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Experience a 2-hour sunset sail on the historic Schooner Applejack in Boothbay Harbor for just $59.95, with stunning views, wildlife sightings, and a friendly crew.
Boothbay Harbor’s Schooner Applejack Sunset Sail Tour offers a charming and intimate way to enjoy Maine’s scenic coastline. Priced at $59.95 per person, this 2-hour excursion departs from 15 Wharf St and promises a memorable experience aboard Boothbay’s oldest windjammer. With an impressive rating of 5.0 out of 5 from 19 reviews, it’s clear this tour is a favorite among visitors. The tour is booked on average 36 days in advance, highlighting its popularity, especially during the sunset hours.
What makes this sail truly stand out is its personal touch. The crew invites guests to help hoist sails or take the wheel, making it a participatory adventure rather than just a passive ride. The stunning coastline views, combined with the chance to spot porpoises, osprey, bald eagles, and harbor seals, appeals to nature lovers and photography enthusiasts alike. The deck offers a 360-degree view from every seat, ensuring everyone gets a great perspective of the scenery.


The Schooner Applejack is renowned for being Boothbay Harbor’s oldest windjammer, adding historical charm to your sunset voyage. The vessel’s beautiful design and history are appreciated, with some reviews noting the interest in its past. While more details about the ship’s history could enhance the experience, the crew’s enthusiasm makes up for it.
This boat’s small group size, with a maximum of 14 travelers, ensures a cozy atmosphere. The friendly crew is praised for their knowledge and approachability, creating a relaxing environment to enjoy Maine’s coastal beauty.
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The tour begins at 15 Wharf St, a convenient location near public transportation. After boarding, the sailing route takes you past Burnt Island Light, Squirrel Island, Ram Island Light, and the outer islands of Boothbay. The route is perfect for those wanting to combine scenic views with light navigation.
Views of local boats setting lobster pots or hauling catches provide a lively, authentic maritime experience. The sunset, often with a pink moon glow, enhances the natural beauty, making the moment ideal for photography.
During the sail, the crew’s knowledgeable narration enriches the experience. This includes insights about the lighthouses, local marine life, and historic sites. Keep an eye out for harbor porpoises; several reviews mention seeing pods of dolphins as the boat returns.
Birdwatchers also appreciate spotting ospreys and bald eagles, especially in the calm evening light. Harbor seals are occasionally seen lounging on rocks or swimming nearby, adding to the sense of being immersed in nature.

Unlike larger or more passive tours, the Applejack sail encourages guests to get involved. Many reports highlight the fun of helping hoist sails, blowing bubbles at neighboring boats, or taking turns at the wheel. This active participation makes the experience especially appealing for families and groups wanting a hands-on maritime adventure.
The crew’s friendly and knowledgeable approach ensures that even first-time sailors feel comfortable and engaged. This dynamic adds a layer of fun that sets it apart from more traditional sightseeing cruises.

Guests are welcome to bring their own snacks and non-alcoholic drinks, which can be enjoyed on deck. Alcoholic beverages are available for purchase, with a selection of beer, wine, and liquor. Restroom facilities are onboard, making the trip comfortable for all.
The small size of the vessel means you’ll find plenty of space to relax and soak in the views. The open deck offers unobstructed sightlines, ideal for enjoying the sunset and taking photographs.

The sail’s route takes you past notable landmarks such as Burnt Island Light, a classic Maine lighthouse, and Squirrel Island, a popular landmark in the harbor. The outer islands provide scenic backdrops and opportunities to glimpse marine wildlife.
Navigating past these points, the crew shares informative stories and facts about each location. The route’s flexibility means you experience calm waters and beautiful vistas—especially as the sun begins to set, casting a warm glow over the coastline.
Since Maine weather can shift rapidly, passengers are advised to bring a light jacket or sweatshirt. The tour’s confirmation is received upon booking, and it operates most days, unless weather conditions are unfavorable. If canceled due to bad weather, guests are offered a full refund or the option to reschedule.
Service animals are allowed onboard, and the tour is suitable for most travelers. With a maximum of 14 guests, the experience remains intimate and personal. Make sure to arrive at the meeting point on time to avoid missing your spot.

Reviews repeatedly praise the friendly crew, particularly mentioning Captain Shawn, Captain Kate, Captain John, and Captain Dawson, all recognized for their knowledge and engaging storytelling. Guests appreciate the opportunity to learn about the area’s history while enjoying the peaceful voyage.
The stunning sunset views and the chance to spot wildlife like porpoises and eagles add a magical touch. The participatory sailing experience elevates it from being just a sightseeing cruise to a hands-on adventure.
This sunset sail is perfect for families, couples, or small groups who want to enjoy Maine’s coast in a relaxed atmosphere. It’s especially suited for those interested in marine wildlife, history, or simply unwinding on the water. The small group size, interactive nature, and beautiful scenery make it a top choice for those seeking a personalized and memorable Maine experience.
“What an experience! My best time ever on a boat. Gorgeous boat and lovely town but what made it unique was the Captain. What an incredible man with…”
Is alcohol allowed on the boat?
Guests can bring their own non-alcoholic drinks. A selection of beer, wine, and liquor is available for purchase onboard.
What is the maximum number of travelers?
The tour hosts up to 14 guests, ensuring a cozy and personal experience.
What should I bring?
A light jacket or sweatshirt is recommended due to Maine’s unpredictable weather. Bringing snacks and drinks is encouraged, but no alcohol is permitted unless purchased onboard.
Can children participate?
Yes, the tour is suitable for most travelers, and children of all ages are welcome with a ticket.
What highlights make this tour special?
The participatory sailing, stunning sunset views, and wildlife sightings such as porpoises and eagles are among the main attractions that set this experience apart.