An hour from DC. Crabcakes on the water. The Naval Academy. The Chesapeake doing what the Chesapeake does.
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.
Is Annapolis Right for Your Trip?
The honest answer from a DC/Bethesda family that has been making this drive for generations.
Steamed Crabs at Cantler’s
Whole blue crabs, Old Bay, brown paper on the table, a mallet, a beer, and an hour of picking. The full Maryland experience. Messy, communal, the actual way Marylanders eat crabs. Lines are worth it.
Search Hotels → Search on ExpediaNaval Academy
338 acres along the Severn River, open to visitors with photo ID. The Chapel, the Crypt of John Paul Jones, Bancroft Hall, noon formation on weekdays during the academic year. Free. Plan two hours.
Search RentalsSailing Charter
Annapolis is the sailing capital of America — more sailboats per capita than any US city. A two-hour sail on the Bay from City Dock is the Annapolis experience no restaurant can replicate.
Search RentalsCross to Eastport
Walk the drawbridge to Eastport for better restaurants, lower prices, and the best view back toward the Annapolis skyline across Back Creek. At least one meal here per visit.
Search Hotels → Search on ExpediaWhy Annapolis
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, 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. The waterfront, the Naval Academy, the historic district, the seafood — it has been doing all of this well since 1649 and shows no signs of needing to try harder.
City Dock & the Waterfront
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 opening toward the Bay. A harbor scene that has looked essentially the same, in its bones, for three centuries. Sailing charters, powerboat rentals, and kayak tours all depart from the City Dock area.
The Naval Academy
The United States Naval Academy occupies 338 acres along the Severn River — a working military installation open to public visitors with photo ID. The Chapel and the Crypt of John Paul Jones (open and free), noon formation on weekdays during the academic year, the USNA Museum in Preble Hall. Check usna.edu for current visitor policies before planning around noon formation.
The Crabcakes
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. Cantler’s Riverside Inn is the Annapolis crab institution — steamed crabs at picnic tables on the Mill Creek waterfront, the full Maryland experience. Lines in season. Cash preferred. Worth it.
Crab season runs May–November, peaking in August and September when crabs are largest and most plentiful. Outside of season, crabcakes are available year-round but whole steamed crabs are a summer and fall experience only.
Where to Stay
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. The history-traveler’s choice.
Chesapeake Bay Waterfront Rental
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.
Search Annapolis Hotels and Rentals
Historic inns downtown, waterfront B&Bs, and Chesapeake Bay properties with dock access. Book early for summer season and the October boat shows.
Where to Eat
Cantler’s Riverside Inn
The Annapolis crab institution — steamed crabs at picnic tables on the Mill Creek waterfront. No frills, real crabs, cold beer. Lines in season. Cash preferred.
Carrol’s Creek Café (Eastport)
Waterfront restaurant in Eastport — views across Back Creek to the Annapolis skyline, excellent crabcakes, the upscale Chesapeake dining experience.
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.
Quick Reference: Annapolis Maryland
| Category | The Answer |
|---|---|
| Distance from DC | About 35 miles via Route 50 — 1 hour normal traffic |
| Best time | May–October for crab season; October for US Sailboat Show |
| The meal | Steamed crabs at Cantler’s — the lines are worth it |
| Naval Academy | Photo ID at main gate; free visitor access; noon formation weekdays |
| On the water | Sailing charter from City Dock — the experience no restaurant matches |
| For dinner | Eastport — walk the drawbridge, better restaurants, best skyline view |
| Parking | Limited downtown — arrive early and walk everywhere from one spot |
| Pair with | Solomons Island — 40 miles south, same Chesapeake character |
Annapolis has been doing this well for a long time. An hour from DC. Crabcakes on the water. The Chesapeake doing what the Chesapeake does.