Discover the Charm of the Schooner Eastwind Sunset Sail in Maine

If you’re dreaming of a peaceful escape along Maine’s rugged coastline, a sunset sail aboard the Schooner Eastwind might just be your next highlight. While we haven’t personally stepped aboard, plenty of reviews show this trip is a beautifully relaxing way to soak in Boothbay Harbor’s scenery. Think sweeping views of lighthouses, playful wildlife, and remote islands only accessible by boat—all wrapped up in a two-hour voyage.
What makes this experience stand out? For one, the full 360-degree deck view means no matter where you sit, you’ll be eye-level with the horizon, soaking in the sights. Plus, the friendly, seasoned crew has been working in Boothbay Harbor for nearly 50 years, and that kind of local knowledge really shows. But, as with anything, there’s a small tradeoff: the tour’s reliance on good weather can mean cancellations, which some travelers have faced.
This sail is perfect for those who want a laid-back, scenic outing that doesn’t require a huge time investment. Whether you’re celebrating a special occasion or simply want a quality way to unwind after a busy day of exploring, this trip has broad appeal. Just keep in mind that if you’re after a detailed narration or a more lively experience, you might find this more serene and observational.
Key Points

- Two-hour duration offers a relaxed but memorable experience without taking up your whole day.
- Full 360-degree views from every seat ensure you won’t miss any of the coastal scenery.
- BYOB and snacks provide flexibility, and a restroom onboard adds convenience.
- Cancellations are weather-dependent, so good weather is key to a smooth trip.
- The tour is limited to 28 travelers, keeping the group intimate yet lively.
- Pricing at $54.95 per person is reasonable for a scenic sunset trip, especially considering the personalized experience.
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Why the Schooner Eastwind Sunset Sail Could Be Your Perfect Getaway

This two-hour sail isn’t just about the journey itself—it’s about the experience of gently gliding past Maine’s iconic coastline. The boat, equipped with an onboard engine, speeds to prime sailing grounds, allowing more time to relax and enjoy the scenery. Once on the water, you’ll love the unobstructed views of lighthouses, fishing lobstermen, and the chance to spot local wildlife.
The boat’s design ensures no view is blocked, so whether you’re sitting at the bow or amidships, you’ll never miss the stunning vistas. The friendly crew, including captains and first mates, are eager to make your experience memorable. They’re attentive without being intrusive, and reviews praise Capt Kate and Captain Sean for their professionalism and warmth.
The Itinerary: A Visual Journey

