Silverlining Sailing Cruises

5.0 (32 reviews)

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Silverlining Sailing Cruises - Sunset Ogunquit, Maine - Boating Near Me

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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!

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.

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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Alan R.

Elite 26 All-Star

16

330

932

1 year ago

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. read more

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Ms D.

0

6

0

3 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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Shelley R.

0

20

5

8 months ago

We had a private 1 1/2 hour sail out of Ogunquit on a beautiful autumn evening. Our captain was great, answered our questions and gave us a lovely sail. read more

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Julie B.

0

3

0

1 year ago

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

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Tricia C.

0

4

3

2 years ago

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! read more

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Rand R.

2

162

2

4 years ago

Great boat Great captain, nice guy and really good stories Great mate Great price Great views Parking can be an issue but they warn you about that ahead of time so come early so you're not stressing read more

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Nelly S.

0

2

0

3 years ago

It was beautiful, fun and educational. Captain Jack is very knowledgeable on nautical information, in addition to marine wildlife and local food and traditions. There are many cruise/sailing choices at Perkins' Cove, but this one is the most unique and the best. Don't miss it!! read more

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Kayla S.

Elite 18

62

92

109

8 years ago

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! read more

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Amy W.

1

35

2

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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Steve M.

0

17

0

3 years ago

Fun cruise with Captain Jack. Great time!

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Denise B.

5

22

1

5 years ago

What a great experience. Captain Jack and crew are the best. He is really full of info regarding his boat, the surrounding area. Can't wait to do this again. read more

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Jaclyn C.

22

39

37

12 years ago

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. read more

Silverlining Sailing Cruises - Sunset view - Boating Near Me

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Imakayak G.

33

38

32

12 years ago

!!!!!!!! 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!! read more

Silverlining Sailing Cruises - The sail - Boating Near Me

Silverlining Sailing Cruises - The Silverling - Boating Near Me

Silverlining Sailing Cruises - In the capable hands of Cap'n Jack - Boating Near Me

Silverlining Sailing Cruises - We're sailing!!!! - Boating Near Me

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Eric S.

Elite 24

11

186

114

9 years ago

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. read more

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Christy F.

11

5

0

6 years ago

What a great way to spend a hot sunny summer afternoon. Capt. Jack's boat was as beautiful as the weather. Jack was engaging with information about the area, the seas and the boats history. Quiet if you wanted to enjoy the peacefulness of the sea. You can bring food and drink aboard to make the trip a real pleasure. read more

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Sami H.

731

4

2

6 years ago

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. read more

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Eric R.

0

7

2

6 years ago

If you want an amazing trip book this gem of a boat. We had a wonderful time. You won't be disappointed with captain Jack. read more

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John G.

2

9

0

19 years ago

Take a sail on the Silver Lining and meet the REAL Captain Jack. Fourteen years ago, my wife and I got married on this beautiful, wooden, 1939 Hinckley 42-foot sailboat and we sail with Captain Jack every time we visit Ogunquit - most recently in late July 2007. For $33 per person (maximum of 6 passengers) you get a 90-minute cruise that takes you from Perkins Cove through the harbor and out into the Atlantic. Once the sails are raised, you're free to walk around the deck, take pictures of yourself standing at the bow with the Ogunquit shoreline in the background, or just sit and sip that bottle 'o rum you brought onboard. It's a totally peaceful, relaxing 90 minutes on the water that you'll never forget. Just tell Captain Jack that John and Kathy sent you and, hopefully, he won't charge more than his regular rate. read more

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Mary J.

0

19

0

5 years ago

We thoroughly enjoyed this relaxing, laid-back experience. Captain Jack and First Mate Keenan were pleasant, knowledgeable, and funny. If you want constant narration, this is not the charter for you. But if you want tranquil smooth sailing, by all means sign up! The scenery around Perkins Cove and Ogunquit is just so beautiful!! There are only 6 passengers, so it never feels crowded. My husband and I are power boaters, so it was nice to enjoy a different way to access the water and see the sights. read more

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Lizzie P.

4

11

0

8 years ago

Terrific way to relax while visiting Ogunquit. Captain Jack was great fun and a great host. We Surprised our mother/grandmother with the 4:30 PM to 6:00 PM sail and the timing couldn't have been better. Bring some wine and cheese and enjoy the beautiful Maine coast! read more

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Stephanie S.

48

57

3

12 years ago

My family & I have been sailing with Captain Jack for years - at least a decade. He is personable & knows a lot about everything, from who's building along the Marginal Way to where his sails were made. His sails are small (no more than 6 guests) and beautiful. Lasting about 1.5 hours, they are the perfect duration. Don't forget to bring your own snacks & beverages. read more

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Tracey H.

