History should not be confined to the pages of a book when there’s a whole world out there waiting to be explored. For the nostalgic traveler, immersing yourself in America’s fascinating past can be a rich and eye-opening journey. History buffs planning their next getaway should look to these historic US cities for their storied pasts, preserved landmarks, notable monuments, and cultural hotspots.

Boston,  Massachusetts

Historic US Cities boston

It would be impossible to leave Boston off this list given, in many ways America’s freedom was born here. The cobblestone streets where the Puritans and Revolutionaries once walked hold stories of the country’s beginning. The first public library, public school, and public park can all be found here. A 2.5-mile marked path called the Freedom Trail winds through the city stopping at 16 of the most famous historic sites. The route includes Old North Church, Paul Revere’s House, the site of the Boston Tea Party, Bunker Hill Monument, and many others. Even after American Independence, Boston remained a hub of both trade and innovation. 

Favorite Boston Tour

A half-day of walking filled with historic stops and small eats at quirky local favorites. The  North End to the Freedom Trail allows you to visit many of Boston’s most famous attractions in the comfort of a small group with a knowledgeable local guide. Stop at Quincy Market, the Old State House (site of the Boston Massacre) as well as the historic wharves on Atlantic Ave. 

Where to stay in Boston 

Omni Hotel Boston at The Seaport (ADD LINK), now stands at the flagship hotel for the city’s vibrant Seaport district, considered the new culinary, cultural and entertainment epicenter.  The ultra modern hotel, which rises 22 stories and takes up an entire city block on Summer Street, is inspired by an art-gallery-inspired and is set to take guests on an inspirational, immersive, journey via curated art installations, its expansive gallery-style lobby and outstanding gastronomy – there’s seven signature restaurants and bars, including a hip indoor/outdoor pool bar and grill and a cool modern take on the traditional sports bar. 

Oldest Restaurants in Boston

Opened in 1654, Green Dragon Tavern is where the Sons of Liberty met to plan The Boston Tea Party. Today, the restaurant is still serving traditional New England seafood dishes like hearty clam chowder. Marliave, the oldest chef-run restaurant in Boston has been serving high-end French food since 1885. 

Charleston, South Carolina


From its distinct place in Civil War history to its charming gardens and grand antebellum mansions, history buffs will be delighted by a visit to Charleston – a year-round destination with warm weather, good old fashioned Southern hospitality and many a wraparound porch for sipping a glass of wine and soaking in a sense of the past. Tour one of America’s most important neoclassical structures, the Nathaniel Russel House, understand the difficult history of the stunningly beautiful Middleton Place, or simply stroll down the cobblestone streets under the cover of palmetto trees. Taking a short boat ride to explore Fort Sumter and stand where the first shots of the Civil War were taken is a must. 

Favorite Tour in Charleston 

The Historic City Highlights Tour is a short tour that gives you an overview of some of the city’s most iconic landmarks like Rainbow Row, Battery Sea Wall and numerous historic churches. Schedule it early in the trip and you can go back and visit the spots that most grabbed your interest. 

Historic Charleston Hotels

An effortless blend of historic charm and modern amenities make The Restoration the perfect landing spot to explore the “Most Charming City in America.” 

Historic Charleston Restaurants

As one of America’s most historic cities, Charleston retains its obsession with seafood and impeccable southern hospitality and The Charleston Grill offers the best of both those things. Don’t miss out on the crab cakes, they’ve been the signature menu item for over 20 years. 

St. Augustine, Florida

Historic US Cities st. augustine

Founded in 1565 by Spanish explorers who were believed to have been looking for the Fountain of Youth, St. Augustine is the longest continuously inhabited European city in the United States. While that story has proven to be mostly untrue, visitors can still make time to see Ponce de Leon’s Fountain of Youth Archeological Park. The historic Colonial Quarter filled with European Colonial architecture is the undeniable highlight along with Castillo de San Marco, the oldest masonry fort in the continental United States situated right on the water and the beautiful St. Augustine Lighthouse. In a state with many well-known attractions, St. Augustine will surprise more than just the history buffs. 

Favorite Tour in St. Augustine

Take a short expertly guided tour through the St. Augustine Old Jail built in 1891. The tour allows for a peek into the cell blocks and the sheriff’s quarters where he and his family once prepared inmate meals. 

Historic Hotels in St. Augustine 

Located in the heart of the St.Augustine Historic District, Casa Monica Resort and Spa exudes Spanish Baroque Revival design and historic charm while offering all of the luxury amenities modern-day travelers and spa-goers have come to expect.

Historic St. Augustine Restaurants 

Much like the rest of the city, St. Augustine’s historic significance is reflected in the food. Heavily influenced by the culinary heritage of the Minorcans, heavily seasoned seafood with a strong focus on local ingredients is the city’s culinary sweet spot. Situated in a 1920’s ice factory the Ice Plant is still hand-chiseling ice for their cocktails. 

Williamsburg, Virginia

Historic US Cities vwilliamsburg

The world’s largest living history museum, a visit to 18th-century Colonial Williamsburg will make you feel as if you’ve transported back in time. Learn to throw an ax, fire a flintlock musket, or just meander through the village to see craftsmen dressed in full costume. Full scale, meticulously accurate historical reenactments take place here for both education and entertainment. No visit to Williamsburg is complete without also visiting nearby Jamestown and Yorktown who both have their own interactive museums – Jamestown Settlement and the American Revolution Museum at Yorktown.

Favorite Tour in Williamsburg

Walk through the eerily-lit streets of Colonial Williamsburg while hearing some Bone-Chilling Ghost stories. An incredible group of storytellers will share tales of the gruesome bloodshed and tragic accidents that occurred in some of the city’s most famous landmarks. 

Colonial Williamsburg Hotels

The iconic Williamsburg Inn, built-in 1937 is located across the street from historic downtown. The hotel teamed up with historians to help replicate period window treatments, wallpapers, and paint colors. The attention to detail is as apparent inside the hotel as it is throughout the city.

Colonial Williamsburg Restaurant 

Enjoying a historically inspired family-style meal here is a favorite pastime. There are many restaurants and taverns in Colonial Williamsburg but of course, we have a few favorites. Shields Tavern for quintessential southern cuisine and a few revolutionary surprises like ale potted beef. The Rockefeller Room is a contemporary fine dining destination that pays homage to the evolution of American cuisine. You can almost taste the past in the roast pork with apple cider gnocchi.