Key West Sailing Trips

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

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

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

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

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

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

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

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

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