Anonymous wrote:OP here. Is there enough to do for four days in St. Michaels? If you are just chilling I'm wondering if the accommodations premium in St. Michaels is worth it.

For me, between hotel amenities (pool, spa, tennis, bikes, kayaks), shops galleries, restaurants, winery, brewery, visiting neighboring towns and possible other seaside activities (sailboat tour, crabbing), there is enough to do.

Anonymous wrote:OP here. Is there enough to do for four days in St. Michaels? If you are just chilling I'm wondering if the accommodations premium in St. Michaels is worth it.

Nearby Easton has several nice restaurants and its downtown is great. It would be easy to spend a day there with St. Michaels as your base. You could see if something is playing at the Avalon theater. From just outside of St. Michaels you can also take the ferry to Oxford, there are a couple of places to eat on the water. Take a book and relax with some ice cream in Oxford!

Have you ever been to Cape May? I’d take the ferry and go there. You could stay there and do a day trip to Philly. And rest, relax the rest of the time.

Brandywine Valley in Pennsylvania

OP here. Is there enough to do for four days in St. Michaels? If you are just chilling I'm wondering if the accommodations premium in St. Michaels is worth it.

Spending time in St. Michael’s without kids would be heaven, to me. It’s only about an hour from Chestertown. You could stay at the Inn at Perry Cabin and enjoy the pool and spa.
Go to the winery and pop into galleries or antique shops. Borrow bikes and go to Tilgman Island. Rent kayaks at Shore Pedal and Paddle. Eat at Limoncello and at Stars (more for the setting than the food on this one).

I would consider a four day cycling trip - staying at various B&Bs…Vermont Country Cycling used to do this.

We are dropping kids off at camp in Chestertown and then will have four days kid-free. I don't want to come back to the DMV--too much driving--but Eastern Shore/Atlantic beaches are not my idea of fun. Can you convince me otherwise? Is there a fancy b&b that's worth it? I'm trying to think through flying somewhere but it's not really enough time and can't chance a late flight for camp pickups.