logo-print
Skip to content

Things To Do In Boston On Vacation

boston hidden gems

Hidden Gems in Boston

One of the most popular vacation destinations in the USA, Boston offers visitors an abundance of history, art, music, dining and cultural attractions. But for many, it’s the lesser known spots and points of interest that draw their attention, the less touristy places that provide totally unique Boston experiences. Check out these hidden gems in and around the city on your next trip.

More Info
boston common

Ultimate Guide to Boston Common

15 Stop 15

Established in 1634, the 50-acre Boston Common is the oldest public recreation area in the country. Colloquially known as “the Common,” the park is one of the gems in the Emerald Necklace, a series of parks, urban open spaces and greenways that meander through several Boston neighborhoods and stretch to Roxbury. Boston Common, situated across from the Massachusetts State House, forms the southern base of Beacon Hill and is delineated by Beacon, Park, Tremont, Boylston and Charles streets.

More Info
boston newbury street

Things to Do Near Copley Square

Named to honor the famed Boston artist John Singleton Copley, this Back Bay neighborhood is well known for its history and iconic architectural structures. Here, you can spend the day enjoying its charms in the way of various cafes, historical points of interest and upscale shops. There is also much to do, see and explore just footsteps away. Here’s a guide to some of the top things to do near Copley Square.

More Info
boston-old-north-church

Oldest Sites To See In Boston On Vacation

Many visitors are interested in seeing all the colonial sites and taking an Old Town Trolley Tour is the most efficient way to accomplish that goal. This guide will help you plan your vacation around the oldest attractions in Boston and give you insights on which trolley stops are most important to visit.

More Info
boston newbury street

Newbury Street

10 Stop 10

Eight blocks filled with salons, boutiques, and fabulous dining. Boston’s Newbury Street has something for everyone. Shops include The Boston Baked Bean, So Good Jewelry, Niketown, Hempest and more.

More Info
boston old state souse

Old State House

5 Stop 5

The Old State House, built in 1713 on the site of the first Town House, is the oldest surviving public building in Boston. The building served as a meeting place for the exchange of economic and local news and was said to be the center of politics in the colonies. The Declaration of Independence was read from the balcony on the east side of the building, and just below it is the spot where the Boston Massacre took place. The Old State House is one of the most important public buildings in the U.S.

More Info
historic north end

Historic North End

2 Stop 2

Welcome to Boston’s Little Italy. The North End is famous for the many authentic Italian restaurants, cafés, espresso bars, and sandwich shops that dot the neighborhood. The area features nearly 100 restaurants, ranging from the authentic Italian and Italian-American family style to Chinese, Thai, and local seafood. After dinner, stop by one of the world famous pastry shops. Mike’s Pastry and Modern Pastry each have their own unique twist on classic desserts. Get there early to avoid the lines!

Boston bunker hill monument

Bunker Hill Monument

3 Stop 3

The Bunker Hill Monument was the first public obelisk in the United States designed to commemorate the Battle of Bunker Hill. The battle was actually misnamed because the majority of the action took place on Breed’s Hill and that is where the monument sits. The monument was begun in 1827 but construction had to be halted and it wasn’t completed until 1843. The architect, Solomon Willard, had the granite for the 221 ft structure brought in from Quincy, Massachusetts.

More Info
boston chinatown

Reasons To Visit Boston

You’re in for an unforgettable adventure. From exceptional food, sporting events and musical venues to what we all know as the Cradle of Liberty, Boston is home to so many fascinating sights and points of interest that your toughest choice will be which ones to experience first. Read on for the most important reasons to visit Boston on your next vacation.

More Info
boston tea party ships meeting house

Must Do Activities For First Time Visitors To Boston

The city of Boston is filled with things to do from visiting popular museums to walking the Freedom Trail. Enjoy Boston’s rich history and see all the sights during your trip. After touring the major attractions, take a leisurely stroll around the Boston Public Garden or stop by for a refreshing drink at Cheers. Conveniently located near the trolley stops, these attractions are must-dos for first time visitors of all ages.

More Info
boston trinity church

Things To Do With Family

If you’re heading to Boston with family, great fun is in store for everyone. The Cradle of Liberty is a wondrous place where old and new mesh beautifully and history and culture abound on every corner. There are a ton of things to do with family including attractions, sights, museums, and activities throughout Boston.

