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Gloucester Point Small-Group Sailing Lesson

Discover the art of sailing during your time in the Williamsburg area with this sailing lesson. Join a small group and head out onto the water with a modern sailboat to learn the basics of sailing. Learn how to build speed, “see” the wind, and boat safety, or simply enjoy a relaxing ride on the water.

About this activity in Gloucester Point

Cancellation policy
Cancellation policy
A full refund will apply if you cancel more than 24 hours before the activity start time. no refund is possible if you cancel less than 24 hours before the activity start time.
Event Policy
Other Policy
Discover the art of sailing during your time in the williamsburg area with this sailing lesson. join a small group and head out onto the water with a modern sailboat to learn the basics of sailing. learn how to build speed, “see” the wind, and boat safety, or simply enjoy a relaxing ride on the water.

Includes

  • Lunch
  • dinner
  • dogs are welcome, and sometimes they attract dolphins (true fact).
  • celebrate your anniversary or birthday with private seating on a cushion up on the bow.
  • photos offered for free of the entire crew at sea, and on the wheel.
  • learn to sail by taking the helm (wheel) to turn the boat.

Excludes

  • No drugs and no cats!

Other

  • Service animals allowed
  • all areas and surfaces are wheelchair accessible
  • transportation options are wheelchair accessible
  • not recommended for travelers with poor cardiovascular health
  • infants and small children can ride in a pram or stroller
  • suitable for all physical fitness levels
  • wheelchair accessible
  • ada accessible with 24-hour notice.
  • shade and padded seat provided.

Customer Reviews

10/10
Based on 10 Reviews
O8345UUamandaa
Aug 26, 2026 10:55:47 PM
Summary: We had a wonderful sailing experience! The captain was friendly, personable, and knowledgeable about the area. He made the trip especially memorable for my dad by letting him take the helm for most of the sail for the first time in almost 30 years - an experience he absolutely loved! The boat was clean and comfortable, and the quiet background music created the perfect atmosphere without being distracting. Communication before and after the trip was also excellent. I highly recommend this sailing expedition to anyone looking for a relaxing, enjoyable, and memorable experience!
Leah_W
Aug 19, 2026 09:16:54 AM
Summary: Thank you Captain Bill! You were awesome! I had a blast in the past! I can’t wait to have more adventures in the near future!
SizzlingSisig
Aug 16, 2026 05:33:05 PM
Summary: We had a group that exceeded the max of 6 but Captain Bill worked with us to have 2 sailboats out to the river at the same time for a private daytime sail with our family. While we were not on the same boat. We shared the same area and we were able to interact while sailing. It was a fantastic experience for us to learn to sail AND learn the history at the same time. We also appreciated the peace and quiet of the ocean - Captain Bill said, no cars honking. The wind and air was fresh! We can’t wait to go back again!

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Know more about Gloucester Point

Visitors consistently mention the excellent service, knowledgeable guides, and memorable experiences. The tour holds an impressive average review score of 10.0 out of 10.0 based on 171 verified traveler reviews, reflecting its strong reputation among guests.
Based on the information reported by the owner or manager, details for the cancellation policy for the Gloucester Point Small-Group Sailing Lesson are as follows: A full refund will apply if you cancel more than 24 hours before the activity start time. no refund is possible if you cancel less than 24 hours before the activity start time. Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the activity description.
Best-rates for the Gloucester Point Small-Group Sailing Lesson starts from $96 per person with includes with all other facilities. Varoom matches every traveler with their perfect place to stay or activity, whether you are traveling with a group, friends, family, or pets.
Yes, certain activities may adjust schedules depending on the season, daylight, or weather conditions.