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Outer Cape Sailing ‑ CLOSED

Wellfleet, MA, USA
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About Outer Cape Sailing
The Original small boat charter in Wellfleet. Daysail or Sunset sail in scenic Wellfleet Harbor with Coast Guard licensed captain. Go ashore on Great Island for picnics, beachcombing, or swimming. Sailing lessons with US Sailing certified instructor. Affordable, private, and fun. "Not Your Typical Cocktail Cruise." Since 2004.
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Outer Cape Sailing
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124Reviews1Q&A
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Ally4377 wrote a review May 2019
NY6 contributions2 helpful votes
We really enjoyed our sail with the Captain! It was relaxing, fun, beautiful and romantic- even though there were the 3 of us! We brought snacks and wine, and enjoyed them as the sun went down. We highly recommend this outfit.
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Date of experience: August 2018
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kc0ads wrote a review Sep 2018
1 contribution
Absolutely beautiful sunset. Captain was great, answered every question you could possible ask. When we first got on the sail boat one of the people in our party attmitted they couldn’t swim and started to freak out. I was thinking “oh god”. The captain was very responsive, reassuring, and calming to our anxious patron. She actually started to enjoy the ride, with the help of the friendly captain. We were the only ones out on the water and he turned around at the perfect time to see the moon rise. We will definitely be back. Perfect for a gift for friends/familyWarning: this is a smaller sailboat so if small spaces or water are not your thing maybe do not do this sail boat ride
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Date of experience: September 2018
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roci5864 wrote a review Sep 2018
Wolcott, Connecticut1 contribution
I took a chance and booked this trip as a birthday present for my boyfriend. We had never been on a sailboat before and I wanted something fun and experiential. We went on the 2:30 excursion on Sunday, July 24. I switched from Saturday to Sunday because of rainy weather and Gary was very accommodating - luckily the trip was not fully booked. There was another couple on board, and Gary was very knowledgeable about the area. It was a little choppy getting to the beach, and we had to shift weight around from one side to the other - at one point I think the boat was angled pretty sharp to one side, but I thought it was fun! If you think you might get queasy, I would recommend Bonine - my boyfriend took some and he was fine. Bring your own cooler of food and drink if you want. The other couple wanted to go look at seals, while we wanted to swim in the bay. So Gary was able to drop us off for a half hour at the beach to go swimming and picnic, while he took the other couple seal watching. The day was perfect! The beach surrounding the bay was very clean, not that many people when we went. The water seemed a little warmer even in late June, maybe because it's circulating in a bay and not affected as much by the ocean. It was a smooth ride back. Nothing negative to say. We really enjoyed this excursion! This was a fantastic experience and I highly recommend Outer Cape Sailing with Gary!
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Date of experience: June 2018
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zhouchen12 wrote a review Aug 2018
1 contribution
The sailing trip with Captain Gary was great. The sailboat was set up as single handed, so Captain Gary operated jib sheets, main sheets and tiler all by himself, which was incredible. It was a very windy day, but he sailed really smoothly. Hopefully we will find time to sail with Captain Gary again!
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Date of experience: August 2018
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NavyGator1982 wrote a review Aug 2018
St. Petersburg, Florida14 contributions2 helpful votes
My wife and I plus another couple took a 4 hour charter and it was perfect. Amazing experience and time. Captain Gary was awesome!
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Date of experience: August 2018
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