Picturesque Annapolis has something for everyone, whether your interests lean towards history, regional food, architecture or charming waterfront views. Fortunately, Annapolis’s compact size makes it easy to sample all of the above in one long weekend. Maryland’s capital city is located about 30 miles from both Washington, D.C., and Baltimore, but world’s away from both bustling cities with its own small-town charm. Here’s a little trivia: The entire city of Annapolis encompasses only 6.7 square miles, but there are more colonial buildings here than any other town in the United States.

Pack your bags for a spring-time escape to this beautiful waterside town. Here’s how to spend your time there.

48 Hours in Annapolis

Brick-lined streets are part of the charm of Main Street, filled with local stores and restaurants on either side. Image: visitannapolis.org

48 Hours in Annapolis

Known as America’s Sailing Capital, quaint Annapolis, Maryland is a treat for boat-lovers. This dock leads to the bustling Main Street. Image: Visitannapolis.org/Kenneth Tom Photography

Day 1

Fly into Baltimore/Washington Airport (BWI) for the closest airport, with a rental car providing the most flexibility for a trip to Annapolis. Where to check in depends on how steeped in history you want to be. Historic Inns of Annapolis has three quaint venues offering 18th-century architecture with up-to-date room amenities. As another option, the new downtown Loews Annapolis blends with other old brick buildings nearby, but has the elegance of a big city hotel inside.

48 Hours in Annapolis

The Governor Calvert House is one of three older homes available as a B&B through Historic Inns of Annapolis.

48 Hours in Annapolis

As a more modern option for overnight stays, the Loews Annapolis has a spacious bar and fitness center.

The best overview of the Annapolis historic district comes from walking the streets, and what’s better than a guide dressed in Colonial garb? The two-hour Four Centuries Walking Tour from Annapolis Tours will take you in the steps of George Washington (it was in the Annapolis State House where he resigned as president in 1783), past 18th Century houses and through the downtown area.

48 Hours in Annapolis

Tour guide Reid Bowman, a retired attorney, explains the historical significance of the Maryland State House on one of his walking tours.

Make sure to spend extra time walking the grounds of the U.S. Naval Academy (note that you must have a U.S. driver’s license or other form of I.D. when passing through the entry gate), a picturesque campus on the water. Hop across the Naval Academy bridge to the Severn Inn for dinner, with views looking back across the Severn River onto Annapolis.

48 Hours in Annapolis

The Naval Academy draws visitors to Annapolis because of its beautiful campus and events.

48 Hours in Annapolis

Navy boats of all sizes can be spotted on the Academy grounds.

48 Hours in Annapolis

Navy officers walk past popular bar Harry Browne’s in downtown Annapolis.

Day 2

To really experience this waterfront town, you need to get in the water. Capital SUP has both stand-up paddleboarding or kayak rentals. They’ll point you to either a quiet waterway for beginners, or seasoned boaters can take off into Annapolis Harbor. When you’ve worked up an appetite, head to an off-the-beaten-path eatery for lunch (few tourists will know about this one): The Point Crab House. This casual waterfront restaurant sits next to a dock along Mill Creek. Their specialty? The lump crab cake sandwich — not surprisingly — although their burgers will also do you right.

48 Hours in Annapolis

Kayaking along downtown Annapolis offers the best views of this waterfront city. Image: visitannapolis.org

48 Hours in Annapolis

No surprise … one of the best ways to get around this water-based city is by water taxi. Image: visitannapolis.org

48 Hours in Annapolis

Crab cakes at The Point — as you would expect in Maryland — are the authentic versions, with lump crab and minimal fillers.

48 Hours in Annapolis

Lunch at The Point, a less touristy destination than many other spots, provides a waterfront view.

Head back to downtown to stroll the shops, or visit the William Paca garden, a pre-Revolutionary War home with acres of parterre gardens and heirloom roses. Afterwards, walk over to Preserve for a drink and dinner, where you’ll be charmed by this Main Street establishment started by a husband-and-wife duo with training from the Culinary Institute of America. They’ll tempt you with grilled Chesapeake Rockfish, Maryland Blue Catfish or Pork and Sauerkraut, which are just a few of their entrées worth trying.

48 Hours in Annapolis

Mom-and-pop stores add to the Norman Rockwell quality of Annapolis.

48 Hours in Annapolis

Wednesday night sailboat races are a colorful sight. Image: visitannapolis.org

48 Hours in Annapolis

May Day festivities include elaborate flower displays all over Annapolis. Image: Carol Weymer

When you’re ready to book your weekend away, check out visitannapolis.org. You’ll find not only suggestions for where to stay, shop and eat, but you’ll also find a calendar filled with fun events, including sailboat shows in both spring and fall, the Crab Feast and the May Day basket competition. Enjoy Annapolis!

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Find more great quick trip ideas in our “Weekend Getaways” section!