Grace Bailey

Offering 5-day and weekend cruises.

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Sail the beautiful flagship Grace Bailey for unmatched, authentic windjamming. Unquestionably the finest example of a 19th-century coaster afloat today, she is listed as a National Landmark.

Built in 1882 and restored in 1990, she is 123 feet overall (81 feet on deck) and has accommodations for 29 passengers. The Grace Bailey has a rich history. The moment you step on board her broad wooden decks, you'll know "this is the real thing", an authentic 19th century sailing ship. This is the same ship that sailed to the West Indies in the Fruit Trade and carried granite to New York City to help build Grand Central Station.

A major restoration was done on this vessel in 1990; every effort was made to preserve its historic integrity while offering maximum comfort to our guests. The original cargo area is divided into sections, each with several private accommodations and a nearby head. A unique feature of this windjammer is the restored 1882 main cabin, complete with handcarved wood paneling and even a piano.


  • Fast and able, frequent winner of both formal and informal races
  • Warm, spacious galley and dining area with two companionways providing easy access to deck
  • Original 1882 main cabin
  • Exceptional headroom throughout
  • Twelve private double cabins with either double bed or two single beds; all with a window or porthole for light and ventilation.
  • Two private single cabins and two pullman beds
  • Four heads below decks, one in each passenger area
  • Fresh, hot-water shower below decks
  • Auxiliary power: yawl boat
  • Ship Layout
  • Accommodations