757 Sailing Charters

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.

08/28/2025

Here are some sunset pictures from the last sunset sail we had.

08/27/2025

I’m letting you in on a little secret.🤫. Sometimes S/V Freedom turns into the love boat! Really cool to watch the transformation. Oh and a beautiful sunset. No dolphins in sight, but I think they enjoyed the sail nonetheless.