Schooner Sunset Sail

No trip to Key West is complete without spending a picturesque afternoon aboard the Appledore II. Imagine lounging on the open deck, drink in your hand, as the boat gently rocks you into a sense of content and restfulness and the sun warms your skin in the cool breeze. Top it all off with the iconic sights of the Key West Historic Harbor and Mallory Square, with views of Fort Zachary Taylor, and you have the perfect afternoon in the making.

Our Schooner Afternoon Sail departs daily at 2 p.m. and follows the coast to the Historic Harbor. Be on the lookout for a glimpse of the Navy Mole where all of the biggest ships dock. While others frantically vie for a water sports activity spot or a place to lounge on the crowded beaches, you can enjoy a hassle-free afternoon sail.

The Distinguished Appledore II

Climb aboard the majestic Appledore II for an afternoon of relaxing in the warm sun. Available to Key West seasonally, the Appledore II is an 89-foot, 2-masted windjammer that was built in the style of the historic schooners of the 19th century, making it a crowd-pleasing and beautiful vessel.

Constructed in the tradition of shipbuilding in New England, the Appledore II was first launched in 1978 from Portsmouth, New Hampshire. On its maiden voyage, Appledore II literally saw the world as it completed an around-the-world exploration adventure as Herb and Doris Smith explored exotic ports, including the Galapagos Islands, Indian Ocean and the Cape of Good Hope. The Appledore II visits Key West every year to provide afternoon and sunset sails to visitors from around the world. In the off-season, the Appledore II sails the New England coast of Maine.

At 19-feet wide, the deck is spacious enough to spread out and bask in the sun. Although the Appledore II can carry up to 49 passengers, the day trip often sets sail well below maximum capacity for the comfort of our guests, providing generous seating areas and plenty of room to relax or roam. Look for the Appledore II to be docked in Key West every year from November to Memorial Day.

A Sail to Remember

Our afternoon sails can often be overlooked due to the overabundance of water sport activities and festivities that we offer through Best on Key West. But the Schooner Afternoon Sail is one cruise you won’t soon forget. Our day sails are perfect for an afternoon alone and away from it all, or cozy up to a loved one on the warm deck and enjoy the day together sipping complimentary wine, beer or sangria. And because this tour is available every day, we often have space for your whole family, wedding party or large group.

Grab your sunglasses and camera and prepare yourself for a luxurious afternoon asea. Fun for the family or ideal for a quick getaway, the historic Schooner Afternoon Sail can take you back in time while you forget your worries.