About Us

Cape Charles Community Sailing, also known as Cape Charles Sailing, was founded by Hannah Twiddy and Mia Guinan in 2019. Following a sail across the Chesapeake Bay, they joined forces to create foundational community collaborations, which still exist today. The sailing school has expanded to host multi-week summer camps that include volunteer and counselor-in-training programs. The camp operates out of Oyster Farm Marina in Cape Charles and has expanded Up the Road to help run the Eastern Shore Yacht and Country Club’s sailing program. The summer camp runs June - August with additional programs starting up in April through October. Fall of 2025 was the inaugural year for the Eastern Shore Sailing Team, this is an after school sailing club open to those that live on the Shore. In addition, we offer Monday night sailing nights, adult learn to sail courses, community events, and regattas. Continued collaborations with local organizations across the Eastern Shore, Hampton Roads, and Northeast NC allow us to provide scholarships that help make sailing accessible to all.

CCCS owe success to the countless friends, family members, and volunteers who dedicate their time and effort to make our sailing camps and events possible. Together, we create an environment where a love for sailing can flourish, ensuring that everyone can enjoy the beauty and adventure of the Eastern Shore’s waters.

Find out a little more about our team below!

A bit about owner and director -Hannah Twiddy

Originally from Elizabeth City, North Carolina, she grew up in a small, grassroots sailing program now known as River City Sailing; of which she used as a guide for the sailing program in Cape Charles. She leads with over 15 years of teaching experience, mostly along the Atlantic-East Coast. Her journey has taken her around the world—both through sailing and through her academic pursuits. Hannah has a PhD in Physiology and Global Health from Old Dominion University. She researches human aging and the benefit of intergenerational activities which focus on living well throughout life. Through international research as a Fulbright Postdoctoral Fellow to Australia and regions of the world known as Blue Zones, she explores environment influence on Healthy Aging. Discovered through her research she believes living well starts at a young age and aims to put academics to practice through teaching sailing and the multitude of lifelong benefits that come with this knowledge. Sailing is one of many intergenerational activities that teaches life lessons and gives freedom to those at any age. Sailing has taken her all over the world and she aims to pass this to the next generation.

In 2026, the Eastern Shore of Virginia Sailing Foundation was created to serve as a 501 (c) 3 to support sailing programs, such as the one in Cape Charles and others on the Shore.

Who is on the dock?

  • Scott Whittaker

    Scott Whittaker moved to Cape Charles late last year, November 2025. He came to us from far across the water (and bridge) in the East Beach area of Norfolk. Scott moved to Virginia Beach in 2017.

    After careers in the US Navy, then moving to a career in water and wastewater treatment Scott recently retired and Cape Charles became the perfect home. The perfect Shore pace of life, great people, and plenty of activities to keep busy. Both Scott and his wife Claudia love the water and being on and in it. 

    Sailing has been a long time passion for Scott having first learned at Camp Seagull 54 years ago! Since then he taught his parents, who bought a 24’ sailboat then made the march to larger and larger sailboats, eventually retiring to their boat and cruising the Atlantic, making the trip across the ocean twice without Scott! Scott brings many years of sailing experience having been an instructor at the Navy Sailing Club Coronado and later crewing for several years in both Jacksonville and Pensacola areas. His latest sailing has been with Sail Time in Norfolk.



  • Neiley Guinan

    Neiley has been with the program since it’s inception, either as a camper, volunteering her time and energy, or helping others learn. When racing, look for her at the finish line!

  • Ethan Dail

    Ethan was our first camper to be US Sailing Level 1 Instructor certified! He is a skilled welder and serves as a mechanic with the sailign camp.

  • Caleb Dail

    Caleb came up through the summer camp program, before volunteering for a year and has moved into the role of assistant instructor. Caleb took home a 1st place in our single hand even during the sunfish regatta in 2025.

  • Jayden Edwards

    Jayden has been devoted to sailing camp since he was a young camper. He has become an expert at sunfish. He is an assistant instructor for our summer camp and sails on our sailing team during the school year.

  • Millicent Smith

    Millicent is an assistant instructor for our 2026 summer sailing camp. She has sailed in our camp as well as Camp Seafarer on the East Coast.

A man and woman standing on a boat deck, wearing sun hats and sunglasses, smiling at the camera. The woman is holding a water bottle, and both are dressed casually in long-sleeve shirts, shorts, and hats.
A group of six people standing on a wooden dock in front of a two-story blue and white building, with a body of water and trees in the background on a sunny day.
Young man standing on a dock at a marina, holding an Italian flag with a blue, white, and green color scheme. There are boats and a blue sky in the background.
Young man in sunglasses and a hat giving two thumbs up on a porch near a body of water with boats and people in the background.
A young girl receiving a prize or certificate from a young man at an outdoor event under a white canopy, with several people watching and taking photos.
Three women smiling for a selfie outdoors on a porch with a roof overhead.
Two young girls sitting on a sailboat with a green and white sail, wearing life jackets and sunglasses on a lake, with another sailboat in the background.
Group of kids standing outside a blue building labeled 'Cape Charles Sailing Camp', with some holding green drawstring bags, and one girl holding a saxophone.
A person standing next to a small sailboat with a decorated sail near a body of water, with a gazebo in the distance against a clear blue sky.
A group of seven young people smiling and posing for a selfie on a dock by a lake on a sunny day with trees in the background.
Man with sunglasses and beard sailing a small boat on the lake, wearing an orange hoodie and a life jacket, with a remote control in his hand, and another small sailboat in the background.
A small sailboat with two people on board, with a colorful striped sail, anchored on a lake with trees in the background under a blue sky with some clouds.
Two women on a boat, one wearing colorful tie-dye shirt and sunglasses, the other wearing white shirt and sunglasses, smiling and giving a thumbs up, with water and sky in the background.
An elderly couple standing together on a dock by the water, both wearing sun hats, sunglasses, and casual clothing. The woman is holding a water bottle and smiling, while the man has his arm around her, both looking at the camera.
Two girls sitting on a boat with a dog, in front of a large sail decorated with red and blue handprints and the text "Charles Community Sailing."
A girl sitting on a porch with a guitar in her lap, petting a white dog with black markings.
A young girl is giving a presentation or speech outdoors under a canopy, with an audience of children sitting on the porch, some taking notes or listening attentively, and a man relaxing on the porch floor.
A person sailing a small boat with a colorful sail on a lake, surrounded by trees.
Person enjoying swimming in a lake, wearing a life jacket.
Person sailing a small boat with a yellow and white sail on a river near a green forest.
Two boys outdoors near a body of water, one standing with sunglasses and a cap, smiling, and the other sitting and looking at something in his hands.
A woman sitting on a boat holding a megaphone and a small cup, smiling, with water and trees in the background.
Group of people, including children and adults, on a dock near water, with some holding boarding passes and luggage, under tents and umbrellas on a sunny day.
Sailboats with colorful sails racing on a lake, with a forested shoreline in the background.
Two children sailing a small boat on a lake, with other boats and sailboats in the background.
Children gathered outside the Cape Charles Sailing Camp entrance, some sitting on the deck and others standing, listening to an instructor.