Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

Sailing in Boothbay Harbor on the historic schooner Apple Jack offers a charming blend of scenic views, wildlife encounters, and maritime history. This 2-hour cruise is ideal for those craving an authentic New England experience without the crowds. From the moment the crew hoists the sails, you’ll feel transported into a classic maritime adventure.

What we love most about this trip is the chance to witness lighthouse vistas and remote islands only accessible by boat, the friendly and knowledgeable crew who make the journey engaging, and the charm of sailing on Boothbay’s oldest windjammer. That said, it’s a short trip, so if you’re after a full-day excursion, this might leave you wanting more. Still, for anyone wanting a relaxed, scenic sail with plenty of authentic touches, this cruise hits the right notes.

This experience suits travelers interested in maritime scenery, local wildlife, and historic vessels. It’s also great for those traveling with family, couples seeking a romantic outing, or solo adventurers eager for a taste of Maine’s coastal charm.

Key Points

• Authentic maritime experience on Boothbay’s oldest windjammer
• Wildlife sightings including porpoises, bald eagles, and harbor seals
• Lighthouse and island views accessible only by boat
• Friendly, knowledgeable crew enhancing the journey
• Flexible booking options with free cancellation and pay later
• Affordable value at $55 per person for 2 hours of sailing

You can check availability for your dates here:

What to Expect on the Schooner Apple Jack

Stepping onto the schooner is like stepping back in time. As the crew begins to raise the sails, a wave of anticipation builds. The majestic vessel, with its tall, billowing sails, glides smoothly away from the dock, catching every breeze. The gentle sound of water against the hull and the fresh coastal air instantly set the mood for a relaxed, scenic cruise.

The Itinerary and Highlights

The main attractions of this cruise are the views and the wildlife. As you slip past Burnt Island Light, you’ll see one of Maine’s iconic lighthouses, guarding the entrance to Boothbay Harbor. The cruise also takes you past Squirrel Island, which is visible only from the water, and the outer islands of Boothbay—a treat for those seeking a sense of remote, untouched beauty.

You’ll likely spot porpoises, often swimming alongside the schooner, and keep an eye out for bald eagles soaring overhead. The crew, including Captain Shawn and crew members like Megan, are praised for their friendly, approachable manner and their ability to share interesting tidbits without overwhelming. As noted in reviews, guests appreciated how the crew pointed out sights and allowed volunteers to help with sails and steering, making the experience interactive.

Wildlife & Scenic Stops

The voyage provides plenty of chances to observe local wildlife—many guests mention spotting harbor seals, and some reviews highlight the crew’s capability of spotting birds of prey like ospreys and bald eagles. The lush, rugged coastline dotted with coastal homes and remote islands offers captivating views that are only visible from the water, giving a sense of discovery.

The Sailing Experience

The sails are the star of the show. Watching the crew hoist and trim the sails adds a tangible sense of history and craftsmanship. Guests are often invited to help out—lifting the sails or steering—adding a fun, hands-on element appreciated by many. The 2-hour duration feels just right: enough time to relax, enjoy the scenery, and learn about the local area without feeling rushed.

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Onboard Comfort and Facilities

The restroom onboard makes the trip comfortable, especially for those who might be concerned about long outings. The availability of alcohol for purchase, including beers, wines, and Bloody Marys, allows guests to enjoy a drink as they soak in the views. Remember, food and non-alcoholic beverages are your responsibility—so consider bringing some snacks or a picnic to enhance the experience.

Value and Booking Details

Priced at $55 per person, this cruise offers excellent value for a scenic, authentic sailing experience. The smaller group size—around ten guests—means a more intimate and relaxed atmosphere, with plenty of interaction with the crew. The flexible booking options, including free cancellation up to 24 hours in advance and reserve now, pay later, make planning easier.

The meeting point is clearly marked at Fisherman’s Wharf Inn, with a prominent sign for the Schooner Eastwind. The cruise ends back at the same spot, making logistics straightforward.

Why This Experience Stands Out

Compared to larger, more commercial tours, this sailing trip emphasizes authenticity and intimacy. The knowledgeable crew—including Captain Shawn and Megan—are frequently praised for their friendliness and expertise. Guests rave about their ability to share insights while maintaining a relaxed, welcoming atmosphere.

The scenery is unbeatable: rugged coastlines, historic lighthouses, and the chance to see wildlife such as porpoises and eagles add a layer of excitement. Many reviews emphasize how beautiful and sparkling the day was, and how the crew’s humor and kindness made the trip memorable.

Authenticity and Unique Touches

Guests often mention that the old schooner itself is a highlight, being the oldest windjammer in Boothbay. Its historic charm, combined with the opportunity to hoist sails, provides an engaging experience beyond just sightseeing.

Who Should Consider This Cruise?

This tour is perfect for nature lovers, history buffs, and anyone wanting a genuine New England maritime experience. It’s also well-suited for families, couples, or solo travelers who appreciate smaller groups and personalized service. Those seeking longer, more comprehensive tours might find this short voyage a bit light, but it’s an ideal introduction to the area’s maritime beauty.

Final Thoughts

The Boothbay Harbor Schooner Apple Jack Daytime Sailing Cruise offers a delightful blend of scenic views, wildlife spotting, and historic charm—all wrapped in a relaxed two-hour trip. The friendly crew, authentic vessel, and picturesque surroundings make it a memorable way to connect with Maine’s coast.

While it may be brief, the experience delivers plenty of photo-worthy moments and authentic maritime ambiance. If you’re visiting Boothbay Harbor and want to enjoy a classic sail, this cruise provides excellent value and a genuine taste of New England’s seaside heritage.

FAQ

Is this cruise suitable for children?
While specific age restrictions aren’t listed, the relaxed, family-friendly atmosphere and interactive sailing make it suitable for children comfortable around water and open to light adventure.

What should I bring?
Bring a hat, sunscreen, and a jacket—coastal weather can change quickly. It’s also wise to have some snacks and non-alcoholic beverages if you want to extend your enjoyment.

Are drinks available onboard?
Yes, alcohol such as beer, wine, and Bloody Marys can be purchased during the cruise. Soft drinks and snacks are also available.

Is the cruise weather-dependent?
Yes, sailing is subject to weather conditions. You can cancel up to 24 hours in advance for a full refund if the weather cancels the trip.

How long is the cruise?
The voyage lasts approximately 2 hours, with starting times available depending on the day.

What is included in the price?
Your ticket covers the sailing, onboard restroom access, and the scenic experience. Food is not included, so bring your own if desired.

How many people are on each trip?
Guests typically number around 10, creating an intimate, friendly atmosphere.

Are volunteers allowed to participate?
Yes, volunteers can help with sail hoisting and steering, making for a more interactive adventure.

Is there a specific dress code?
No formal dress code—just wear comfortable, weather-appropriate clothing and sturdy shoes.

This detailed review should help you decide if a scenic boat ride in Boothbay Harbor on the Apple Jack schooner is right for you. Whether you’re after wildlife sightings, historical ambiance, or simply a relaxing day on the water, this cruise offers a truly memorable experience.

You can check availability for your dates here: