Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience a relaxing 2-hour schooner sail in Key West with a full open bar, guided by knowledgeable crew, departing from Mallory Square for a peaceful adventure.


This sailing excursion on the Appledore schooner offers a balance of classic maritime charm with modern comforts. The $79 price covers approximately 2 hours of sailing and includes a full open bar. Starting at 200 William St, the tour begins at 1:30 pm, providing a leisurely late-afternoon escape from the buzz of Key West.
Designed for those who enjoy participating in sailing activities, the tour invites guests to help raise the sails and try their hand at the wheel. The modern schooner boasts spacious decks and comfortable accommodations, making the experience both relaxing and engaging.
Enjoy being on the water? Here are other boat experiences we've looked into in Key West

The tour begins at Mallory Square, a lively waterfront hub famous for its sunset celebrations and vibrant street performances. While visitors typically associate the area with evening festivities, this sail departs in the early afternoon, offering a different perspective of the waterfront’s charm.
The Key West Historic Seaport serves as the second stop, providing scenic views of the colorful old buildings, shops, and restaurants. This area is a bustling marina that perfectly captures the maritime spirit of Key West and sets a picturesque backdrop for the sail.

The Appledore schooner is a two-masted vessel reminiscent of 19th-century trading ships, yet equipped with modern amenities. Its spacious decks ensure comfort during the calm, peaceful cruise, which is particularly appreciated on days with good weather.
The crew receives high praise for their interest, attentiveness, and passion for sailing. They offer historical information about the vessel and the area, enriching the experience with stories of maritime tradition. This personal touch adds a layer of educational value to the cruise.

One of the standout features of this tour is the full open bar available to guests over 21. This includes a wide selection of alcoholic beverages, sodas, and bottled water, ensuring everyone stays refreshed.
The crew’s friendly attitude enhances the social atmosphere onboard, making it easy to relax and enjoy the scenic surroundings. The attention to service is evident, and the bar complements the peaceful, leisurely pace of the sailing.
Multiple reviews highlight the calm and peaceful nature of the sailing experience. The beautiful weather on the day of the trip contributed to a serene voyage, with gentle breezes and smooth waters.
Participants are encouraged to engage actively with the sailing process, which adds a fun and authentic element. Helping raise the sails and taking the wheel provide a hands-on feel that many guests appreciate, especially those interested in maritime traditions.
For more beverage-focused experiences, here's what we've covered in Key West
This tour accommodates up to 49 travelers, ensuring a more intimate experience without feeling crowded. The meeting point is conveniently located at 200 William St, and service animals are permitted onboard.
Since the tour is designed to be relaxing and accessible, most travelers can participate. The sailing duration of about 2 hours means it’s suitable for those looking for a short, light adventure rather than a full-day commitment.
The tour depends on good weather conditions; if canceled due to poor weather, participants are offered a full refund or alternative date. Cancellation is free if made at least 24 hours in advance; cancellations within 24 hours are non-refundable.
This flexible policy gives peace of mind, especially in Key West where weather can be unpredictable. Since the sailing is non-stop, the focus stays on enjoying the serene voyage rather than multiple stops or long journeys.
This sail appeals to those seeking a peaceful, engaging water experience with a touch of maritime history. The participatory elements like raising sails and steering add a fun layer of involvement. Coupled with the full bar and palpable crew enthusiasm, this tour offers a balanced mix of relaxation and activity.
The price point makes it accessible for most travelers, and the high rating of 5.0 based on 65 reviews reflects consistent satisfaction. It’s especially suited for adults who appreciate scenic, tranquil sailing with social opportunities.
“It was a peaceful and beautiful sail. . Great historical information from Captain! The Crew was super nice!”
How long is the schooner sail?
The sailing duration is approximately 2 hours with no stops along the way.
Is food included in the tour?
No, the tour does not include food; it features a full open bar, soda, and bottled water.
What is the meeting point?
The tour starts at 200 William St, Key West, with a start time of 1:30 pm.
Can I participate in sailing activities?
Yes, guests are encouraged to help raise the sails and try steering the schooner.
Is the tour suitable for children?
The tour is designed for most travelers, but most alcohol service is for guests over 21 years of age.
What happens in case of bad weather?
If canceled due to weather, participants are offered a full refund or reschedule. The experience requires good weather to proceed.
The Schooner Appledore Day Sail in Key West offers a relaxing yet participatory way to enjoy the water and the iconic maritime environment. With friendly crew, stunning views, and an inclusive bar, it promises a memorable afternoon on the Gulf of Mexico.