What to Expect on a Group Sailing Charter
Group sailing charters at Inn at Perry Cabin run for two hours aboard one of three vessels from the Inn's fleet: the Starbright Alerion Sport 38, the Starlight Alerion Express 33, or the Harbor Star Andreyale 33 French Canal Commuter. Each vessel accommodates up to six passengers and is captained by one of the Inn's experienced crew members who know the Miles River and the Chesapeake Bay intimately. Morning departures leave at 10:00 am and return by noon, giving guests the rest of the day to explore St. Michaels or settle in at the Inn. Afternoon charters run from 1:00 pm to 3:00 pm and are a relaxed way to spend a midday on the water. Evening charters are timed to the sunset, which on the Miles River is the kind of thing guests come back year after year to see from the water. All group sailing charters depart directly from Inn at Perry Cabin's private dock on the Miles River in St. Michaels, Maryland. No separate marina, no extra travel. Just a short walk from the Inn to the dock and you are on the water.
Group Sailing for Corporate Retreats
and Team Outings
Beyond leisure travel, group sailing charters at Inn at Perry Cabin are a genuinely effective option for corporate retreats, team building outings, and incentive travel groups staying at the Inn. A two-hour sailing charter on the Chesapeake Bay has a way of breaking down the usual dynamics of an offsite meeting and creating the kind of shared experience that people actually remember. The Miles River setting, the Forbes Four-Star quality of the vessels and crew, and the ease of organizing sailings through the Inn's Guest Services team make group charters a low-effort, high-impact addition to any corporate or group retreat itinerary at the Inn. For larger groups or private vessel buyouts, our Private Charters page covers full-fleet options including the Hinckley Five Star motor yacht and the historic 1902 Stanley Norman Skipjack.
