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.

Windward Sailing
Booking unavailable on Tripadvisor

Want other options you can book now?
63Reviews2Q&A
Traveler rating
  • 62
  • 1
  • 0
  • 0
  • 0
Traveler type
Time of year
Language
Selected filters
  • Filter
  • English
Popular mentions
David S wrote a review Jul 2021
4 contributions
We booked the catamaran for 10 people (3 families with grandparents, parents and children). This is our second time going out with Captain Tony (3 years ago) and we loved it so much, we wanted to repeat. We were lucky enough to arrange a sunset cruise last week for 2 hours. The boat was as nice and clean as before, the weather was beautiful and the sunset on the water was spectacular.
Read more
Date of experience: July 2021
Helpful
Share
Karin B wrote a review Jul 2021
St. Johns, Florida55 contributions11 helpful votes
Thank you for a wonderful sail under the careful watch of Captain John and Windward Sailing. We had a beautiful tour and learned a lot about the inlet between Amelia and Cumberland Island. Our teens enjoyed conversation, the thrill (!) and even the quiet of a beautiful sailboat.
Read more
Date of experience: July 2021
Helpful
Share
Rachel wrote a review Jun 2021
New Jersey30 contributions13 helpful votes
We had a wonderful 4 hour sail on Windward Sailing’s catamaran. It’s not a large boat but certainly roomy enough. It has a head and two lovely seats on the bow that give you the best view ever! We loved laying in the nets up in the bow as well. Coleman was a wonderful Captain, full of interesting knowledge of the area, delightfully friendly, and kept us entertained the whole trip. The only thing I felt was missing was food and drink. For the price, it should have included drinks and snacks and/or sandwiches.
Read more
Date of experience: June 2021
Helpful
Share
Aaron K wrote a review May 2021
SmalltownUSA2 contributions
Magnificent day at sea! Vessel pristine, skipper excellent host. Highly recommend. Great tour about the islands, skipper seasoned sailor and great tour guide.
Read more
Date of experience: May 2021
Helpful
Share
larmc5 wrote a review Apr 2021
Dothan, Alabama130 contributions74 helpful votes
Treat yourself to a private catamaran charter with Windward Sailing. Hands down it is one of our most favorite things to do. Relaxing fun with experienced captain. Already planning our next trip!
Read more
Date of experience: April 2021
Helpful
Share
Previous
123456