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2 days in Annapolis

Westlake, Ohio
Level Contributor
1 post
3 reviews
5 helpful votes
2 days in Annapolis

I am visiting Annapolis with my 14 year old in a few weeks. We plan to tour the Naval Academy but I don’t have a good handle on where else to go to “see the city,” have a shorter history type tour, cruise the bay, eat seafood (which we both LOVE). Where have been favorite go-to’s to get a good vibe of the city?

2 replies to this topic
Baltimore, MD
Destination Expert
for Baltimore
Level Contributor
1,646 posts
84 reviews
101 helpful votes
1. Re: 2 days in Annapolis

I can spend the day in the historic district walking, shopping and eating but not sure that a 14 year old would enjoy that type of day. There are self guided tours available.

The Annapolis Maritime Museum if you want to learn about the history of the Chesapeake Bay and waterman. I believe the still do skipjack tours.

I definitely recommend getting out on the water, preferably in a sailboat. Out of town guests recently went out on the Woodwind for a 2 hour sail and thoroughly enjoyed themselves.

If don't mind driving about 5 miles from downtown, I recommend Cantler's Riverside Inn for steamed crabs, more "authentic" than some of the places downtown, great crab cakes too. If you don't want to drive, crab cakes are what you want order. I like the atmosphere at Eastport's Boatyard Bar and Grill.

Don't miss homemade pop tarts for breakfast at the Iron Rooster and pies for dessert at Dangerously Delicious Pies.

Level Contributor
462 posts
54 reviews
27 helpful votes
2. Re: 2 days in Annapolis

Great ideas and to add a few more…try the visitors center on West Street and maybe take the trolley tour around town to get a sense of the town. The water taxi from City Dock is a short but fun ride. I agree with Cantlers for crabs but you may also consider Mikes Crab house on Riva Road.. if you are walking in town, go thru the Market House near the docks, Kilwins Ice Cream is a definite stop for me. Mason’s Lobster has amazing lobster sandwiches ( not an Annapolis thing) but truly amazing. Besides Iron Rooster, try Chick and Ruth’s for breakfast, a tourist must. Plus the food is great. Wednesday and Saturday evenings, on west street, a few restaurants participate in Dinner Under the Stars. Walking around in the evening is pretty “neat” also. If you are there Thursday-Saturday and you have a car, try the Dutch Market…an Amish Market and restaurant to include baked goods, fresh meats and gift shop. Enjoy your visit, the food and city.

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