Schooner Grace Bailey

Sailing aboard Schooner Grace Bailey offers a classic Maine windjammer experience, where travel is powered by wind, tide and seamanship rather than engines. Grace Bailey carries forward a long maritime tradition along Maine’s coast. Windjamming invites guests to slow down and take part in life under sail—raising canvas, watching the crew work the rigging and feeling the rhythm of open water. Multi-day charters include time exploring secluded harbors and islands, enjoying meals prepared on board and relaxing on deck as the schooner glides quietly through Penobscot Bay. The experience blends history, hands-on sailing and unhurried coastal travel.