How to spend the ultimate weekend in Boston

The birthplace of the American Revolution, Boston is one of the most historic cities in the United States. It’s home to the country’s oldest public park, university, public library and many other firsts that have given it a unique place in the nation’s cultural and political identity. 

Modern Boston overflows with creativity and innovation in every field imaginable, from literature, music and cuisine to technology, medicine and architecture. I grew up in the nearby suburbs, and every time I visit the city, there are new things to discover, different cultural influences and evolving neighborhoods to explore, even as the city’s identity remains firmly and uniquely Bostonian.

• When to arrive: Arrive on Thursday evening to be ready to start your Boston adventure on Friday morning. Spring (April-May) and autumn (September-October) are the most pleasant, temperature-wise, and have the added beauty of blooming flowers or turning leaves, but these same features also make them very popular times of year for visitors. Summer is another busy tourist season, but the typically hot and humid weather can get oppressive. 

• How to get from the airport: Assuming you’re traveling with easily manageable luggage, the cheapest way to get from Logan International Airport to Boston and neighboring Cambridge is by city subway and/or bus. Plan your trip on the Massachusetts Bay Transit Authority website (MBTA, or simply “the T” to locals). 

• Getting around town: Boston traffic is notoriously horrific, so plan to rely on public transportation and your own two feet during your visit. The city is quite compact and walkable, but if you anticipate making extensive use of the MBTA system, you may want to buy an unlimited 24-hour or seven-day travel pass.

• Where to stay: There’s no getting around it; accommodations in Boston are expensive. But with only a weekend to explore, you’ll want to be fairly close to the action. The Harborside Inn is a relatively (for Boston) budget-friendly converted 19th-century warehouse with an excellent central location. For a splurge with character, The Liberty is a luxury hotel rather ironically housed in a converted former jail. 

• What to pack: You’ll be walking a lot, so comfortable shoes are essential. Casual clothing is perfect for sightseeing and exploring, but pack something a bit dressier if you’re planning to go out for a nice dinner, show or drinks at an upscale bar. 

Thursday

Evening: If you’ve arrived early enough to have some time to explore after checking into your accommodation, the Trillium Beer Garden on the Rose Kennedy Greenway is a great spot for a casual first evening in Boston during the warmer months. In colder weather, Trillium’s year-round taprooms at Fort Point and Fenway are good alternatives. 

Friday 

Morning: Start your day with a visit to the Boston Public Market on Hanover Street, where you can enjoy such treats as freshly baked cider donuts, sweet and savory crêpes, or sourdough bagels, along with other products from local artisan producers. 

How to spend the day: Dive into Boston’s revolutionary past by walking the 2.5-mile Freedom Trail, which winds past key historic sites, starting at the Boston Common, America’s oldest public park. Follow the red line in the pavement through downtown Boston, past locations such as the Old State House, Faneuil Hall, and the Old North Church.

In the North End, be sure to stop for a cannoli at Mike’s Pastry, a venerable Boston institution just a block from the Paul Revere House, where the Revolutionary War hero lived in close quarters with his very large family. Nearby, Monica’s Mercato is an Italian grocery and deli that serves up the city’s best sub sandwiches. 

From the North End, the Freedom Trail continues across the Charles River to Charlestown, where attractions include the Bunker Hill Monument and Museum, as well as the USS Constitution, the world’s oldest commissioned warship still afloat.

Dinner: After walking around all day, you’ve likely built up an appetite, so it’s a good thing Boston has plenty of outstanding restaurants to choose from. Head to the Seaport, a once-derelict industrial area that in recent years has been redeveloped into a thriving residential and business district with excellent dining options, including the flagship harborside location of Legal Sea Foods, an iconic Boston chain.

It has indoor and seasonal outdoor dining at ground level and a year-round top-floor deck. Nearby, The Barking Crab also serves delicious fresh seafood in a very casual clam shack-style environment overlooking the Fort Point Channel.  