More Info
boston tea party ship museum december

Things to Do in the Winter

When the temperature starts to drop and the winter season begins, there’s still plenty of fun to be had in Boston. Whether visiting many of the city’s most popular indoor attractions or enjoying events and other seasonal activities, here are some of the top things to do during winter in Boston.

More Info
swan ride unique things to do boston

Things to Do in Boston During the Spring

Spring is in the air! And you know what that means – warm days filled with sunshine, inviting you to get out and enjoy all there is to do and see in Boston. Read on for some of the top things to do in Boston during spring. Take a Ride on a Swan Boat
. Nothing says “welcome spring!” like the opening of the Swan Boats at the Boston Public Garden. It has been more than 130 years since the Swan Boats made their first voyage on the beautiful waters of the lagoon. This family-owned business has been welcoming guests for generations and is one of the city’s most unique and beloved traditions.

More Info
boston louisburg square

Things To Do In The Fall

Fall is the perfect time of the year to visit Boston, the summer heat has waned and the air is light and cool. Depending on what month you go, you may also get to witness the leaves changing. Here are some fun things to do in Boston in the fall season.

More Info
things to do with kids

Things To Do With Kids

Looking for the most efficient and entertaining way to visit many of the things to do in Boston with kids? Look no further because Old Town Trolley Tours offers parents a relaxing way to tour all the best attractions in Boston for kids. Parents don’t have to worry about searching for directions to the New England Aquarium, driving to the Museum of Science, or finding parking while traveling from all of Boston’s best attractions. Our hop on and hop off trolley tours allow the parents to concentrate on having fun with their kids instead of worrying about logistics.

More Info
boston public garden

Things To Do In The Summer

If you’re in Boston, you are at the epicenter of American history. There are so many activities and attractions in this city, including educational points of interest and others that are just plain fun. Since it’s summer, you’re probably on the lookout for things to do that are cool during the heat of the day.

More Info
boston-events-calendar-may

How To See Boston in 2 Days

Your friends who have traveled here might say you need more than 2 days in Boston to see all the best attractions, but many of the attractions only require 30 minutes to an hour for a tour. This means that you can easily visit five Boston attractions per day and still have time for three leisurely meals; and we all know how important it is to eat the great food in Boston! Here’s a recommended itinerary from our travel planners who know all the shortcuts.

More Info
boston trinity church

How to See Boston in 1 Day

The city of Boston is one of the most visited destinations in the country and with good reason. Millions of people come each year to experience the rich heritage that comes alive on practically every corner, the abundance of cultural attractions, entertaining venues and diverse dining scene. If you only have one day to explore Boston, jump on the Old Town Trolley and follow these recommended stops to see the best of the city.

More Info
boston new england sports museum

New England Sports Museum

4 Stop 4

The New England Sports Museum is located on the 5th and 6th floors of the TD Garden. This Boston attraction features exhibits organized by sport, including hockey (Boston Bruins, Hartford Whalers, and Olympics), basketball (Boston Celtics), football (New England Patriots), and baseball (Boston Red Sox). Concourse galleries also feature boxing, rugby, soccer and artifacts from the Boston Marathon. The museum has life-size statues of Carl Yastrzemski, Bobby Orr, Larry Bird, and Harry Agganis, an old Boston Garden hockey penalty box, and thousands of other items.

boston bank of america pavilion

Blue Hills Bank Pavilion

19 Stop 19

One of Boston’s premier concert venues, the Pavilion, is open seasonally from May through October. From Tony Bennett to K.D. Lang to Bonnie Raitt to Jay-Z; they have all played at the Bank of America Pavilion, and this year’s lineup looks just as exciting as past years. With a perfect Boston Harbor location and many outstanding “sea oriented” restaurants located nearby, as well as a cutting edge New York style steakhouse, Del Frisco’s, spending an evening in the Seaport District can be a real Boston experience. When the concert is over, visit Harpoon Brewery and Beer Hall just 100 yards away from the Pavilion.

boston childrens museum

Boston Children’s Museum

17 Stop 17

The Boston Children’s Museum is a not-to-be-missed interactive experience for kids. The museum has offered innovative, educational, and fun exhibits for children and families for more than 90 years. Exhibits range from A to Z, focusing on arts, culture, and science. Kids can rock climb, work in a child-size construction zone, paint in an art studio, or even act in a short play.

