A Weekend in St. Michael’s, Maryland

17th May 2009

I’ve been dying to go to St. Michael’s, Maryland ever since I watched Wedding Crashers a few years ago which was filmed there. It’s a lovely little town about an hour drive from Annapolis. If you’re a fan of boating, it should be on your list of must-visits.


As far as I’m concerned, there is only one place to stay in St. Michael’s: The Inn at Perry Cabin. It is an absolutely beautiful hotel owned by the Orient-Express company. I stayed in the newer section of the hotel that was added a few years ago. My room featured a beautiful marble bathroom with a soaking tub, and the closet was made of teak and looked like the inside of a boat cabin (so beautiful!). My room also had a lovely sitting area with a fireplace, a nice desk overlooking the bay and beautiful framed images of sailboats everywhere. I was in heaven!


The hotel also has a lovely spa and pool, and meticulously manicured gardens. We borrowed bikes and explored the entire property – you could get lost for hours wandering around.


We ate breakfast and lunch at Perry Cabin everyday which was great, but for dinner we checked out a new restaurant in town each night. We started with the Crab Claw, which is a big tourist destination. It sits right on the water in town – you couldn’t ask for a more scenic spot to dine. The food and service are both great – nothing fancy, but a great place to go if you’re in the mood for crab. They serve them right on the table and you can crack them with wooden mallots – so fun!

The second night we had dinner at Market House, a great new place within walking distance of Perry Cabin. The food was wonderful and very reasonably priced. My favorite part was the wine selection – you pick out any bottle you want just like you would in a liquor store and the waitress opens it for you at the table. Every bottle in the restaurant is under $20!

Last, but not least we tried Ava’s Pizzeria and Wine Bar. I had the award-winning Shrimp Puttanesca with creamy polenta. It was good, but I didn’t think it was award-winning. The rest of the table tried a variety of pizza and pasta dishes – all wonderful.

See and Do

St. Michael’s, Maryland is all about life on the water – sailing, fishing, crabbing, etc. While you’re there it is absolutely vital that you do two things: go on a chartered boat (power or sailboat) for the day and visit the Chesapeake Bay Maritime Museum. The Museum has an amazing collection of wooden boats and a great education facility for children. Even if you’re not a boat lover, it’s fascinating to investigate the boat restoration facility and admire the beautiful job the museum has done to restore its collection of historical boats.

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