One Of 'America's Prettiest Cities' Is A Cozy East Coast Beauty With Old Town Europe Vibes

Founded in 1649 and named after the British Princess Anne, the Maryland city of Annapolis is hailed as one of "America's prettiest cities," according to Forbes. Its well-preserved cobblestone streets and picturesque waterfront showcase the perfect blend of history and modernity, and its architecture seamlessly transitions from colonial Baroque to Georgian styles. Nicknamed the Sailing Capital of the World, it will come as no surprise that this city is home to the U.S. Naval Academy and boasts a longstanding maritime history.

Located on the Chesapeake Bay, Annapolis is full of good food, art, history, and culture, making it the perfect destination for anyone hoping for a laid-back atmosphere. From its waterfront to its narrow, winding streets, this city promises no shortage of things to do or comfortable places to stay. Offering a number of historic B&Bs and trendy hotels, the city oozes 18th-century vibes without sacrificing modern convenience.

Spring in Annapolis brings mild temperatures and vibrant colors as the flowers begin to bloom. It also offers the chance to see the Annapolis Film Festival and Maryland Day celebrations. Summer is typically hot and is peak tourist season, particularly for sailing enthusiasts, and winter brings cozy charm and festive lights adorning the historic streets. While Annapolis is pretty all year round, you could also visit in the fall, when the autumn leaves make for scenic walks and the best photos. While on your East Coast fall getaway, avoid crowds at Swallow Falls State Park, Maryland's "top hidden gem" for foliage views.

With the highest concentration of 18th-century buildings in the U.S., Annapolis is something of a living museum. The Maryland State House stands as a testament to the city's historical significance and is the oldest state capitol still in continuous use. It is open to public viewing every day from 8:30 a.m. to 5 p.m., and you can take a self-guided tour of the building to delve into its importance throughout history. Throughout the year, the Maryland State House also holds various exhibitions.

The city's identity is deeply intertwined with its maritime history, as shown by the sailboats dotting the harbor. The Annapolis Maritime Museum offers insight into the city's nautical past through interactive displays and organizes sailboat cruises that offer further views of the quaint waterfront. Various other sea tours are also available, with many running daily and lasting anywhere between 40 minutes and a few hours, allowing you to take in the old-world atmosphere of the city from a new perspective.

While there are many American cities that will make you feel like you're in Europe, Annapolis offers a backdrop of old-time charm. Whether you choose to wander the streets or dive into some of the many opportunities to travel back in time, the European vibes in Annapolis are everywhere, from the brick-lined roads and colorful houses of Pinkney Street to the City Dock that looks like a small coastal town plucked straight out of Europe.

Despite maintaining its historical character, Annapolis also offers plenty of modern amenities. Its combination of well-preserved American history and European-inspired architecture and ambiance makes it a welcoming destination that embodies East Coast beauty. While you may choose to visit for its aesthetic appeal, Annapolis is a desirable place to live for its atmosphere and a melting pot of art, food, and activities.

The city's vibrant, contemporary culture sits comfortably alongside its historical roots in its thriving arts scene, with numerous galleries and public art installations. The Future History Now project works with disadvantaged youths to create murals around the city, and the new Guardians of the First Amendment Memorial honors five journalists from The Capital newspaper. The city also offers dance shows at the Ballet Theatre of Maryland and regular theater performances at the Compass Rose Theater and the Annapolis Summer Garden Theater.

Similar to how Baltimore, Maryland, is an underrated foodie destination in America, Annapolis' hidden culinary landscape boasts a diverse range of food, ranging from traditional Chesapeake Bay fare to modern, innovative dining experiences. Given the proximity to the sea, it is unsurprising that Annapolis is home to many seafood restaurants. The crab cakes and mussels at the nautical-themed Boatyard Bar and Grill are particularly popular; alternatively, the speakeasy-themed DRY 85 offers an extensive drink menu with a popular blue cheese and fig burger.