How to spend the ultimate weekend in Boston

14.10.2024 - 21:51 / lonelyplanet.com

Oct 11, 2024 • 7 min read

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. 

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