Captain clay

Captain Clay Dingledine is a native to Virginia’s Northern Neck and first began his sailing adventures at age 13. With an adventurous soul, he eventually moved to other cities, countries and even land-locked states but the shores of the Chesapeake Bay always beckoned him back. 

And now he is ready to share his knowledge and love for life on the water with others. Captain Clay is certified to Instruct for the American Sailing Association. Ask him about his high-school sailboat racing days, his trip to the Florida Keys, or his Atlantic passage from Bermuda to Norfolk. Clay has also travelled extensively for surf, including Puerto Rico, California, Mexico, Costa Rica, Ecuador, and the entire eastern seaboard from Maine to Florida.

First mate Jarrah

Jarrah joined the Sail & Surf crew in 2025 as an apprentice. He makes an excellent deckhand on Pisces and his enthusiastic and positive outlook has proved a priceless addition to overall well-being of our business.