3 days in Annapolis Itinerary

3 days in Annapolis Itinerary

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— 2 nights


Annapolis ©
Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S.
Shop till you drop at Olivins and Fifer Orchards - Farm, Country Store and CSA. Explore hidden gems such as Flag Ponds Nature Park and Eastern Shore Brewing. You'll find plenty of places to visit near Annapolis: Running Hare Vineyard (in Prince Frederick), St. Michaels (Lyon Distilling Company, Spas & Wellness, & more) and Harvest Ridge Winery (in Marydel). The adventure continues: pause for some photo ops at Maryland World War II Memorial.

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Expect a daytime high around 41°F in January, and nighttime lows around 28°F. Finish your sightseeing early on the 20th (Sun) to allow enough time to travel back home.

Things to do in Annapolis

Wineries Shopping Trails

Side Trips

St. Michaels, Running Hare Vineyard, Flag Ponds Nature Park, Fifer Orchards - Farm, Country Store and CSA, Harvest Ridge Winery
Highlights from your plan
Flag Ponds Nature Park ©
Flag Ponds Nature Park
Lyon Distilling Company ©
Lyon Distilling Company
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse