My husband and I are planning a road trip in June. Solo, no kids, and we are approx. a 5 hour drive away to the southwest. I'd love any suggestions on what to visit, where to stay, good restaurants, etc.
We'll have about 5 days and love a good adventure.

Visit Annapolis. Stay at the Maryland Inn. Walk through the Naval Academy. Eat lunch at Buddy's Crabs and Ribs or at Cantler's Riverside. Shop on Main Street or Maryland Avenue. Monday night Jazz Jam at the Maryland Inn. Go to Rams Head Tavern for good live music, good food and local brewed beer. Chart House is good for cocktails.

Visit harbor in Baltimore. Lot's to do.

On Eastern Shore stay at Inn at Perry's Cabin. Top notch. St.Michaels is vaguely interesting. All others areas around Bay area are pretty boring for a tourist. Uh oh! Wife coming. Gotta Go!

I think the Eastern Shore is pretty quiet, but if that;s what you want it's a great place to go. If Perry Cabin is too pricey, go one town farther to Oxford and stay at the Robert Morris Inn. Have you read Mitchner's "Chesapeake"?? The area has a lot of history as well as wonderful crabcakes!! It's been a long time since we were there--I'd love to go back.

I second (or third) the Inn at Perry Cabin; great rooms and ambience, beautiful grounds (even a croquet court) and bikes to ride into St. Michaels. While in St. Michaels ("vaguely interesting" sells it a bit short, there is a morning's worth of interesting shops to explore), rent a skiff and cruise around the inlets in the area for a few hours. To see the "real" Cheasapeake, take the ferry from Smith Point/Reidville, VA or Crisfield, MD to Smith Island. It's an all-day adventure and a trip back in time.

The Inn At Perry Cabin is a favorite getaway of ours. It is very pricey, so you may choose not to stay there- however, I recommend a visit to the Inn for lunch or dinner. That way you can enjoy the ambiance of the inn and be served a delicious meal.
I haven't done it, but I understand that you can take a boat to Oxford from St Michaels.