Boston, Massachusetts — one of the oldest cities in the US, is where history meets modernity, sports are a religion and seafood is a must-have on the menu. In addition, the Atlantic Ocean is just a short drive away, and you have a sweet spot of appeal for travelers of all preferences.
A hub of innovation, culture and American heritage, Boston represents the heart of New England. The charismatic city sees over 22 million visitors each year.
AAA has been helping members plan trips to Boston for decades and our in-depth Boston travel guide is packed with hotel recommendations, excellent entertainment ideas and delicious dining destinations to help you start dreaming up your perfect trip.
Getting to Boston
Anchoring the northeastern U.S. with Connecticut and Rhode Island to the south and Connecticut to the North, Boston is easily accessible from several transportation hubs in major cities and international ports of call.
By Air
Just 15 minutes outside Downtown Boston is Logan International Airport (BOS). You’ll also find alternatives in the smaller Manchester-Boston Regional Airport (MHT) and the Rhode Island T.F. Green International Airport (PVD) in Providence.
By Rail or Train
Amtrak has three convenient stations in Boston, all within a two-mile radius. They are centrally located in most city accommodations.
- South Station (BOS): South Station is the northern terminus of the busy Northeast Corridor
- North Station (BON): North Station is the gateway to many historical sites
- Back Bay Station (BBY): Boston Back Bay, MA Amtrak Train Station is served by Acela Express, Northeast Regional and Lake Shore Limited trains
How to Get Around Boston
Travel like a local or dust off your favorite walking shoes; either way, Boston was built for exploring and provides plenty of stress-free ways to traverse all of the sites.
Take a Drive
Boston is one of the country’s oldest cities and so are many of the roadways. Its narrow and winding roads make navigating, especially for an “out-of-towner,” challenging. If you choose to rent a car, we recommend opting for a compact version, which will come in handy for parking.
Travel Like a Local By Subway
Natives will tell you – leave the car and embrace Boston’s robust public transport system, a character of the city in itself. The Massachusetts Bay Transportation Authority, affectionately known as "The T," efficiently connects the city. The Red, Orange, Blue and Green Lines make stops at nearly all of the popular city sites, making navigating more straightforward for visitors.
Stretch Your Legs
Boston is widely considered one of the most walkable cities in the United States. Many of its most popular sites and attractions are centrally located, allowing you to make the most out of a daytime itinerary.
Best Time to Visit Boston
Boston sees distinct shifts in weather through the seasons but maintains itself as a year-round destination with well-known events and festivals throughout the year. The city never truly stops and most of its attractions stay open no matter the season, the best time to visit Boston depends on what your priorities are and what you would like to see on your visit to Beantown.
Fall
Fall is the season for leaf peeping in Boston, with natural spaces like the Boston Commons, Harvard’s campus and Boston’s Public Gardens turning on the colors to maximum saturation. Daytime temperatures are still hovering in the 70s in September but drop down into the low 50s in November. One of the can’t-miss fall events is the Head of the Charles Regatta rowing race on the Charles River in October.
Winter
Bostonians are notoriously hardy folks and you’ll find not much stops when the weather shifts from sunshine to snowflakes. The city averages 9 to 14 inches of snow a month through the winter season and if you’re aiming for a white backdrop to your travel photos, January is your best bet. Daytime highs run in the high 30s and low 40s, so pack accordingly. Can’t-miss events during the winter include the Boston Winter Festival at City Hall Plaza and the Boston Tea Party Reenactment in mid-December.
Spring
From March to May, Boston is blooming. Cherry blossoms, magnolias and tulips are bursting throughout the city as daytime temperatures warm to the low 60s and 70s. Spring is the best time of the year to visit for great photos and comfortable weather. Can’t-miss events in spring include opening season baseball games at Fenway Park and the notoriously popular St. Patrick’s Day Parade in March.
Summer
Summer is the perfect season to put “America’s Walking City” to the test. Daytime temperatures top out in the comfortable 80s, making it ideal to tour the historical sites or tour the Charles River Esplanade by kayak or paddleboard. Can’t-miss events in summer include the Seaport Summer Cruise Series, which sees world-renowned musical acts aboard boats and the Boston Kite & Bike Festival.
Top Things to Do in Boston
Boston is a city that caters to every type of traveler. For history buffs, the city is a living museum with its well-preserved colonial architecture and historical sites; art enthusiasts will enjoy both historical and contemporary installations and outdoor enthusiasts will revel in the city’s many green spaces.
