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.

Galene

Meet Galene, a 1968 Columbia 36’ built in nearby Portsmouth, Virginia. On the brink of being forgotten and destroyed, Captain Clay acquired Galene in 2017 and spent three years on a total refit. Outfitted with modern amenities and safety equipment, yet still maintaining her classic look, Galene is ready to get you on the water with comfort and style.

Galene is equipped with ample space for watching a sunset on the bow or relaxing in the living space below decks.

Modern amenities include LED lighting, multiple USB ports for charging phones and devices, bluetooth speakers, electronic chartplotters and even solar panels, just to name a few.

For more information on specific gear multi-day trips, check out this page.

Pisces

Pisces was custom built on the Chesapeake Bay in the 1990’s. She was designed with a simple elegance, to sail safely and comfortably over the horizon. She has enjoyed several trips to the Caribbean and after seven years of sitting unused, Clay and his close-nit community of friends and family helped breathe new life into Pisces.

Pisces is spacious and stable, offering a prefect platform for larger groups to enjoy sailing on the Bay. She contains 3 private cabins with a bonus cabin for kids.

Jarrah callister

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.