Know Before You Go

Holiday Tours

From its colonial beginnings and revolutionary past, Boston has since been one of America’s most essential and diverse cities in the USA. Visiting Boston is great any time of year; but this year, winter just got even better! For the first time, you’ll be able to take in the fun and merriment of the holiday season on an Old Town Trolley Holiday Lights and Sights Tour! You’ll have a front-row seat as you experience the dazzling lights and splendor of the season, riding through town as carolers fill the night air with music. Add complimentary seasonal beverages and snacks, and you’re all set for what promises to be a new holiday tradition in Beantown!

Complete Guide to Back Bay Boston

Famous for its picturesque streets lined with remarkable Victorian brownstones, Boston’s Back Bay is considered by many to be one of America’s most beautiful neighborhoods. While enjoying the many architectural wonders, trendy restaurants and shops here, it may be hard to imagine that at one time the area was nothing more than a bay that became a marshy flat during low tide. Today, the Back Bay, located along the Charles River, is one of Boston’s most expensive neighborhoods—and home to upscale shops, art galleries, boutiques and bars.

Check out this guide to all you can do and see when you’re here:

Complete Guide to Boston Cruise Port

One of America’s most historically rich and attraction abundant cities, Boston is the destination of choice for travelers from all corners of the globe. A popular tourist hub, the cruise port is always brimming with activity with its nearly half a million visitors per year. Whether you’re arriving by cruise, departing on a cruise or a visitor who’s looking for ways to enrich your Boston vacation, the cruise port is an ideal starting point! Here’s a guide to help you plan out all you can see and do while in the area.

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.

Ultimate Guide to Boston Common

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.

Quincy Market

This festival marketplace offers over 150 shops, restaurants, and merchant carts in the three buildings surrounding Faneuil Hall, North Market, Quincy Market, and South Market. Quincy Market, the center building, is a great gathering spot and place for lunch, with over 35 stands offering a global food selection. During the summer months, street performers often entertain the crowds around the marketplace. Jugglers, clowns, puppeteers, musicians, and magicians are just a few types of entertainers that can be seen on the cobblestone promenade.

Approximate Time to Allow: 1 1/2 hours for lunch and shopping

Harvard University

Founded in 1636, Harvard is the oldest university in the United States. Among its graduates are seven U.S. Presidents of the United States: John Adams, John Quincy Adams, Theodore and Franklin D. Roosevelt, Rutherford B. Hayes, John F. Kennedy and Barack Obama. The campus is distinguished by a diverse collection of historic buildings and the acclaimed Harvard University Museums.

Harvard Square, Cambridge

Things To Do In Beacon Hill Boston

One of Boston’s oldest neighborhoods, Beacon Hill is known for its charming, narrow cobblestone streets, federal style row houses and gaslit streetlamps. It’s also considered to be one of Boston’s most desirable and expensive residential areas in the city. A visit to Boston isn’t complete without a stop here. Whether to shop, dine or wander about admiring the architecture and numerous historic sites, there are so many things to do in Beacon Hill.

Things To Do In Boston Near Faneuil Hall

Built in 1742 at the site of the old town dock, Faneuil Hall was the location of town meetings in colonial Boston. It is often referred to as “the Cradle of Liberty” because it was here that Samuel Adams, James Otis and other leaders in the American Revolution made speeches against British oppression.

Know Before You Go

Boston Attractions

Explore Boston attractions with Old Town Trolley Tours. Hop on and off at interesting places to visit and maximize your vacation time.

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.

The Best Shopping in Boston

It’s big, noisy, a touch chaotic, dynamic, a force in academia and easily one of the most classic American cities in the lower 48. Every inch of Boston seems to be entrenched in history and worthy of a story you might hear at the neighborhood pub. The accent, the oysters, the clam ‘chowda’, the perennially winning professional sports teams, all of it amounts to things only this city can claim. You want museums? Institutions of higher learning? Great public parks and green spaces? They got them in bulk here. It’s the kind of city that gets better the longer you’re willing to explore it. Of course, without question, Boston is a shoppers paradise. From every upscale brand, major department store to mom and pop shops that sell items you can’t get anywhere else.

Fun Facts About Boston

Everyone knows that Boston is one of the most historically abundant cities in the United States. And while we’ve all heard the stories of the midnight ride and the Boston Tea Party, there are some fun facts that many folks don’t know about Beantown.

Boston Restaurant Guide

Old Town Trolley guide to top-rated Boston restaurants. If you’re a foodie, click on the link to learn about local dives and popular places to eat in Boston.

Boston Cruise Excursions

Welcome to Boston!

Boston is a beautiful city filled with historic sites that helped shape colonial America. Maximize your time for sightseeing by taking Boston shore excursions with Old Town Trolley. Whether you take the 1.5 hour tour purchased from your ship excursion desk, or take the 1.75 hour tour with on-and-off privileges purchased from Old Town Trolley directly, you will have time to shop, visit Boston attractions, and find your way to some of our most famous landmarks.

Boston Field Trip Tours

Our Historical Tour is geared to all ages and takes you through Boston while recounting the history of our beautiful city. Your conductor will tell stories from the past while weaving in current events and happenings as well by mixing the old and the new.

Our Sons and Daughters of Liberty Tour is geared toward middle school students and focuses on The Revolutionary War time and history. It is an interactive tour with a costumed character on board and two stops along the way.

