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Boston is more of a "big town" than a "big city." It's not overwhelming in size but can be that much more confusing to navigate. If you can avoid traffic, however, nothing is too far apart, and there is quite a lot to see and do. The key to Boston is its abundant and distinctive neighborhoods, which between them offer something pretty much for everyone. The main thing is not to try and do everything and putting so much pressure on yourself you forget to enjoy your vacation.
Downtown is the historic heart of the city, and if all you have is half-a-day your "must do" activity is simply following The Freedom Trail from Boston Common to "Little Italy" the North End, which is also America's oldest residential neighborhood. Your "should do's" are Beacon Hill, which is full of tranquil "old money" charm that is best experienced just by leisurely wandering through it; and Back Bay which has a "new money" commercial flavor and larger Parisian-style boulevards. They are idyllically divided by the Public Garden / Boston Common and all together serve as a scenic "other-half-of-the-city" experience.
In most other cities the other neighborhoods might themselves become a main attraction. However, in Boston (by comparison) you can think of them as "nice to do" and explore them selectively based on individual tastes and matching interests. Charlestown is quiet and residential but perfect for those who want to double-down on the history. Cambridge is more chaotic (and technically a different city) but an obligatory pilgrimage for would-be intellectuals and currently-are hipsters. Chinatown has heroically fought off gentrification and remains defiantly authentic. The South End is for foodie's that don't want Italian but should not be confused with South Boston (Southie) which was historically Irish but is becoming rapidly Yuppie. Fenway is for baseball if you're a sports fan and for museums if you're not. Last but not least Seaport is the newest neighborhood in Boston full of the trendiest hotspots fighting with each other in hopes of someday becoming longtime staples.
Avoid driving when possible and wear comfortable shoes. Stay downtown or near public transportation instead of renting a car. Hotels and food can be pricey, but the museums are generally a good value and many offer free admission days. Some of the Best Things To Do In Boston are actually very affordable...
The only thing in Boston more brutal than the architecture are the prices. Fortunately, many of the most memorable experience don't cost a penny. Other than The Freedom Trail, here's our recommendations for after (or before) tour activities.
Walk across the Bridge or (for a better view) take the ferry from Long Wharf, every 15 minutes, daily until 6:00. ($3.70)
Glide across the lagoon in a pedal-powered swan boat, a beloved Boston tradition since 1877.
Rent a bike and cruise the scenic path along the Charles River with stunning city views.
Take the free water shuttle across the harbor for unbeatable skyline views and authentic Latin cuisine.
Stroll Boston's most fashionable street, lined with boutiques, cafés, and Victorian brownstones.
Walk the Harborwalk from Seaport to Charlestown, enjoying waterfront views and harbor activity.
Capture Boston's most photographed street—a cobblestone lane on Beacon Hill with gas lamps and charm.
Explore the iconic golden-domed State House with free guided tours showcasing marble halls, historic chambers, and stunning architecture.
Explore the iconic golden-domed State House and pay homage to the "Sacred Cod" with free guided tours showcasing marble halls, historic chambers, and stunning architecture.
1.5 mile walk through 10 historic sites on Beacon Hill that tell the story of Boston's 19th-century African American community.
Take the MBTA Commuter Rail to explore charming towns outside Boston like Salem, Concord, or Rockport for a scenic day trip.
Each neighborhood has its own unique character and charm. Click any card to discover what makes it special.
Downtown
Boston's bustling center featuring the Freedom Trail, historic sites, theaters, and the financial district.
North End
Boston's oldest neighborhood, famous for authentic Italian restaurants, historic sites, and the annual St. Anthony's Feast.
Beacon Hill
Gas-lit streets, brick sidewalks, and Federal-style rowhouses make this Boston's most picturesque neighborhood.
Back Bay
Victorian brownstones, world-class shopping on Newbury Street, and architectural gems like Trinity Church.
Charlestown
Home to the USS Constitution and Bunker Hill Monument, this waterfront neighborhood blends history with modern charm.
Cambridge
Across the Charles River, home to Harvard and MIT, with vibrant squares, bookstores, and innovation.
Chinatown
Authentic Asian cuisine, traditional markets, and the ornate Chinatown Gate welcome you to this vibrant district.
West End
Home to TD Garden (Celtics & Bruins) and the Museum of Science, this is where excitement happens.
Fenway
Legendary Fenway Park, world-class museums, and a lively college atmosphere define this iconic area.
South End
Trendy restaurants, art galleries, and the largest Victorian brownstone district in the country.
East Boston
Diverse community with stunning harbor views, authentic Latin cuisine, and easy airport access.
South Boston / Seaport
Working-class roots meet modern development along the waterfront. Famous for St. Patrick's Day parade.