Start from 45 curated places around Annapolis, MD, then choose the recommendations that fit your guests.
Restaurants & cafés
Vin 909 Winecafe
A converted Eastport bungalow doing a daily-changing, locally sourced menu around brick-oven pizza and an unusually deep, fairly priced wine list. It is the neighborhood spot people get jealous of, small enough that the wait is the price of admission.
Osteria 177
A polished Main Street Italian-Mediterranean room that has held the upper-end dinner slot in town for years, strong on house pasta, seafood crudo, and a serious wine cellar. This is where locals book the anniversary dinner.
Trails & outdoors
Quiet Waters Park
A 340-acre county park south of town with paved loop trails through woods down to overlooks on the South River and Harness Creek. The main loop is flat and easy, with miles of unpaved offshoots for anyone who wants more.
Greenbury Point
A 231-acre conservation peninsula at the mouth of the Severn, with sand-and-stone loop trails past the historic radio towers and out to wide water views opposite the Naval Academy. It feels remote despite being minutes from downtown.
Things to do
Annapolis Maritime Museum
A small museum in a former oyster-packing house on the Eastport waterfront, telling the Chesapeake's working-water story with a hands-on bent. It runs sailing programs and a historic skipjack you can actually board.
Banneker-Douglass-Tubman Museum
Maryland's official African American heritage museum, set in a former 1874 church near Church Circle, covering the state's Black history from slavery through the civil rights era. Admission is free and the exhibits are tightly curated.
Landmarks & sights
United States Naval Academy
The 338-acre working campus the city is built around, where midshipmen drill on Worden Field and the green-domed Chapel anchors the skyline. The visitor center runs guided walking tours led by retired officers that get you into the Yard you can't otherwise wander freely.
Maryland State House
The oldest state capitol still in continuous legislative use, and the only one that once served as the U.S. capitol, where Washington resigned his commission in 1783. The Old Senate Chamber has been restored to look exactly as it did that day.