Like Newport, smaller and older
Annapolis: 48-Hour Escape from Washington, DC
Colonial brick port and sailing capital on the Chesapeake, with the Naval Academy and a 1700s downtown of cobbled streets.
Annapolis: Colonial brick port and sailing capital on the Chesapeake, with the Naval Academy and a 1700s downtown of cobbled streets.
At a glance
Annapolis, District of Columbia is a 45 min drive from Washington, DC, best visited April-June or September-October. Like Newport, smaller and older. Top things to do: United States Naval Academy, Maryland State House, City Dock and Ego Alley. Where to eat: Cantler's Riverside Inn, Galway Bay. Stay at Annapolis Waterfront Hotel or Historic Inns of Annapolis.
68
of 100
Escape score
A solid 48 hours
A short drive for what you get.
- Drive
- 45 min from Washington, DC
- Best window
- April-June or September-October
- Typical stay
- ~$223/night
Escape score: what there is to do and eat (40%), typical weekend lodging cost (30%), drive time (25%), rounding (5%). Computed from our own guide data, never from paid placement.
Why here
Annapolis is a city of 40,000 on the Severn River where it meets the Chesapeake Bay, 45 minutes east of DC. It has more 18th-century brick buildings than any city in the country, a working sailing harbor, and the United States Naval Academy anchoring one end of town. The Maryland State House is the oldest in continuous legislative use, and George Washington resigned his commission there in 1783. The downtown is a walkable grid of cobbled streets, sail lofts, and crab houses, and the docks fill with sailboats in summer.
Annapolis was the capital of the United States for a few months in 1783 to 1784, the only city to ever hold that title officially outside of Philadelphia, New York, and DC. The Continental Congress met in the State House, and it was here that George Washington resigned his military commission, the act that set the precedent for civilian control of the military. The Naval Academy, founded in 1845, anchors the east end of town with the Beaux-Arts Bancroft Hall, the largest dormitory in the world. Sailing is the other institution, Annapolis is the self-proclaimed sailing capital of the country, and regatta season fills the harbor from April through October.
A weekend in Annapolis is a brick-and-water weekend. Walk the cobbled streets and the State House, tour the Naval Academy, watch the sailboats at City Dock, and pick crabs at Cantler's across the bridge. Come April through June or September through October. Two nights lets you add a beach afternoon at Sandy Point State Park on the bay.
The plan
48 hours in Annapolis
Same town, two different weekends. Pick the arrival that matches your Friday.
Friday, on arrival
Check inAnnapolis Waterfront Hotel
From ~$260/night
The only hotel directly on City Dock. Sailboats out the window, walkable to the Naval Academy and every brick street. The central sailing-port base.
Leave Washington, DC after work: the 45 min drive lands you here in the evening.
Friday night
Dinner, then the main streetCantler's Riverside Inn
Across the bridge in Horn Point, a classic Maryland crab house. Pick crabs on brown paper, the crab cakes and the oysters are the orders. The real Eas...
Eat first and walk it off after. Most small-town kitchens stop seating by 9.
Saturday morning
First stopUnited States Naval Academy
Free, photo ID required. Walk the Yard, see the Naval Academy Chapel and John Paul Jones's crypt, and the museum in Preble Hall. 1-2 hours. The Beaux-...
Saturday midday
LunchGalway Bay
On Maryland Avenue, the Irish pub the locals fill. The fish and chips, the shepherd's pie, and a pint are the moves. Walkable from the State House.
Saturday afternoon
Second stopMaryland State House
Free. The oldest state capitol in continuous legislative use, finished in 1779. See the Old Senate Chamber where Washington resigned his commission, a...
Sunday morning
Last stop, then homeCity Dock and Ego Alley
Free. The working waterfront where Spa Creek meets the harbor. Watch the sailboats come and go, then walk up to the brick streets of Main and Maryland...
45 min back to Washington, DC still leaves you the afternoon.
Timings are a suggestion, not a schedule. Shift the whole plan by how late you leave.
The Basecamp
Where to stay in Annapolis
Annapolis Waterfront Hotel
The only hotel directly on City Dock. Sailboats out the window, walkable to the Naval Academy and every brick street. The central sailing-port base.
Historic Inns of Annapolis
The Maryland Inn and two sister inns, 1700s brick buildings on State Circle, a short walk to the State House and the harbor. The colonial stay.
