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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.

            1. I think you will have a great time in Annapolis. Here are a few suggestions:

              49 West Coffeehouse: for some good joe, and delicious treats. Very eclectic, artsy and not too far from the Westin.

              Aromi D'Italia - Right near the harbor, enjoy the wide variety of gelato.

              Osteria 177 - Our favorite dining spot in the historic district. Coastal Italian-Mediterranean Cuisine. Elegant dining right on Main Street. Excellent, fresh food with a wide variety. Plenty of seafood offerings.

              Boatyard Bar & Grill - In Eastport, a sailor's bar/restaurant with decent food, fun atmosphere, large selection of libations. You'll often overhear tales from very salty dogs who may have traveled in from New England, Africa, even Australia.

              Davis' Pub- A total local dive right near the water in Eastport. If you want to be a part of the Eastport experience, plunk yourselves down at an outside picnic table, order some juicy burgers and super crisp fries, and enjoy the local scene while sipping on some cold beer.

              Definitely ditto on Pusser's for a drink and/or Ram's Head, but f the weather is not great, you may want to have a drink at the Chart House if it is not packed with diners waiting for tables. The two story glass in the bar overlooks the harbor and historic Annapolis (in Eastport). A water taxi can deliver you right to the dock. Also near your hotel is Jerry's Seafood. I wouldn't eat there, but would go to the roof top bar for a drink.

              As for other activities......Main Street and upper West Street houses most of the restaurants, shops, boutiques, eateries, etc. A great place for a stroll. Don't forget to walk around State Circle and visit Maryland Avenue which also has some interesting shops.

              I would stop into the Visitor's center which is off of Church Circle almost across the street from Ram's Head Tavern. They will have a map, and other information where you can do your own walking tour. There are many historical buildings that you don't have to tour but walking the cobblestone streets and seeing the architecture is worthwhile. You may want to take a quick peek inside the State House, visit the Naval Academy (the visitor's center is right on the water with interesting artifacts and displays). You can walk the campus which is beautiful but an ID is required for entry.

              Get out on the water either with Watermark Cruises, Woodwind I & II schooners, or power the vessel yourself in rented kayaks, sea doo's or small powerboats.

              The Market house has some interesting vendors now so take a peek in there. It is right on the water. Also, there is a small Farmer's Market on Sundays in a parking lot to the right of Ego Alley as you stand facing the water.

              Enjoy your time and happy Anniversary!

              5 Replies
              1. re: BontheC

                What's in the market now?????? Last time I was over there it was empty after the big chain madness that had been in there...

                1. re: ktmoomau

                  Not sure if you are familiar with Homestead Gardens in Davidsonville, but it is one of the largest and finest nurseries in the state if not the region. They also sell all kinds of garden and outdoor related products. They are currently selling some plants and local veggies and fruits (peaches, tomatoes, corn etc.) Atwaters bakery has taken over about 3-4 stalls and is offering all kinds of wonderful breads, pastries, pies, sandwiches, jams, honey, and other goodies. There is a flower shop there now and Viccaro's Italian Pastry/bakery is still there. It looks a bit disheveled but at least there seems to be a pulse.

                  1. re: BontheC

                    Yeah, I wish they would get the seafood guys back, but that sounds like a major improvement.

                    1. re: ktmoomau

                      Well initial negotiations had mentioned bringing in Annapolis Seafood Co. which has about 5 outlets now. They offer fresh fish, local crabs, seafood, shellfish at the stores in a market setting, but they also prepare them offering seafood baskets with fries, coleslaw and hushpuppies. They are local so it would be nice to see them join the mix..

                      1. re: BontheC

                        They are ok... I liked the guys that used to be in there, they had character, but someplace with soft shell sandwiches and crabcakes that is casual that you could eat on the dock definitely has appeal to locals who work in the area (and the transient State House types) and tourists so I hope that works out. Such a shame what happened there.

              2. DH and I spent our anniversary (#1) in Annapolis last July, and stayed at the Westin - very nice hotel, though (as some noted) a bit off the beaten path. The lobby Starbucks wasn't open on the weekend mornings but there's one just outside the hotel.

                We had brunch Sat at Chick and Ruth's Delly - http://www.chickandruths.com/ - be prepared for crowds and noise but it is definitely a fun experience.

                Dinner Sat was at Reynolds Tavern - nice people but food was only so-so for the prices, I wouldn't recommend it.

                Lunch Sun was a mess of crabs at Cantlers. We got there just after they opened at 11 to avoid the crowds. These were the best crabs I've had in a long time... and exactly the right atmosphere.

                1. I'm grinning as I read your post. My husband and I are going to Annapolis this weekend (early Sept.) for a getaway, love food and drink, and are staying at the Westin. We have visited Annapolis many, many times, sail out of Back Creek, and can't go there without dinner at O'Leary's. Not sure if it qualifies as "foodie," but the food is good (skip the flown-in-from-Hawaii fish and concentrate on what's local--soft shells if they're on the menu) and the service is great. We've also enjoyed Carrol Creek Cafe and second the advice on avoiding most downtown restaurants, especially on a late summer weekend when it will be mobbed. We've enjoyed O'Brien's for drinks, Pusser's is fun but can be very crowded. Brunch at McGarvey's for great bloody mary's (brunch is served Sunday only). Shopping: if you like pottery you have to go the Annapolis Pottery. Sightseeing: in addition to what's already been offered, go to the State House--full of history--the Paca house for gardens if you enjoy that, stroll some of the back streets downtown for the ambiance. And by all means get out on the water, even if it means booking one of those touristy boat trips.

                  1. We had great breakfast / brunch in the Treaty of Paris restaurant on the top of Main street just off the Church Circle. The eggs benedict on crab cakes are unbeatable. It is not an outdoor place, it is quite dark and the atmosphere is not very hip AND it is a hotel restaurant; however I think it was the best thing I have eaten for a long time.
                    For dinner, I can recommend McGarveys and Edgewater restaurant. Both are very casual, the latter a little run down and way out of the center but with the most lump crab meat in crabcakes so big that you will be full from just one.
                    Also there was what looked as a really nice wine bar just down from our hotel (the Loews) on the West street.