2025 SUMMER CRUISE SEASON

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Spring - Early Summer

June 6th & 7th - New Shoreham, RI. Block Island

Dinner at The Barn on June 6th at 6pm.    
Port Captain: Nick and Stephanie Durgarian 

June 27th - Montauk, NY on Long Island 

Ocean Club Montauk, an all-day dining destination for sweeping waterfront views, just-caught seafood, open-fire Braai grilling, and the best local, in-season ingredients—all prepared in the Hamptons’ most expansive open kitchen by Chef Jarad McCarroll 
Port Captain: Jim and Holly Mascolo

June 28th - Montauk, NY on Long Island 

Star Island Grill features breakfast, lunch and dinner menu that includes the freshest local seafood, the best hamburgers, barbecue and home-style dinners. Outdoor games, casual dining. Group dinner at Star Island Grill
Port Captain: Jim and Holly Mascolo

Summer Cruise east to Martha’s Vineyard

Depart Watch Hill on July 14th, 2025

July 14th - Gosnold, Ma on Cuttyhunk Island 

Dock Party and Lobster Boil 
Port Captain: Please contact [email protected] for information

July 15th & 16th - Vineyard Haven or Edgartown, MA on Martha’s Vineyard

Dinner at EYC July 15th @ 6pm, Cocktails @ 5pm
Port Captain: Gerry and Joan Gorman
 

July 17th - Padanaram Harbor, Dartmouth, MA

Dinner at New Bedford Yacht Club 5pm cocktails on the lawn, 6pm Dinner inside the club. Moorings available at NBYC, email Bob for reservations [email protected]. Slips may be available at the South Wharf Yacht Yard through Dockwa.
Port Captain: Bob and Nancy Kiel
 

July 19th - Return Watch Hill Harbor 

Cocktail reception on the deck @ WHYC - July 19th, 2025 @ 5:30pm

Fall Cruise 

Sept 11th - Connecticut River, Essex, CT

Dinner at Essex Yacht Club
Port Captain: Please contact [email protected] for information

Sept 12th - Dering Harbor, Shelter Island, NY. 

Sept 13th - Sag Harbor, NY, Sag Harbor Yacht Club

Dinner at local restaurant in Sag Harbor details to come.
Port Captain: Jim and Holly Mascolo