Eastern Shore Maryland 3-Day Family-Friendly Road Trip

Day 1: Exploring Annapolis

Annapolis, Maryland

8:00AM

Breakfast at Iron Rooster

Start your day with a hearty breakfast at Iron Rooster in downtown Annapolis, known for its delicious breakfast dishes and cozy atmosphere.
Iron Rooster is located in Annapolis' historic district, easily accessible by foot.
50 USD, 1 hour

10:00AM

Tour the U.S. Naval Academy

Visit the U.S. Naval Academy to learn about its history and see the impressive campus. Don't miss the stunning Chapel and Museum.
The U.S. Naval Academy is a short walk from Iron Rooster.
Free, 2 hours

1:00PM

Lunch at Boatyard Bar & Grill

Enjoy a seafood lunch at Boatyard Bar & Grill overlooking the harbor. Try their famous crab cakes for a taste of Maryland.
Boatyard Bar & Grill is a 10-minute drive from the U.S. Naval Academy.
80 USD, 1.5 hours

3:00PM

Explore Historic Annapolis

Take a leisurely stroll through the charming streets of Historic Annapolis, lined with colonial buildings, boutique shops, and art galleries.
Walk from Boatyard Bar & Grill to Main Street in the historic district.
Free, 2 hours

6:00PM

Dinner at Preserve

Indulge in a farm-to-table dining experience at Preserve, known for its innovative dishes using locally sourced ingredients.
Drive to Preserve restaurant located in Annapolis.
120 USD, 2 hours
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Day 2: St. Michaels Adventure

St. Michaels, Maryland

9:00AM

Breakfast at Blue Crab Coffee Co.

Start your day with a delicious breakfast at Blue Crab Coffee Co., a cozy cafe known for its artisanal coffee and pastries.
Blue Crab Coffee Co. is located in the heart of St. Michaels.
30 USD, 1 hour

11:00AM

Visit Chesapeake Bay Maritime Museum

Explore the rich maritime history of the Chesapeake Bay region at the Chesapeake Bay Maritime Museum, featuring exhibits on boats, oysters, and lighthouses.
Walk from Blue Crab Coffee Co. to the museum along the picturesque waterfront.
25 USD, 2 hours

1:00PM

Lunch at Carpenter Street Saloon

Savor a seafood lunch at Carpenter Street Saloon, a local favorite known for its crab soup and friendly atmosphere.
Carpenter Street Saloon is a short walk from the museum.
60 USD, 1.5 hours

3:00PM

Wine Tasting at St. Michaels Winery

Experience a wine tasting session at St. Michaels Winery, where you can sample a variety of locally produced wines in a charming setting.
Drive to St. Michaels Winery for a delightful wine tasting experience.
50 USD, 1 hour

5:00PM

Explore St. Michaels Main Street

Take a leisurely stroll along St. Michaels Main Street, lined with boutique shops, art galleries, and charming cafes perfect for souvenirs and snacks.
Walk from St. Michaels Winery to Main Street.
Free, 1 hour

7:00PM

Dinner at Ava's Pizzeria & Wine Bar

Enjoy a relaxed dinner at Ava's Pizzeria & Wine Bar, known for its delicious wood-fired pizzas and extensive wine selection.
Ava's Pizzeria & Wine Bar is located in the heart of St. Michaels.
100 USD, 2 hours
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Day 3: Exploring Easton and Return to Annapolis

Easton, Maryland

9:00AM

Breakfast at Rise Up Coffee Roasters

Start your day with a gourmet breakfast at Rise Up Coffee Roasters, known for its artisanal coffee and freshly baked pastries.
Rise Up Coffee Roasters is located in downtown Easton.
40 USD, 1 hour

11:00AM

Explore Avalon Theatre

Discover the historic Avalon Theatre, a cultural hub in Easton hosting live performances, movies, and events that showcase the local arts scene.
Walk from Rise Up Coffee Roasters to Avalon Theatre in downtown Easton.
20 USD, 2 hours

1:00PM

Lunch at Out of the Fire

Enjoy a farm-to-table lunch at Out of the Fire, a cozy restaurant known for its seasonal menu and rustic charm.
Out of the Fire is a short walk from Avalon Theatre.
70 USD, 1.5 hours

3:00PM

Drive back to Annapolis

Embark on a scenic drive back to Annapolis, enjoying the picturesque views of the Eastern Shore landscape along the way.
Drive from Easton to Annapolis.
Gas Cost, 2 hours

6:00PM

Dinner at Vin 909

Conclude your road trip with a delightful dinner at Vin 909, a cozy wine bar and restaurant offering a selection of fine wines and delicious small plates.
Head to Vin 909 in Annapolis for a memorable dining experience.
150 USD, 2 hours
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