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Silverlining Sailing
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Traveler Overview
  • Excellent96%
  • Very good2%
  • Average1%
  • Poor1%
  • Terrible0%
Travelers talk about
“captain jack”(48 reviews)
“silver lining”(11 reviews)
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Perkins Cove Road, Ogunquit, ME 03907
+1 207-646-9800
Most Helpful Positive Review
Reviewed October 11, 2014

My wife and I have sailed several times with Captain Jack on the Silverlining. Captain Jack is also the owner of the boat and keeps it very clean and well maintained. The captain and his first mate Elliot are very friendly and knowledgeable about sailing,...More

6  Thank JAC02048
Most Helpful Critical Review
Reviewed August 16, 2017 via mobile

I sailed the silver lining with my family (including 2 small children) and it was less than satisfactory...The captain almost sailed right into another charter boat which was carrying it's own passengers...Very scary and unsafe experience. Not impressed. Will be sure to sail a different...More

1  Thank sammybabyy
Jack G, Owner at Silverlining Sailing, responded to this reviewResponded August 18, 2017

Madame, I am very sorry to hear that you had an unsatisfactory experience while sailing out of Perkins Cove. However, you and your family were not on our boat. I see that you also wrote a glowing review for 'the gift" I am assuming your...More

Reviews (135)
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All reviews captain jack silver lining beautiful boat sailing experience sunset sail real beauty true sailing amazing experience relaxing afternoon great adventure great captain maine coast perkins cove ogunquit area mother nature lobster new england
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1 - 10 of 132 reviews
Reviewed 2 weeks ago

Our sail on The Silver Lining was as good as we hoped for. It was really an excellent experience. Captain Jack is knowledgeable about Perkins Cove and the coast nearby for sure, and he made it a very interesting and fun time in addition to...More

Thank JJB105
Reviewed October 9, 2018

Captain Jack was awesome! We were so impressed with the quality and the appearance of this 1938 sailing craft. Care and perfection are an obvious "musts" of the upkeep of the boat. He does an amazing job of keeping the boat "original". We thoroughly enjoyed...More

Thank AMP0907
Reviewed September 13, 2018 via mobile

We took the 11:30 cruise with Silverlining sailing out of Perkins Cove in Ogunquit. The boat itself is a beautiful maintained sloop and one of the things we appreciated is that they limit each trip to only six guests so that the boat is not...More

Thank grbroucek
Reviewed September 6, 2018

We found Silverlining Sailing in the "local activities" section of the guide book in our cabin in York. We booked a sunset cruise on a small sailboat. The day of the cruise, Silverlinings called us and said the sea was too rough and the sail...More

Thank Alexis James B
Reviewed September 5, 2018 via mobile

Delighted to spend 2 hours relaxing on the water in good hands with a very competent, experienced and charming Captain. Look forward to returning!

Thank kalis43
Reviewed September 4, 2018 via mobile

My friend and I booked a 2 hour sail just for fun and relaxation. Silverlining did not disappoint. The boat was absolutely beautiful. We were fortunate enough to have perfect sailing weather. Everything was just as described. Would definitely recommend!

Thank ErinM2790
Reviewed September 1, 2018 via mobile

My husband is an experienced sailor and this was my first time on a sailboat. The captain and mate were super friendly and the boat ride was amazing. I definitely made the right choice booking this sailing trip for my family.

Thank Aliza S
Reviewed August 27, 2018

This is a magnificiant boat, smaller than other option (which are nice) but this one is great. Reserve in advance, always quite full. The captain is knowledgeable, and you feel what sailing means. It can be cold on the water, bring sweather. La meilleure expérience...More

1  Thank chalifouxh
Reviewed August 12, 2018 via mobile

This trip was the highlight of our week in Ogunquit. Jack and Julian could not have been nicer. Total relaxation, beautiful view of the coast. Could not ask for more!

Thank pckeefe1207
Reviewed August 12, 2018 via mobile

I invited 2 friends sailing recently, one who was concerned as he is not a “boat person”. After spending 2 hours on The Silverlining, he wants to make sure that I book again next summer. The boat is extremely well maintained, a real beauty, and...More

1  Thank Howard D
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Questions & Answers
Ask a question
Annette G
July 9, 2018|
AnswerShow all 2 answers
Response from JackG386 | Property representative |
I’m sorry Annette, we are full on Thursday, our next available space would be Sunday at 9;30
Kayla S
June 18, 2018|
Response from JackG386 | Property representative |
This is up to your discretion. Most people do,some don’t. If you tip the captain,he shares with his crew. Thanks for asking.
February 23, 2018|
Response from JackG386 | Property representative |
Hi, I would reserve several weeks in advance. Times and fees vary please visit our web site for more information