Read more
Key West Wild Dolphin Sail and Shallow-Water Snorkel
4 hours Spend a gorgeous Florida day in the transparent, azure waters aboard a snorkeling and dolphin-viewing sailing tour. Cruise on a large catamaran that accommodates up to half its passenger capacity for an enjoyable voyage to observe wild dolphins hunting and frolicking with their infants, and snorkel shallow water coral reefs, wreckage sites or...Read more
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
2 hours Admire the exquisitely painted sky during this luxurious sunset cruise in Key West. Make remarkable memories as you embark on one of Sebago's modern sailing catamarans, sipping sparkling wine or your favorite cocktail and indulging in shrimp cocktail on your voyage to the ideal spot for sundown gazing. You'll be mesmerized by twilight views...Read more
Key West Sunset Champagne Catamaran Cruise
1 hour 30 minutes Witness the renowned sunset over Key West from a 1.5-hour catamaran sail. While you bask in the dusk vistas of the ocean as the sun sets, sip some complimentary wine, champagne, beer, sangria or margaritas on board the vessel. As you cruise across the water, appreciate sights of the island with a chilled beverage in hand — an ideal way to...Read more
Key West Full-Day Power Adventure: Sailing & Watersports Package
6 hours This Key West experience allows you to relish all the island has to give. Hop aboard a stylish catamaran over the tranquil waters of the Gulf of Mexico and pick from a variety of aquatic activities, including kayaking through backcountry mangroves, snorkeling in sheer waters, parasailing along the renowned Key West waterfront, and...Read more
Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West
2 hours Witness the beauty of a Key West sunset on board the Sandie...Read more
Key West Snorkel and Sunset Sail: Rum n' Reggae
3 hours This Caribbean-styled journey presents two dream experiences that Key West is renowned for - a vivid coral reef and gorgeous sunsets. Revelers can look forward to savoring rum punch, listening to the vibrant reggae music, and exploring a vivid tropical island reef habitat on this exhilarating snorkel and sunset...Read more
Schooner Key West Day and Sunset Cruises with Full Bar
2 hours Sail Key West on an impressive 2-masted schooner, just as the daring explorers of the 19th century did, while indulging in the lavish, modern comforts of a passenger schooner. Spacious and cozy decks offer you a thrilling voyage. Witness the crew haul up the sails and become part of this ancient practice by aiding them with...Read more
Sunset Sail in Key West with Beverages Included
1 hour 30 minutes Key West is renowned for its incredible sunsets and Floridays is well-known for our extraordinary, serene champagne sunset cruise. Our dedication to providing exemplary service and meticulous attention to detail on the voyage at dusk is legendary. Being out in the ocean for a Key West sundown experience is like being INSIDE the...Read more
Private Afternoon Snorkel with Sunset Sail
4 hours - Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's amazing natural wildlife with up to five others, before sailing back to shore at...Read more
Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings
2 hours 30 minutes Our Captain’s Choice Dolphin Watch Sunset Sail is the ideal VIP sailing experience! Limited to a select group of passengers, this 2.5 hour sail is more akin to a private cruise than a group tour and is one of the top activities in Key West.
As we leave behind the Historic Seaport, search for famous Key West sites such as renowned...Read more
Key West Sunset Snorkel Sail with Open Bar, Live Music, and Appetizers
3 hours Indulge in this 3 hour twilight excursion. We will sail to the top reef locale in Key West, where you can take a dip and savor an evening snorkel. If you're not up for swimming, no problem - the bar is open! Grab yourself a draft beer or glass of wine & take in the scenery. After finishing your snorkeling adventure we'll set off on an...Read more
Key West Schooner Backcountry Eco-Tour: Sail, Snorkel & Kayak
5 hours Embark on an unforgettable adventure, setting sail from Key West's Historic Seaport in our classically-styled schooner. Discover the wonders of the Gulf of Mexico as you explore its pristine waters, snorkel over a unique patch reef in the backcountry and kayak through untouched mangrove islands. Refuel with snacks and refreshments...Read more
Florida Keys Afternoon Reef Snorkel & Sail Adventure
3 hours Come join us on a snorkeling journey to explore the only living coral reef in North America! We have some incredible reefs located on both the north and south sides of Key West; every site offering its own unique experience. The trip is about an hour long out to the reef, with an additional hour for our return voyage back to our dock. Our crew...Read more