Meet Our Fleet in St. Michaels, Maryland

A Nautical Heritage Rooted in the Chesapeake Bay Since 1819

Founded in 1819 by Navy man, seafarer, and hometown hero Samuel Hambleton, the nautical heritage of Perry Cabin runs deep, a fact that is reflected in every vessel of our esteemed fleet. Hambleton's connection to the water was not incidental. He was a decorated officer of the United States Navy and a key figure in the Battle of Lake Erie, and the property he built on the Miles River carried that maritime spirit from its very first days. More than two centuries later, that spirit is alive in a fleet of sailing yachts, motor vessels, and a historic 1902 skipjack, all available for private charters, group sailings, and guided excursions on the Chesapeake Bay.

The breadth and beauty of the fleet is a matter of pride and careful cultivation. From the timelessness of the historic Stanley Norman Skipjack to sleek Alerion sailing yachts, a classic Friendship 40, and a custom Hinckley Talaria 55 motor yacht, we have something for every seasoned sailor and first-time guest alike. All vessels depart from Inn at Perry Cabin's private dock on the Miles River in St. Michaels, Maryland, roughly 90 minutes from Washington D.C. and Baltimore.

Stargazer, a Friendship 40

The Friendship 40 is gorgeously designed, fast, and built to an unmatched quality. Flawless fore and aft decks and a low-profile cabin top provide 360-degree views from the helm, giving every passenger an unobstructed look at the Miles River and the open Chesapeake Bay beyond. The spacious cockpit with three deep settees provides a luxurious seating area well suited for private charters and longer sailing excursions.

Teak coaming and detailing take you back in time to a more graceful era of sailing, while the shallow draft allows for remote cruising in the quieter reaches of the Eastern Shore. Combined with the large sail plan, the Stargazer is an exceptionally fast and responsive vessel, equally at home on a brisk morning sail or a golden-hour sunset cruise on the Chesapeake.

Starbright, Alerion Sport 38

Starbright is equipped to accommodate a full weekend cruise on the Chesapeake Bay and is one of the most versatile sailing vessels in our fleet. Her traditional topsides are coupled with an advanced underbody and rig built for performance in the variable winds common on the Miles River and the open Bay.

A fully roached mainsail on a carbon fiber mast is efficient and effective, and a single-line reefing system allows easy adjustment when the wind picks up without breaking from the experience. The self-tacking jib boom enables efficient use of the jib on all points of sail, making Starbright an ideal choice for guests who want an active sailing experience without the complexity.

Starbright's gracefully contoured cockpit comfortably seats as many as eight passengers, making her a popular choice for private group charters and intimate celebrations on the water. Her separate rear cockpit provides complete control with electric winches and all sail handling right at hand.

Starlight, Alerion Express 33

Starlight turns heads with her sheer classic overhangs, thoroughly modern underwater shape, and low coach roof. She pairs purity of line with unsurpassed performance, with an ability to single-hand and the capability to sail comfortably in all kinds of wind and weather on the Chesapeake Bay. This is the perfect sailing vessel for guests who do not want to wait for a narrow window of ideal conditions to get out on the water.

The easy setup and stowage of this boat means more time sailing the Miles River and less time at the slip. Whether the goal is a two-hour private sailing charter, a half-day excursion, or a full-day voyage along the Eastern Shore coastline, Starlight delivers a clean, responsive, and genuinely enjoyable sail every time.

Midnight Star, a Tadorne 26

Launched in 1991, the Midnight Star drew immediate interest and admiration when she first appeared, and she continues to turn heads on the Miles River today. The hull and deck are made of polyester with a teak and varnished mahogany finish, giving her a warmth and craftsmanship rarely found on modern production vessels. Eight meters strong, she comfortably welcomes up to six guests on board for private charter sailings on the Chesapeake Bay.

The self-draining cockpit is large and spacious, and every line, halyard, sheet, reefing system, engine handle, and furling control is within arm's reach of the helmsman, making her easy to manage in all conditions. Beneath the roof, the atmosphere in the cabin is warm and convivial, finished with satin-varnished mahogany by talented craftspeople. The Tadorne is a fast, stiff sailboat, and one of the most characterful vessels in the fleet.

