This 7 day Maryland self-drive loop takes you from the bustling piers of Charm City to the historic foothills of the Blue Ridge Mountains, finishing in America’s sailing capital.
Days 1–2: Waterfront Culture in Baltimore
Begin your road trip in Baltimore. Spend your first afternoon exploring the bustling Inner Harbor and marveling at the marine life inside the world-renowned National Aquarium. As evening falls, wander the historic cobblestone streets of Fells Point for a classic dinner of fresh Maryland blue crabs.
On Day 2, dive into the city's rich history and culture. Start with a morning tour of Fort McHenry National Monument, the historic birthplace of the national anthem. In the afternoon, explore the stunning collections at the Walters Art Museum or enjoy a panoramic view of the city from the top of Federal Hill Park before dining in the trendy neighborhood of Mount Vernon.
Days 3–4: Historic Charm & Nature in Frederick
Drive one hour west to Frederick, a city known for its beautiful architecture and vibrant arts scene. Spend Day 3 exploring the remarkably preserved 50-block historic district, filled with independent boutiques, antique shops, and local art galleries. Walk along Carroll Creek Park, featuring unique linear water gardens and local craft breweries.
On Day 4, visit the fascinating National Museum of Civil War Medicine. Afterward, take a short drive north to Catoctin Mountain Park for a scenic hike to Chimney Rock, or view the picturesque Cunningham Falls. End your day with a farm-to-table dinner in downtown Frederick.

Days 5–6: Maritime Heritage in Annapolis
Drive southeast to Annapolis, Maryland’s capital. On Day 5, take a guided walking tour of the prestigious United States Naval Academy and admire the historic Maryland State House, the oldest state capitol in continuous legislative use.
Spend your final day on the water. Embark on a scenic Chesapeake Bay cruise, or rent a kayak to explore the harbor. Conclude your trip with a stroll around Ego Alley at City Dock, soaking in the views of passing sailboats while enjoying a waterfront dinner.
7 DAY MARYLAND SELF DRIVE TOUR
From London
Including
Return direct flights with British Airways from London to Baltimore
Standard Car Hire including full insurance
2 nights at 4* Marriott Owings Mills Metro Centre, Baltimore Metro Area, King Room, Room Only
2 nights at 4* Visitation Hotel Frederick, King Room, Room Only
2 nights at 3* The Governor Calvert House at Historic Inns of Annapolis, King Room, Room Only
Prices from £1,379 per person (based on 2 adults sharing)
or
From Scotland
Including
Return flights with Iceland Air from Glasgow to Baltimore via Keflavik
Standard Car Hire including full insurance
2 nights at 4* Marriott Owings Mills Metro Centre, Baltimore Metro Area, King Room, Room Only
2 nights at 4* Visitation Hotel Frederick, King Room, Room Only
2 nights at 3* The Governor Calvert House at Historic Inns of Annapolis, King Room, Room Only
Prices from £1,329 per person (based on 2 adults sharing)
or
From Ireland
Including
Return direct flights with Aer Lingus from Dublin to Washington, D.C
Standard Car Hire including full insurance
2 nights at 4* Marriott Owings Mills Metro Centre, Baltimore Metro Area, King Room, Room Only
2 nights at 4* Visitation Hotel Frederick, King Room, Room Only
2 nights at 3* The Governor Calvert House at Historic Inns of Annapolis, King Room, Room Only
Prices from Euro 1,589 per person (based on 2 adults sharing)