0

7

0

8 years ago

We did the 2-4pm sail and had a very relaxing afternoon on the water. We packed a cooler of snacks and Mimosa to celebrate our friends upcoming wedding. Captain Jack and the crew were friendly and fun, by the end of the sail we felt like old friends. We have sailed other boats but this one was by far the best experience yet. We will be back again for sure!!!! read more

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Jay D.

0

7

3

11 years ago

Don't ask, just do it. We had the best sailing tour aboard this boat. It was so relaxing to be on the water with no sound of an engine. The captain is a true professional and is happy to answer any sailing questions or question about the area in general. The sailboat is amazing; beautifully restored and comfortable. Anyone who is interested in a boating tour in Maine needs to take this trip! Don't hesitate, it will be the highlight of your trip for sure. Call ahead to book your slot because spots seem to fill quickly. He allows 6 people per outing which gives this activity a very personable feel. Do yourself a favor and book today! read more

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Emma K.

1

6

2

10 years ago

Captain Jack and Dan were both amazing. My family went out off Perkins Cover and had the perfect day sailing. Jack and Dan were extremely genuine, telling great stories and giving us great insight into sailing and restaurants around the area. I highly, highly recommend taking a sailing trip on the Silverlining if you are in the South Maine area! Thanks guys!!! read more

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Mary M.

1

116

5

10 years ago

We thoroughly enjoyed sailing with Captain Jack on his beautiful sailboat. $40 dollars a person and it was well worth it. The Captain and his Mate Bryan were very personable and friendly. We learned a lot about Maine during the trip and had fun. We would definitely sail with Silverlining Sailing Cruises the next time we return to Maine. Just 6 guests at a time for 1 1/2 or 2 hours. read more

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Lucie B.

0

3

0

14 years ago

We had a great experience on a 90-minute sunset cruise on The Silver Lining. Captain Jack is very knowledgable about the area, from it's glacial past to present day. He only accepts 6 passengers on the 42-foot sloop, which makes for a comfy intimate sail that feels like a private charter. There were only 4 passengers when we went out. Peaceful. Quiet. Relaxing. A great way to experience Maine's southern coast! read more

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Deepinder G.

0

2

0

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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Jody W.

0

5

1

11 years ago

Our family had an amazing time on our sunset cruise. We can't recommend it highly enough. The 6-person maximum makes for an intimate and unique experience. Captain Jack is both the consummate professional and the most hospitable captain. We loved learning about the history of his vessel and chatting with him and his first mate - Alex. Unfortunately the time flew by too fast on what was a perfect evening and sunset. Don't miss this highlight of Ogunquit - book in advance!!! read more

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Mary Ann R.

1

35

0

10 years ago

a wonderful sail, Captain Jack is such an experienced and accomplished sailor that you will immediately be at ease. We had a wonderful time and enjoyed every minute, including our opportunity to meet and talk with such a a friendly and engaging Captain. If you are anywhere close and want a great sailing experience, go to Silver Lining Cruises in Perkins Cove, Oqunquit ME. read more

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Tobias R.

0

4

0

14 years ago

My only complaint is that we didn't take a long enough cruise. We went out for 1.5 hours and it was a blast. Captain Jack has a beautiful 42' boat and his crew was great. Absolutely a great way to spend some time in Ogunquit. read more

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Joe H.

0

3

0

14 years ago

An incredible value for an unforgetable afternoon. Jack and his crew offer a tremendously wonderful experience from start to finish. So excited to have finally found that elusive 'friend with a boat.' Can't wait for our next trip. read more

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Cindy B.

2

60

29

11 years ago

Amazing experience! Captain Jack and his First Mate, Alex, were awesome! We had a wonderful time and they were the perfect hosts! Very relaxing and they made you feel right at home! Did a 2 hour sail, had a blast! read more

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More info about Silverlining Sailing Cruises

Ogunquit, ME 03907
Directions
(207) 646-9800
Call Now
Visit Website
http://www.silverliningsailing.com

Payment methods

Does Silverlining Sailing Cruises take Bitcoin?

No, Silverlining Sailing Cruises does not take Bitcoin.

Does Silverlining Sailing Cruises take credit cards?

Yes, Silverlining Sailing Cruises takes credit cards.

Indoor Amenities

Does Silverlining Sailing Cruises allow dogs?

No, Silverlining Sailing Cruises does not allow dogs.

Outdoor Amenities

Does Silverlining Sailing Cruises have bike parking?

Yes, Silverlining Sailing Cruises has bike parking.

Does Silverlining Sailing Cruises have parking?

Yes, Silverlining Sailing Cruises has parking options.

Other Amenities

Is Silverlining Sailing Cruises wheelchair accessible?

No, Silverlining Sailing Cruises is not wheelchair accessible.