Graduate Annapolis
Boutique hotel on West Street, a 10-minute walk to the Naval Academy and City Dock. Nautical-themed rooms and a rooftop bar. The mid-century downtown base.
What to do
United States Naval Academy
Free, photo ID required. Walk the Yard, see the Naval Academy Chapel and John Paul Jones's crypt, and the museum in Preble Hall. 1-2 hours. The Beaux-Arts Bancroft Hall is the largest dormitory in the world.
Learn more ↗Maryland State House
Free. The oldest state capitol in continuous legislative use, finished in 1779. See the Old Senate Chamber where Washington resigned his commission, and the Rotunda. 45 minutes.
Learn more ↗
City Dock and Ego Alley
Free. The working waterfront where Spa Creek meets the harbor. Watch the sailboats come and go, then walk up to the brick streets of Main and Maryland Avenue. The postcard of Annapolis.
Learn more ↗Pack for Annapolis
Dock & fishing kit
Curated for docks, charters, and working waterfronts in Annapolis.
Tackle box organizer
Compact trays that survive the charter boat.
See price on Amazon →Polarized fishing sunglasses
Cuts the water glare so you can actually see the fish.
See price on Amazon →Fishing pliers with lanyard
Hooks, split rings, and line cutters on one tether.
See price on Amazon →Collapsible cooler
Folds flat in the trunk, carries the catch and the drinks.
See price on Amazon →As an Amazon Associate, book2escape earns from qualifying purchases.
Where to eat
Cantler's Riverside Inn
Across the bridge in Horn Point, a classic Maryland crab house. Pick crabs on brown paper, the crab cakes and the oysters are the orders. The real Eastern Shore dinner in town.
Galway Bay
On Maryland Avenue, the Irish pub the locals fill. The fish and chips, the shepherd's pie, and a pint are the moves. Walkable from the State House.
Most reviewed on Yelp
The most-reviewed restaurants in Annapolis. A solid indicator of where locals actually eat.
Boatyard Bar & Grill
Seafood
Iron Rooster
American, Breakfast & Brunch
Cantler's Riverside
Seafood, Crab Houses
Review counts and ratings are curated from Yelp and may change over time.
Go even deeper
Side trips near Annapolis
Once you've settled into Annapolis, these nearby towns are close enough to fold into the same weekend without moving your basecamp.
5 min from Annapolis
Eastport
Across the Spa Creek bridge, technically a separate village that fought a mock war of independence from Annapolis. The maritime vibe, the boatyards, and the best waterside bars in town.
20 min from Annapolis
Sandy Point State Park
20 minutes east on the bay, the beach at the foot of the Bay Bridge. A swim and a picnic, and the closest real sand to Annapolis, with the bridge towers behind you.
On the calendar
Coming up in Annapolis
Events happening in town, refreshed weekly.
Refreshed weekly
Dec 6
Annapolis Chocolate Binge Festival
Annapolis · First block of West Street
Indulge in decadent chocolate treats, warm drinks, family activities, and seasonal craft vendors on historic downtown streets. It provides a sweet and lively kickoff to winter holiday exploring in the state capital.
Getting there
Drive logistics
From DC, take US-50 east to exit 24 (Rowe Boulevard). ~32 miles, about 45 minutes. Park at the Noah House Garage and walk the downtown, the brick streets are narrow and the parking is tight.
Drive time
45 min
Best time
April-June or September-October
Questions & Answers
Annapolis weekend FAQ
Annapolis is about 32 miles east of DC, roughly a 45-minute drive via US-50 east to the Rowe Boulevard exit.
Yes, free with a photo ID. Visitors walk the Yard, the Naval Academy Chapel, John Paul Jones's crypt, and the museum. Hours vary, check the USNA visitor center before you go.
Annapolis is the capital of Maryland, home of the United States Naval Academy, and the sailing capital of the Chesapeake, with more 18th-century brick buildings than any American city and a walkable colonial downtown.
Yes. At 45 minutes, Annapolis is the closest small-town weekend from DC, with the Naval Academy, a walkable colonial brick downtown, and the sailing harbor, all doable in a relaxed 2-night trip.
Not once you arrive. The State House, the Naval Academy, City Dock, and the brick main streets are all within a 15-minute walk, and the parking garages sit at the edge of the walkable core.
The Dispatch
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