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Silverlining Sailing Cruises

5.0 (36 reviews)
Closed • 9:30 am - 8:00 pm

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Alan R.

Excellent experience with Silverlining. The ship was beautiful and they only allow 6 guests which make for a more comfortable experience. Captain Jack and his crew were friendly, great with kids, and very knowledgeable. This was easily worth every dollar. They sail at various times and can be tailored towards a more romantic evening or more family experience.

Sunset Ogunquit, Maine

This was our second sunset sail with Captain Jack and his crew George. Smooth sailing, beautiful boat, and wonderful host. We plan to sail with him again whenever we are in OGT. Highly recommend!

Kayla S.

I took my wife on a sunset sailing cruise with Silverlining for a birthday gift. We arrived at the designated time and boarded the vessel on time. Captain Jack was pleasant but didn't really interact with us much. He spent most of the trip talking with our sailing mates about Florida and how awful it is, and also deterred them from moving to Maine. While the conversation wasn't pleasant, the cruise was gorgeous and relaxing. It isn't something we plan to do again soon, but is probably great for tourists to the area. PS - Maine IS a wonderful place to live, even if your tour guides won't tell you that!

Sunset view
Jaclyn C.

Beautiful sunset sail. Jack, the captain is extremely friendly and pleasant. He allows 6 people at once so it isn't overcrowded and there's plenty of room to move around. The boat ride is slow and relaxing and the sunset is beautiful. We got a slightly longer boat ride than expected due to lack of wind which I definitely did not mind at all.

The sail
Imakayak G.

!!!!!!!! Sometimes words just don't adequately express an experience. This is such a case. $38 is a bargain price for a whole lot of remarkable. This was the highlight of my vacation! Exhilarating experience. Nothing can top the feeling of flying across the ocean at a wicked angle under a deep blue sky with sails whipping overhead. Awesome, awesome adventure. Want more!!!! Captain Jack and his First Mate were warm and personable. Felt like we were among friends. Felt very safe as we sailed at high speeds and crazy ass angles across the Atlantic. Do this!!

Eric S.

Fantastic, relaxing time aboard the Silverlining! Beautiful historic sailboat with a really nice crew. They let us bring a nice bottle of wine aboard to enjoy while we cruised the coast prior to sunset - even kept the white on ice for us. Can't say how much we really enjoyed it - was perfect.

Captain Jack and Elliot we're beyond great. We did the sunset sail, brought a bottle of rose and enjoyed a great ride. I would highly recommend anyone visiting the area schedule (in advance as they do book up quickly) a sail with Silverlining.

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5 months ago

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2 years ago

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8 months ago

We had a great experience with silver lining sailing cruise! It was our first time on a sailing cruise and a fun adventure!

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1 year ago

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1 year ago

Great, friendly crew, made the experience picture perfect! Will absolutely sail again!

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2 years ago

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8 years ago

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3 years ago

We had a wonderful sail this afternoon. With only 6 passengers, there is plenty of room. It was a lovely day. I highly recommend this trip.

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3 years ago

Fun cruise with Captain Jack. Great time!

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12 years ago

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9 years ago

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6 years ago

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19 years ago

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14 years ago

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14 years ago

Awesome cruise, very friendly and knowledgable captain and great value. Highly recommend this to anyone in the area.

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11 years ago

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Ask the Community - Silverlining Sailing Cruises

Review Highlights - Silverlining Sailing Cruises

“. Just tell Captain Jack that John and Kathy sent you and, hopefully, he won't charge more than his regular rate.”

Mentioned in 22 reviews

Read more highlights

The Gift Sailing - A great day of sailing on the maine coast

The Gift Sailing

(13 reviews)

On the annual Maine vacation my family takes, my husband and I decided on a whim to go sailing. We…read moreare huge fans of all things sail, we have a tiny boat ourselves and love to go out on huge boats we have no chance of owning ourselves. While the trip left early (we found ourselves scratching our heads, standing on the dock twenty minutes early), the mistake was an honest one and the boat turned around to pick us up. Once we actually boarded things were off to a good start! I loved that they didn't crowd the boat- we've been on a couple trips on other vessels where every last spot gets taken and you find yourself making serious body contact with strangers. Yes, there was the usual older gentleman sailing aficionado type that wanted to make sure everyone onboard knew how much of a sailing expert he was, but eventually even he settled in... The captain of The Gift is personable and interesting and very chill. There was no need to force conversation, but he was ready with a story, cool facts and answers to questions whenever needed. A couple of people got sick, and the crew was very considerate first pretending not to notice for privacy's sake and then offering water. One thing to note is that the protocol for this sail trip seems to be going out on the water and kind of wandering around. This isn't a trip that happens in the same exact routine way, five times a day, every day of the year. I think this is a great feature, but if you're looking for memorized facts about the coast and one set route of touristy sightseeing, this isn't the trip for you. This one is just about hitting the water and enjoying the wind!

I wish zero stars was an option, as my family had a horrible experience. There were no positive…read moreaspects, but most importantly, the sail is run in an unsafe, irresponsible manner. The boat is small and shabby, and there's insufficient comfortable seating, which meant that some of our party had to be uncomfortably perched on the side of the boat. We couldn't hear anything the entire sail, although we were told we didn't miss much) and for one person, this included the quietly mentioned instructions to move our feet before we turned. Why this wasn't explained loudly before we even left the cove, is beyond me. This led to him almost being pulled off the boat, and with a terrible rope burn that required medical treatment. The "crew" could not have been less concerned, and expressed nothing but annoyance. Even if this had not occurred, the sail would have been painfully boring if we weren't all trying not to vomit from the rough waves. We sailed straight out, straight back in, and then repeated. There truly couldn't have been less effort put in to the experience. Bottom line, if you value safety and competence, avoid this boat at all costs.

Silverlining Sailing Cruises - boating - Updated November 2026

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