Painted city portrait of St. Michaels, MD — the Hooper Strait Lighthouse & Chesapeake Bay Maritime Museum harbor, informed by Henri-Edmond Cross. — the Hooper Strait Lighthouse & Chesapeake Bay Maritime Museum harbor

ASTRO Experiences · St. Michaels, MD

Experiences in St. Michaels, MD

Curated local experience providers on the ASTRO Network — tours, outings, food, and events worth remembering.

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ASTRO Network Geography

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Location: St. Michaels, MD×

Photo by Robert So
Luxury Boat Tours, Private Charters, Kayaking, Sailing Lessons
Inn at Perry Cabin
St. Michaels, MD Area
The Inn at Perry Cabin, built in 1815, offers guided boating experiences from its private waterfront marina on the Miles River in St. Michaels, Maryland. The fleet includes historic sailing yachts and motor vessels suitable for sunset sails, sightseeing, and special occasions exploring the scenic Chesapeake Bay. Enjoy effortless luxury and coastal adventure with personalized service from an experienced waterfront resort.
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Sailing Charters
St. Michaels Sailing Charters
St. Michaels, MD Area
Set sail from historic St. Michaels on the Chesapeake Bay aboard a classic sailing ketch or modern catamaran. Choose between the intimate, traditional Lady Patty or spacious, stable Epiphany. This sailing experience combines Miles River beauty, wildlife spotting opportunities, and Chesapeake traditions for an unforgettable escape.
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Marina
Chesapeake Bay Maritime Museum
St. Michaels, MD
The Chesapeake Bay Maritime Museum Marina is a Members-Only Marina located along St. Michaels Harbor and the Miles River. It offers 55 slips with electric, pump-out service, climate-controlled showers, Wi-Fi, picnic tables, and bicycles. A CBMM membership at the Mariner level or above is required to use the facilities. Visitors can make reservations for overnight or hourly docking.
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Private Chef, Event Catering
Chef Melissa
St. Michaels, MD Area
Offers private chef services for in-home dining, weekly meal prep, and event catering, bringing expertly crafted cuisine to clients' homes or special occasions.
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Photo by Calvin Seng
Boat Tours (Tiki Bar)
Love and Dreams Bay Cruises
St. Michaels, MD Area
Provides 1.5-hour leisurely tours on a Floating Tiki Bar boat around St. Michaels harbor and the Miles River, offering complimentary snacks and non-alcoholic beverages.
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Boat Tours, Water Taxi, Kayak/Bike/Paddleboard Rentals
St. Michaels Harbor Shuttle & Tours / Shore Pedal & Paddle
St. Michaels, MD Area
Provides boat tours, water taxi services, and rentals for kayaks, stand-up paddleboards, and bicycles, with options for eco-historical tours and sunset cruises.
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Marina
Saint Michaels Harbour Inn, Marina and Spa
St. Michaels, MD
Saint Michaels Harbour Inn, Marina & Spa is a year-round luxury inn situated on the historic harbor of St. Michaels, Maryland. The marina offers 52 transient boat slips, available for arrivals by boat or for docking for the day, during a stay, or for the whole season. Visitors can also explore on-site boat charters.
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ASTRO Network Geography

Inn at Perry Cabin

St. Michaels Sailing Charters

Chesapeake Bay Maritime Museum

Chef Melissa

Love and Dreams Bay Cruises

St. Michaels Harbor Shuttle & Tours / Shore Pedal & Paddle

Saint Michaels Harbour Inn, Marina and Spa