Coastal Sailing Weekend to Block Island or Cuttyhunk Island

Set sail from Warwick, Rhode Island, on a two-day coastal sailing weekend that blends hands-on learning with island exploration along the New England shore. This intimate journey aboard a comfortable 42-foot Bavaria monohull offers a unique chance to sharpen your sailing skills, embrace the rhythm of the sea, and discover two captivating island destinations: Block Island and Cuttyhunk Island. Starting at Greenwich Bay Marina in Warwick, this experience promises a balance of education, relaxation, and discovery for sailing enthusiasts aged 18 to 75.

Warwick, situated in Rhode Island, is perfectly positioned to access the coastal gems of Block Island and Cuttyhunk Island, both reachable within a 33 to 39 nautical mile sail. Block Island, often described as a pork chop-shaped landmass, boasts 32 miles of hiking trails, dramatic 250-foot-high coastal cliffs, and sparkling ocean vistas. Its lively history and vibrant summer culture create an engaging backdrop for daytime exploration or sunset strolls.

Meanwhile, Cuttyhunk Island offers a quieter, more secluded retreat with pristine shoreline and peaceful landscapes, perfect for those seeking to detach from everyday life. Under the guidance of experienced instructors, guests become active crewmembers—helping sail the boat, navigating, and getting hands-on experience without pressure or tests. The weekend starts Friday evening with a rendezvous and navigational prep at Greenwich Bay Marina, followed by setting out early Saturday morning.

Depending on weather conditions, you'll practice sailing maneuvers, anchoring techniques, and enjoy unhurried time at your island destination. Evenings feature relaxed dinners aboard, fostering a convivial atmosphere among fellow adventurers. The all-inclusive weekend covers cabin accommodations (each priced per cabin), provisioning with two lunches and one onboard dinner, and expert instruction.

As this is a sailing school, passengers are encouraged to participate fully, bringing a sleeping bag and towel, and following guidance for onboard life. The experience fosters camaraderie, skill growth, and a profound connection to the coastal environment. Whether seeking a new sailing challenge, a coastal escape, or a chance to share the sailboat experience with like-minded travelers, this weekend cruise stands out for its blend of education, island immersion, and accessible adventure from Rhode Island’s shores.

Its small group size and professional mentorship ensure a rewarding experience that captures the essence of New England’s maritime heritage. Book your place for a summer weekend that promises wind in your hair, salt on your skin, and some of the most scenic sailing New England offers.