More Info
boston theater district

Boston Theater District

6 Stop 6

More than a dozen theaters are clustered in the Boston Theater District. On Warrenton Street or Shear Madness Alley, the Charles Playhouse is home to the Blue Man Group, as well as Shear Madness, the country’s longest running non-musical play. Other theaters include the Colonial, Shubert, Orpheum, Opera, Emerson Majestic & Wilbur, most of which were built in the grand architectural style of early 1900s performance halls. These beautifully restored Boston gems, some intimate, some grand, host critically acclaimed productions.

More Info
boston chinatown

Chinatown

6 Stop 6

Chinatown in Boston is the only historic Chinatown in New England. The area first became populated by Chinese immigrants in the early 1890’s. Before that, the area was settled by White Anglo-Saxon Protestants. Irish, Jewish, Italian, and Syrian immigrants also all lived in the area at one time or another because of the low cost of housing and job opportunities in the area. In the late 19th century, manufacturing plants moved into the area and remained active through the 1990’s.

More Info
boston public library

Boston Public Library

8 Stop 8

As the oldest large free-lending library in America, the Boston Public Library was designed as a “palace for the people.” The McKim building includes a children’s room, the first in the country, and a sculpture garden with an arcaded gallery surrounding it. When facing the Copley Square side, the library façade resembles a 16th century Italian palace. Bates Hall is the library’s magnificent reading room, named after the library’s original benefactor Joshua Bates.

boston massachusetts state house

Massachusetts State House

15 Stop 15

In the distinctive gold-domed building atop Beacon Hill, the past meets the present. On weekdays, you can discover Massachusetts’ history on a free tour of the center of the state government. The building, completed in 1798, was designed by Charles Bulfinch to replace the Old State House.

In addition to housing the state government, the State House also displays various portraits of governors, murals depicting the state’s heritage, and statues inside and on its grounds. The building is recognizable because of its dome sheathed in copper and covered by 23 karat gold, as seen in the film The Departed.

boston common

Boston Common

14 Stop 14

Boston Common was established in 1634 and is on the List of National Historic Landmarks. Today, this expansive green space is the starting point of the Freedom Trail and the anchor of the Emerald Necklace, a system of connected parks that winds through various Boston neighborhoods. Its long history includes being used as a campgrounds for British Troops, the site of public executions and the place where several notable visionaries and leaders gave legendary speeches including Martin Luther King Jr., Pope John Paul II and Gloria Steinem. Today, Boston Common is still a place for many public gatherings, festivals, events, concerts and sports as well as a pleasant place to jog, bike and walk while enjoying the pretty scenery. Located at the foot of Beacon Hill.

copley place

Copley Place

10 Stop 10

Copley Square, named after the American portraitist John Singleton Copley, is a historic focal point of this busy commercial area. A bronze statue of Copley can be found on the northern side of the square. Nearby Boylston Street offers shopping and attractions plus Newbury Street features upscale boutiques and restaurants in its quaint 19th century townhouses.

boston seaport district

Boston Seaport District

18, 18a, 19 Stop 18, 18a, 19

Located on Boston’s waterfront, just across from downtown and not far from the airport, the Seaport District is one of the city’s most burgeoning neighborhoods. If you were looking at a map, you’d find this area stretches from the harbor to Fort Point Channel and into South Boston to East and West First Streets. It includes the four neighborhoods of Fort Point, Fan Pier, the Convention Center, and the Marine Industrial Park.

More Info
boston acorn street

Acorn Street

14 Stop 14

One of the most photographed streets in the city, Acorn Street offers visitors a reminiscent ride back to colonial Boston. It was on this lovely street that 19th century artisans and trades people lived and today the row houses are considered to be a prestigious address in Beacon Hill.

boston charles river esplanade

Charles River Esplanade/Hatch Shell

14 Stop 14

Charles River Esplanade is one of the many examples of land set aside in Boston for public enjoyment. During the summer you can catch a free concert or play at the Hatch Shell, or watch the rowers practice in the Charles River as you stroll in the park.

boston cambridge

Cambridge

13 Stop 13

Visit Cambridge and explore The M.I.T. Museum, Massachusetts Institute of Technology (MIT), and Harvard Square.

