7-Day Maryland Adventure: From Historic Sites to Coastal Charm

Day 1: Historic Baltimore

Baltimore, Maryland on July 1, 2025

9:00am

Breakfast at Blue Moon Cafe

Enjoy a hearty breakfast at this popular local spot known for its creative pancakes and classic American breakfast fare, open from 7am to 3pm.
USD15, 1h0m

10:30am

Visit National Aquarium

Explore diverse marine life including sharks, dolphins, and tropical fish in one of the nation’s top aquariums, open from 9am to 6pm.
USD39.95, 2h30m

1:30pm

Lunch at Phillips Seafood

Delight in Maryland’s famous crab dishes and fresh seafood overlooking Baltimore’s Inner Harbor, open from 11:30am to 9pm.
USD30, 1h0m

3:00pm

Explore Fort McHenry National Monument

Visit the historic fort that inspired the U.S. national anthem; the site offers exhibits and scenic waterfront views, open 9am-8pm.
USD15, 1h30m

5:00pm

Stroll Inner Harbor Promenade

Enjoy a relaxing walk along the harbor, with shops, street performers, and picturesque boat views.
Free, 1h0m

7:00pm

Dinner at Thames Street Oyster House

Savor Chesapeake Bay oysters and classic seafood dishes in a cozy setting open until 10pm.
USD40, 1h30m
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Day 2: Maritime Annapolis

Annapolis, Maryland on July 2, 2025

8:00am

Breakfast at Miss Shirley’s Cafe

Start with popular Southern-inspired breakfast dishes in a lively atmosphere, open from 7am to 3pm.
USD20, 1h0m

9:30am

Tour U.S. Naval Academy

Discover the history and tradition of the Naval Academy with guided tours available from 9am to 4pm (closed Sundays).
USD0, 2h0m

12:00pm

Lunch at Carrol’s Creek Cafe

Dine on waterfront while enjoying fresh seafood and an extensive wine list, open 11:30am to 9pm.
USD35, 1h0m

2:00pm

Visit Maryland State House

Explore the oldest state capitol still in continuous legislative use, open 9am-4pm Monday-Saturday.
Free, 1h0m

3:30pm

Annapolis Historic District Walk

Wander charming 18th-century streets lined with shops, galleries, and cafés.
Free, 1h30m

6:00pm

Dinner at O’Learys Seafood Restaurant

Enjoy fresh local seafood and classic Maryland crab cakes open until 9pm.
USD40, 1h30m
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Day 3: Sailing & Shopping

Annapolis, Maryland on July 3, 2025

8:30am

Breakfast at Baker’s Street

Grab fresh pastries and coffee from this beloved neighborhood bakery, open 7am to 1pm.
USD12, 0h45m

9:30am

Sailing Tour of Chesapeake Bay

Relax on a 2-hour sailing tour offering beautiful views of the bay and Annapolis harbor.
USD80, 2h0m

12:00pm

Lunch at Annapolis Market House

Sample a variety of local foods from vendors in this historic market open 9am-6pm.
USD15, 1h0m

1:30pm

Shop City Dock and Main Street

Browse boutique shops and art galleries in the heart of Annapolis.
Free, 2h0m

4:00pm

Visit William Paca House and Garden

Tour this historic Georgian mansion and beautifully maintained gardens, open 10am-4pm.
USD10, 1h0m

6:30pm

Dinner at Lemongrass

Enjoy upscale Asian fusion dishes in a romantic waterfront setting, open until 9pm.
USD45, 1h30m
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Day 4: Charming Eastern Shore

St. Michaels, Maryland on July 4, 2025

7:30am

Breakfast at St. Michaels Coffee & Ice

Start your day with fresh pastries and specialty coffee, open 7am to 3pm.
USD10, 0h45m

8:30am

Drive to St. Michaels (from Annapolis)

Travel approximately 1 hour east to the historic town famous for maritime heritage.
Gas USD15, 1h0m

9:30am

Visit Chesapeake Bay Maritime Museum

Explore exhibits on the bay’s history, boatbuilding, and culture, open 9am to 5pm.
USD15, 2h0m

