Maine’s coastline offers some of the most memorable sailing experiences on the East Coast. With charming harbors, lighthouse-lined shores, and abundant wildlife, it’s a destination that invites you onto the water. Whether you’re interested in a relaxing sunset cruise, a lively day sail, or a wildlife-focused excursion, Maine has options that fit different tastes and budgets. From the classic schooner experience on the Applejack to wildlife sightings on the Eastwind, each tour provides a window into Maine’s maritime charm.
In this guide, we’ll explore the top four boat tours available in Boothbay Harbor. We compare their highlights, value, and what makes each one special. If you want to hoist sails or just sit back and enjoy the scenery, we’ve got you covered. We’ll help you decide which cruise suits your interests, whether you’re a seasoned sailor or a first-time visitor. And if you’re planning ahead, we’ll share practical tips for booking and best times to go.
1. Schooner Applejack Sunset Sail Tour in Boothbay Harbor
This 2-hour sunset sail aboard the Schooner Applejack in Boothbay Harbor is a favorite for those seeking a classic Maine maritime experience. The tour (which you can check out here) offers an engaging mix of relaxation and activity. You’re encouraged to help hoist sails or take turns at the wheel, making it more than just a sightseeing cruise. As the sun dips, the boat slips past Burnt Island Light, Squirrel Island, and the outer islands, with chances to spot porpoises, Bald Eagles, and harbor seals along the way.
What makes this tour stand out is its focus on hands-on sailing and the opportunity to learn from an experienced crew. The $59.95 per person price includes a scenic voyage through calm waters, with top reviews praising the knowledgeable crew and breathtaking views. It’s ideal for travelers who want a personal touch and a chance to participate actively. The sunset timing offers a romantic backdrop, perfect for couples or small groups.
Potential drawbacks include its limited duration—at around 2 hours, it’s a quick outing. But that’s enough time for a memorable sunset without feeling rushed. Bottom line: this sail offers authentic sailing with a friendly crew, making it a great choice for active adventurers and sunset lovers alike.
2. Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
If you prefer a more relaxed, daytime experience, this 2-hour day sail aboard the Schooner Eastwind (available here) is a superb option. The tour starts from the central Boothbay Harbor waterfront, putting you close to the town’s shops, inns, and eateries. The focus is on offering a classic sailing adventure with plenty of opportunities to enjoy the scenery—lighthouses, fishing lobstermen, and remote islands only accessible by boat.
This cruise stands out because of its long-standing reputation—almost 50 years of experience—and its popularity in national publications. The $54.95 price reflects a quality experience with a crew that’s both friendly and knowledgeable. The boat’s design emphasizes comfort and scenic viewing, making it perfect for families or anyone wanting a leisurely sail. During the trip, expect to see wildlife such as seals and dolphins, with many reviews highlighting the crew’s attentiveness and the beautiful views.
On the downside, because it’s a shorter, daytime trip, it may not appeal if you’re looking for a romantic sunset or evening ambiance. But for those interested in a laid-back, scenic cruise with expert insights into the local maritime environment, this tour offers excellent value.
3. Schooner Eastwind Sunset Sail to see the Maine Coastline
For those wanting to combine the beauty of a Maine sunset with the charm of a sailing schooner, this 2-hour sunset cruise aboard the Schooner Eastwind (also available here) is a standout. The trip promises a relaxing voyage along Boothbay Harbor’s coast, with views of lighthouses, fishing lobstermen, and wildlife, similar to the day sail but with the added magic of sunset colors.
What makes this sunset sail special is its reputation for delivering a serene, picturesque experience. Priced at $54.95 per person, it’s an affordable way to enjoy an iconic Maine evening. The crew, including Captain Kate and first mate Meghan, are praised for their attentiveness and friendliness, ensuring a smooth ride. The focus is on enjoying the scenery and the peaceful atmosphere, making it ideal for couples or anyone looking for a romantic setting.
A minor consideration is that sunset cruises are weather-dependent, and clouds can obscure the view. But if the weather cooperates, you’ll leave with a treasure trove of beautiful memories. Bottom line: this experience offers a peaceful conclusion to a day in Boothbay Harbor, perfect for romantic outings.
4. Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
Lastly, for those wanting a lively, hands-on sailing adventure, this 2-hour day sail on the Schooner Applejack (check it out here) offers a delightful experience. The boat, Maine’s oldest windjammer, takes you past Burnt Island Light, Squirrel Island, and the outer islands. Participants are encouraged to help hoist sails or take a turn at the wheel, making it a truly participatory outing.
What sets this tour apart is its combination of history and activity. At $54.95 per person, the experience not only offers scenic views but also a taste of Maine’s sailing heritage. Many reviews highlight the crew’s professionalism and the opportunity to steer the boat—great for active travelers or families with kids eager to learn about sailing. Wildlife sightings such as porpoises, ospreys, and bald eagles add a special touch.
The main limitation is that, being a 2-hour sail, it might feel a bit brief for those craving a longer adventure. But for a fun, engaging day on the water, this tour hits the mark. Bottom line: it’s perfect for anyone wanting to participate actively and enjoy Maine’s maritime history firsthand.
How to Choose
When selecting the best boat tour in Maine, think about your priorities. If you want a romantic, scenic evening, the Eastwind Sunset Sail is hard to beat. For a more active, hands-on experience with a historic schooner, the Applejack day sail delivers a lively adventure. Budget travelers will appreciate the similar price points of the day and sunset sails, but if wildlife is your priority, consider the day sail for opportunities to see seals and dolphins.
Booking early is recommended, especially for sunset cruises or weekends in high season. Check the weather forecast, as Maine’s coastal conditions can change quickly and impact your experience. Think about your physical readiness—some tours encourage participation, so if you’re less mobile, a relaxed daytime sail might suit you better.
Final Thoughts
From romantic sunset cruises to lively, participatory sails and wildlife-watching adventures, Maine’s boat tours offer a rich variety of options. The Applejack sunset sail provides a classic, hands-on experience with spectacular views. The Eastwind day and sunset sails stand out for their reputation and scenic beauty, catering to both daytime relaxation and evening romance. Meanwhile, the Applejack day sail combines history and activity, perfect for adventurous visitors.
No matter which you choose, these tours give you a chance to experience Maine’s coastal beauty from the water—an essential part of any trip here. If I had to pick, I’d say go for the sunset sail if romance and stunning scenery are your priorities, or the active schooner adventures if you want to learn about sailing and Maine’s maritime history firsthand. Book early, set your expectations for great views and friendly crews, and enjoy a memorable day on Maine’s legendary waters.