The 5 Best Day Trips From Washington, DC

Annapolis, the capital of Maryland, is chock-full of prestigious historic sites
Annapolis, the capital of Maryland, is chock-full of prestigious historic sites | © Mira / Alamy Stock Photo
Washington, DC is the pulsing hub of the federal government, what with emblematic landmarks such as the White House and Supreme Court taking center stage. Named after America’s first president and founding father, the capital city has a current of political and historical energy flowing throughout its streets that draws over 20 million visitors annually. If you’re looking to escape the crowds for the day, you can easily do so with the seaside and sun-dappled wine country located just a matter of hours away by car.


Jutting out into the mouth of the Severn River, Annapolis has a rich maritime history. Its thriving shipping industry attracted many wealthy merchants who lay down roots with grand mansions – and many of these 18th-century structures still stand today. The Maryland capital is peppered with prestigious sites, including the red-brick Maryland State House, Romanesque St Anne’s Church and Beaux-Arts Naval Academy that sits on the waterfront.

ToursOriginal Annapolis Seafood Crawl
From $69 per person
2 hours
4.5 (10)

Home of the oyster-roasting and sock-burning traditions – where locals celebrate the spring equinox with a feast of oysters (and by burning their worn winter socks) – Annapolis is the perfect place to tuck into the renowned seafood of Chesapeake Bay. On this tour, you’ll be whisked round the city on an e-cruiser, learning about its absorbing history and sibling rivalry with the community of Eastport. You’ll also stop at a number of local restaurants along your journey, giving you the chance to sample seasonal seafood such as oysters, clams, mussels and crabs – all locally caught.


Known as Charm City to some and the birthplace of the Star-Spangled Banner to others, enchanting Baltimore is a patchwork of diverse neighborhoods. Many famous figures have called the city home, including master of the macabre Edgar Allen Poe, and jazz icon Billie Holiday. The city’s jaw-shaped coastline bites into the Patapsco River, lined with the fashion boutiques of Fells Point (as seen in Sleepless in Seattle) and the aquarium, planetarium and buzzing bars of the Inner Harbor.

ToursFells Point Food Tour
From $73 per person
3 hours 30 minutes

If you’re not sure where to start but you’re eager to dig into some of Baltimore’s best foodie fare, then look no further than the friendly buzz of Fells Point. A local guide will provide an insider’s perspective as you lose yourself in the salty aromas of this historic-meets-hip neighborhood. Along the way you’ll drop into a selection of enticing eateries, including family-run restaurants serving up classic Baltimore-style pit beef and palate-pleasing Spanish tapas. Small groups ensure your experience remains as personalized as possible – and that there’s more than enough food for even the most ravenous traveler.

Chesapeake region

In fictional terms, the Chesapeake region has a less than savory reputation – being the setting of the famous Hannibal book, film and TV series. In reality, however, the coastal region is better known for its mix of busy ports, dense forests and native wildlife and flora. Most notable among these are the blue crabs and oysters that have transformed it into a hub of the seafood industry.

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ToursChesapeake Region Wine Tour
From $97 per person
5 hours

Quench your thirst and curiosity on this wine-fueled exploration of Maryland’s Eastern Shore. Taking you around the best wineries that Chesapeake has to offer, the tour delves into the inner workings of vineyards and introduces you to the local vintners who run them. As you learn about the craft of winemaking, you’ll also get the chance to sample some of the reds and whites. Upgrade to include a cheese plate or charcuterie board to enhance the taste even more (and soak up some of the vino).


The striking skyline of Frederick looks like the zig-zag of a heart monitor, set with the pointed spires of its historic churches. The city is filled with fragments of its Civil War past – immortalizing the conflict with sites such as the Monocacy National Battlefield and National Museum of Civil War Medicine. Go for a rummage in the old-world treasure trove of the city’s 200 antique stores to find grand mementos, including grandfather clocks and authentic armoires.

ToursWalking Tour of Frederick – the Crossroads of Maryland
From $15 per person
2 hours

History buffs will be entirely in their element as they follow historian guide Don through a city awash with evidence of its battle-worn past. The semi-professional photographer will demonstrate his passion for the subject as he leads you, rain or shine, round Frederick’s most historic sites. Stops include an Evangelical Lutheran church, the bucolic stretch of Carroll Creek Park and colonial City Hall – a storied structure with a collection of legend-has-it mysteries to delve into. As the rich heritage of the city is chronicled in engaging detail, you’ll learn of its transformation from German settlement to revitalized city.

Mount Vernon

Named after the sprawling estate of George Washington, Mount Vernon is one of Baltimore’s oldest neighborhoods and a designated National Historic Landmark District. Its towering centerpiece is the original Washington Monument, set among manicured Beaux Arts parks lined with stately homes. The area offsets an affluent suburban culture with historical institutions such as the Neo-Renaissance Peabody Library and a vibrant LGTBQ nightlife scene.

ToursLocal Food Tour of Mount Vernon
From $108 per person
4 hours 15 minutes

No trip to a destination is complete without a taste of its culinary delights or a delve into its past – and on this tour you can do both. Your guide will lead your small group past elegant Victorian homes and moody Gothic churches, providing anecdotes and interesting facts along the way. There will also be regular stops to indulge in a bite to eat. Fill up on local food, and wash it down with a boozy beverage and stories about the diverse architecture of the city.