Stroll the Grounds of Harvard
Stroll through the prestigious Harvard University, starting at the iconic Harvard Yard, the oldest part of the campus. You'll also want to stop at Massachusetts Hall, the oldest surviving building at Harvard and one of the two oldest academic buildings in the United States. The statue of John Harvard, also known as the "Statue of Three Lies" due to the inaccuracies inscribed on its pedestal, is also a great iconic stop. If you prefer a guided option, booking an official tour is a great option.
Take a Boston Hop-on Hop-off Tour
If your legs need a break or you have a short timeframe, the Boston Hop-on Hop-off Tour is the way to go. With 14 stops around Boston, you can see Boston at your own pace with unlimited rides. When you take a seat on the trolley, the guide will share interesting historical details and entertaining anecdotes about Boston's history.
Explore Boston’s Chinatown
Boston’s Chinatown is one of many cultural hotspots throughout the city. It is most definitely a hub of Boston’s strong food culture. Hand-pulled noodles, Peking Duck and hot pots that will transport you across the world are all here along Beach Street. If you happen to be in town in January or February, you won’t want to miss the Chinese New Year celebrations, complete with firecrackers, dumplings and lion dances.
Walk Inside Paul Revere’s House, the Oldest Building in Boston
One of the most popular stops in Boston's North End is the city's oldest building, dating back to around 1680. Paul Revere’s House is preserved as the starting point of Paul Revere’s famous “midnight ride” in 1775 to alert his compatriots of the approaching British forces.
The house has served various purposes over the years, including a bank, grocery store and cigar factory, but has most recently been restored to serve as a museum, showcasing 17th-century architecture and original artifacts like Revere's silverware and the era’s historical documents.
Sample the Brews at the Samuel Adams Boston Brewery
If you’re looking for a drink and a little bit of beer history, head to the Jamaica Plain neighborhood to sample beers at the Samuel Adams Boston Brewery. Take a guided tour through the production process where the brand first began, learn about the history of brewing and enjoy a barrel-aged beer with cheese pairing.
Outdoor Activities in Boston
Boston boasts an all-season appeal for outdoors enthusiasts whether you want to float, hike, or ride a swan. These are just a few of the can’t-miss outdoor activities in Boston.
Hike the Freedom Trail
Not so much a rugged hiking trail as it is a well-maintained path through historical sites, the Freedom Trail is the perfect tour through Boston’s historic sites.
The 2.5-mile-long path weaves through the city, passing by 17 locations, including museums, churches, meeting houses, burying grounds, parks, a ship and noted historic markers collectively narrating the story of the American Revolution.
Kayak Along the Charles River Esplanade
Arguably one of the best, 360-degree vantage points of the city is from the Charles River afloat a kayak. The Charles River Esplanade is a public park stretching three miles along the river banks. Calm conditions make it a perfect way for the family to take in the Boston skyline, Cambridge, the Harvard University Campus and Fenway Park.
Where to Stay in Boston
Boston’s accommodations cover the gamut from luxurious hotels to budget-friendly “apartment hotels,” B&Bs and even houseboats. Here are a few AAA Diamond-designated options.
The VERVE Boston Natick, Tapestry Collection by Hilton
- Address: 1360 Worcester St, Natick, MA
- Diamond-designation: Three Diamond
- Best For: Pop culture enthusiasts
This boutique hotel brings a stylish pop culture atmosphere, with each elevator stop boasting a specialized theme relating to art or music; a nostalgic arcade gaming experience even takes over one of the floors. Inspired by the culinary legend Julia Child, the in-house restaurant serves a generous breakfast buffet every morning, making for a uniquely scenic start to the day.
Seaport Hotel® Boston
- Address: 1 Seaport Lane, Boston, MA
- Diamond-designation: Four Diamond
- Best For: Sustainability
The Seaport Hotel is an upscale experience packaged within certified EcoRooms & EcoSuites. The Seaport features an indoor heated pool, two restaurants and a full bar. Some rooms on the higher floors give sweeping views of Boston Harbor or the cityscape. Located just steps from the waterfront, it’s perfect for accessing Boston’s green spaces.
