A pier and lighthouse in St. Michael's
Waypoints Annapolis

Top Destination Spotlight: Coastal Charm in St. Michaels

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Once a colonial trading post, St. Michaels has become a popular waterfront tourist destination. The charming historic town on Mayland’s Eastern Shore has plenty of activities, sights, and restaurants to explore. With a little over 1,000 full-time residents and just 25 nautical miles from Annapolis, St. Michaels is the perfect charter trip getaway.

St. Michaels is home to several marinas including St. Michaels Marina and St. Michaels Harbour Inn Marina & Spa which both offer boat slips, refueling facilities and spas. Whichever marina you choose, it’s a great place to dock and start exploring the mainland.

  • Steamed crabs
  • A historic building in St. Michael's

Talbot Street runs through St. Michaels and on it you will find colonial-style architecture and rows of local shops, restaurants, and bars. Stop by Awful Arthur’s Seafood Company to dine on seafood staples like oysters and shrimp. They even have a pet-friendly outdoor patio so you can bring your furry friends!

It wouldn’t be a trip on the Chesapeake Bay without having some Maryland Blue Crabs. The Crab Claw offers fresh crabs with beautiful views of the Miles River. They also provide free dockage while dining if you call ahead to reserve your slip.

The Chesapeake Maritime Museum is a must-see stop. The museum takes guests on an interactive journey through Maryland’s maritime history. It’s also one of the few places that holds historical displays of the Chesapeake Bay and its culture. The Hooper Strait Lighthouse is a favorite exhibit for museum guests to explore.

The streets have large wide shoulders that bicycle riders use to get up and down the peninsula. If you didn’t bring a bike, shops like TriCycle and Run rent and deliver bikes to riders of all experience levels.

Visit the many boutique stores and bring a little piece of St. Michaels home with you. Pemberton Pharmacy is an old-fashioned working pharmacy and gift shop that is filled with Maryland-themed mementos, Chesapeake Bay Outfitters offers a large selection of coastal clothing and items, and it’s no surprise that a town steeped in so much history is also home to several antique shops like Iron Will Woodwork.

Are you ready to plan your charter trip to St. Michaels? Our charter specialists can help you plan your trip whether for a day or several nights. Contact us today!