More Info
boston harvard square

Harvard Square

13 Stop 13 (617) 495-1573

Harvard Square is an intellectual and offbeat area with a mix of languages, ages, and cultures. Its streets are lined with coffeehouses, independent bookstores, cinemas, and music stores. The centerpiece of the area, Harvard University, is the oldest institution of higher learning in America, established in 1636. Its long list of famous alumni includes seven presidents of the United States. The campus is distinguished by a diverse collection of historic buildings and the acclaimed Harvard University Museum offers expansive collections. For information, visit the University Events & Information Center on Massachusetts Avenue.

boston historic ballpark

Historic Ballpark

12 Stop 12 open 9am-4pm

Get your behind the scenes look at America’s most legendary ballpark, Boston’s Historic Ballpark. Visit the place where Carlton Fisk hit one of baseball’s most famous homeruns, walk the same warning track once strolled by Ted Williams, and even touch the beloved “Green Monster.” Tours leave hourly from the Souvenir Store on Yawkey Way seven days a week.

More Info
boston symphony hall

Symphony Hall

9 Stop 9

The Symphony Hall in Boston, Massachusetts is considered one of the top concert halls in the world because of its impressive acoustics. The Boston Symphony Orchestra and the Boston Pops share the hall. The Symphony Hall was designed through a collaboration of architects McKim, Mead and White and assistant professor of physics at Harvard University, Wallace Clement Sabine. Sixteen Greek and Roman statue replicas line the walls of the hall and Beethoven’s name is inscribed over the stage. The Symphony Hall’s organ, a 4,800 pipe Aeolian-Skinner, is also considered to be one of the best in the world. It was installed in 1949 and is autographed by Albert Schweitzer.

boston museum of fine arts

Museum of Fine Arts (MFA)

9 Stop 9

The Museum of Fine Arts in Boston is one of the largest museums in the U.S., housing the second largest permanent museum collection in the Western Hemisphere. The museum is affiliated with the School of the Museum of Fine Arts and the sister museum, the Nagoya/Boston Museum of Fine Arts, in Nagoya, Japan. The Museum of Fine Arts offers a fine permanent collection from the masters of American painting as well as a vast selection of works of art from all important periods; it also hosts special exhibits on loan from around the world.

More Info
boston prudential center skywalk

Prudential Center Skywalk

11 Stop 11

The Boston Skywalk Observatory is located on the 50th floor of the Prudential Center. From this vantage point you have sweeping 360-degree views of the city and beyond. On a clear day, you can see the mountains of New Hampshire. The Skywalk offers a state-of-the-art Antennae Audio Tour pointing out historic and cultural attractions, and special interactive, audiovisual exhibits on Boston history and architecture.

More Info
copely square

Things To Do In Copley Square Boston

8 Stop 8

Copley Square, named after the American portraitist John Singleton Copley, is a historic focal point of this busy commercial area. A bronze statue of Copley can be found on the northern side of the square. Nearby Boylston Street offers shopping and attractions plus Newbury Street features upscale boutiques and restaurants in its quaint 19th century townhouses.

boston museum of science

Museum of Science (MOS)

4 Stop 4

Boston’s Museum of Science, located on the Charles River Basin, has over 500 interactive exhibits and a variety of live presentations throughout the day. The museum also features a planetarium, New England’s only domed IMAX, a theater of electricity with one of the world’s largest Van de Graaff generators, and exhibits from the original Computer History Museum. Beginning with a collection of men sharing scientific interests in the early 1830’s, the museum still houses some of the artifacts that were originally stored and displayed.