Residence Inn by Marriott
- Address: 370 Congress St, Boston, MA
- Diamond-designation: Three Diamond
- Best For: Luxury
If you’re looking to splurge on accommodations, the Residence Inn by Marriot in Downtown Boston will not disappoint. Nestled within a historic structure dating back to 1901, the harmonious fusion of historical charm and contemporary industrial design are on full display. Previously serving as a sugar and molasses warehouse, the guest rooms are characterized by original brick walls, lofty ceilings with visible wooden beams and large windows.
Where to Eat in Boston
While the local food landscape of the city is built around seafood, you’ll find a little bit of everything, all of it infused with a distinct Boston flavor. From the hip vegan spots in Jamaica Plain to the fine dining of Beacon Hill, there are plenty of famous Boston foods to fill up your breakfast, lunch and dinner plans. Many local favorites also boast AAA Diamonds, so be sure to add one or all of them to your Boston itinerary.
Cantina Italiana
- Address: 346 Hanover St.
- Diamond-designation: Approved
- Reservations: Suggested
- Cuisine: Italian
Cantina Italiana, established in 1931, is one of the oldest restaurants in Boston’s historic North End. Operated by brothers Chuck and Fiore Colella, it serves classic Italian dishes like caprese, risotto and parmigiana. Known for its hearty cuisine and welcoming atmosphere, it remains a local favorite.
Legal Harborside
- Address: 270 Northern Ave, Boston, MA
- Diamond-designation: Approved
- Reservations: Suggested
- Cuisine: Seafood
Legal's flagship restaurant boasts panoramic waterside views, presenting three distinct dining experiences across its three floors – one of which is the roof deck; This is an eatery you’ll want to return to more than once. Each of these levels offers a unique take on seafood cuisine.
The menu features beloved New England seafood staples such as fried clams, lobster rolls, baked scrod and raw oysters, much of which is sourced locally.
Mamma Maria
- Address: 3 North Square, Boston, MA
- Diamond-designation: Four Diamond
- Reservations: Suggested
- Cuisine: Italian
Boston has a rich Italian history that began with the steady influx of Italian immigrants in the late 1860s. Mamma Mia is an edible ode to Boston’s past with an imaginative Italian menu featuring a fusion of fresh local and regional ingredients. The four-season terrace on the second floor boasts views of the historic North Square. The outdoor terrace, nestled in the city’s famous cobblestone streets, completes the “only in Boston” experience.
Boston Photo Spots
Boston is an undeniably picturesque city with its blend of historic charm and modern elegance. Beautiful cobblestone streets, quaint brownstones and iconic landmarks like the Paul Revere House and Old North Church make it easy to get a great shot for the photo album. Here are just a few of the best photo spots in Boston.
1. Fan Pier Park
On any given day, you’ll find Fan Pier Park busy with amateur (and professional) photographers. Panoramic views of the city skyline against the Boston Harbor, sailboats dotting the water and local city wildlife make it the perfect backdrop for an Instagram photo or a printed one. Sunset and sunrise photos are especially popular in the park.
2. Boston Public Garden
Boston Public Garden boasts over 80 species of plants and flowers, an abundance of regional and exotic trees and the famous statue of George Washington on his horse. You could spend all day taking photos in Boston Public Gardens.
3. Copley Square
Copley Square is a rich optical tapestry of architectural styles, from the modernist design of the Hancock Tower to the historical grandeur of the Boston Public Library and the Old South Church. In the center of the square, you'll find a stately fountain, which makes for a lovely photo backdrop.
4. Commonwealth Avenue Mall
This beautiful, tree-lined parkway stretches from the Boston Public Garden to Kenmore Square, offering a myriad of photo opportunities along the way, from statues and memorials to elegant rows of Victorian brownstone homes.
This photo spot changes with the seasons, with the spring bringing lush greenery and blooming flowers in contrast to the fall when stunning hues of red, orange and yellow light the scene in fiery tones.
Boston Day Trips
Boston's strategic location makes it an excellent home base for day trips to various East Coast sightseeing destinations. Its proximity to numerous historic and scenic locations in New England means that you can revisit the Witch Trials of Salem one day while basking in Maine’s famous lobster rolls the next. Here are some popular day trip options under two hours away from the city center.
1. Portland, Maine
Portland is a charming seaside city located just a two-hour drive north of Boston. Cobblestone streets, particularly in the captivating Old Port District, are home to boutiques, quaint pubs and atmospheric cocktail bars, like the exceptional Jewel Box or Blyth & Burrows. It is also a magnet for food enthusiasts across the country.
