It's going to be hard to put into words what a great experience we had while sailing on the silver lining cruise. First the boat is a museum piece, if you love sailboats this is what all sailboats should measured against. We left the dock and your on this beautiful boat and the captain is yelling you the history of the boat and the what's we were in and the next thing you know your in the Atlantic sailing. The boat is so smooth and stable you can't believe the boat is heeling over. I own a sailboat, this was one of the best days of sailing I have ever experienced! I would highly recommend sailing the Silver lining when in Perkins cove Maine read more

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This was our second time with Silverlining. Once again it did not disappoint. Captain Jack and Mike were the best. It has the look and feel of being on a friend's sailboat. I would recommend this to anyone just looking to chill with "friends". read more

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

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

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

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

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

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

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

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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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.

Fun cruise with Captain Jack. Great time!

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

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!!!!!!!! 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

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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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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

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

Silverlining Sailing Cruises - Boating Near Me

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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

Silverlining Sailing Cruises - Boating Near Me

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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

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

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

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

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

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

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

Silverlining Sailing Cruises - Boating Near Me

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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

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

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

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

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

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

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

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