cruise-in-company for sail and power

Annual Cruise

The Annual Cruise presents members with among the best opportunities the Club offers to make new friendships and foster old. Typically one week in duration and usually in August, destinations can involve staying within Long Island Sound, or traveling to Narragansett/Buzzards Bays and the islands of Nantucket and Martha's Vineyard. And every few years, the cruise heads to Maine where it will be in 2017. Participants include both power and sail, member owned and member chartered yachts. And when interest permits, the sailboats may engage in some casual non-spinnaker point-to-point racing!

Winter Cruise

Typically held every other year, the winter cruise involves members chartering boats for one week somewhere warm! In 2015, the club members sailed the British Virgin Islands; in 2017, the cruise explored the islands of St. Martin, Anguilla and St. Barths. Our 2019 winter cruise took participants one-way, from the island of St. Vincent south/southwest through the Grenadines, and ended at Port St. Louis Marina at the southwestern end of Grenada.


Held over Labor Day weekend, the Mini-Cruise combines a short family-oriented day race with an overnight raft-up and a race home the following day.

Cruising Squadron

The Cruising Squadron organizes short day-long and weekend cruises for power and sail. The Squadron encourages non-boat owner members participation either as guests aboard a member boat or by land. Venues typically include the bays and harbors along the north shore of Long Island and south shore of Connecticut but have also included New York Harbor and lower Manhattan. The Squadron promotes camaraderie among members through on the water activities and group dining either at reciprocal yacht clubs or notable restaurants at our destination.

Overseas Trophy

For meritorious cruising achievement by an Indian Harbor member
2014 Nikita - Michael Tierney