12:00pm

Lunch at The Crab Claw Restaurant

Enjoy fresh crab and seafood with a view of the Miles River, open 11:30am to 9pm.
USD30, 1h0m

1:30pm

Explore downtown St. Michaels

Shop local boutiques, art galleries, and enjoy scenic harbor views.
Free, 2h0m

4:00pm

Relax at Saint Michaels Harbour Inn & Suites pool

Unwind with a swim and peaceful harbor views.
Free (hotel guests), 1h30m

6:30pm

Dinner at A Little Taste of Heaven

Savor creative American dishes using local ingredients, open until 9pm.
USD40, 1h30m
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Day 5: Historic Oxford Visit

Oxford, Maryland on July 5, 2025

8:00am

Breakfast at Carpenter Street Saloon

Enjoy a casual breakfast in this popular local tavern, open 7am to 2pm.
USD15, 1h0m

9:00am

Drive to Oxford

Short 20-minute drive to the quaint riverside town with rich history.
Gas USD5, 0h20m

9:30am

Oxford Museum and Town Walking Tour

Visit the museum and enjoy a self-guided walking tour of historic buildings and waterfront paths.
USD5, 2h0m

12:00pm

Lunch at The Robert Morris Inn

Dine in one of Maryland’s oldest inns with waterfront views and hearty meals, open 11:30am to 8pm.
USD30, 1h0m

1:30pm

Take a Kayaking Tour on the Tred Avon River

Enjoy a guided 2-hour kayak excursion exploring the scenic coastline and wildlife.
USD50, 2h0m

4:00pm

Return to St. Michaels

Drive back to St. Michaels for the evening.
Gas USD5, 0h20m

6:00pm

Dinner at St. Michaels Crab & Steak House

Experience fresh seafood and steak options in a cozy atmosphere, open until 9pm.
USD40, 1h30m
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Day 6: Frederick's Heritage & Nature

Frederick, Maryland on July 6, 2025

7:30am

Breakfast at Brewer’s Alley

Start your day with a hearty breakfast and excellent local brews, open from 7am.
USD18, 1h0m

8:30am

Drive to Frederick

Approximately 1.5-hour drive northwest from St. Michaels.
Gas USD20, 1h30m

10:00am

Downtown Frederick Walking Tour

Explore historic architecture, antique shops, and art galleries in this charming town.
Free, 2h0m

12:00pm

Lunch at Volt

Experience creative American cuisine in a historic setting, open 11:30am to 2pm.
USD45, 1h0m

2:00pm

Visit National Museum of Civil War Medicine

Discover the history of medical practices during the Civil War, open 10am to 5pm.
USD10, 1h30m

3:30pm

Walk Catoctin Creek Park Trail

Enjoy a scenic nature walk along the creek with peaceful surroundings.
Free, 1h0m

6:00pm

Dinner at The Tasting Room

Dine on farm-to-table dishes in a cozy downtown location, open until 9pm.
USD40, 1h30m
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Day 7: Columbia & Departure

Columbia, Maryland on July 7, 2025

8:00am

Breakfast at Bread & Chocolate

Enjoy artisan breads, pastries, and gourmet coffee at this popular bakery, open 7am to 2pm.
USD15, 1h0m

9:30am

Drive to Columbia

About 45-minute drive south from Frederick to Columbia.
Gas USD10, 0h45m

10:15am

Visit Merriweather Post Pavilion and Lake Kittamaqundi

Walk around scenic Lake Kittamaqundi and explore the area near the famous outdoor concert venue.
Free, 1h30m

12:00pm

Lunch at Giant Food Court or local eateries in Columbia Mall

Casual dining with many options suitable for a variety of tastes.
USD15, 1h0m

1:30pm

Visit Robinson Nature Center

Explore interactive exhibits and trails designed to educate about the local environment, open 9am-5pm weekdays.
USD6, 2h0m

4:00pm

Finish and departure

Conclude your Maryland trip or head to the airport/train station as needed.
Varies, Varies
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