More Info

Cheers Bar

7 Stop 7

The historic landmark pub was transformed from a long-standing neighborhood gathering spot for locals into one of Boston’s must-see stops for visitors after gaining notoriety as the location of the popular 1980’s TV sitcom, Cheers. The Cheers Pub was founded in 1969 and was discovered in 1981 by Hollywood couple Mary Ann and Glenn Charles. During their visit, they photographed the interior and exterior of the pub, which they gave to the set designer back in Hollywood to replicate for the set of the show. Cheers premiered on NBC in 1982 and remained on the air for 11 seasons, receiving over 100 Emmy nominations over the years. The pub eventually changed its name to Cheers to avoid confusion.

boston public garden

Boston Public Garden

6 Stop 6

The landscaped, 24-acre Boston Public Garden, established in 1837, was the first public botanical garden in the U.S. The Public Garden contains lovely manicured paths, the famous “Make Way for Ducklings” statues, a 4-acre pond with swans and a variety of other birds, and several memorable statues throughout. You can enjoy a leisurely ride aboard the Swan Boats, pedal-powered gondolas which have been in operation during the summer months since 1877.

More Info
boston uss constitution

USS Constitution and Museum

3 Stop 3 open Closed on Mondays during the off season.

Launched in 1797, the USS Constitution is the oldest commissioned warship still afloat. Crisscrossing the globe, this three-masted frigate participated in the Barbary War off the coast of North Africa and sailed the Caribbean in search of pirates. She earned her nom de guerre Old Ironsides during the War of 1812 when enemy cannonballs bounced off her resilient wooden hull. Docked in the Charlestown Navy Yard, the famous ship is a floating museum open to public. It is also a stop on the on the Freedom Trail and the Old Town Trolley.

More Info
boston paul revere house

Paul Revere House

2 Stop 2

Built in 1680, the unimposing wooden house at 19 North Square is the oldest house in downtown Boston. The 3-story building was the home of silversmith and Boston Patriot Paul Revere from 1770-1800, previously housing the parsonage of the Second Church of Boston. Revere sold the house in 1800 and it became a tenement with the ground floor used for shops and various businesses over the years. In 1902, Revere’s great-grandson purchased the property and restored it so that it could be opened to the public. In 1908, after restoration by architects and preservationists, the Paul Revere House opened to the public as one of the earliest historic house museums in Boston and the U.S.

More Info

New England Aquarium

1 Stop 1

The New England Aquarium, situated on the scenic Central Wharf, has more than a dozen exhibits that highlight hundreds of different species from around the world. Attracting 1.3 million visitors each year, the Boston Waterfront attraction recreates natural habitats ranging from reefs and tide pools to rocky shorelines. In addition to its exhibits, the aquarium offers Whale Watch excursions that take visitors 30 miles east of Boston to Stellwagen Bank where you can see whales, dolphins, sea birds and other marine life. The aquarium also has an IMAX® Theater that features films of animals and their habitats, 3-D movies and first-run feature

More Info
boston freedom trail

Freedom Trail

15 Stop 15 open Mon-Sat

Relive history and discover our nation’s fascinating past and the American Revolution as you walk along Boston’s Freedom Trail. On this 2.5-mile, red-lined brick route, you’ll stroll your way to churches, burial grounds, museums and meeting houses, each with a compelling story that played a significant role in the shaping of America.

More Info
boston harbor cruise

Boston Harbor Cruises

1 Stop 1

Boston Harbor Cruises has been introducing visitors to the Boston Harbor since 1926. Today they are New England’s oldest and largest cruise company. Boston Harbor Cruises offers Whale Watching, Sightseeing, Lighthouse, and Sunset Cruises, in addition to fast ferries for private functions and general entertainment. Boston Harbor Cruises also runs The Landing, Boston’s only fully outdoor patio bar and a great spot to enjoy drinks and the view of the Boston harbor. There’s no reason to trek to Boston’s Historic Ballpark when you can catch a Red Sox game on TV from the waterfront!

More Info
boston faneuil hall

Faneuil Hall

1 Stop 1 (617) 426-6500 open 7 Days a Week

One of Boston’s most well known historic sites, Faneuil Hall Marketplace was constructed in 1742 and served as a marketplace and meeting hall since it first opened its doors. Named after the wealthy merchant who provided funding for the hall, Peter Faneuil, this significant structure has been the site of many important and inspirational speeches by famed Americans, including Samuel Adams. When visiting Boston, a stop here is definitely a must do.

More Info
Up
Back to top