7-Day Maryland Itinerary

The Ultimate Maryland Family Vacation: Kid-Friendly Adventures, Beaches & History

Theme: A mix of historic sites, scenic coastal drives, outdoor adventures, and world-famous seafood across Maryland.

Best Time to Visit: Spring (April-June) or Fall (September-October) for mild weather and fewer crowds.

Day 1: Arrive in Baltimore & Explore

Fly into Baltimore/Washington International Thurgood Marshall Airport (BWI).

Top Things to Do in Baltimore:

Visit the Inner Harbor – Home to the National Aquarium & historic ships.

Tour Fort McHenry National Monument – The birthplace of the Star-Spangled Banner.

Catch an Orioles Game at Camden Yards (Seasonal).

Try Local Craft Beer at Heavy Seas or Union Craft Brewing.

Dinner at Nick's Fish House or LP Steamers – Enjoy Maryland blue crabs!

Overnight in Baltimore.

Day 2: Annapolis – Maryland's Capital & Sailing City

Drive from Baltimore to Annapolis (45 min).

Top Things to Do in Annapolis:

Tour the Maryland State House – The oldest state capitol still in use.

Visit the U.S. Naval Academy – Walk through this historic military campus.

Take a Sailing Cruise on the Chesapeake Bay.

Try Crab Cakes at Cantler's Riverside Inn.

Overnight in Annapolis.

Day 3: Chesapeake Bay & St. Michaels

Drive from Annapolis to St. Michaels (1 hour).

Top Things to Do in St. Michaels:

Visit the Chesapeake Bay Maritime Museum.

Go Kayaking on the Miles River.

Wine Tasting at St. Michaels Winery.

Dinner at The Crab Claw – A classic waterfront seafood spot.

Overnight in St. Michaels or nearby Easton.

Day 4: Assateague Island & Ocean City Beach Day

Drive from St. Michaels to Assateague Island (2 hours).

Top Things to Do at Assateague Island National Seashore:

See the Wild Ponies Roaming the Beach.

Relax on the White Sand Beaches.

Bike Along the Scenic Island Trails.

Drive to Ocean City, MD (30 min).

Top Things to Do in Ocean City:

Walk the Ocean City Boardwalk – One of the best on the East Coast.

Try Thrasher's French Fries & Dumser's Dairyland Ice Cream.

Ride Amusement Park Rides at Trimper's (Seasonal).

Overnight in Ocean City.

Day 5: Deep Creek Lake & Western Maryland

Drive from Ocean City to Deep Creek Lake (4.5 hours).

Top Things to Do at Deep Creek Lake:

Rent a Boat or Go Kayaking on the Lake.

Hike at Swallow Falls State Park – See Maryland's tallest waterfall!

Skiing & Snow Activities (Winter Only) at Wisp Resort.

Dinner at Mountain State Brewing Co.

Overnight in Deep Creek Lake.

Day 6: Antietam Battlefield & Harpers Ferry

Drive from Deep Creek Lake to Antietam National Battlefield (2 hours).

Top Things to Do at Antietam:

Tour Antietam National Battlefield – Site of the bloodiest battle of the Civil War.

Walk the Sunken Road ("Bloody Lane").

Drive from Antietam to Harpers Ferry, WV (30 min).

Top Things to Do in Harpers Ferry:

Hike Maryland Heights Trail – Amazing views of the Potomac River.

Explore the Historic Town & John Brown's Fort.

Overnight in Frederick, MD.

Day 7: Frederick & Return to Baltimore

Explore Frederick before heading back to Baltimore (1 hour).

Top Things to Do in Frederick:

Walk Through the Historic Downtown.

Visit a Craft Brewery Like Flying Dog Brewery.

Explore Catoctin Mountain Park (Optional Stop).

Drive to BWI Airport (1 hour) & Depart.

Fly home from Baltimore.

Total Drive Time:

Approx. 15-18 hours of driving across Maryland.