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Outer Cape Sailing

Closed Now: 08:30 - 20:30
Open today: 08:30 - 20:30
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Review Highlights
Perfect

Absolutely beautiful sunset. Captain was great, answered every question you could possible ask... read more

Review collected in partnership with this attraction

Reviewed 2 weeks ago
kc0ads
Great Experience - Fantastic Time!

I took a chance and booked this trip as a birthday present for my boyfriend. We had never been on a... read more

Reviewed 2 weeks ago
roci5864
,
Wolcott, Connecticut
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Traveller Overview
  • Excellent93%
  • Very good4%
  • Average3%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain gary”(13 reviews)
“small boat”(5 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: 08:30 - 20:30
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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 reviewscaptain garysailing experiencesmall boatday sailouter capegreat captainprivate saillovely afternoonmagnificent sunsetsunset cruisewellfleet harborhighlight of our tripamazing experiencelow tidelots of funwindskiing
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1 - 10 of 122 reviews
Reviewed 2 weeks ago

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
Thank kc0ads
Reviewed 2 weeks ago

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

Thank roci5864
Reviewed 3 weeks ago

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
Thank zhouchen12
Reviewed 3 weeks ago

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
Thank NavyGator1982
Reviewed 3 weeks ago

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
Thank KEEP_KIDS_SAFE
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded 3 weeks ago

Thanks a lot! Glad you enjoyed it.

Reviewed 3 weeks ago

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

Thank Gwendolyn H
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded 3 weeks ago

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 3 weeks ago 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

Thank Jared T
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded 3 weeks ago

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 4 weeks ago

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

Thank CelticCail
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded 3 weeks ago

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 4 weeks ago

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
Thank vivigcouture
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded 3 weeks ago

Thanks a lot!

Reviewed 4 weeks ago

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

Thank ebport
GaryFlo, Owner at Outer Cape Sailing, responded to this reviewResponded 3 weeks ago

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
18 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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