Harbor Star, an Andreyale 33 French Canal Commuter

Explore the most remote, pristine reaches of the Miles River and Chesapeake Bay aboard Harbor Star, an Andreyale 33 French Canal Commuter with genuine character and serious capability. Boasting a roomy cockpit and an elegantly appointed salon with large beveled glass windows and a satin-mahogany finish, she easily accommodates up to six passengers plus crew in comfort well above the standard motor charter experience.

With a shallow draft and 100-hp diesel engine, Harbor Star reaches top speed at a whisper-quiet 18 knots, making her ideally suited for brisk two-hour motor cruises, half-day outings, and full-day private charters exploring the waterways of Maryland's Eastern Shore. She is particularly well suited for guests who want to reach quieter anchorages and less-traveled stretches of the Bay that larger vessels simply cannot access.

Five Star, a Hinckley Talaria 55'

Five Star is the flagship of the Inn at Perry Cabin fleet and one of the most capable and distinctive motor yachts available for private charter on the Chesapeake Bay. A unique and highly customized Hinckley Talaria 55 Flybridge, she is powered by an optional Mann V-12 engine package capable of reaching 40 knots, making her the fastest vessel in the fleet and well suited for the Explore the Chesapeake excursion that takes guests from St. Michaels to Annapolis by water. She boasts a full helm station on the flybridge for open-air cruising and an inside steering section in the pilothouse for year-round comfort.

The interior is elegantly finished in gloss varnish with raised-panel custom detailing throughout, setting a standard of refinement that reflects the Forbes Four-Star quality guests expect at Inn at Perry Cabin. Five Star is available for private charters, half-day and full-day voyages, and the Skip the Bridge package that brings guests directly to the Inn by water from the Annapolis area.

Stanley Norman Skipjack: A National Historic Vessel on the Chesapeake Bay

We are proud to include the 1902 Stanley Norman Skipjack as the most historically significant vessel in our fleet. Listed on the National Register of Historic Places, the Stanley Norman is one of the last remaining skipjacks of the thousands that once worked the Chesapeake Bay dredging oysters for the regional watermen economy. Built by boat builder Otis Lloyd of Salisbury, Maryland, and named after his two sons, she carries more than 120 years of Chesapeake Bay maritime history in her hull and rigging.

Today, the Stanley Norman serves as a living teaching vessel at Inn at Perry Cabin, welcoming guests aboard for the Skipjack Legacy Voyage, the seasonal Oyster Dredging Experience, and the Rum Running on the Skipjack evening with Lyon Rum. For every ticket sold aboard the Stanley Norman, $10 is donated to 4ocean to support ocean cleanup and marine conservation efforts.

FAQs

How many vessels are in the Inn at Perry Cabin fleet, and what types are available?

The Inn at Perry Cabin fleet includes seven vessels, featuring four sailing yachts, two motor vessels, and the historic 1902 Stanley Norman Skipjack.

The sailing yachts include:

Stargazer – Friendship 40
Starbright – Alerion Sport 38
Starlight – Alerion Express 33
Midnight Star – Tadorne 26

The motor vessels include:

Harbor Star – Andreyale 33
Five Star – Hinckley Talaria 55

All vessels are available for private charters, with select options also used for group sailings and guided excursions on the Miles River and Chesapeake Bay.

Can I book a specific vessel for a private charter on the Chesapeake Bay?

Yes, specific vessels can be booked for private charters based on availability, group size, and experience type.

Charters are offered in two-hour, half-day, and full-day options from April through October, with the Hinckley Five Star available through November.

For bookings, contact Guest Services:
Phone: 443.258.2228
Email: [email protected]

Where do all sailing and motor charters depart from?

All charters depart from Inn at Perry Cabin’s private dock on the Miles River in St. Michaels, Maryland, so no additional travel is required.

Address:
308 Watkins Lane
St. Michaels, MD 21663

The Inn is approximately 90 minutes from Washington, D.C. and 75 minutes from Baltimore.

What is the difference between a private charter and a group sailing at Inn at Perry Cabin?

A private charter offers exclusive use of a vessel with flexible timing, route, and onboard arrangements tailored to your preferences.

A group sailing is a shared, captained two-hour experience where guests join others on board.

Group sailings typically operate on Starbright, Starlight, and Harbor Star, while private charters are available across the full fleet, including the Stanley Norman Skipjack and Hinckley Five Star.