757 Sailing Charters

06/06/2026

Thank You For Sailing With Us

After many wonderful years on the water, we want to share that our sailing charter business has officially closed following the sale of The Freedom.

We are incredibly grateful for the support of our guests, friends, and community who trusted us to be part of their adventures and special memories. It has been our privilege to share the beauty of sailing with so many amazing people.

Thank you for your business, support, and memories we’ve created together.

God Bless,
Captain Tommy & Captain Robert

04/05/2026

Some of these folks are from Pennsylvania. Beautiful day on the water. Saw a few birds, some other boats, but not really busy on Hampton Roads today.

04/01/2026

Third times a charm. These fine folks altered their house with a large flashing light. Last 2 times they went sailing with us, we had a hard time finding their house. Pretty easy to find this time. 😉😂

04/01/2026

09/19/2025

Beautiful day for a sail! No fishing on this sail, but plenty of dolphins and some Phish fanatics. Several of these folks came all the way from the west coast just to sail with us. Seriously, the concert was just an add on. 😉

09/19/2025

Posting this from last week before the storm. Local folks who won a sail from Virginia Youth Sailing located on Fort Monroe.

08/30/2025

Wow! Three-peat customers! Great sailing today. First time to Thimble Shoal in a long time. Saw camera shy dolphins from a distance.

08/30/2025

Last sail was a solemn occasion and a fond farewell! The family requested no pictures. But they were okay with pictures of the dolphins that showed up on our way out and back.

08/29/2025

Took these Hampton U. Alumni by HU, but was so busy avoiding boat traffic I forgot to take pictures. They had a good time.

08/28/2025

Here are some more pictures from a few sails ago.