New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Free AI trip planner

3 Days in Maryland's Eastern Shore

3 Days in Maryland's Eastern Shore Itinerary

Last updated: 2024 Jun 14

Exploring Saint Michael's Charm

Morning
Start your day with a delicious breakfast at The Inn at Perry Cabin by Belmond, known for its elegant ambiance and exquisite cuisine. After breakfast, visit the historic The Crab Claw Restaurant for a taste of local seafood and waterfront views.
Afternoon
Spend your afternoon exploring the maritime history of Saint Michael's with a visit to the Chesapeake Bay Maritime Museum. Dive into the local culture with a wine tasting experience at Miles River Yacht Club.
Evening
Enjoy a delightful dinner at Bistro St. Michaels, offering a blend of French and American cuisine in a cozy setting. End your evening with a stroll along the charming streets of Saint Michael's.
Bedtime
Find amazing hotels in Saint Michael's.

Discovering Maryland's Culinary Scene

Morning
Indulge in a leisurely brunch at Bistro 112, known for its farm-to-table dishes and welcoming atmosphere. After brunch, explore the local art scene at The Galley showcasing works by regional artists.
Afternoon
Head to Foode for a unique dining experience featuring locally sourced ingredients and creative dishes. After lunch, take a relaxing walk along the waterfront and enjoy the scenic views.
Evening
Dine at Limoncello Italian Restaurant & Wine Bar for a taste of authentic Italian cuisine paired with a selection of fine wines. Wrap up your evening with a nightcap at Bartlett Pear Inn, known for its cozy ambiance and craft cocktails.
Bedtime
Find amazing hotels in Saint Michael's.

Outdoor Adventures in Maryland

Morning
Start your day with a hearty breakfast at Ava's Pizzeria & Wine Bar, offering a variety of breakfast options to fuel your day. Embark on a kayaking adventure along the Miles River with Saint Michael's Kayak Tour, exploring the natural beauty of the area.
Afternoon
For lunch, savor the flavors of the bay at Gourmet by the Bay, known for its fresh seafood and waterfront dining experience. After lunch, visit the Saint Michael's Winery for a tasting of local wines.
Evening
Conclude your trip with a memorable dinner at Theo's Steaks, Sides & Spirits, a steakhouse known for its prime cuts and elegant ambiance. Raise a toast to your Maryland adventure at this iconic dining spot.
Bedtime
Find amazing hotels in Saint Michael's.

Adjacent Cities

kayakFind the right stay during your trip.
Got a question about your trip?