Classic Day Sail

There is no experience in Key West quite like our Key West sailing excursions. It's one thing to be out at sea on a regularly engine powered boat, but it's a completely different experience to ride out to sea aboard a sailboat. And with the Adirondack III, a 80-foot wooden schooner, the experience of sailing takes on a completely new level.

At parts romantic and at parts nostalgic for the era of sailboats, the Adirondack III is the kind of boat you dream of being on. You can see its massive sails looming in the distance, but now you too can be on board the Adirondack III on our unforgettable Classic Day Sail.

Sailing is not the most common way to go out on the waters of Key West, but it is definitely one of the most preferred ways. Once you enjoy the experience of being on a sailboat, you will understand the attraction that these boats have over boats that are powered by engines. On board a sailboat, you get a quieter boat ride that is both peaceful and exciting. It is exciting because you get to first see the massive sails go up, and then you get to witness them as they catch hold of the breeze and let the air guide the way.

People of all ages love being on the Adirondack III for an early afternoon sail. It is one of the few boats in Key West that offers a sailing experience at this time of the day. This is an ideal time to head out to sea if you want to experience the year-round warm weather and the sunny days that Key West is known for. The Classic Day Sail departs the harbor in the early afternoon, right as the day is at its warmest and the sun at its highest point. Don't worry, even on the hotter days of summer, the sea breeze of the Gulf of Mexico offers you a welcomed reprieve. You will feel completely at peace as the balmy sea breeze strokes your hair and the scent of the salty waters infiltrates your olfactory senses.

On the Classic Day Sail aboard the Adirondack III, you will get to experience a full hour and a half of sailing in the calm waters that surround Key West. The schooner's journey will depend on that particular day's wind and water conditions, but you will definitely get to do some Key West sightseeing. The Day Sail typically sails past the historic Fort Zachary Taylor, the exuberant Mallory Square, and the picturesque Sand Key Light Tower.

Bring your camera for this sightseeing tour and maybe even bring some binoculars since you will likely be able to see all kinds of marine life and animal wildlife off in the distance. Many of our guests spot pods of dolphins, sunbathing sea turtles, and soaring water birds.

The Classic Day Sail is great for guests of all ages. Drinks such as beer, wine, champagne, and soda are provided on board for the extremely low cost of $1 per beverage. Guests are also encouraged to bring some food on board for a snack or even a full on lunch. The Adirondack III schooner offers plenty of space for guests who want to have lunch on board, and you can pick up a to-go lunch from the nearby and highly popular Schooner Wharf Bar and restaurant.