Boothbay Harbor Schooner: Maine Coastline Sailing

46 Ratings

Boothbay Harbor

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Experience Boothbay Harbor’s best sunset sail. Explore Maine’s coastline, lighthouses, and wildlife aboard the Schooner Eastwind. Book your unforgettable two-hour voyage today.

Duration: 2 hours

Cancellation: 24 hours

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Highlights

Boothbay Harbor Region - Our docks are centrally located in the historic waterfront of Boothbay Harbor. Just steps away, you’ll find excellent inns, shops, restaurants, and various water activities. We collaborate with and support our waterfront community and are eager to guide you to all the wonderful experiences nearby.

What's Included

BYOB drinks and snacks (non-alcoholic)
On-board restrooms

What's Not Included

Gratuities
Alcoholic beverages

Additional Information

Sail away from it all on your two-hour voyage aboard Boothbay Harbor’s schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape.
Our goal is for you to experience the best two-hour classic sailing trip in the world. We have been working on this experience in…

Location

20 Commercial St

Commercial Street

In Boothbay Harbor, please look for the sign that says "Schooner Eastwind."

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings

4.6

(46 Ratings)

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1 star

Storyteller639064

Jul 8, 2025

Beautiful Night in Boothbay! - Christina and Josh were great. Both were energetic which made the sail even more enjoyable. Their interaction while working together was entertaining and lighthearted. Would love to come back! Thanks for a great night!

Review provided by Tripadvisor

Nicole_c

Jul 5, 2025

An enjoyable experience with excellent views - 10 out of 10 experience! The captain and his mates were helpful and friendly. The schooner was clean, beautiful and well maintained. We went along the coastline and enjoyed some beautiful weather and views. They had refreshments (at a cost) and a restroom on board.

Review provided by Viator

Leigh_f

Jun 28, 2025

Beautiful Cruise - Friendly, professional sailing. Lovely scenery in Boothbay Harbor. Luke and Christine did a great job!

Review provided by Viator

E1967tvsandyw

Jun 24, 2025

Super relaxing and beautiful! - Great 2 hour sunset sail. Beautiful day and Captain Josh and first mate Merson were both terrific. Definitely worth the spend and a great way to see Booth Bay Harbor and surrounding islands from the sea.

Review provided by Tripadvisor

Markm50

Jun 13, 2025

Pleasant evening on the water… - Very enjoyable couple of hours spent on a beautiful old sailing ship off Boothbay Harbour. Crew were professional and very pleasant, taking time to move and chat among the different patrons on board. Scenery was quite beautiful whilst the sun went down. There wasn’t as much physical activity in hoisting the sails as hoped - think this was down to it being TOO windy. With passenger safety paramount I think the skipper limited this activity, conditions weren’t that choppy and there was no issues moving around the vessel whilst underway. Might be a little boring for youngsters but sometimes it’s just nice to sit back and enjoy the scenery 😀👍

Review provided by Tripadvisor

D4837rybrianc

Jun 5, 2025

Live life! - Capt. Josh, Brian and Christina were like being out with family. Sunset Eastwind on June 5th from 6:30 to 8:30 pm was great. The love and respect for history of boats, nature and way of life is clear when you really meet the crew. Don't pass up the chance to go out with them and always keep asking questions! They are great at telling what they know and have experienced and are young and still seeking their own answers. We wish them all the best in their journeys.

Review provided by Tripadvisor

Bwilkin

May 29, 2025

Recommend it - Captain Josh, Christina and Brian were wonderful. The three were friendly and quite knowledgeable of the area. The sunset was fantastic. We highly recommend it!

Review provided by Tripadvisor

Taylor_c

May 27, 2025

Quintessential Maine Experience - This was one of our favorite experiences from the trip. We took the first sail of the season and while it was still cloudy, it was a great experience! Josh and Luke made the trip fun and interactive for the small group on the boat. We saw a lighthouse, the smaller islands, and seals. It was so quiet and peaceful out on the water.

Review provided by Viator

Dougpk7094zc

Oct 13, 2024

Sunset Sailboat Trip - As part of a 25th wedding anniversary trip to Maine, the sunset trip was an awesome highlight. The crew was pleasant and answered a ton of questions about the area, the lobster industry and sailing. The ship was clean and felt safe.

Review provided by Tripadvisor

Libby_h

Jun 22, 2025

Be aware! - Be aware! Our experience was cancelled due to weather which is completely understandable. What is UNACCEPTABLE is that we were not notified in ANY way so we drove 4 hours for NOTHING. The attendant MJ, was just plain nasty. We arrived 15 minutes early and she spoke to us like we were idiots for not knowing it was cancelled. When I asked why we weren't notified she said, "I have 27 people to call". It was 10 minutes before departure time. We left disappointed.

Review provided by Viator

Check Availability

From $60

up to 12 guests

1 - Adult