This 2.5-mile (4-kilometer) walking path winds past many of Boston’s historical landmarks from the colonial and revolutionary eras. Marked with a red brick line, the path carries you through the heart of the city. Visit Faneuil Hall, explore the city’s Old State House, and see the site of the Boston Massacre before ending up in modern-day Boston at Copley Square. There are 16 set stops on the Freedom Trail, but the path allows for flexibility to explore the city at your own pace.

Boston is full of museums, both large and small. Make sure to hit the major players, like the Museum of Fine Arts and the Isabella Stewart Gardner Museum, famous for its eclectic collection housed in an Italian-style villa. Afterward, dive into the region’s unique cultural history at spots like the Harvard Museum of Natural History. For a bargain on a day or two of museum trips, pick up a sightseeing pass, such as a Boston CityPASS.

Boston is a baseball town, and games are held at the iconic Fenway Park. Home of the Boston Red Sox, the park is an impressive site, even when it’s not baseball season. On a guided tour of Fenway, you can visit the roof deck that overlooks right field, see the famous 37-foot (11-meter) “Green Monster” as well as “Pesky’s Pole,” and learn why these highlights are significant to Red Sox history.

Boston is home to a large Irish and Italian population, and the Italian community once congregated around the North End neighborhood. With its dense brick buildings, twisting side streets, and many restaurants, Boston’s North End is a unique place to spend the afternoon. Visit the many churches in the area (including the Old North Church), stop by historical sites like the Paul Revere House, and taste the wide range of traditional Italian and American Italian food, including pizza.

Explore Charles River Esplanade, a beautiful park on the south bank of the Charles River Basin. Then, consider getting out on the river itself inside renovated World War II-era amphibious vehicles known as "ducks." Pass the Boston Garden, the Boston Common, Beacon Hill, and Bunker Hill on land before driving off-road and into the river to get a water-side view of the city. For a comprehensive experience of the city, the Duck Boat Tours have it covered.

Massachusetts is one of the top whale-watching spots in the world and you can admire these majestic animals up close from Boston via boat. Cruise around the Stellwagen Bank National Marine Sanctuary at the mouth of Massachusetts Bay to spot whales and other marine life with the help of a naturalist guide. The area is a feeding ground for humpback, fin, minke, pilot whales, dolphins, sea birds, and more.

The city that served as the setting for Cheers definitely knows its beers. Bars and taverns dot the city, one of the oldest being J.J. Foley's Cafe. Raise a few pints of local beer in the city’s historic drinking holes and hear stories about Boston's past. You can also swing by a brewery like Samuel Adams or Harpoon to learn about the Boston brewing process and taste these famed local beers.

Play a part in one of Boston’s milestone moments at the Boston Tea Party Ships and Museum. This experiential floating museum lets you reenact the night of December 16, 1773 when patriots dumped imported tea from ships in protest against British taxes—an event that ultimately sparked the 1775 American Revolution. After joining costumed compatriots, dress up and board a replica ship to throw mock tea crates overboard before exploring the artifact-filled museum.

Wedged between the Charles River and Massachusetts State House, Beacon Hill is one of Boston’s oldest and most picturesque neighborhoods. Stroll its steep cobbled streets past elegant Federal-period houses, dip into the restaurants, coffee houses, and boutiques of upscale Charles Street, and admire much-photographed Acorn Street, a picture-perfect sliver of colonial-era Boston.

Boston’s revolutionary past has left it with many poignant historical sites. Visit the Boston Massacre plaque commemorating the colonists shot by British soldiers here in 1770. The nearby Granary Burying Ground houses the graves of those killed and other notable Bostonians, as does the spooky, centuries-old Copp’s Hill Burying Ground. All three typically feature on Freedom Trail tours, while the graveyards are stock-in-trade for Boston’s ghost excursions.