Now booking for Cape Charles summer 2024!

Check out our Store for new Windsong merch you can rock all year long! We’ve got hoodies, t-shirts, blankets, mugs, ornaments, and a lot more!

Sailing from Cape Charles Town Harbor, near The Shanty restaurant!

Experience your own unique sailing adventure on the Chesapeake Bay aboard the traditional Schooner Windsong!

Relax with a beer or glass of wine while we sail the smooth waters of the Chesapeake Bay, or take a hands-on approach and help the crew set sails and helm the boat.

We can also offer custom special event and full day adventures!

Circa 2005 with Chris Gateley at the helm.

Windsong has a long history!

Check out the logs kept by the former owners, Chris and Sue Gateley, as they sailed her under the beautiful name Sara B from 2004 to 2020.