How to Spend Three Splashy Days in Annapolis, Maryland
The charming maritime enclave offers fun on and off the water.
Ego Alley in Annapolis, Maryland / Photograph by Bob Peterson
Looking for great getaways from Philly this summer? Consider Annapolis, Maryland. This maritime enclave offers fun on and off the water. Below, our favorite ways to explore the city and its shores. And if you want even more travel ideas, click here.
Day One in Annapolis
A room at the Graduate / Photograph by David Mitchell
Just a short drive from Philly, Maryland’s capital city is a charming coastal gem. Take the refreshingly rural Route 301 down to the Bay Bridge, an impressive four-mile steel span over the Chesapeake Bay. Choose a hotel near the action, like the Graduate by Hilton (rooms from $199), and stroll toward the waterfront. Annapolis is eminently walkable. Stop into the Maryland State House for a self-guided tour of the oldest legislative building still in active use in the United States. Pop into the Parley Room, a ’20s-themed joint with great drinks and outdoor seating, and wrap up your evening with wine and modern small plates at Level or a burger at Dry 85 (the whiskey list here goes 100 deep).
Day Two in Annapolis
Graduation at the U.S. Naval Academy / Photograph courtesy of U.S. Naval Academy
Power up with a hearty breakfast at Miss Shirley’s Cafe, a Maryland institution with a Southern twist. Spend the morning at the shops around Ego Alley, especially Reclaimed of Annapolis, where they reimagine nautical and architectural salvage into modern home goods. Schedule a tour at the beating heart of Annapolis, the U.S. Naval Academy. Allow a few hours to explore the historic grounds, and do not miss the stunning crypt of Revolutionary War hero John Paul Jones. Just outside Gate 1, happy hour at the Goat features seafood-forward Mexican cuisine with killer margaritas in a cozy corner space.
Day Three in Annapolis
The Maryland Inn, with the State House in the background / Photograph by Bob Peterson
Buzzy Old Fox Books & Coffeehouse opens early with java, pastries, and a delightfully curated and browsable store. A guided tour of the centrally located Museum of Historic Annapolis provides a smart and quick overview of the region’s history. Grab an oversized homemade pop-tart from Iron Rooster on your way over to the 18th-century William Paca House, a Georgian mansion with the city’s most gorgeous garden — a picturesque spot for your last afternoon.
Travel Journal: 4 Can’t-Miss Aquatic Activities in Annapolis
Rent a kayak or paddleboard from Capital SUP. / Photograph courtesy of Capital SUP
1. Hop on a harbor tour with Watermark. Get a unique view of the Naval Academy and city from atop the double-decker Harbor Queen.
2. Rent a kayak or paddleboard from Capital SUP and explore the calm waters around Nautilus Point. Early birds can book a sunrise session.
3. The Annapolis Maritime Museum & Park is a one-stop aquatic shop featuring engaging exhibits and offering beautiful sunset cruises on a historic skipjack.
4. You can’t leave Annapolis without a waterfront meal. The Choptank offers the ultimate in fresh seafood, creative cocktails, top-notch service, and harbor views.
Published as “Escaping to Annapolis, Maryland” in the June 2025 issue of Philadelphia magazine.
