What a great experience! I am so glad that my wife booked this trip for us. It was such a great time. The captain was great as was her first mate. She did a fantastic job sailing, having good conversation, and keeping things fun. She also knew a lot about sailboats in general and explained the differences in the other sailboats we passed. Lots of safety aboard and they do a great job having the visitors help with the needs of the boat. It was absolutely gorgeous that day and we could not have had better conditions to sail. Wind was good. Water was good. Times were good! We got to see a bunch of lighthouses and many wildlife too. All in all, a good way to spend a day on the water. They do sell booze if you want a drink. You only live once, do the things!! I would do it again in a heartbeat!! '26 - 32 read more

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I took my 1 year old grandson (and his parents..lol) on the Eastwind. We wanted a short trip due to his age and attention span. He had the best time and even got to steer the boat!! (long enough for a cute picture) Skipper and mate were amazing and the mate was an encyclopedia of local knowledge. I highly recommend this to anyone in the area. read more

We went on a sunset cruise on the Applejack with Luke and Christy. They were both very personable and made our trip very enjoyable. We learned a lot about the bay and the ship. The boat and crew made sure everyone was safe and they took care of the needs of all of us. The cruise was very relaxing and peaceful. Highly recommend this experience. read more

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Sara Josh and Marison were a fantastic crew. Highly recommend the sunset cruise. Ask Marison to tell you all about bagpipe lore. read more

Schooner Eastwind - Boat Charters Near Me - Boothbay Harbor, Maine

Everything was a great it was easy to get your ticket before hand check in was easy. Captain Luke and crew were very nice and did a fantastic job. My husband even got to help put up the sails!! It was a very fun relaxing enjoyable time! read more

Schooner Eastwind - My husband helping put up the sails. - Boat Charters Near Me - Boothbay Harbor, Maine

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Wonderful staff and crew! This was a bucket list item for my husband and I. We had an incredible time! read more

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This is actually a review of Eastwind's sister vessel, the AppleJack. Our sunset cruise was textbook-perfect. Capt. Katie and her crew were so much fun... entertaining, personable, very knowledgeable of the islands and harbor, and totally focused on our having a Large Time. They took extra time to cruise around a moored old vessel, the "Niagara," explaining its presence and history. And the cost was more than reasonable! This tour is a MUST DO when you're staying in B'Bay. -Moe and Donna read more

Schooner Eastwind - Sunset view from AppleJack - Boat Charters Near Me - Boothbay Harbor, Maine

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Staff excellent! Luke and Simeon were excellent sailors and just lovely people! Competent and extra kind to the two children on board! We didn't get a good sail because the wind was down, but amazing views and a seal and two porpoises! read more

What a great way to send an afternoon on the water at a reasonable price. We took the early afternoon two hour cruise. Beautiful views, relaxing, and they had drinks available modestly priced. Would love to go again. Highly recommend. read more

Beautiful susnset cruise. The Captain and Mandy were awesome and friendly. Loved being able to help raid the sails. Beautiful night sailing in Boothbay Harbor. Would do it nightly if I could. read more

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What an amazing sail around Boothbay Harbor! The Captain and crew were skilled and knowledgeable. We were lucky to sit near the Captain during the cruise, and he gave us a great history of the bay as well as answering all of our questions. The 2-hour cruise was so relaxing, and we were able to see a bay porpoise on our sail. The ship does have a bathroom (head) onboard, and selection of soft drinks, wines, beers, and cocktails for those who want a little extra. We would highly recommend the Eastwind and would love to go back next time we are in Maine! read more

Great sailing experience. The weather was great. The captain and first mate were wonderful.

