Maine’s rugged coastlines, historic lighthouses, and abundant wildlife make it one of the best places in the U.S. for boat tours and cruises. Whether you’re after a peaceful sunset sail, a lively day trip, or a wildlife encounter, Maine offers options that suit all kinds of travelers. The Schooner Applejack Sunset Sail in Boothbay Harbor stands out for its romantic atmosphere, while the Eastwind offers a classic daytime schooner experience. For those who want to combine relaxation with sightseeing, these tours provide an authentic taste of Maine’s maritime charm. The range of options means you can enjoy a quiet evening watching the sun dip below the horizon or a lively day spotting seals and porpoises.
If you’re looking for a true Maine adventure, you’ll want to consider not only the scenery but also the vibe. Some tours, like the sunset sail, are perfect for couples or celebrating special occasions, while the daytime schooner is great for families or anyone eager to raise the sails. All of these experiences give you a chance to see Maine from the water, where the coast reveals its real character—wild, beautiful, and full of life.
Quick Overview
This list covers four top boat tours in Maine, with options ranging from sunset sails to wildlife cruises. Each offers a unique perspective on Boothbay Harbor’s beauty, with some emphasizing history and scenic views, and others focusing on interactive sailing experiences. For a romantic evening, check out the Schooner Applejack Sunset Sail. If you want a lively, hands-on day cruise, the Schooner Eastwind 2 Hour Day Sail is a perfect pick. For those seeking a classic Maine sailing experience with stunning coastlines, the Eastwind Sunset Sail delivers. And for a more relaxed, traditional day sail, the Applejack 2-Hour Day Sail is excellent.
1. Schooner Applejack Sunset Sail Tour in Boothbay Harbor
At number 1 on our list, the Schooner Applejack Sunset Sail is a perfect choice for a romantic evening or a peaceful way to end your day in Boothbay Harbor. This tour lasts about 2 hours and costs $59.95 per person. On this cruise, you’ll join the crew on Boothbay’s oldest windjammer, helping hoist sails or taking a turn at the wheel if you want. The route takes you past Burnt Island Light, Squirrel Island, Ram Island Light, and the outer islands—offering plenty of chances to spot porpoise, Osprey, Bald Eagles, and harbor seals.
What makes this sail special is the chance to participate actively in the sailing process while enjoying the calm waters at sunset. The crew, including Captain Shawn and First Mate Marison, are genuinely friendly and knowledgeable, making the experience both fun and informative. Reviews highlight the beautiful evening scenery and the captain’s impressive seamanship, with several describing it as a “gorgeous boat and lovely town.” The focus on authentic sailing and the opportunity to help makes this tour a hit for those who want a hands-on maritime experience.
Bottom Line: This tour is ideal if you’re after a romantic, scenic, and interactive sailing experience with a friendly crew and stunning sunset views.
2. Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
At number 2, the Schooner Eastwind 2 Hour Day Sail offers a relaxed, scenic cruise perfect for soaking in the Maine coastline. For around $54.95, you’ll enjoy a roughly two-hour sail that takes you past lighthouses, fishing lobstermen, and remote islands accessible only by boat. This tour is deeply rooted in the local community—almost 50 years of experience support its reputation as one of the best in Boothbay Harbor.
The crew, including Captain Sherman and Meghan, are praised for creating an authentic and enjoyable experience. They give guests the opportunity to raise the sails, making it interactive even for young children—one review mentions a 6-year-old getting to help hoist the sails. Guests appreciate the friendly crew and the opportunity to see seals and a dolphin, adding a touch of wildlife excitement.
If you’re interested in exploring Maine’s coast, this cruise provides excellent value with its focus on classic sailing and local storytelling. The docks are at the heart of Boothbay Harbor, putting you close to shops, restaurants, and other water activities.
Bottom Line: This trip is perfect for those who want a relaxing, interactive sailing experience with opportunities to see wildlife and learn about the area’s maritime culture.
3. Schooner Eastwind Sunset Sail to see the Maine Coastline
Number 3 on our list, the Eastwind Sunset Sail is a two-hour cruise that delivers an immersive experience of Maine’s rugged coast. For $54.95 per person, this tour takes you past lighthouse-beaconed islands, fishing boats, and possibly wildlife like seals and eagles. Captain Sean and crew work hard to provide a memorable trip, with reviews praising the enthusiasm and professionalism of the team.
What sets this cruise apart is its strong focus on scenic views and a peaceful atmosphere. During sunset, the views of the Maine coastline look especially stunning, making it ideal for romantic evenings or photographers. The crew’s extensive experience, combined with the boat’s traditional charm, adds an authentic sailing feel.
Guests frequently mention feeling “safe and well cared for,” with many describing the trip as “wonderful” and “exceptional.” The boat’s location in Boothbay Harbor means you’re steps from the town’s best inns and restaurants, making this a very convenient option.
Bottom Line: Perfect for travelers seeking a relaxing sunset cruise with superb scenery and a friendly crew, especially if you want a more tranquil experience.
4. Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
The last in our lineup, the Applejack Day Sail provides a classic Maine sailing experience. For $54.95, this 2-hour cruise offers the chance to help hoist sails and navigate past Burnt Island Light, Squirrel Island, and Ram Island Light. Like the sunset sail, this voyage delivers opportunities to spot porpoise, Osprey, Bald Eagles, and harbor seals.
What makes it stand out is its focus on active participation. Many guests enjoy the hands-on sailing, which adds a layer of engagement to the relaxing scenery. The boat is described as “beautiful,” and the crew as “wonderful,” providing a fun and informative experience. It’s especially good for those who want to experience Maine’s maritime culture firsthand.
While the trip is shorter and focused on daytime activity, reviews mention the opportunity to see wildlife and enjoy the cool ocean breeze. It’s a solid choice for travelers who prefer interactive sailing over passive sightseeing.
Bottom Line: This tour offers a hands-on sailing experience with excellent wildlife viewing and a friendly crew—ideal for active travelers.
How to Choose Your Maine Boat Tour
When picking between these options, consider your priorities: Do you want a romantic sunset or a lively day sailing? If you’re after a special evening experience, the Applejack Sunset Sail offers that magical moment. For active participants or families, the Eastwind Day Sail allows you to assist with the sails and see wildlife up close. Those seeking scenic tranquility should look at the Eastwind Sunset Sail for breathtaking coast views.
Budget is also a factor—most tours fall within the $54.95 to $59.95 range, but the experiences differ greatly. Be sure to book early during peak summer months, especially for sunset cruises, which are popular for special occasions. Also, check the weather forecast and dress in layers, as Maine weather can change quickly.
Final thoughts
Maine offers a wide spectrum of boat tours and cruises that highlight the state’s rugged coastlines, abundant wildlife, and rich maritime heritage. For a romantic evening, the Applejack Sunset Sail provides a beautifully relaxing experience, while the Eastwind options deliver more active, scenic days on the water. If you want to combine scenic views with wildlife sightings, any of these tours will satisfy your curiosity and sense of adventure.
Remember, booking early increases your chances of snagging your preferred time, especially in peak season. No matter which tour you choose, you’re sure to leave with a deeper appreciation for Maine’s seafaring traditions and spectacular coast. Happy sailing!