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Outer Cape Sailing

Closed Now: 8:30 AM - 8:30 PM
Open today: 8:30 AM - 8:30 PM

Outer Cape Sailing
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Traveller Overview
  • Excellent93%
  • Very good4%
  • Average3%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain gary”(31 reviews)
“sailing trip”(8 reviews)
“sunset sail”(15 reviews)
About
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...more
Closed Now
Hours Today: 8:30 AM - 8:30 PM
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Suggested duration: 2-3 hours
Contact
Town Pier, Wellfleet, MA 02667
Website
+1 508-237-4012
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Reviews (123)
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All reviews captain gary sailing trip sunset sail outer cape small boat great sailing wellfleet harbor great weather lovely afternoon beach excursion answered our many questions smooth ride hour cruise magnificent sunset perfect location amazing experience private beach
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1 - 10 of 122 reviews
Reviewed 5 September 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 4 September 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 31 August 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 28 August 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 27 August 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 28 August 2018

Thanks a lot! Glad you enjoyed it.

Reviewed 27 August 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 28 August 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 26 August 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 28 August 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 25 August 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 28 August 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 24 August 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 28 August 2018

Thanks a lot!

Reviewed 24 August 2018

It's all about the captain! We had dicey weather that threatened to keep us ashore, but we agreed to give it a shot, and the sail was wonderful. Gary kept us chatting the whole way on a variety of different topics, from sailing to teaching...More

Date of experience: August 2018
Thank ebport
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded 28 August 2018

Thanks for being good sports about the weather, and for the great review. I enjoyed your company.

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Questions & Answers
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deidrey2014
19 June 2018|
Answer
Response from GaryFlo | 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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