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Anniversary weekend trip to Annapolis

My husband and I have scheduled a weekend getaway in Annapolis in mid Sept to celebrate our 10 yr wedding anniversary. We are early 40s and love good food and drink. Neither of us have been before. We are staying at the Westin and would like to take in all Annapolis has to offer.

Looking for recommendations for brunch/lunch restaurant - fun cafe with outdoor seating and good beer/wine selection would be ideal, any sightseeing/shopping we must do, and most importantly best dinner in town for celebrating a special occasion. A modern foodie restaurant - seafood and fresh/local ingredients with good atmosphere.

Also hints on fun place for a drink after dinner would be welcome. Thank you!

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  1. Glad to hear you'll be visiting our wonderful town. Bear in mind that the Westin is at the edge of the "historic" downtown area, but is still within walking distance (about 20 minutes) of the City Dock area via West Street. But I think your better dining options are away from the dock area.

    For a good wine bar, check out the Purple Tooth, just a few blocks from your hotel. They have limited food but is a nice place to unwind over a glass or two of wine. Interesting architecture inside as well.

    For good seafood I recommend O'Learys, a few minutes across the Spa Creek bridge in the Eastport neighborhood. Reservations recommended.

    A few places NOT to try: Buddys Crabs n Ribs; Wild Orchid Cafe.

    1. I like lewnes steak house in eastport, just over the bridge from the annapolis harbor. They have great steaks and seafood. I also like to have a couple of cocktails while sitting outside at the docside bar at the Marriot called Prusser's Pub. You can watch the boats an the people in annapolis harbor and it is very relaxing.

      1. Agree - Pusser's for drinks and viewing, get the $6 daily special glass of wine at Purple Tooth, Tsunami, Aqua terra or Kinkaid's new place for dinner (O'Leary's sounds too boring for what you're looking for), afternoon beer in the back patio at Ram's Head. At your hotel, Carpaccio has outdoor seating (never been though).

        1. I echo the recommendations for Lewnes and O'Leary's and suggest you also take a look at the following:

          Cantler's: very casual, mostly outdoor, traditional Maryland crabs and seafood.

          Harry Browne's: beautiful spot directly on State Circle and across from the State House; it's a formal, traditional place.

          Les Follies: superb, classic French food.

          Jalapenos: loads of Spanish (and a few Mexican-inspired) tapas

          Mike's Crab House: straight-down-the-middle Maryland crab house

          Most of the spots downtown are "touristy" and should be avoided. But the downtown can be a colorful, fun place to spend an evening; there are only a couple of places worth trying: McGarvey's, Cafe Normandie, Joss. Avoid all the others.

          1. My boyfriend and I spent our anniversary in Annapolis last year and had a really great dinner at Caroll's Creek. It was nice to sit ouside, overlooking the water and eat delicious seafood. I highly recommend it.