4 Best Boat Tours & Cruises In Maine

The 4 Best Boat Tours & Cruises in Maine

Maine offers some of the most scenic and authentic boat experiences on the East Coast. Its rugged coastline, picturesque islands, and abundant wildlife make it a prime destination for boat lovers. Whether you’re dreaming of a sunset sail with a historic schooner or eager to spot harbor seals and porpoises, Maine’s waters won’t disappoint.

One standout experience is the Schooner Applejack Sunset Sail in Boothbay Harbor, which combines a classic windjammer cruise with breathtaking views at dusk — perfect for romantic evenings or folks who want a genuine Maine adventure.

The Eastwind offers equally charming options, with a focus on wildlife sightings and local storytelling. For those short on time but wanting to get a real feel for the coast, all four tours deliver memorable outings.

Quick Overview

This list features four top boat tours and cruises in Maine, each with its own appeal. For a classic sunset experience aboard a historic schooner, check out the Schooner Applejack Sunset Sail.

If you’re looking for a relaxed day sail to explore Boothbay Harbor’s wildlife and coastal scenery, the Schooner Eastwind 2 Hour Day Sail is a fantastic choice. For a more scenic, wildlife-focused voyage, the Schooner Eastwind Sunset Sail offers breathtaking views at dusk.

Lastly, the Schooner Applejack 2-Hour Day Sail is perfect for families and first-timers wanting a shorter, friendly cruise.

1. Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Starting with a classic sunset sail in Boothbay Harbor, the Schooner Applejack offers a memorable experience aboard Maine’s oldest windjammer. This 2-hour cruise is highly rated with a perfect 5.0/5 based on 19 reviews, which speaks to its popularity. As you glide past Burnt Island Light, Squirrel Island, and the outer islands, you’ll be treated to scenic views only accessible by boat.

The crew encourages you to help hoist sails or take the wheel, making it more interactive than your average cruise. Keep your eyes peeled for porpoise, osprey, bald eagles, and harbor seals, all common sightings along this route.

What makes this tour stand out is the combination of history, hands-on sailing, and the opportunity to enjoy Maine’s famous sunset.

Captain Shawn and First Mate Marison are noted for their friendly, knowledgeable approach, and many reviews highlight the “lovely evening” and “incredible man with the most experience at sea.” The price of $59.95 is reasonable for the quality and length of the experience, especially given how much you get to participate.

Bottom Line: If you want a romantic sunset with a touch of adventure and history, this cruise is a top pick. It’s perfect for couples or anyone who wants to see Boothbay Harbor from the water with a true sailing experience.

2. Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

For those looking for a relaxing daytime cruise, the Schooner Eastwind offers a 2-hour voyage that emphasizes wildlife, coastal scenery, and local flavor. Priced at $54.95, this tour provides excellent value considering its reputation as “the best 2-hour classic sailing trip in the world.” The crew supports a hands-on experience, giving you the chance to raise the sails and learn about the area.

This cruise is highly praised for its authentic local storytelling, with reviewers mentioning helpful guides like Sherman and Meghan. One even noted that their young child helped hoist the sails, making it a memorable family activity. The route takes you past lighthouses, working lobster boats, and remote islands only accessible by boat, offering a true glimpse of Maine’s maritime life.

One reviewer appreciated the friendly crew and noted, “Saw seals and a dolphin,” which underscores the rich wildlife sightings on this trip. The central location in Boothbay Harbor means everything is within easy reach, making it ideal for a short, scenic escape.

Bottom Line: If you want an interactive, family-friendly sailing adventure with local charm and wildlife sightings, this is an excellent choice. It’s perfect for travelers who want to learn and engage without a lengthy commitment.

3. Schooner Eastwind Sunset Sail to see the Maine Coastline

Rounding out the list is the Schooner Eastwind Sunset Sail, which offers a similar 2-hour experience but emphasizes spectacular evening views of Maine’s coast. This cruise, rated 4.5/5 based on 33 reviews, is praised for the friendly crew, beautiful scenery, and relaxed atmosphere.

For $54.95, it gives travelers a chance to unwind and take in the rugged coastline, lighthouse views, and the chance to spot fishing lobstermen at work.

Capt. Sean and crew like Simon, are noted for their attentiveness and ability to make guests feel safe and included. During sunset, the landscape transforms, making this an ideal trip for photographers or anyone wanting a peaceful yet visually stunning experience. Many guests mention that they enjoyed the opportunity to see the coast at the best time of day, with some wishing for a longer trip.

The itinerary supports the idea of a laid-back, scenic cruise with great storytelling, making this a popular choice for those seeking a tranquil end to their Maine day.

Bottom Line: For a relaxing sunset cruise with plenty of wildlife and coastal scenery, this tour delivers a memorable Maine evening. It suits travelers who love photography, quiet moments, or simply unwinding with a view.

4. Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Finally, the Schooner Applejack offers a straightforward 2-hour day sail that highlights Maine’s maritime charm. Priced at $54.95, this cruise is ideal for first-timers, families, or anyone wanting a quick but authentic taste of Maine sailing.

The boat, Maine’s oldest windjammer, sets a course out past Burnt Island Light and Squirrel Island, giving you the chance to spot harbor porpoises, ospreys, bald eagles, and seals.

What makes this tour stand out is the participatory element — you can help hoist sails or take the wheel — and the focus on local landmarks and wildlife. Reviewers mention the “beautiful boat” and “opportunity to steer the boat,” making it especially appealing to kids or those new to sailing.

The boat’s historic charm and friendly crew create an engaging environment, and the 2-hour length is suitable for those with limited time or who want a quick escape from town. It’s a great introduction to Maine’s coastal waters.

Bottom Line: For a short, interactive sailing experience in Boothbay Harbor, this cruise checks all the boxes. It’s perfect for families, novices, or anyone seeking a breezy, fun outing.

How to Choose the Right Maine Boat Tour

Selecting the best boat experience depends on your interests, time, and budget. If you’re after a romantic sunset with historical charm, the Schooner Applejack Sunset Sail is hard to beat. For a family-friendly hands-on adventure, the Eastwind Day Sail offers engaging wildlife sightings and local storytelling.

If your goal is to relax and enjoy Maine’s coast at dusk, the Eastwind Sunset Sail provides stunning views and a peaceful experience. For a quick, participatory outing, the Applejack Day Sail is excellent.

Consider your budget, the amount of time you want to spend, and whether you prefer wildlife spotting, sailing, or scenic views. Booking early is advised, especially in peak summer months, to secure your preferred date and time.

Final Thoughts

Maine offers a wonderful variety of boat tours and cruises that highlight its rugged coastline, abundant wildlife, and sailing traditions. For a romantic sunset, the Applejack cruise is hard to beat. If you want an interactive family experience, Eastwind’s day sail combines fun with education. For those seeking serenity and scenic beauty, the sunset cruises provide a peaceful, picturesque escape.

No matter which cruise you choose, you’re in for a taste of Maine’s maritime spirit. Book early, pack your camera, and get ready for some unforgettable moments on the water.