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

Experience a 2-hour Maine schooner day sail from Boothbay Harbor, with opportunities to help hoist sails and spot wildlife like porpoise and bald eagles.

The Schooner Applejack offers a 2-hour day sail departing from Boothbay Harbor in Maine, priced at $54.95 per person. This tour is perfect for those seeking an engaging, scenic experience on the water, with the option to help hoist sails or take the wheel. The small group size — a maximum of 14 travelers — ensures a personal atmosphere, while the included restroom and BYOB policy add practical comforts. The tour is most often booked 32 days in advance, reflecting its popularity among visitors eager for authentic sailing.
While the voyage provides stunning views of Burnt Island Light, Squirrel Island, and other outer islands of Boothbay, it also offers a chance to observe local wildlife like porpoise, osprey, bald eagles, and harbor seals. The experience balances relaxation and activity, making it suitable for a wide range of travelers, especially those interested in sailing and coastal scenery.

The Applejack schooner is recognized as Boothbay Harbor’s oldest windjammer, adding historical charm to the experience. The crew is described as wonderful and knowledgeable, creating a warm, inviting atmosphere. From the cool air to the length of the journey, the reviews highlight the relaxing nature of the sail combined with interactive opportunities like steering the boat.
This tour offers a balance of scenic beauty and hands-on involvement. Whether you are a sailing enthusiast or simply someone looking to enjoy the coast from the water, the Applejack provides a memorable Maine adventure. The small group size ensures an intimate experience, where everyone can engage with the crew and take in the sights without feeling crowded.

The itinerary takes you out past Burnt Island Light, Squirrel Island, and Ram Island Light, alongside the outer islands of Boothbay. These lighthouse views are classic Maine sights, with the sails providing a picturesque backdrop. The outer islands are notable for their rugged beauty and seaside charm.
A highlight of the route is the chance to spot wildlife as the schooner glides past local boats engaged in lobster potting and fishing. The marine life and bird sightings contribute to the authentic coastal experience. While the weather on the day can influence the wind strength, the beautiful conditions reported in reviews suggest a pleasant cruise most days.
One of the main attractions of this day sail is the opportunity to see wildlife up close. Expect to glimpse porpoise, often seen playing around the schooner, and birds like oysters and bald eagles, soaring overhead. The harbor seals are also commonly spotted resting on rocks or swimming nearby.
Wildlife sightings are a common occurrence, adding an extra layer of interest to the voyage. The natural setting plus the unobstructed views make this a particularly appealing activity for nature lovers or those wanting a peaceful escape into Maine’s coastal environment.
The meeting point for the tour is at 20 Commercial St, Boothbay Harbor, a central location easily accessible near public transportation. The tour operates with a maximum of 14 travelers, creating an intimate atmosphere where everyone gets a chance to participate.
The service animals are allowed onboard, and the confirmation of booking is received at the time of reservation. The tour is designed to be accessible for most travelers, with most participants able to enjoy the experience.
The sailing experience includes a restroom on board, which is a practical benefit during the two-hour voyage. Guests are welcome to bring their own non-alcoholic drinks and snacks — a great way to enjoy a picnic-style experience at sea.
Alcoholic beverages are not included but are available for purchase onboard. The selection includes beer, wine, and liquor, allowing guests to enhance their cruise with a drink of choice.
The tour can be canceled free of charge if done at least 24 hours in advance. This flexible policy offers peace of mind in case of bad weather or other unforeseen circumstances. If canceled due to poor weather, guests are offered a reschedule or a full refund.
Since the tour is popular and most often booked 32 days ahead, early reservation is recommended to secure a spot. The weather-dependent nature of sailing means that confirmation is contingent on favorable conditions on the day.
The reviews speak highly of the relaxing atmosphere and the interactive elements of the tour. Passengers enjoy the chance to steer the schooner or help hoist the sails, providing a hands-on experience that enhances the overall enjoyment.
The scenic views, combined with the opportunity for wildlife sightings and engaging crew, create an experience that feels both authentic and leisurely. The small group size fosters a personal connection with the crew, making the sailing feel more like a shared adventure than a routine tour.
This sail caters well to a wide audience, especially those interested in coastal scenery, nautical activities, and wildlife. It is suitable for families, couples, and solo travelers who appreciate a relaxed pace combined with interactive sailing.
The price point and duration make it an accessible option for those looking for a short but memorable escape on Maine’s waters. The nature and wildlife viewing opportunities are a particular draw for outdoor enthusiasts.
The Schooner Applejack 2-Hour Day Sail offers a quintessential Maine experience — classic coastal views, wildlife sightings, and hands-on sailing. Its affordable price, small group size, and friendly crew make it a welcome choice for visitors seeking an authentic maritime adventure.
While weather conditions can influence the experience, the generally beautiful conditions reported make this tour a reliable option most days. It’s a great way to connect with Maine’s maritime culture and enjoy a peaceful slice of the coast.
“Excellent experience! Would recommend to anyone! Beautiful boat and wonderful crew! We enjoyed the cool air and the length of the journey! We also …”
Is the tour suitable for children?
Yes, the tour is accessible for most travelers, including children, especially those interested in sailing or wildlife.
Can I bring alcoholic drinks?
No, alcohol is not included but can be purchased onboard. The tour allows BYOB non-alcoholic drinks and snacks.
What should I bring?
Wear comfortable clothing suitable for outdoor sailing, and bring sunscreen and sunglasses. You may also wish to bring a light jacket in case it’s windy.
How many people are on the schooner?
The maximum group size is 14 travelers, ensuring an intimate, personal experience.
What is the meeting point?
The tour begins at 20 Commercial St, Boothbay Harbor.
What happens if the weather is poor?
If canceled due to bad weather, guests are offered a full refund or rescheduling.
Is the tour wheelchair accessible?
The available information does not specify accessibility details; contact the provider for specific needs.
How far in advance should I book?
Most bookings are made around 32 days before the scheduled date, so early booking is advisable.