Annapolis, Maryland
The Chesapeake town that DC families have been escaping to for generations — and still can’t stop going back to.
In this guide
01 — Why Annapolis
The Chesapeake town that DC families have been escaping to for generations.
Annapolis sits at the mouth of the Severn River where it meets the Chesapeake Bay — Maryland’s state capital, home to the United States Naval Academy, and one of the best-preserved colonial towns in America. For generations of DC and Bethesda families, it was the day trip: an hour south on Route 50, a walk through the historic district, lunch on the water, crabcakes and cold beer, and the particular pleasure of a town that has been doing this gracefully since 1649.
Growing up in the DC/Bethesda area, Annapolis was part of the rhythm of summer — day trips for seafood, a family friend with a house on one of the coves outside the city, the kind of waterfront property that dotted the Chesapeake shore for miles, boats at the dock, waterskiing on the Bay in the afternoon. That’s Annapolis as a way of life for a certain generation of mid-Atlantic families, and it still delivers on that promise for anyone who makes the drive.
“Annapolis is what happens when a colonial port town becomes a sailing capital becomes a food destination — without ever losing the thread of what made it worth visiting in the first place.”
02 — City Dock & the waterfront
The heart of everything.
City Dock is where Annapolis announces itself — a working harbor at the end of Main Street, sailboats and powerboats tied up at the slips, the Maryland State House visible on the hill behind, the water of the Severn River opening toward the Bay. It’s a harbor scene that has looked essentially the same, in its bones, for three centuries.
The Chesapeake Bay from the water
The real Annapolis experience — for anyone who can arrange it — is being on the water. Sailing charters, powerboat rentals, and kayak tours all depart from the City Dock area. The Chesapeake from the water, with the Annapolis skyline and the Naval Academy behind you, is the view that explains why this town has been a sailing capital for two centuries.
04 — The crabcakes
The whole point. And they hold up.
A Maryland crabcake is a specific thing — blue crab, minimal filler, broiled or lightly fried, the crab itself doing all the work. Annapolis is one of the best places to eat one while looking at the water the crab came from.
Steamed crabs vs crabcakes
The full Maryland experience is steamed blue crabs — whole crabs, Old Bay, brown paper on the table, a mallet, a beer, and an hour of picking. Messy, communal, the actual way Marylanders eat crabs. If you have time for only one seafood meal in Annapolis, steamed crabs is the one to choose.
05 — Where to stay
Historic inns, waterfront hotels, and Bay properties.
Historic Inn — Downtown
Historic Inns of Annapolis
Three connected historic properties in the heart of downtown — the Maryland Inn, Governor Calvert House, and Robert Johnson House. Walking distance to City Dock, the Naval Academy, and the State House.
Best for: history travelers, couples, the walkable downtown experience
Full-Service Hotel
Westin Annapolis
Full-service hotel within walking distance of City Dock — pool, spa, modern amenities. The comfortable contemporary option in downtown Annapolis.
Best for: those who want full-service amenities
Vacation Rental
Chesapeake Bay Properties
A waterfront house on one of the coves around Annapolis — with a dock, a kayak, and the Bay out the window — is the DC-family tradition done right. The real Annapolis experience for families and groups.
Best for: families, groups, the authentic Chesapeake experience
06 — Where to eat
Waterfront seafood, Main Street dining, and the crabcake conversation.
Cantler’s Riverside Inn
The Annapolis crab institution — steamed crabs at picnic tables on the Mill Creek waterfront, the full Maryland experience. No frills, real crabs, cold beer. The lines are worth it. Cash preferred.
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Carrol’s Creek Café
Waterfront restaurant in Eastport — views across Back Creek to the Annapolis skyline, excellent crabcakes, the upscale Chesapeake dining experience. Reservations recommended.
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O’Leary’s Seafood Restaurant
Eastport’s beloved neighborhood seafood restaurant — consistent, excellent, the local’s choice for a proper seafood dinner. Has been doing this right for decades.
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Chick & Ruth’s Delly
The Annapolis institution since 1965 — enormous sandwiches, the Pledge of Allegiance recited every morning at 8:30am, a diner that has fed generations of state politicians and Naval Academy families.
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Rams Head Tavern
The downtown anchor — craft beer, good pub food, live music venue. The gathering place for an Annapolis evening that wants to end with music.
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07 — Things to do
On the water, in the history, and along the streets.
Sailing charter on the Chesapeake
Annapolis is the sailing capital of America — more sailboats per capita than any US city. Sailing charters depart from City Dock regularly. A two-hour sail on the Bay is the Annapolis experience that no restaurant can replicate.
Naval Academy tour
The Chapel, the Crypt of John Paul Jones, Bancroft Hall, noon formation if timing allows. Free visitor access with photo ID. Plan two hours minimum.
Walk the historic district
Maryland Avenue, State Circle, Church Circle, Main Street — one of the best-preserved 18th century streetscapes in America. The Maryland State House (1779, oldest state capitol in continuous legislative use) is open to visitors.
Eastport — the other Annapolis
Cross the Spa Creek drawbridge for better restaurants, better bars, and the best view of the Annapolis skyline from across the creek. More local, less tourist-oriented. At least one meal here per visit.
Kayak the creeks
The Severn River, Back Creek, and the coves around Annapolis are excellent kayaking territory — sheltered, scenic, a completely different perspective on the city. Rentals at City Dock.
08 — Practical tips
What to know before you go.
One hour from DC
About 35 miles from downtown DC via Route 50 East — an hour in normal traffic, longer on summer Friday afternoons.
Parking is limited
Downtown parking garages fill quickly on weekends. Arrive early. The historic district is compact enough that wherever you park, you walk everywhere anyway.
Naval Academy visitor rules
Photo ID required at the gate. Check usna.edu for current policies before planning your visit around the noon formation.
Crab season runs May–November
Blue crab season peaks in August and September — largest and most plentiful crabs. Outside of season, crabcakes remain excellent but whole steamed crabs are summer/fall only.
Eastport for dinner
Walk the drawbridge to Eastport for at least one meal — better restaurants, lower prices, the best view back toward the Annapolis skyline.
US Sailboat Show in October
The largest in-water boat show in the country — spectacular if boats are your thing, very crowded if they’re not. Know the dates before booking your October visit.
Quick Reference
The Chesapeake town that never needed to reinvent itself.
Annapolis has been doing this well for a long time — the waterfront, the colonial history, the Naval Academy, the seafood, the sailing. It doesn’t need to try to be something new because what it is has been working since 1649. For DC and Bethesda families, it’s been the day trip and the weekend escape and the summer ritual for generations. For good reason.
An hour from DC.
Crabcakes on the water.
The Chesapeake doing what the Chesapeake does.