Explore maryland with our 4-day road trip itinerary​

Discover the two faces of Maryland on this four-day road trip that takes you on opposite sides of the Chesapeake Bay, the country’s largest estuary with a watershed that encompasses six

states and the District of Columbia. An appealing urban vibe permeates the bay’s Western Shore, where Maryland’s small but bustling capital charms with the grandeur of a military academy and

a scenic harbor awash with sailboats. Cross the Chesapeake Bay Bridge to the Delmarva Peninsula, which Maryland shares with Delaware and a slice of Virginia, and the vibe shifts

dramatically. Here, on the Eastern Shore, the pace slows, and Maryland’s inviting rural side unveils itself. Think pastoral landscapes, marshes harboring waterfowl, and waters rich with

oysters, crab and rockfish. Historic waterman communities still thrive, and the inspiring story of a Black heroine from pre-Civil War days unfolds. You get a beach day on the Atlantic, too,

and plenty of opportunities to indulge in fresh seafood and crab feasts along the way. Alamy Stock Photo DAY 1: ANNAPOLIS ​Start your adventure in the sailing haven of Annapolis, home to the

U.S. Naval Academy (USNA) and Maryland’s capital. Brick-paved streets lined with vintage storefronts and 18th century brick houses give this bayside city of 41,000 people all kinds of

charm.  Begin with a walking tour of the USNA downtown for a peek at a midshipman’s life. See the nautical-themed stained-glass windows at the Naval Academy Chapel, the crypt of hero John

Paul Jones, lauded as the father of the U.S. Navy, and more. Ninety-minute tours depart from the Armel-Leftwich Visitor Center hourly from 10 a.m. to 3 p.m. Monday-Saturday and from 11 a.m.

to 3 p.m. Sundays. Also on campus, don’t miss the Gallery of Ships at the Naval Academy Museum, which has an impressive collection of warship models from the 17th, 18th and 19th centuries.

Tour information with enhanced braille descriptions of the grounds is available on loan from the visitor center. Less than a mile away, the Maryland State House dates to 1779, making it the

country’s oldest statehouse still in continual use. Look up to discover the most notable architectural feature of this handsome Georgian structure: the wooden dome, constructed in 1794

without nails; wooden pegs reinforced by iron straps hold it together. On lively Main Street, a few blocks south, lovingly preserved buildings from four centuries house restaurants, bars,

galleries and shops for every budget. At Local by Design, you can buy everything from inexpensive decorative pottery to pricier fine art, all created by local artisans. Kitschy shops sell

affordable souvenirs. Annapolis Ice Cream Company is a must-stop for a tasty treat, especially if you’re traveling with the grandkids; it has been voted the town’s best ice cream for 18

years straight. As the sun sets, embrace locals’ favorite pastime: sailing. Take in unparalleled views of Annapolis from aboard the 74-foot Schooner Woodwind on a two-hour Chesapeake Bay

sail. Feel the cool breeze in your hair as you smell the salt-tinged aroma of the water. But the schooner isn’t wheelchair-friendly, so a better option might be one of the 40-minute

sightseeing cruises offered by Watermark on bigger boats with wider gangway ramps and level entrances.  For dinner, indulge in the bay’s bounty at Boatyard Bar & Grill, a favorite of

local sailors across the harbor from downtown in the Eastport district. Try the Open Faced Crab Dip Samich, made with Maryland lump blue crab. The seafood served up in restaurants on this

coast isn’t necessarily cheap, but it’s guaranteed to be fresh. Try local merchants in and around the bay area for inexpensive options.