Starting at the heart of Boothbay Harbor’s historic waterfront, the tour’s dock location in Boothbay’s bustling center is ideal. Surrounded by shops, inns, and restaurants, you can easily make this sail part of a larger day of exploring. Once aboard, the boat’s quick transit to the sailing grounds means you won’t spend a lot of time in transit, giving you maximum time to relax and enjoy.
The core of the experience is the sunset (or the scenic daytime sail), which offers a wonderful opportunity for photography and quiet reflection. As you glide past remote islands and watch lobstermen work, the entire scene feels authentic and timeless. One reviewer mentioned that the views during sunset were “gorgeous,” emphasizing how this time of day enhances the experience’s natural beauty.
The Onboard Experience: What to Expect
Snacks and Drinks: You’re welcome to bring your own non-alcoholic drinks and snacks, adding to the casual, picnic-like vibe. For those wanting a little something stronger, alcoholic beverages are available for purchase onboard, including beer, wine, and liquor.
Restroom Facilities: Having a restroom onboard is a big plus for comfort on this relatively short trip. It’s not a full-service bathroom, but it’s sufficient for a two-hour sail.
Group Size and Atmosphere: With a cap of 28 travelers, the tour maintains an intimate feel. This makes it suitable for couples, small groups, or solo travelers who enjoy a relaxed, friendly environment. The small size also ensures that everyone gets good views and space to enjoy the sail.
Weather Considerations: Since the tour depends on good weather, cancellations can happen if conditions turn unfavorable. Luckily, they offer a full refund or the option to reschedule if that occurs. This is worth keeping in mind when planning your trip, especially in Maine’s unpredictable climate.
The Realities of the Experience: Insights from Reviews
Many guests have praised the stunning views and the friendly crew. For instance, one reviewer loved how Captain Sean made the trip exceptional, describing him as “awesome,” while another called out crew member Simon for being “amazing.” These personal touches can elevate what might seem like a simple boat ride into a memorable moment.
A couple of reviews pointed out that a bit more commentary during the cruise would enhance the experience, especially for those interested in local landmarks. While the boat doesn’t offer narrated commentary, the scenic views themselves are engaging enough for most.
However, it’s worth noting that one guest experienced a cancellation with no notice. While rare, it’s a reminder to check the weather forecast and understand the cancellation policy. The tour’s flexibility—offering full refunds or rescheduling—helps mitigate this risk.
Price and Value: Is It Worth It?
At $54.95 per person, the price strikes a good balance considering the full two-hour experience, boat amenities, and the opportunity to view Maine’s coast from a prime vantage point. Compared to other scenic activities, it’s a reasonable way to enjoy a memorable sunset without a hefty price tag.
What you’re paying for is more than just the scenery—it’s a chance to unwind, take photos, and enjoy Maine’s natural beauty in a relaxed setting. If you’re someone who appreciates scenic vistas and the gentle rhythm of sailing, this trip offers solid value.
Who Should Consider This Tour?
This sail is ideal for those looking for a peaceful, scenic experience rather than a high-energy or narrated tour. It’s particularly suited for couples, small groups, or solo travelers who want to appreciate Maine’s coastline at sunset. Because it’s not explicitly marketed as family-friendly, younger children might not find it as engaging unless they love being on boats and sightseeing.
If you’re celebrating a special occasion or simply want a tranquil break from busy sightseeing, this is a wonderful choice. It’s also a lovely way to wind down after exploring Boothbay Harbor’s shops and restaurants.
Final Thoughts
The Schooner Eastwind Sunset Sail offers a gentle, scenic escape that captures the essence of Maine’s coast. The full panoramic views, friendly crew, and relaxed pace make it a worthwhile outing for anyone wanting to embrace the maritime beauty of Boothbay Harbor. While weather-dependent cancellations can be frustrating, the overall experience is likely to leave you with lasting memories of Maine’s rugged shoreline and peaceful waters.
For those who enjoy quiet moments, stunning vistas, and a touch of nautical history, this sail hits the right notes. Just be prepared for the weather and bring along some snacks and drinks for a truly personalized experience. Whether for a romantic sunset, a peaceful afternoon, or a small group adventure, this trip is definitely worth considering.
Schooner Eastwind Sunset Sail to see the Maine Coastline
“Weather and sunset was gorgeous. The only thing that I wish they would add to the cruise is narrating your whereabouts a little bit. Throughout th…”
FAQ
How long is the tour?
The cruise lasts about 2 hours, so it’s a perfect short outing without taking up your whole day.
Can I bring my own drinks and snacks?
Yes, you’re welcome to bring BYOB non-alcoholic drinks and snacks onboard, which adds a personal touch to your trip.
Are alcoholic beverages available?
Yes, a selection of beer, wine, and liquor can be purchased during the sail.
Where does the tour start?
The meeting point is at 20 Commercial St, Boothbay Harbor, right in the heart of the waterfront.
What’s included in the price?
The ticket price covers the sailing experience and restroom access onboard. Gratuities are not included.
What if the weather isn’t good?
The tour requires good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund.
How many people does the boat hold?
The vessel limits group size to 28 travelers, ensuring a comfortable, intimate atmosphere.
Is this suitable for children?
While not specifically marketed as family-friendly, children who enjoy boats and scenic views should be comfortable on this trip. Keep in mind, it’s a relaxed, adult-oriented experience.
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