I went on September 20, 2020 for a ride on the Eastwind Schooner and it was a great time. Friendly crew and there were only 4/5 others on the boat with me. Decently priced and BYOB (!!!) Captain and first mate were informative about any questions and gave us tidbits about the boat and scenery. Also, I am typically not a boat person and even get car sick - but I had no sea or motion sickness on this trip. The crew know what they are doing. Covid Safety: Everyone wore their mask while getting on, then we took them off while seated. Typically they allow everyone to help with the sail, but obviously no 'hands on' experience ATM. read more

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OUTSTANDING! What a wonderful cruise, ship captain Sean(Shawn?) and his mates Max and Jada were super warm, attentive and welcoming. They were extremely involved with the guests and Sean is a wealth of knowledge and charm. The Eastwind is a beautiful boat lovingly built by a boat building couple not on a factory assembly line. The crew invites you to bring food onboard, we got great sandwiches from Marcello's a few blocks away, and they sell a nice selection of soft drinks, beers, wines and cocktails during the cruise at reasonable prices. Schooner Eastwind was the highlight of our four day visit to Maine and I highly recommend it. read more

Captain and crew were excellent. Boat was beautiful. It wasn't crowded. Maybe 20 passengers. Drinks were available onboard for nominal price. Wonderful excursion. read more

Great sailing experience. The crew was terrific, I was able to take the helm for a short time. read more

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A very pleasant time was enjoyed on a two hour Sunset Cruise on a nice hand built schooner. They were at full capacity (28 people) but that was never an issue, and there was space to move about. They allow you to bring your own refreshment, and that makes the entire experience more enjoyable and a bargain! Wonderful scenery, perfect weather, smooth sailing and and a nice Sauvignon Blanc. Kudos to Captain Paul and 1st Mate Jared for keeping things interesting. read more

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Captain Dawson and Cody were excellent! They were both knowledgeable and friendly. We had a gorgeous sail and saw a beautiful sunset. We highly recommend getting aboard one of the Schooners and enjoying the ride! read more

Took the sunset cruise aboard the Eastwind. Was a beautiful night for a sail and the captain and first mate were terrific and the schooner was an amazing vessel. Our only disappointment was the timing. Because of planned fireworks they cut our tour short to add a fireworks viewing sail at 8:45. The cruise was supposed to be from 6:30-8:30 but we were back in dock my 8:15. read more

Hate to say it, but last summer was such a disappointment. I have grown up taking cruises on both the Eastwind and the Bay Lady. The captain complained about putting the sails up, (we have been on sails with them up and down, really doesn't matter as long as the company is good) but he just complained consistently about putting them up which soured the mood for everyone. Needless to say, it was a quiet trip with a group of disappointed people. The captain basically berated our group for using the bathroom ONCE, and told us to stop drinking anything so we would stop having to use the facilities. My family has probably spent around $500 a summer on this boat and we will be forgoing the trip this year. Try the Pink Lady/Island Lady instead for sunset cruises/reggae cruises. read more

Covid actually helped this trip be enjoyable. Because of limited numbers being allowed on the sail boat, it was an extremely hot day and not over crowded. The captain and crew member were so kind and helpful with answering questions. I was nervous to go on, but by the end ready to go again! read more

Schooner Eastwind - Boat Charters Near Me - Boothbay Harbor, Maine

We were so excited for this schooner trip!! We had the last trip of the day , so I imagine the captain was tired. Said there wasn't enough wind to put up the sails & it would just take so much time...... blah, blah, blah....well we go out a little ways & there was definitely enough wind for the sails. He even said so. U can bring alcohol onboard & there was a group with one loud, drunk guy that was just obnoxious. Not enjoyable at all. So, this trip was a basic boat ride with a drunk guy. Do this again? No thanks. read more

I saw this boat sail past our condo every night for a week! I finally talked my husband into going and he absolutely loved it. We have fallen in love with Boothbay and plan to keep coming back . This town is filled with great people and good food and nice cool weather ( what else could you possibly want?) I would highly recommend a trip at sunset on the Schooner / the views were amazing. The captain and first mate were so nice and we were able to bring our own cooler with refreshments. This is a perfect adventure to plan for your next trip to Boothbay Harbor. Worth the expense read more

Schooner Eastwind - Beautiful sailing at sunset - Boat Charters Near Me - Boothbay Harbor, Maine

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Great sail out on a beautiful evening! Capt. John and Megan were great. Funny, engaging and knowledgeable on the history of the harbor.

