St. Michaels/Tilghman Island

It’s the town with a refined charm that hints of Martha’s Vineyard. Though locals might be shy to draw this comparison, the smalltown waterfront vibe, bucolic layout, mom and pop shops, hip eateries, upscale lodging, and elite shopping can’t be denied and make St. Michaels, and by extension Tilghman Island, a pleasure-cruiser’s paradise.

The St. Michaels harbor offers the more protected anchorage of the duo-destination, located just inside the Miles River, off Eastern Bay. If you’re visiting for the day or maybe an overnight, dropping anchor in the

North or South Anchorage in the river or within the adjacent coves may be the easiest bet. From your vessel, you can hail the water taxi on VHF channel 71 to visit the town. There’s plenty of slips available, too, for longer stays. Between the Chesapeake Bay Maritime Museum and several marinas, there’s no shortage of docking amenities.

You’ll find plenty to enjoy when on land. Walk the streets surrounding the harbor and duck into art galleries and ateliers, fashion-forward clothiers, wine bars, craft breweries, and refined restaurants. For history buffs, you’ll find the Chesapeake Bay Maritime Museum’s floating fleet of vessels, expansive maritime exhibitions, working shipyard, and the 1879 Hooper Straight Lighthouse a delight.

Between the Inn at Perry Cabin and the St. Michaels Harbour Inn, Marina & Spa there are pampering services and fine dining—even golf, so bring your clubs. On most weekends during summer and fall seasons, there could be a culinary festival, outdoor concert, farmers’ market, ghost tours, sailing races, and more events. The St. Michaels Maryland Business Association (stmichaelsmd.org) has the full rundown how to get the most out of your visit.

To the south, Tilghman Island sits at the mouth of the Choptank River. The best spot to settle in is, perhaps, within Knapps Narrows—the slice of channel that creates the island proper. Private and public docks line both its sides, and there are a couple larger marinas at either end. Harris Creek is protected, also popular, and features the renowned Wylder Hotel on its waterfront. For your town excursion, we recommend hopping on your stowaway/folding bicycle to navigate between the island’s charming B&Bs, cozy restaurants, and tucked-away parks and nature sites.