48 Hours in Boston

Day One

Morning

Start off your day with one of Boston’s most famous restaurants. The Paramount in Beacon Hill is well-known for its breakfast. Served up cafeteria-style, expect all the staples—omelets, pancakes, French toast and more. Or, grab breakfast at Parker’s Restaurant. Specialties on the menu include the American breakfast—two fresh eggs, breakfast potatoes and smoked ham—as well as corned beef hash, a Boston Benedict and more.

After breakfast, explore the antique shops and specialty stores that line Charles Street. Boston Antiques Co. is a great choice for those looking for decorative arts, while Artifaktori is the place to be for vintage clothing. You might also check out some of the historical buildings in Beacon Hill, like the Nichols House Museum, which dates back to 1804, or the Boston Athenaeum, one of the oldest independent libraries in the United States.

Afternoon

After working up an appetite from walking around, head to Sam LaGrassa’s. This family-run shop is only open for lunch on weekdays, but it’s worth stopping by for specialty sandwiches like the jalapeno chicken, pastrami po’boy and Santa Fe barbecue chicken. Or go to The Tip Tap Room on Cambridge Street. The steak frites are a standout, as are the burgers (try the turkey option for a lighter version).

After eating, the Freedom Trail is waiting. This 2.5-mile path winds through downtown Boston, passing by 16 locations significant to the history of our nation. Learn about the American Revolution by visiting churches, meeting houses and more.

Or, take to the water for a different kind of tour—Boston’s Duck Tours are partially on land and partially on the water, cruising around Boston Harbor for a different perspective on the city’s rich history.

Evening

Head over to the nearby the Union Oyster House for dinner. This restaurant boasts the distinction of being the country’s oldest eatery, having started serving food in 1826. It’s even housed in a building dating back to before the revolution. Along with grilled oysters and oysters Rockefeller, this spot also has plenty of delicious lobster dishes—try the lobster ravioli for a truly decadent experience.

Another option for supper is The Tap Trailhouse, also located near the Freedom Trail. Expect classic pub fare like burgers on the menu alongside tons of brews.

To finish off the night, explore Faneuil Hall Marketplace, which has plenty of shops, live entertainment and even houses three historic market buildings. For those who opted out of the Duck Tours, you might also stroll around Boston Harbor—sunsets are particularly beautiful reflected on the water.

Day Two

Morning

For a quick breakfast, head to nearby Boston Brewin’ Coffee for espresso drinks, chai lattes or fresh smoothies. The café’s pastries make for a quick and delicious light breakfast. If you’re looking for heartier fare, however, try The Friendly Toast. From breakfast burritos to homemade bread in flavors like cayenne-cheddar, cinnamon-raisin and more, this spot has plenty of options for the most important meal of the day.

Next, hop on an Old Town Trolley Tour, which stops at a variety of Boston’s most fun landmarks—Fenway Park, Copley Square and even Cheers, the bar made famous by the television show of the same name. You might also opt to visit the nearby Boston Public Garden, a beautiful garden in the middle of the city full of sculptures—including the famous Make Way for Ducklings, based on the beloved children’s novel.

Afternoon

For lunch, Stephanie’s on Newbury has light options—think gazpacho, wedge salads and Thai lettuce wraps—as well as decadent options like lobster rolls, buffalo chicken sandwiches and fish and chips, so you’re sure to find what you’re looking for. You might also try The Parish Café for a wrap or sandwich—and best of all, some alfresco dining out on the patio and in the sunshine.

While in the area, check out Newbury Street which is full of cute boutiques and stores to satisfy any taste, from the high-end (like Chanel and Cartier) to unique spots you won’t find in any other city.

Yet if you’re craving a bit of tranquility, head to the Boston Public Library. This gorgeous building has plenty to offer besides books, including beautiful architecture and paintings, as well as an afternoon tea held in the courtyard.

Evening

The North End of Boston is known for a plethora of amazing Italian restaurants, so book a table at Bricco, which boasts a relaxed atmosphere and mouthwatering entrees like braised duck breast, veal and more. Or, head to Lucca, also in the North End. Options include pan-seared scallops, fresh rigatoni and—for dessert—tiramisu with toasted hazelnuts or a dark chocolate cannoli.

Finish your trip with some cocktails. Parker’s Bar offers barrel-aged cocktails, from rye Manhattans to tequila old fashioneds, as well as classic Moscow mules and other fun libations, like the Botanical Crush.

Lolita Cocina & Tequila Bar in Back Bay also has a fun atmosphere, with dim pink lighting, small plates and fruit cocktails—think: peach sangrias, watermelon mojitos and more.

If you’re lucky, you might even be able to catch a show at one of Boston’s numerous venues, like The Beehive, which is always buzzing with blues and jazz musicians, or The Plough & Stars. For something completely unique, head to Lizard Lounge, which boasts great cocktails and amazing live poetry readings.

If you have more time...

Head to the Mapparium, a three-story globe made of stained glass at the Mary Baker Eddy Library that explores the world’s geography in a fun, visually-pleasing presentation. Kids especially will love this spot.

Or, for more history, make your way to Dorchester Heights for great views of downtown and the harbor. It was also the sight of an important American Revolution-era battle in which American forces were able to capture the area and get a key victory.

You might also visit the New England Aquarium, home to more than 2,000 animals, fun educational events and exhibits covering everything from tide pools to freshwater animals to tropical fish.

The Omni Parker House concierge team contributed to this article.