Grab an authentic Maine lobster roll at the Portland Lobster Company or Miller Brother’s Seafood, then walk it off by strolling along Portland Pier.
2. Salem, Massachusetts
Just a short forty-minute skip up the Eastern Seaboard and you’ll find yourself sent back to the 1692 Witch Trials. Today, the residence turned museum of Judge Corwin, who oversaw the trials, draws inquisitive visitors. The Salem Witch Village is another draw to explore that era where modern witches lead tours and you can explore a replica of a village from the time of the trials.
3. Providence, Rhode Island
Providence, the capital of Rhode Island, is an excellent destination for a family-oriented day trip. You won’t be in the car long at just an hour away and there is plenty to do to accommodate small travelers. A little people-friendly itinerary may feature a visit to the Providence Children's Museum or Roger Williams Park Zoo for hands-on exhibits or a trip to the Roger Williams Park for its beautiful gardens, walking paths, playgrounds, carousel village and the Museum of Natural History and Planetarium.
Visiting Boston on a Budget
Boston is a great city to visit on a budget, with a walkable layout that allows you to save on transport, affordable food options that cater to a large population of college students and a variety of price points for accommodations. Here’s how to approach travel to Boston on a budget.
1. AAA Member Discounts
Did you know that AAA members are offered numerous benefits and discounts during their travels? Members can access many exclusive travel benefits, including lower-price attraction tickets, discounts on rental cars and even massive savings on accommodations with local hotel partners.
2. Look for the Free Experiences
Boston offers a variety of free activities that are perfect for visitors on a budget. Here are some of the best free things to do in Boston.
- The Freedom Trail: This 2.5-mile-long path takes you through 16 historical sites in Boston, including the Massachusetts State House, Paul Revere's House and the USS Constitution Museum.
- Green Spaces: The Boston Public Garden and Boston Common are two of the city's most beautiful green spaces. Go for a picnic, grab some family photos and revel in the city's natural treasures.
- Boston Public Library: Not only is this building one of Boston’s architectural gems, but the library also offers free tours highlighting its history.
- Faneuil Hall Marketplace: While shopping here isn't free, the atmosphere is. Think street performers and historic surroundings with a side of people-watching.
- Charles River Esplanade: Enjoy a walk, run, or bike ride along the Charles River Esplanade, all with a front-row seat to the stunning cityscape.
Travel Tips for Boston
Whether you're a seasoned globetrotter or embarking on your first visit to the city, careful planning is key. Here are a few tips to make the most of your Bostonian getaway.
Bring Your Walking Shoes
You might be surprised how easy it is to get caught up in Boston’s wandering cobblestone lanes. Bring your walking shoes, even if you don’t intend on being on foot for the day. You never know where Boston’s serendipity will lead you.
Learn Some Local Lingo
We’ve all heard about the classic Boston accent, but there is also some slang that you should know. Here are a few phrases you’ll only hear in Boston.
- Dunkies: A nickname for Dunkin' Donuts, a Boston breakfast institution.
- The T: Short for MBTA (Massachusetts Bay Transportation Authority), Boston's subway system.
- Southie: A nickname for South Boston.
- Bubbler: A term used by some Bostonians for a water fountain.
- The Hub: A nickname for Boston, derived from the phrase "The Hub of the Universe," coined by writer Oliver Wendell Holmes in the 19th century.
- The Pike: The Massachusetts Turnpike (I-90), which runs between the city and the western part of the state.
What to Pack for Boston
Packing for Boston should be done according to the seasons. There are a few things that should be in your carry-on bag no matter what.
Basic Items to Pack for Your Boston Getaway
- Comfortable walking shoes
- Backpack
- Hat
- Camera
- Travel documents/ID/health insurance card
- Medication
- Maps of historical locations
- Travel toiletries
- Phone/computer/chargers
- Exercise clothing (if you’re planning to enjoy the numerous outdoor activities in the area)
- Clothing for layering by the season.
- Light rain jacket
Plan Your Ultimate Boston Vacation with AAA
Book your Boston trip with a AAA agent today. Our travel agents make planning a trip easy, with access to vacation packages and a la carte planning options for every budget. Use your AAA membership to access exclusive travel benefits and use Trip Canvas for travel inspiration.