Group Sailing Charters in St. Michaels, Maryland
Sail the Miles River with Good Company
There is something about being on the water that makes strangers feel like old friends by the time the dock comes back into view. Our group sailing charters on the Miles River are designed exactly for that kind of morning, afternoon, or evening. Perfect for solo travellers, couples, and small groups looking to get out on the Chesapeake Bay without booking an entire vessel to themselves, these captained group charters offer a genuine sailing experience aboard some of the most beautifully maintained vessels on the Eastern Shore of Maryland. You will not be on a tour boat with a microphone and a crowd.
You will be on a proper sailing yacht with a small group of fellow guests, a seasoned captain, and the Miles River opening up ahead of you toward the Chesapeake Bay. Whether you are visiting St. Michaels for the first time or returning for the season, a group sailing charter is one of the simplest and most satisfying ways to spend a few hours here. Come along for a captained group charter and experience this little corner of the Eastern Shore coast the way it was meant to be experienced, from the water, together.
The Details
Captained group two-hour charters (up to 6 passengers)
Starbright, Starlight, and Harbor Star
10:00 am - 12:00pm | 1:00pm - 3:00pm
Evening charter based on sunset
Rates
April - October, 2026
Monday - Thursday | 9:00am - 4:00pm | $105 per passenger
Monday - Thursday | 4:00pm - 9:00pm | $120 per passenger
Friday - Sunday | 9:00am - 9:00pm | $140 per passenger
All charter cruises are subject to MD sales (6%) and amusement tax (10%)
*There is a surcharge of 10% on all our Motoring Vessels.
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.
FAQs – Group Sailing Charters at Inn at Perry Cabin
What is included in a group sailing charter at Inn at Perry Cabin?
A group sailing charter includes a fully captained two-hour sailing experience aboard one of the Inn’s sailing or motor vessels on the Miles River and Chesapeake Bay.
Each charter accommodates up to six passengers per vessel, and food and beverage arrangements can be customized through the Guest Services team at the time of booking.
How is a group sailing charter different from a private charter at Inn at Perry Cabin?
A group sailing charter is a shared experience where individual guests or couples join others on board for a captained two-hour sail.
In contrast, a private charter offers exclusive use of the entire vessel with full flexibility in timing, route, duration, and food and beverage arrangements.
Private charters are available across the full fleet, including the Hinckley Five Star and the Stanley Norman Skipjack.
Can non-hotel guests book a group sailing charter in St. Michaels?
Group sailing charters are primarily offered to guests staying at Inn at Perry Cabin. However, day visitors may be able to join based on availability.
To confirm availability, contact Guest Services:
Phone: 443.258.2228
Email: [email protected]
Are group sailing charters available for corporate retreats and team building events?
Yes, group sailing charters are ideal for corporate retreats, team building activities, and incentive travel groups staying at the Inn.
For larger groups or exclusive experiences, private charter options are available across the full fleet.
To discuss requirements and availability, contact Guest Services:
Phone: 443.258.2228
