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Outer Cape Sailing

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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Hours Today: 8:30 AM - 8:30 PM
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Outer Cape Sailing
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Reviews (124)
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All reviews captain gary outer cape sunset sail sailing trip small boat wellfleet harbor great lesson beach excursion smooth ride magnificent sunset perfect location great sail amazing experience private beach great afternoon picnic lunch family experience
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Reviewed May 19, 2019

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.

Date of experience: August 2018
Thank Ally4377
Reviewed September 4, 2018

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...More

Review collected in partnership with this attraction
Date of experience: September 2018
Thank kc0ads
Reviewed September 3, 2018

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...More

Date of experience: June 2018
Thank roci5864
Reviewed August 30, 2018

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...More

Review collected in partnership with this attraction
Date of experience: August 2018
Thank zhouchen12
Reviewed August 28, 2018

My wife and I plus another couple took a 4 hour charter and it was perfect. Amazing experience and time. Captain Gary was awesome!

Review collected in partnership with this attraction
Date of experience: August 2018
Thank NavyGator1982
Reviewed August 26, 2018

We thoroughly enjoyed the suset cruise with Captain Gary! A quiet sail around the Bay with a stop in the perfect place to watch the sun set, and the full moon rise while we enjoyed the snacks and wine that we brought. Gary was knowledgeable...More

Review collected in partnership with this attraction
Date of experience: August 2018
Thank KEEP_KIDS_SAFE
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded August 27, 2018

Thanks a lot! Glad you enjoyed it.

Reviewed August 26, 2018

We had a wonderful time sailing with Gary. He knows the bay like the back of his hand and can find fun trips to take even in difficult weather. We caught a striped sea bass while we were out the other day. Out at Jeremy...More

Date of experience: August 2018
Thank Gwendolyn H
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded August 27, 2018

Thanks for the great review and providing some details that I sometime forget to mention such as fishing when fish are feeding in harbor, birds nesting, seals swimming, great shell collecting and warm water to swim in, all at Jeremy Point.

Reviewed August 26, 2018 via mobile

I spent a week sailing with Gary, taking a beginning sailing course. Despite having taken courses from another organization, I did not feel confident in my abilities. His clarity and patience allowed me to finally feel comfortable on the water. Anyone who Has the chance...More

Date of experience: August 2018
Thank Jared T
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded August 27, 2018

Jared, thanks for the great review! it was a pleasure working with you. You are far better than you think you are. You really got the feel for it last week.

Reviewed August 24, 2018

I booked the OTHER sailing out of the exact same point to the exact same point for the morning we went out but that captain e-mailed to say he had a "scheduling conflict" for that day. Um, isn't the point of us reserving our spot...More

Date of experience: August 2018
Thank CelticCail
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded August 27, 2018

Thanks for the detailed comments and positive review. It was very rough that day, and you were good sports to go. I was definitely focussed on sailing the boat. You raise some good points about the leaning of the boat in high winds, and the...More

Reviewed August 24, 2018

Garry had fun stories to tell as well as knowledge of the area. The secluded beach is beautiful and the waters are warm. Lovely day!

Review collected in partnership with this attraction
Date of experience: August 2018
Thank vivigcouture
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded August 27, 2018

Thanks a lot!

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Questions & Answers
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deidrey2014
June 18, 2018|
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Response from Gary F | Property representative |
Service dog is allowed onboard, but only on private sail. Also not allowed onshore at Jeremy Point due to bird nesting. Dog Gone Charters in PTown is more dog friendly. Capt Gary
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