Does Silverlining Sailing Cruises have free WiFi?

No, Silverlining Sailing Cruises does not have free WiFi.

From the Business

Specialties

1 1/2and 2 hour Private and semi private sailing excursions on classic wooden sailing vessel.

History

Established in 1983.

While limiting each cruise to six passengers, Silverlining Sailing has be providing fun and relaxation to thousands of customers annually in an uncrowded, intimate setting. Sailing 5 times daily at 9:30, 11:30, 2, 4:30 and 6:30. Reservations are suggested

Meet the Business Owner: John T.

50 years of sailing experiences USCG licensed captain since age 19 Repairs,restores and assists in building wooden boats during the off season

More Info

Hours

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 21 reviews

Read more highlights

Finestkind Scenic Cruises

(76 reviews)

Great lobster tour. Perfect amount of time to see activity and not too much else going on. Very…read morenice crew and what a nice ride and view!

We did a 1pm Nubble Light cruise September 3, 2025. It was the perfect early fall day--sunny,…read moreclear, temps in the low 70s--for a cruise down the coast to see the lighthouse from all the other angles you can't from Sohier Park. Captain Bob was our captain, and Matt narrated the journey (among other things like getting drinks). Matt was an EXCELLENT tour guide. The historic stories were fascinating, and we felt we learned so much! He was hilarious, too. The vessel itself was sturdy & clean, and I felt very safe. What a thoroughly enjoyable experience! We'll be checking out other tours next summer.

The Gift Sailing

(13 reviews)

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.

Great bunch of guys , good local flavor fair price, you'll love it just do it. It's one thing to go…read moreon a motorboat on the coast of Maine, but it's another thing to sail.

Casco Bay Custom Charters

(20 reviews)

I highly recommend Casco Bay Custom Charters…read more We sailed with them for a special family event in July 2020. We gathered to release our father's ashes at sea. The team we worked with to plan the event were flexible with our plans including location, departure, and the actual release. They provided helpful information about purchasing a biodegradable urn and how to structure our minimal program - especially as we had young children participating (ages 4-11). They will work with you to create your ideal experience.

Our small family really enjoyed this private charter experience. The crew was super friendly and…read morevery knowledgeable. The boat was comfortable and the tour included some hardy snacks and drinks. Would highly recommend this company to anyone looking for a private Charter tour in the area.

Cove Runner

(1 review)

We took a trip from Perkins Cove to Kennebunkport as a way to sightsee and add something different…read moreto our annual trip to Ogunquit. Captain Bob is friendly, courteous, communicated well for planning, and has a nice boat for a party of 4-6. We would love to do another trip with Captain Bob.

Bunny Clark Deep Sea Fishing

(26 reviews)

You can't find a better boat anywhere! In short, the captains (Tim and Ian) are exceptional as is…read morethe mate (Danny)! They practically put the fish on the hook for you. If there's ever been an asshole on the boat, o haven't encountered him or her and it's hard to miss someone when the boat is capped at 20 fishermen. My dad has been going out on the Bunny Clark since the 80s and me with him since age 12. When I was young we started with a 3 hour tour then increased over time. My dad used to do the marathon trips but now sticks with the extreme day and this has become an annual or semiannual trip for us together, maybe with a friend or two. The vessel is basic (exactly what is needed) but the people and experience are exceptional. Bring cash to tip the mate who will filet your fish for you plus extra if you want to buy flies, bait, and put into any of the pools they may have going. Parking nearby is $10 per car in Perkins Cove which you can't beat.

Was great! Never been deep sea fishing but Boyfriend insisted i go for day and to say the least…read morewill definitely go again. Crew on boat VERY helpful and attended to everyone on boat. Crew had great personalities and I laughed so much. Thank you to them for a awesome day and experience.

Sail ME

(8 reviews)

Great experience...we did an afternoon sail, which was great. . Loved our cruise...boat was great…read moreand loved the small group experience. Very relaxing and the crew was informative and really knowledgeable. Would highly recommend...you won't be disappointed.

Beautiful afternoon on the water! So relaxing, would highly recommend to anyone visiting town…read more Amazing captain and crew, very knowledgeable and friendly. Perfect way to spend a summer afternoon!

Salty Lewer Fishing

(12 reviews)

Bryan is knowledgeable, experienced and showed a lot of patience with this inexperienced fisherman…read more The fish just weren't biting that morning, none of the other charters had much success, either. What matters is that we got an individualized fishing trip - it's called fishing, not catching!

Had a great time! Caught some fish and enjoyed the ride. Just went for a casual outing, not a…read moreserious day of fishing. The 2 hour tour was the perfect length and so enjoyable!

