Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

When it comes to exploring Maine’s coastal charm, a sailing cruise on a historic schooner ranks high among the unforgettable ways to take in the region’s natural beauty. The Boothbay Harbor Schooner Apple Jack Daytime Sailing Cruise offers a laid-back yet captivating glimpse of the area’s rugged coastline, remote islands, and vibrant wildlife. While we haven’t personally set sail, reviews and detailed descriptions paint a vivid picture of what travelers can expect from this two-hour adventure.

What makes this experience stand out? First, the chance to see iconic lighthouses and islands only accessible by boat is a real draw. Second, the knowledgeable and friendly crew ensures all guests feel comfortable and informed. Lastly, sailing on Boothbay’s oldest windjammer adds a sense of history and authenticity to the trip. One possible consideration is that the tour is relatively short, which might leave some wanting more time on the water. Still, for those seeking a relaxed, scenic outing in Maine’s famed harbor, this cruise hits the sweet spot. It’s especially ideal for travelers who appreciate maritime history, wildlife spotting, and stunning coastal views without a hefty price tag.

This experience made our article of 8 Of The Best Cruises And Boat Tours In Boothbay Harbor.

Key Points

• Authentic Maine experience aboard the region’s oldest sailboat
• Wildlife sightings include porpoises, bald eagles, and harbor seals
• Expert guides and crew make for an engaging, informative trip
• Iconic lighthouses and islands only visible from the water
• Affordable at $55, offering excellent value for a scenic adventure
• Flexible booking options with free cancellation and pay later policies

You can check availability for your dates here:

What to Expect on the Schooner Apple Jack

This two-hour voyage is designed to deliver a relaxed yet engaging sail through Boothbay Harbor’s scenic waters. From the moment the crew hoists the sails, a sense of adventure takes hold. The schooner Apple Jack is a classic, beautifully maintained vessel, known as the oldest windjammer in Boothbay. Its billowing sails and traditional design evoke a real maritime spirit that’s hard to find elsewhere.

As the schooner glides away from the dock, you’ll notice how the gentle lapping of waves against the hull becomes a calming backdrop. The crew, led by knowledgeable guides, will point out key sights such as Burnt Island Light, a lighthouse that’s a Maine icon, and Squirrel Island, a remote, picturesque spot only accessible by boat. Several reviewers, including Sharon, highlight the crew’s friendly attitude and the well-paced commentary, which strikes a perfect balance—informative without being overwhelming.

The Journey and Key Stops

Your voyage begins at Fisherman’s Wharf Inn, where a clearly marked boarding area makes the process smooth. The boat, typically carrying around 10 passengers plus crew, ensures an intimate atmosphere without feeling crowded. As you set sail, the focus turns to the surrounding landscape. Expect to see rugged coastlines dotted with historic lighthouses—a quintessential Maine scene.

One of the trip’s highlights is the chance to spot wildlife like harbor porpoises, eagles, and seals. According to reviews, guides are quite adept at pointing out these animals, adding a lively, natural element to the cruise. Nancy mentions that her crew was “kind, knowledgeable, helpful, and funny,” making the experience both educational and entertaining.

Hands-On Sailing Experience

For those interested in participating, the crew encourages volunteers to help hoist sails or take the wheel. This involvement isn’t mandatory but adds an element of fun for those eager to get a hands-on experience. It’s a great way to feel connected to the boat and learn more about the sailing process, especially on a vessel with such historic importance.

Wildlife and Scenic Highlights

Imagine cruising past Burnt Island Light, standing sentinel over the harbor, and catching glimpses of Squirrel Island, a quiet refuge for seabirds and visitors alike. The outer islands, like Ram Island Light, provide dramatic backdrops for photos and quiet contemplation. The views of coastal homes—some seemingly perched right on the cliffs—are only visible from the water, giving a rare perspective on the area’s charming seaside communities.

Wildlife sightings are a major bonus. Reviewers like Susan described the day as “beautiful and sparkling,” with the crew impressively attentive to wildlife, pointing out soaring bald eagles and harbor seals. The presence of porpoises adds a playful element, making the cruise dynamic and lively.