You can help raise the sails and learn how to steer the boat or enjoy bottled winter (or bring something stronger) and sit back for the gorgeous sail, narrated with cool trivia by the Captain Paul and Seaman Bob. We really loved our two hour schooner ride. Even saw a seal, porpoises, and osprey:) Super stable, 65 foot sloop. read more

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We had a beautiful evening sail and enjoyed talking to the captain/crew. The sunset was gorgeous! Perfect way to end the busy day. After the outing, we walked up to the hill to the Thistle Inn and had the best dinner of our vacation on the lovely patio. read more

This was my first time on a sailboat! Boothbay Harbor has many different sailboat trip options. I am glad that my boyfriend and I choose this option. The trip is so relaxing and the captain and his mate were so kind and funny. The trip was really enjoyable. Booth bay Harbor is so beautiful and this sailboat makes for a great ride. The trip only allows a certain amount of people on sailboat which is an added bonus..it was not crowded. The price of this sailboat was lower than the other sailboats offered in Boothbay Harbor! read more

Excellent sailing August 3 with Captain Paul and Jared. Never sailed before so their operation of the boat was interesting as well as the sites. Very personable and great value. read more

Schooner Eastwind - Boat Charters Near Me - Boothbay Harbor, Maine

just got back from a july 4th trip and took a schooner ride on the 4th with a couple gal friends AWESOME! it was a hot sunny day and we had a cooler with some wine and beer and some cheese and crackers - no problem! the boat was amazingly beautiful and we ended up in countless pics as people on other boats took pics of us! the owner and his mate (young gal with short hair) were lovely and friendly and would chat about whatever you wanted to and knew so much about the shoreline and area we saw an eagles nest and multiple lighthouses and even a seal! worth every penny and i am encouraging anyone who goes to the area to go on this boat! thank you captain bill! read more

Do take this trip! It's worth every penny! We sailed with Sean (the Captain) and Jerry (the mate). It was an absolutely fabulous experience. We had seen the Eastwind sailing the harbor, it is beautiful to watch from afar, even better to actually be on board. Sean and Jerry are low key, knowledgeable, witty and great sailors. Sean was kind enough to pick the one child on board to steer, it was a nice experience for all on board to watch him with the little boy, who was captivated by the experience. There are many choices in Boothbay Harbor, lots of large sightseeing boats, but this was a very unique experience. Maybe 18 guests on board, plenty of room. Because of its 6000 lb keel, the boat rides very evenly and smoothly....every once in awhile we hit some big boat swells which made it more fun, but mostly, it was just a blissfully tranquil sail, coming close to Burnt Island, and Squirrel Island, so we could see the natural habitats, including one bald eagle and plenty of osprey. Well worth the money, and the very best experience!! read more

We had an excellent sail on the Eastwind July 10th with Captain Joe and Mate Mike. It was a highlight of the summer!! Could not have been better in fact it was perfect!! Verna and Ralph Staples read more

The boat is absolutely beautiful, a classic old school wooden schooner. The captain and first mate were friendly, knowledgeable and professional. It didn't hurt that we had a gorgeous early fall day to go out for a sail! It was a great experience! read more

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A good time was had by all. The Captain and Crew (Bob) were great sailors and tour guides. It was a good experience from purchasing our tickets through disembarking. We look forward to doing it again. read more

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We had a wonderful sunset sail yesterday on the beautiful Eastwind. Such fun listening to Doris talk about your time sailing around the world on the boats her and her husband built. read more

Schooner Eastwind - Beautiful night for our sunset sail. - Boat Charters Near Me - Boothbay Harbor, Maine

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Great experience and highly recommended. My wife even got to hoist sails and steer the schooner. So informative and relaxing. Go see Cindy at the ticket booth, she is awesome. We had Captain Tom, Mike and Bob taking great care of us on the trip. They even have blankets & jackets if it gets chilly. Have fun! read more