OP here. Geat ideas. I was thinking about 60min drive the most.
To those who suggested Baltimore, is there nice cozy hotels you'd recommend? Thank you

Anonymous wrote:Any of the B and Bs on Tilghman Island. Less expensive than St Michaels and just as beaitiful!

You don’t do B&Bs for ROMANTIC weekends away. Why do people suggest this?

Pendry Baltimore.

Believe it or not, if you're flexible on timing, you can do pretty inexpensive beach trips to Miami. I often get RT airfare on American from DCA to MIA for around $130 each (I've gone as low as $100), and if you stay in a city hotel in Brickell (not in South Beach), you can get nice hotels really cheap (like the JW Marriott Marquis or Mandarin Oriental). Rental cars are also cheap in Miami; you can get convertibles for dirt cheap down there.

The Ashby Paris, VA

Charlottesville (wineries, hiking, lots of restaurants)
Little Washington (wineries, the inn, sperryville, skyline drive, nearby caverns)
Roanoke (couple cool museums, nice little zoo, hiking)

Berkeley Springs in West Virginia. My boyfriend and I love staying at the Highlawn Inn. They have a few nice restaurants and spas. It's a cute, quiet town and only about 90 minutes from DC

Any of the B and Bs on Tilghman Island. Less expensive than St Michaels and just as beaitiful!

bedford springs - take your sexiest/naughtiest lingerie

Inn at Perry Cabin. And take your hottest lingerie

Anonymous wrote:how old are you and what are you into makes a difference... and your budget does too of course... B&B plus hiking, wineries... williamsburg, baltimore, st michaels (inn at Perry Cabin type places), salamander resort (close but also $$$), the inn at little washington, camping at skyline drive, weekend in Philly, annapolis...

+1

I thought the hyatt chesapeake resort was crappy. Fine for work conferences, not a couples' weekend getaway.

how old are you and what are you into makes a difference... and your budget does too of course... B&B plus hiking, wineries... williamsburg, baltimore, st michaels (inn at Perry Cabin type places), salamander resort (close but also $$$), the inn at little washington, camping at skyline drive, weekend in Philly, annapolis...

How about the other side of the bridge from Annapolis— St Michael’s. Inn at Perry Cabin is beautiful! Or Cambridge— the Hyatt resort, right on the water with its own little beach. Really not far away.

Baltimore. Charolottesville.

Boyfriend of a few months suggested a weekend getaway. We both have busy schedules and other responsibilities and I'd like to stay in the area and considering Annapolis or Chesapeake beach.
Any suggestions? Places to visit?

Thank you.