Join the Excitement of Racing Sailboats at Holmes Hole Sailing Association!

For 50 years, Holmes Hole Sailing Association has welcomed sailors of all levels. Bring your boat and experience the thrill of racing on Vineyard Sound. Join us today and become part of our vibrant sailing community, where fun and camaraderie await every sailor, regardless of experience!

5/8/20241 min read

A sailboat with a large blue and black striped sail glides across a vast expanse of calm water. Several other sailboats with colorful sails are visible in the background, scattered across the sea. Sunlight reflects off the water, creating a shimmering effect.
A sailboat with a large blue and black striped sail glides across a vast expanse of calm water. Several other sailboats with colorful sails are visible in the background, scattered across the sea. Sunlight reflects off the water, creating a shimmering effect.

Sail, Race, Enjoy