5 Scenic Maryland Day Trips by Private Chauffeur

Why a Chauffeur Changes a Scenic Day Trip

A scenic drive is only relaxing if someone other than you is watching the road. Hand the driving off to a chauffeur and a long day trip turns into something closer to a private tour — you can watch the Chesapeake go by instead of the mile markers, and nobody has to be the designated sober driver on the way back from a winery stop. Here are five routes we run often enough to have opinions about the best order and timing for each.

1. The Eastern Shore and St. Michaels

A drive across the Bay Bridge to St. Michaels and the surrounding Eastern Shore towns is a full-day trip built around the Chesapeake Bay Maritime Museum, waterfront lunch spots and the area's small-town main streets. The Bay Bridge itself can back up badly on summer weekends, and a chauffeur who tracks the crossing's typical congestion windows can save real time versus guessing.

2. Antietam National Battlefield and Western Maryland

The drive out to Antietam near Sharpsburg covers some of Maryland's most dramatic rural scenery along the way, through rolling Washington County farmland. It pairs naturally with a stop in historic Frederick on the return, making a full day out of what would otherwise be a long there-and-back drive for one stop.

3. Annapolis and the Chesapeake Waterfront

A shorter trip, but one worth doing properly: Annapolis's historic downtown, the Naval Academy grounds and a waterfront lunch make for a relaxed half-day or full-day outing, especially pleasant in a vehicle that can wait curbside while you explore on foot rather than circling for parking in a historic district built before cars existed.

4. Harpers Ferry and the Potomac Confluence

Just across the Maryland line in West Virginia, Harpers Ferry's position at the confluence of the Potomac and Shenandoah rivers makes for a dramatic day trip from the Baltimore-Washington area, with a scenic drive through western Montgomery and Frederick County farmland on the way.

5. A Maryland Wine Country Loop

Several of Maryland's wineries cluster in the Frederick and Carroll County countryside, and a chauffeured loop through two or three of them removes the one real obstacle to a proper wine-tasting day: needing a sober driver for the ride home. See our Maryland wine tour transportation page for how we typically structure a multi-stop tasting day.

Booking One of These Trips

Each of these runs well as an hourly, as-directed reservation — one chauffeur and vehicle for the full day, with stops added or adjusted as the day goes. Sedans suit a couple, and an SUV or Sprinter van works better for a group wanting to do the trip together.

Call 877-609-1919 or book an hourly day trip for any of these routes.