We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Outer Cape Sailing

Town Pier, Wellfleet, MA 02667
Save
Review Highlights
Great Private sail

I highly recommend this sail to anyone looking for a nice, peaceful inexpensive sailing experience... read more

Reviewed 5 September 2017
jackiepalmieri
,
Stratford, Connecticut
Sailing into a magnificent sunset with a great captain

One of the great things about Cape Cod is the sunset and a wonderful way to see this sunset is from... read more

Reviewed 3 September 2017
Leonard H
,
New Haven, Connecticut
Read all 77 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
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.
  • Excellent93%
  • Very good5%
  • Average2%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain gary” (18 reviews)
“sunset sail” (9 reviews)
“great sailing” (5 reviews)
Closed Now
Hours
Hours Today: 8:30 a.m. - 8:30 p.m.
Suggested Duration: 2-3 hours
LOCATION
Town Pier, Wellfleet, MA 02667
Write a ReviewReviews (77)
Traveller rating
Traveller type
Time of year
Language
All reviews
"captain gary"
in 18 reviews
"sunset sail"
in 9 reviews
"great sailing"
in 5 reviews
"outer cape"
in 18 reviews
"sailing experience"
in 4 reviews
"lovely afternoon"
in 2 reviews
"wellfleet harbor"
in 6 reviews
"answered our many questions"
in 2 reviews
"great conversation"
in 2 reviews
"hour cruise"
in 2 reviews
"great company"
in 2 reviews
"once in a lifetime"
in 2 reviews
"local history"
in 3 reviews
"saw seals"
in 2 reviews
"low tide"
in 2 reviews
"wind"
in 15 reviews
"sails"
in 6 reviews
Filter

1 - 10 of 77 reviews

Reviewed 5 September 2017

I highly recommend this sail to anyone looking for a nice, peaceful inexpensive sailing experience. Gary our captain was very friendly, interesting and accommodating. If your looking for a nice private sail definitely check this one out. Can accommodate up to 6 people.

Thank jackiepalmieri
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 3 September 2017

One of the great things about Cape Cod is the sunset and a wonderful way to see this sunset is from the deck of a boat. We had that great experience thanks to Gary and his sailing prowess and thorough knowledge of Wellfleet Harbor. We...More

Thank Leonard H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 30 August 2017

Gary was a great captain. The wind was kind of quiet the day we went, but we had a fun sail around the harbor.

Review collected in partnership with this attraction
Thank Matthew K
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
See more reviews
Reviewed 29 August 2017

Alex was an excellent captain. Knowledgable and professional. He certainly knows his way around Wellfleet Bay.

Review collected in partnership with this attraction
Thank danielcR9853CZ
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 23 August 2017 via mobile

Thank you Captain Gary, we had a wonderful time sailing out to Jeramy's point, seeing the seals was awesome! Wonderful trip !! Where be back next year !!!

Thank Colleen D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 20 August 2017

Great afternoon of sailing! Captain was a terrific host. Definitely worth it when visiting the Cape!

Review collected in partnership with this attraction
Thank GreatSailing
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 20 August 2017

Thank you to Capt Alex for an enjoyable day! He provided expertise and flexibility to do what our group preferred (more sailing, less time at the beach). Would definitely sail w them again!

Review collected in partnership with this attraction
Thank eflatow
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 19 August 2017

Great evening sail- enjoyed being part of the adventure. Captain Gary was an expert who willingly explained the basics of sailing as we went. Chose the perfect out of the way nook for watching the sunset,

Review collected in partnership with this attraction
Thank Heather B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 18 August 2017

Had a great sunset sail with Captain Gary! Gary was very knowledgeable about Wellfleet and it's history. He was a skilled sailor and a good teacher. I had not been sailing for a while, and he let me guide the boat back to the pier...More

Thank johndowney2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 17 August 2017 via mobile

We booked the private sail to Jeremy Point with 2 adults and 3 kids age 6-9. It was a beautiful trip to a gorgeous beach. Our guide was pleasant an knowledgeable. Overall a great experience.

Thank Rebecca K
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Nearby
Nearby HotelsSee all 4 hotels in Wellfleet
Mainstay Motor Inn
52 reviews
1.89 km away
Even’tide Resort Motel and Cottages
190 reviews
5.24 km away
Wellfleet Motel
238 reviews
6.33 km away
Blue Dolphin Inn
264 reviews
6.90 km away
Nearby Restaurants
Ceraldi
168 reviews
.12 km away
Mac's Shack
546 reviews
.60 km away
Winslow's Tavern
475 reviews
1.03 km away
The Wicked Oyster
419 reviews
1.10 km away
Nearby Attractions
Wellfleet Public Library
45 reviews
1.16 km away
Wellfleet Harbor Actors Theater
45 reviews
1.06 km away
Mayo Beach
46 reviews
.42 km away
Uncle Tim's Bridge
9 reviews
.08 km away
Questions & Answers
Get quick answers from Outer Cape Sailing staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines
Submit