Tilghman Island
On Maryland’s Eastern Shore, 12 miles southwest of St. Michaels
The scoop: Just three miles long and a mile wide, Tilghman Island is an intoxicatingly serene mix of low-key Chesapeake Bay waterman’s town and burgeoning summer retreat. The northern end, with its crab boats, skipjacks (the last commercial sailing fleet in North America), oyster house and tackle shop, has changed little over the years. But the rest of the island is becoming popular with retirees and summer guests.
Drive time: Just under three hours.
Accommodations: The island offers a smattering of quirky and comfortable overnight options. For outstanding food and drink and sublime bay views, try the Tilghman Island Inn (pictured below; 21384 Coopertown Road; 410-886-2141, tilghmanislandinn.com; $125-$300/night), a Wine Spectator favorite. A delight for gourmands and couples alike, the Chesapeake Wood Duck Inn (Gibsontown Road at Dogwood Harbor; 800-956-2070, woodduckinn.com; $149-$229/night) is a 19th-century boarding house turned B&B.
Don’t miss: Board the oldest working sailboat in the country for a two-hour excursion with Wade Murphy on his skipjack the Rebecca T. Ruark (410-886-2176). He’ll fill you in on the ecology of the bay and dredge you an oyster straight from its waters (sans ice and cocktail sauce).
