Romantic 5-Day Honeymoon Itinerary in Maryland

Day 1: Charming Annapolis

Annapolis, Maryland

9:00 AM

Breakfast at Miss Shirley's Cafe

Start your day with a delicious Southern-inspired breakfast featuring their renowned Crab Cake & Eggs.
Head to Miss Shirley's, located near the waterfront.
USD30, 1.5 hours

10:30 AM

Explore the U.S. Naval Academy

Enjoy a guided tour of this historic academy, rich in architecture and military history.
Walk to the nearby Academy entrance.
USD0, 2 hours

12:30 PM

Lunch at Galway Bay

Savor a hearty Irish lunch while enjoying views of the harbor.
Just a short walk from the Naval Academy.
USD50, 1.5 hours

2:00 PM

Visit the Maryland State House

Discover the history of Maryland's government in this beautiful and historic building.
Located a 10-minute walk from Galway Bay.
USD0, 1 hour

3:30 PM

Relax by the waterfront

Take a leisurely stroll along the Annapolis waterfront and enjoy the picturesque views.
Just a few steps away from the State House.
USD0, 1 hour

5:00 PM

Check-in at the Historic Inns of Annapolis

Unwind in your romantic hotel which blends history and modern comforts.
A short drive from the waterfront.
USD200, 1 hour

7:00 PM

Dinner at The Iron Rooster

Indulge in comfort food favorites with a modern twist as you enjoy a cozy dinner.
Just a 5-minute drive from the Inn.
USD70, 1.5 hours
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Day 2: Vibrant Baltimore

Baltimore, Maryland

8:00 AM

Breakfast at Blue Moon Cafe

Start your day with their famous stuffed French toast—an absolute must-try!
Drive approximately 30 minutes from Annapolis to Baltimore.
USD35, 1.5 hours

10:00 AM

Visit the National Aquarium

Discover the wonders of marine life at one of the best aquariums in the country.
A short drive from the cafe, park at the aquarium.
USD40, 2.5 hours

1:00 PM

Lunch at Phillips Seafood

Relish Maryland crab cakes and seafood specialties with a waterfront view.
Located near the aquarium.
USD60, 1.5 hours

3:00 PM

Explore the Inner Harbor

Stroll around the picturesque harbor, enjoying views of boats and historic ships.
Walking around the Inner Harbor.
USD0, 2 hours

5:00 PM

Check-in at Sagamore Pendry Baltimore

Enjoy your luxurious hotel offering an excellent spot for relaxation.
Short drive from the harbor.
USD300, 1 hour

7:30 PM

Dinner at Ouzo Bay

Delight in Mediterranean cuisine and fresh seafood in a stylish setting.
Nearby, just a 5-minute walk.
USD85, 2 hours
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Day 3: Beach Bliss at Ocean City

Ocean City, Maryland

8:00 AM

Breakfast at The Dough Roller

Enjoy a classic beach breakfast with pancakes and fresh fruit.
Drive from Baltimore to Ocean City, about 3 hours.
USD30, 1.5 hours

9:30 AM

Relax at Ocean City Beach

Spend the morning lounging on the sandy beach or enjoying water activities.
Head directly to the beach from the restaurant.
USD0, 3 hours

12:30 PM

Lunch at Fish Tales Bar and Grill

Dine on fresh seafood with a beautiful view of the bay.
A 5-minute walk from the beach.
USD60, 1.5 hours

2:00 PM

Explore the Boardwalk

Stroll along the iconic boardwalk, filled with shops and entertainment.
Head to the boardwalk adjacent to the beach.
USD0, 2 hours

4:00 PM

Check-in at Hilton Ocean City Oceanfront Suites

A comfortable and romantic hotel right by the ocean.
Short walk from the boardwalk.
USD250, 1 hour

7:00 PM

Dinner at The Shark on the Harbor

Relish some of the best local seafood in an upscale atmosphere.
A short drive from your hotel.
USD80, 2 hours
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Day 4: Artsy Easton

Easton, Maryland

9:00 AM

Breakfast at The BBQ Joint

Savor a hearty breakfast of BBQ brisket and eggs—perfect fuel for the day.
Drive from Ocean City to Easton, approximately 1 hour.
USD35, 1.5 hours

10:30 AM

Visit the Academy Art Museum

Explore a variety of exhibits showcasing local and international artists.
Short drive from your breakfast location.
USD10, 2 hours

1:00 PM

Lunch at Scossa Restaurant & Lounge

Indulge in Italian cuisine with locally sourced ingredients.
Just a brief drive from the museum.
USD65, 1.5 hours

3:00 PM

Explore Easton’s Historic District

Stroll the charming streets and appreciate the local shops and architecture.
Walking around the downtown area.
USD0, 2.5 hours

5:30 PM

Check-in at the Tidewater Inn

Experience this historic inn with all the comforts of a romantic getaway.
Short walk from the Historic District.
USD220, 1 hour

7:30 PM

Dinner at The Farmers Market Restaurant

Dine on fresh, local farm-to-table dishes in a relaxed atmosphere.
Just a short walk from the Inn.
USD75, 2 hours
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Day 5: Charming Frederick

Frederick, Maryland

9:00 AM

Breakfast at The Diner

Enjoy a classic breakfast with fresh coffee in a charming diner setting.
Drive from Easton to Frederick, about 1.5 hours.
USD30, 1.5 hours

10:30 AM

Visit the National Museum of Civil War Medicine

Learn about the history of medicine during the Civil War in this fascinating museum.
A short drive from the diner.
USD10, 1.5 hours

12:00 PM

Lunch at The Wine Kitchen

Enjoy a delightful lunch with local wines and seasonal dishes.
Close by the museum.
USD60, 1.5 hours

2:00 PM

Explore Historic Downtown Frederick

Stroll through the historic streets filled with shops and art galleries.
Just a short drive from the restaurant.
USD0, 2 hours

4:00 PM

Visit Baker Park

Relax in this beautiful park or enjoy a peaceful walk along the winding paths.
A quick drive from downtown.
USD0, 1.5 hours

6:00 PM

Farewell Dinner at The Tasting Room

End your honeymoon with a romantic dinner featuring farm-fresh cuisine and fine wines.
A short drive from Baker Park.
USD90, 2 hours
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