After dark: Boston is well-known for its cultural offerings, from concerts to theater and other performing arts. If you haven’t booked ahead, the Bostix booth at Faneuil Hall Marketplace is a good place to score last-minute deals on available shows. 

Saturday 

Morning: Now that you’ve explored Boston’s early history, it’s time to jump forward in time by heading to the Back Bay, a neighborhood built on reclaimed land in the 19th century. Get your blood flowing with a morning walk along the Charles River Esplanade, then grab some coffee and a pastry at Boston-born Tatté Bakery on Charles Street. Or fuel yourself for another busy day with a late breakfast at delightful Beacon Hill Books & Café on Charles Street (reservations recommended).

How to spend the day: The Back Bay is home to two of Boston’s finest art museums, the gorgeous, eclectic Isabella Stewart Gardner Museum and the monumental Museum of Fine Arts (MFA), both housing world-class collections. The Gardner Museum operates on a timed admission system, so reserve tickets in advance to avoid disappointment.

If art isn’t your thing, perhaps nearby Fenway Park, the nation’s oldest Major League baseball stadium, is. Buy tickets well in advance if you want to catch a Boston Red Sox game. Guided ballpark tours are available year-round when there’s no game on. 

When you’re done immersing yourself in whichever iconic Boston treasure you’ve chosen, head back in the direction of downtown, strolling past the elegant 19th-century brownstones lining leafy residential Commonwealth Avenue and Newbury Street, one of Boston’s most famous shopping streets.

Stop for ice cream at JP Licks or try Sonsie if you’re hungry for a meal. Detour a few blocks to Copley Square, home to historic Trinity Church and the Boston Public Library, one of the city’s architectural treasures, well worth a look inside. Rest your feet in the lovely Boston Public Garden in preparation for the evening’s activities.

Dinner: If you’re willing to splurge for something distinctive, book a table at Yvonne’s, a gorgeous, half-hidden downtown supper club serving fabulous drinks and tasty dishes designed for sharing. Alternatively, head to the South End neighborhood for a diverse array of options, including excellent Asian food at Myers + Chang and Spanish tapas at Toro.

After dark: You’ve seen a bit of Boston at street level, now it’s time to see the city from above. Make your way to View Boston at the Prudential Center, the city’s second-highest building, to admire the 360-degree panorama.

Choose between the floor-to-ceiling windows of the indoor viewing area on the 52nd floor or from the open-air rooftop terrace and bar one level below. It’s a great spot to admire the sparkling lights of the city and perhaps even a beautiful sunset. 

Sunday

Morning: When in Boston, it would be a shame not to cross the Charles River to Cambridge, a vibrant city in its own right and home to two of the world’s most prestigious universities, Harvard and the Massachusetts Institute of Technology (MIT).

A morning walk across Memorial Drive from the Longfellow Bridge to Massachusetts Avenue is a good way to start your day, with views of the Back Bay skyline across the river. If you need a morning pick-me-up, pop into your nearest Flour Bakery, an immensely popular local chain with numerous branches in Boston and Cambridge.

How to spend the day: Founded in 1636, Harvard is the oldest and most storied institution of higher learning in the United States. Familiar from countless movies and TV shows, the original section, Harvard Yard, has grassy quadrangles surrounded by red-brick buildings and the monumental Widener Library. Nearby are several excellent museums belonging to the university, including the Harvard Art Museums and the Harvard Museum of Natural History.

The commercial district around Harvard Square has become gentrified and less quirky in recent decades but remains a good place to grab a bite to eat or indulge your sweet tooth at LA Burdick, known for its fine handcrafted chocolate, including its amazingly rich drinking chocolate. Avid readers should make sure to pop into the Harvard Book Store, one of the Boston area’s best. 

There’s plenty more to see and do, but by now, it’s probably time to hop back on the T and make your way back to Logan Airport. Perhaps you’ll spend the flight dreaming about all the things you want to see and do the next time you visit. Whenever you’re able to come back, this captivating city will be waiting, ever-evolving yet always quintessentially Boston.