New England Eco Adventures

(6 reviews)

Great experience! Make sure to read the details of the meeting point ahead of time, since the bar…read moreaddressed suggested is several storefronts down from where you need to be. The email is helpful. The boat is comfortable and the crew did an amazing job of circling each point of interest both ways, and making sure folks on the "good" side stayed seated so everyone could see at all times. The speed of the boat is amazing. Really a fun experience. You will be reminded to tip MANY times, just FYI.

New England Eco Adventures Portland. Amazing!!!! Up close hump back whale (Mom and calf) Photos and…read morevideo speak for themselves

Breakwood Fishing Adventures

(1 review)

Larry and Matt did a wonderful job trimming a large maple tree that was encroaching on our house in…read moreWells ME with some branches already touching the roof. They also removed another dead tree behind our home and cleaned everything up beautifully! I was impressed with their combination of friendliness and professionalism. In addition, Larry and Matt provided expert opinions on the safety status of a few other trees growing close to our home. We will definitely work with Breakwood Tree adn Excavation again in the future when needed. Thanks!

From the owner: We are a Fishing Charter/Guide Service. Fishing for all species specializing in Trophy Striped Bassread more

Captain Joe's Cruises

(7 reviews)

We had an absolutely fabulous time with Captain Joe over 4th of July weekend. Perfect date night…read moreactivity! Very pleasant ride up the Saco River and back down to the ocean. The views were amazing. Joe was so personable, accommodating, and knowledgeable. We loved learning all the fun facts he had to share with us. Would definitely go again next time we visit Maine.

The whole package, love, love, love! Joe is probably one the friendliest and knowledgeable people…read morein Maine. As a native he knows a lot of the local history and loves to share it with his passengers. He truly has a passion for boating and entertaining. Joe offers the sweetest boat tours. My boss rented a boat just like this for a corporate event and it was a huge hit! Tips: Fishing poles are provided but let them know about fishing in advance so the best bait can be supplied. There's an emergency bathroom on the boat but a better bathroom to use is at the marina and he's able to make stops. Let him know before you get on if you want to swim and he'll take you to a great swimming spot. I use a floaty in the water because I get nervous and it was fine. The boat fits comfortably four adult guests and five if one guest is a child. The boat ride was quite relaxing. We stayed in the river and only ventured into Saco Bay once Captain Joe determined it was going to be a comfortable for everyone.

Why does Yelp recommend reviews?

Hundreds of millions of reviews are posted on Yelp, and our automated recommendation software works in the background to showcase the reviews that it …

5 reviews that are not currently recommended

The reviews below are not factored into the business's overall star rating.

Rose M.

10

3

0

9 years ago

This was the highlight of a fabulous Maine vacation! Capt Jack is a local and is very knowledgeable in things from from sailing, to real estate, to the lobster business, and more, keeping us entertained throughout our sunset cruise. He's been doing this for 25 years but seems to enjoy every trip. Afterwards, we just couldn't stop talking about how great it was. And if you have any fear of sailing, fear not. It was a peaceful, almost flat sail. All you hear is the water moving. If you are a sailing enthusiast, you'll be sure to love this classic Hinckley, I believe the oldest existing one on the water. He may let you talk the helm. And its a bargain - less than our dinner! I can't wait to go back! read more

Quinny Q.

0

1

0

8 years ago

Amazing Adventure!! "Bachelorette - The Day After"!! We set sail at 2pm on Sunday (the day after the bachelorette), beautiful weather and very relaxing afternoon on the water. We packed a cooler of snacks and Mimosa's to celebrate the upcoming wedding. Captain Jack and the crew were friendly and fun, by the end of the sail we felt like old friends. We have sailed other boats but this one was by far the best experience yet. We will be back again for sure!!!! read more

Christian C.

0

9

0

8 years ago

Captain Jack will get you high tonight...and take you to your special island! We lucked out having the boat to ourselves on a windy sunset-swept ocean - perfect sailing conditions. Captain Jack has been sailing for almost 38 years and it shows in his level of experience. I If you are looking for sailing and nothing else, go with Captain Jack. The boat itself is a relic of WWII and made entirely of wood! read more

Johnny S.

0

2

0

5 years ago

This was an absolute blast for me and my family. Capt. Jack and his First Mate Livy were fun and knowledgeable about sailing and Ogunquit. They were a pleasure to talk to. The sailboat was big and comfortable. The sail itself was relaxing and pleasurable with an easy pace on the sea and a smooth sail. This was definitely one of the highlights of my trip !!! read more

Wendy M.

337

6

2

9 years ago

Our second year sailing on Captain Jack's beautiful wooden boat. Loved hearing how he got started and the details about his boat which is the oldest working sailboat made by Hinkley. He's a great host and told us about a restaurant off the beaten path that was wonderful. Highly recommended! read more

Silverlining Sailing Cruises - boating - Updated May 2026

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