Group Charters

Group Sailing Charters in St. Michaels, Maryland

Sail the Miles River with Good Company

Our group sailing charters on the Miles River are perfect for solo travelers, 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. 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.

Reserve your experience through the Concierge Team by calling 443.258.2228 or emailing [email protected].

RESERVE YOUR VOYAGE

 

Overview

Captained group two-hour charters
(up to 6 passengers)

Group charters take place on the Starbright, Starlight, and Harbor Star

 

 

Availability

April  - October, 2026

10:00 am - 12:00 pm | 1:00 pm - 3:00 pm

Evening charter based on sunset

 

Rates

Monday - Thursday | 9:00 am - 4:00 pm | $105 per passenger
Monday - Thursday | 4:00 pm - 9:00 pm | $120 per passenger
Friday - Sunday | 9:00 am - 9:00 pm | $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

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.

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. 

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. 

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.