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.

Day Sail Charters
Booking unavailable on TripAdvisor

Want other options you can book now?
All photos (4)
All photos (4)
Full view
Traveller Overview
  • Excellent100%
  • Very good0%
  • Average0%
  • Poor0%
  • Terrible0%
27 Jul 2017
“Put it on your Bucket List!”
26 Jul 2017
“July 25 17”
Sail with Captain Doug aboard Bay Breeze! From the novice to the expert! Aboard Bay Breeze everyone is part of the crew. Trim the sails and take a turn at the tiller or just relax and be the "lookout." Times and length of sail are flexible.
Suggested duration: 2-3 hours
3801 Main St, Chincoteague Island, VA 23336-1809
+1 757-336-5271
Improve This Listing
Reviews (6)
Filter reviews
6 results
Traveller rating
Traveller type
Time of year
See what travellers are saying:
Updating list...
Reviewed 27 July 2017

Such a FUN time!!! You won't regret it. Booking the trip was easy peasy with Nancy and Captain Doug was professional, safety conscious and knowledgeable of the area. Took so many BEAUTIFUL photos of the sailing day. Terrific for both kids and adults. No one...More

Date of experience: August 2016
Thank Barbara K
Reviewed 26 July 2017 via mobile

Had an absolute blast. LOVED that Doug let us be hands on. He is a great teacher. Very patient. Good conversation. Nancy was a great coordinator our conversations prior to the trip felt as if I was speaking to a life long friend. Both Doug...More

Date of experience: July 2017
Thank raineyrock
go2ci, Owner at Day Sail Charters, responded to this reviewResponded 28 July 2017

Thank you so much for the nice review. We had a great time, too. Thanks for sailing with us! Hope to see you both again. Good luck with the Catalina 22!! :) Nancy & Captain Doug

Reviewed 31 August 2016

Don't miss this experience of sailing around Chincoteaque . This is a little bit out of the box ( not you're Disney type) but an easy, fun, exciting sail with Captain Doug. Our group of 4 had zero sailing experience and became part of a...More

Date of experience: August 2016
1  Thank Lorinsofia
go2ci, Owner at Day Sail Charters, responded to this reviewResponded 28 July 2017

Thank you for your great review! So happy you enjoyed the trip! Hope to see you again! Nancy & Captain Doug

Reviewed 27 June 2016

Captain Doug Cunningham is a sailor par excellance! We really enjoyed sailing with him on the "Bay Breeze!" His boat is clean and shipshape. We took the "hands on" sailing experience and thoroughly enjoyed ourselves. We were a party of 5 adults (four 50+), one...More

Date of experience: June 2016
1  Thank WB6NCO
go2ci, Owner at Day Sail Charters, responded to this reviewResponded 29 June 2016

Hi~ Thanks so much for the nice words! We are so glad that you and your crew had a good time! The winds cooperated and it was a beautiful day! Captain Doug had a great day, too! Hope to see you again if you are...More

Reviewed 27 September 2015

While on vacation in Chincoteague, you have to sail with Captain Doug on the Bay Breeze. He is a wonderful host and Captain. We all had turns sailing, the day out was fun and very educational. The sail boat is spacious and comfortable. A hands...More

Date of experience: September 2015
1  Thank bklassen1961
go2ci, Owner at Day Sail Charters, responded to this reviewResponded 29 September 2015

We are so happy that you had a good time! Thank you for the nice review! We hope to see you if you visit Chincoteague again! Captain Doug and Nancy

Reviewed 1 September 2015

After many visits to Chincoteague Island and other boat trips, my wife and I decided to take a sailing trip. We searched online and found Day Sail Charters. Nancy was wonderful to set up a same day trip after checking the weather forecast. She and...More

Date of experience: August 2015
4  Thank B-E1990
go2ci, Owner at Day Sail Charters, responded to this reviewResponded 29 September 2015

Thanks for the great review. We are glad that you had a good time! Hope to see you on your next trip to Chincoteague! Captain Doug and Nancy

View more reviews
Nearby HotelsSee all 20 nearby hotels
Marina Bay Hotel & Suites, an Ascend Hotel Collection Member
167 reviews
.01 miles away
Anchor Inn
118 reviews
.04 miles away
Waterside Inn
931 reviews
.09 miles away
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
351 reviews
.20 miles away
Nearby RestaurantsSee all 61 nearby restaurants
Right Up Your Alley
240 reviews
.42 miles away
Poseidon's Pantry Gourmet Grocery & Deli
312 reviews
.86 miles away
Bill's Seafood Restaurant
2,278 reviews
.32 miles away
Mister Whippy
916 reviews
.85 miles away
Nearby AttractionsSee all 78 nearby attractions
Chincoteague Island Library
43 reviews
.39 miles away
Chincoteague Cultural Alliance
31 reviews
.56 miles away
Tryfan Gallery
16 reviews
.41 miles away
Questions & Answers
Get quick answers from Day Sail Charters staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines