Private Charters

Private Charters on the Chesapeake Bay in St. Michaels, Maryland

Personalized Luxury Excursions on the Miles River and Chesapeake Bay

A private charter at Inn at Perry Cabin means the vessel is yours. No shared deck, no other guests, no fixed route unless you want one. Just you, your group, a seasoned captain, and the full expanse of the Miles River and Chesapeake Bay ahead of you. Whether you are planning a romantic sunset sailing for two, a family outing on the water, a marriage proposal aboard a classic sailing yacht, a corporate group excursion, or simply a few private hours on the Bay with people whose company you actually enjoy, our captained private charters deliver an experience that no landlocked itinerary can replicate. 

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

 

Overview

Captained private 2 hours, half-day & full-day charters

Available April - October 2026

Private charters take place on the Stargazer, Starbright, Starlight, Five Star, and Harbor Star.

Customize your experience with food and beverage offerings from our boat menu, arranged in advance through Guest Services.

 

Rates

Starbright, Starlight & Harbor Star

Flat Rates per vessel | $700 - $1050 - $1300

Stargazer 

Flat rates | $800 - $1150 - $1500

Stanley Norman Skipjack 

Flat rate | $3100

Five Star (Available through November)

Flat rates| $1500 - $2200 - $3200

*All charter cruises subject to MD sales (6%) and amusement tax (10%)
*There is a surcharge of 10% on all our Motoring Vessels.

 

What to Expect

Private charters are available on six vessels, ranging from intimate two-person sailing yachts and a 55-foot Hinckley Talaria motor yacht, to the nationally registered 1902 Stanley Norman Skipjack—one of the Chesapeake Bay's last surviving oyster dredgers.

Every private charter departs directly from that dock, with no marina transfer, no separate reservation, and no logistics to manage beyond contacting our Guest Services team. 

From romantic Miles River sunset sails and family-friendly Bay excursions to engaging corporate retreats and milestone celebrations, our private charters and Forbes Four-Star waterfront resort create unforgettable experiences for any occasion.

Our Private Charter Fleet

Inn at Perry Cabin's private charter fleet includes six distinct vessels, each chosen for its character, quality, and ability to deliver a genuinely memorable experience on the Miles River and Chesapeake Bay.