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Practical Details and Value

Priced at $55 per person, this cruise offers excellent value considering the length, scenery, and expert guidance. It’s a relaxing way to enjoy Maine’s coastline without the need for strenuous activities or long excursions. The ticket includes access to the restroom onboard and the option to purchase alcoholic beverages like beer, wine, or Bloody Marys, which many guests enjoy during the trip.

What to Bring

To make the most of your sail, pack a hat, sunscreen, and a jacket—Maine weather can change quickly, and being prepared ensures comfort. You’ll also want to bring your own food and non-alcoholic drinks, as these aren’t included, giving you the freedom to enjoy a picnic or snack at your leisure.

Meeting Point and Booking

The meeting point is straightforward, marked by a “Schooner Eastwind” sign at Fisherman’s Wharf Inn. The activity is flexible in terms of booking, with options for free cancellation up to 24 hours in advance, and the ability to reserve now and pay later, making planning easier.

Authentic and Well-Reviewed Experience

The reviews reinforce the cruise’s reputation as a friendly, scenic, and well-organized activity. Sharon appreciated the clear instructions and the fact that volunteers could lend a hand, adding a participatory touch. Nancy called it “a perfect day,” and Susan described the crew as “knowledgeable and helpful,” emphasizing the quality of guides.

The small group size ensures a cozy atmosphere, and the historic schooner adds a layer of authenticity that larger, more commercial tours might lack. The experience isn’t just about sightseeing—it’s about feeling connected to Maine’s maritime heritage.

Who Will Love This Tour?

This cruise appeals to a broad range of travelers. Wildlife enthusiasts will love the animal sightings, while history buffs appreciate the schooner’s heritage. Families, couples, or solo travelers seeking a relaxing water-based activity will find it a perfect fit. It’s ideal for those who want a low-key, scenic, and informative outing without the hassle of complicated logistics or high costs.

If you’re after a romantic escape, a family-friendly adventure, or simply want to see the Maine coast from a different perspective, this cruise offers genuine value and beautiful memories.

FAQs

What is the duration of the cruise?
The cruise lasts about 2 hours, with specific start times depending on availability.

Is the cruise suitable for children?
While not explicitly stated, the relaxed nature and small group size make it suitable for most ages, especially those interested in maritime scenery and wildlife.

Can I bring my own food?
Yes, bringing your own food and non-alcoholic drinks is recommended, as they are not provided on the boat.

Are alcoholic beverages available onboard?
Yes, you can purchase beer, wine, and Bloody Marys during the cruise.

What should I wear?
Bring a hat, sunscreen, and a jacket for changing weather conditions.

Is the boat accessible for people with mobility issues?
This detail isn’t specified, so it’s best to check directly with the operator if you have specific accessibility needs.

How many people typically participate?
The boat typically hosts around 10 passengers plus crew, ensuring an intimate experience.

What are the cancellation policies?
You can cancel up to 24 hours in advance for a full refund, providing flexibility in case your plans change.

The Boothbay Harbor Schooner Apple Jack Daytime Sailing Cruise offers a wonderfully authentic taste of Maine’s maritime heritage. With its friendly crew, stunning coastal views, and wildlife sightings, it’s a memorable way to enjoy a peaceful two hours on the water. The moderate price point and flexible booking options make it accessible for most travelers looking to add a scenic, maritime adventure to their Maine itinerary.

If you’re after a relaxed, scenic outing that combines natural beauty with a touch of history, this cruise is an excellent choice. It’s particularly well-suited for those who love wildlife, scenic vistas, and a story-rich experience aboard a classic schooner. Expect a friendly atmosphere, knowledgeable guides, and plenty of picture-worthy moments—all in a setting that captures the true spirit of Maine’s coast.

This cruise is a fantastic, budget-friendly way to see Maine’s iconic sights from the water while enjoying the company of a passionate crew and a historic vessel.

You can check availability for your dates here: