St. Michaels

Nestled on Maryland’s Eastern Shore, St. Michaels is one of the most charming waterfront towns you’ll visit. Its heart, South Talbot Street, is lined with quaint boutiques, cozy cafés, and incredible restaurants – perfect for an afternoon of wandering and discovering local favorites.

Below are a few of our personal recommendations, but half the fun is just strolling, exploring, and finding your own hidden gems along the way!

Breakfast & Coffee

  • Eat Sprout

  • Rise Up Coffee Roasters

  • The Blue Crab

  • The Galley

Lunch

  • Ava’s Pizzeria and Wine Bar

  • Corah’s Corner

  • Crab Claw

  • Foxy’s Harbor Grille

  • Stars at the Inn at Perry Cabin

Dinner

  • Bistro St. Michaels

  • Limoncello Restaurant and Wine Bar

  • Plates 208

  • Ruse

  • Theo’s Steaks, Sides & Spirits

Easton

9 miles from St. Michaels

Easton is a charming small town known for its tree-lined streets, art galleries, and welcoming vibe. The town blends history with a lively local scene with local cafés, boutique shopping, and a thriving arts community. Just minutes from the water, it’s the perfect mix of laid-back Chesapeake Bay charm and small-town elegance.

Breakfast & Coffee

  • Breakfast in Easton

  • Rise Up Coffee Roasters

  • The Ivy

  • Weather Gage

Lunch & Dinner

  • Hunter’s Tavern in the Tidewater Inn

  • Legal Assets

  • Out of the Fire

  • Tiger Lilly

  • Wardroom