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Address: Town Pier, Wellfleet, MA 02667
Phone Number: +1 508-237-4012
Website
Today
8:30 am - 8:30 pm
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Hours:
Sun - Sat 8:30 am - 8:30 pm
Recommended length of visit: 2-3 hours
Description:

Daysail or Sunset sail in scenic Wellfleet Harbor with Coast Guard licensed...

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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TripAdvisor Reviewer Highlights

Read all 26 reviews
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Amazing day sailing with Outer Cape Sailing

Booked this hoping for something different to do while on vacation. Now it will be a go to every year. Had the best time. Gary was informative, knowledgeable and made the... read more

5 of 5 starsReviewed yesterday
ColoradoCapelover
,
Colorado
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26 Reviews from our TripAdvisor Community

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Showing 26: English reviews
Colorado
Level Contributor
24 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed yesterday NEW

Booked this hoping for something different to do while on vacation. Now it will be a go to every year. Had the best time. Gary was informative, knowledgeable and made the outing all we hoped for. Our bonus was that we were able to go to the submerged island of Billingsgate Island due to the extreme low tide. Highlight for... More 

Helpful?
Thank ColoradoCapelover
Providence, Rhode Island
1 review
5 of 5 stars Reviewed 3 days ago NEW

Took a sailing lesson from Outer Cape Sailing...fantastic teacher, patient and explained sailing terms terms and boating terms and beginning sailing very well. It was really very windy for our first lesson but he guided us through each step and we had a blast! Can't wait for Lesson 2!

Review collected in partnership with this attraction

Helpful?
Thank jan s
Pittsburgh, Pennsylvania
1 review
5 of 5 stars Reviewed 5 days ago NEW via mobile

We had a fantastic afternoon with Gary! His boat and skipper skills were perfect! This is not your normal pleasure cruise around the harbor on a large boat with lots of others. This was a real sailing experience in a private setting!!! Our kids (ages 7 & 11), my husband and I had a wonderful time! Gary was very knowledgeable... More 

Helpful?
Thank rjjyates
GaryFlo, Owner at Outer Cape Sailing, responded to this review

Thank you so much for your kind review. It was a beautiful day, and I'm glad you had such a good time. You forgot to mention two attempted hat rescues, one successful! :-) Best wishes, Capt. Gary More 

Springdale, Arkansas
1 review
5 of 5 stars Reviewed 6 days ago NEW

Very nice for 3 people. Little jaunt out to the island for cheese and wine (bring your own)was great. Captain was pleasant and capable. I recommend for good value. Do not recommend for more than 3 guests.

Review collected in partnership with this attraction

Helpful?
Thank Diana P
Level Contributor
42 reviews
18 attraction reviews
common_n_attraction_reviews_1bd8 15 helpful votes
3 of 5 stars Reviewed 1 week ago via mobile

I had been on a sailboat sunset cruise before which was amazing so my expectations were high...sorry to say I was disappointed. The sailboat is small and it was hard to get comfortable. The captain kept asking us and another couple to help with ropes to the sails the entire sail time. The boat was cluttered and my shoes got... More 

Helpful?
Thank Mascarell
Cambridge, Massachusetts
1 review
5 of 5 stars Reviewed 1 week ago

We had a great time on this day sail trip. We were more than 6 (max number of people that can fit on a boat) so Gary arrange another boat for us with one of his colleague. Since the second boat arrived a bit late with half of us in it, Gary let us stay longer than usual on Point... More 

Review collected in partnership with this attraction

Helpful?
Thank sarahlV8409UC
GaryFlo, Owner at Outer Cape Sailing, responded to this review

Thanks Sarah! It was a beautiful, fun day. Capt. Gary More 

1 review
5 of 5 stars Reviewed 2 weeks ago via mobile

We went on the sunset sail. It was very relaxing and Gary was a great captain. A highlight was seeing the sunset on the water. Very good way to spend the evening!

Helpful?
Thank Stephen F
Wappingers Falls, New York
1 review
5 of 5 stars Reviewed 2 weeks ago

Cap't Gary is awesome! We have been sailing with him for many years, and each year is better than the last. Gary has historical, environmental, and local stories to entertain his visitors, he is easy going and an incredibly safe captain. The best adventure in the area!

Review collected in partnership with this attraction

Helpful?
Thank jenipete
GaryFlo, Owner at Outer Cape Sailing, responded to this review

Thanks Jennifer, So nice to see you and Peter and your kids every year. Capt. Gary More 

Alexandria, Virginia
1 review
5 of 5 stars Reviewed 2 weeks ago

Gary was friendly and provided us with a wonderful afternoon on the water with a quick stop on a private beach where we watched the seals, looked for sea glass, and had a quick picnic. Epic day!

Review collected in partnership with this attraction

Helpful?
Thank alissawendy
1 review
5 of 5 stars Reviewed 3 weeks ago

we went on a afternoon sail from Wellfleet harbor out to Jeremy Point where we stopped at a beach. Our skipper was very informative and pointed out all the nearby attractions while also discussing the basis uses of the lines, sheets, cleats, and sails on his boat. we hope to take sailing lessons with him next year - lots of... More 

Helpful?
Thank Kay B
GaryFlo, Owner at Outer Cape Sailing, responded to this review

Thanks so much Kay, I hope to see you next time for lessons. Capt. Gary More 

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