Hop On Hop Off Boston Tours

We Bostonians take great pride in our city and its rich history, doing our best to preserve the sites and structures that have played an important role in the story of America. For over 30 years, Old Town Trolley has provided Boston sightseeing tours highlighting the best of the city. Hop aboard one of our trolleys and you’ll experience Transportainment , a delightful combination of transportation and entertainment.

Boston Ghost Tours With Ghosts & Gravestones

Old Town Trolley Tours invites you to explore Boston’s darker side aboard the city’s only “frightseeing” ghost tour, Ghosts & Gravestones. You’ll visit the streets where the Boston Strangler once prowled and hear local tales of murder and mayhem, ghosts and ghouls.

Old Town Trolley Tour & Boston Tea Party Ships Package

Buy discount tickets online for the 1 Day Old Town Trolley Tour and Boston Tea Party Ships & Museum. Our exclusive package saves you time and money.

Ghosts & Gravestones Tour

Purchase discount tickets online for the Ghosts and Gravestones Boston tour. Nighttime access into some of the most haunted sites in Boston.

Newbury Street

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.

1-Day Old Town Trolley Tour

Buy discount tickets online for the 1 Day Old Town Trolley Boston Tour. See the best first and learn about all the famous sites with our sightseeing tour.

Getting Around Boston On Vacation

When planning your Boston vacation, keep in mind that while the city is compact and easy to get around, driving your own car is not highly recommended. The streets and neighborhoods can be jumbled and difficult to navigate, especially if you’re not familiar with them. Between the many one-way streets and the confusing layout, you could spend lots of your precious vacation time getting lost and turned around. Read on for some of the top options to get around Boston.

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.

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.

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.

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.

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 fall things to do in Boston this season.

Things To Do With Kids

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 kids including attractions, sights, museums, and activities throughout Boston. 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. There are so many awesome things to do with kids in Boston!

Labor Day in Boston

Residents of Boston typically flee the city during the Labor Day Weekend to Cape Cod and Martha’s Vineyard for the last holiday celebration of the summer. This makes it a great time for vacationers to visit Boston with less traffic and easier access to the attractions. Check out some of the things to do in Boston during Labor Day weekend:

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.

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.

Fort Point Channel

The Channel extends from Gillette Headquarters, home to America’s premier razor manufacturer since King Gillette founded the company over 100 years ago, to the site of the Boston Tea Party on those very waters in 1773 and out into the Boston Harbor. In today’s Boston, the Fort Point Channel is bordered by restaurants, fabulous hotels and water view condos (look at the beautifully mirrored InterContinental Hotel and Residences), as well as attractions like the Children’s Museum and the recently rebuilt Boston Tea Party Ships & Museum.

Boston Children’s Museum

Boston Children’s Museum is the second oldest and one of the most influential children’s museums in the world. For over 100 years it has been engaging children in joyful discovery experiences that instill an appreciation of our world, develop foundational skills, and spark a lifelong love of learning. The Museum’s exhibits and programs emphasize hands-on engagement, learning through experience, and employing play as a tool to spark the inherent creativity, curiosity, and imagination of children. Designed for children and families, Museum exhibits focus on STEAM (Science, Technology, Engineering, Arts, Math), environmental awareness, and health & fitness.

South End Neighborhood

The Boston Center for the Arts is a non-profit performing and visual arts complex in the South End of Boston. The center houses small to mid-sized theater companies, working artists, and arts organizations. The complex includes four theaters, the Mills Gallery, which is a contemporary visual arts space, the Tremont Estates Building, which houses more than 40 artists and 10 non-profit arts organizations, the Cyclorama, the Boston Ballet Building, and the Community Music Center of Boston.

Boston Tea Party Ships & Museum

Located on the Congress Street Bridge, the Boston Tea Party Ships & Museum is an interactive, high tech, floating museum. Unlike anything you’ve ever experienced before, this unique museum sits on a barge in the water, includes tours on restored tea ships and a stunning, interactive documentary that immerses you into the events that led up to the American Revolution. Touch, feel, see and hear what the patriots felt when their passions and angers flared at the injustice of taxation without representation. Participate in multi-sensory exhibits, witness dramatic reenactments by professional actors and historians and discover the true story behind the Boston Tea Party.

Boston Theater District

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.

Chinatown

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.

Boston Seaport District

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.

Acorn Street

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.

Cambridge

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

Harvard Square

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.

Cheers Bar

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.

Freedom Trail

For the average Bostonian, life in the New England colonies during the 17th century was, as you might’ve guessed, not exactly one of ease and leisure. Before they were built by stone or brick masonry, homes were small, dank, drafty and made entirely of wood. This building practice was abolished toward the advent of the 1700s due to the susceptibility of fire. Most of the population subsisted as farmers, the drinking water was unsafe, medicine was still in the Dark Ages, and the average lifespan was just shy of 40 years. These were arduous and challenging times and living under the yoke of an oppressive foreign monarchy would eventually prove too much to bear and, thus, a revolution was born.

Comprised of 16 places of interest, each one a milestone in the evolution of Boston from English colony to independence, the Freedom Trail is an essential component of any trip to Boston. This historic attraction literally lays out Boston’s colonial history before you on the very streets where the city’s most transformative events unfolded several hundred years ago.

The thinking behind the design of the Freedom Trail is attributed to William Schofield, a former travel writer for the Boston Herald. He noticed that visitors eager to immerse themselves in the city’s historic past were having trouble finding the landmarks they were looking for. Schofield proposed a solution – Link the most important sites in a numbered sequence along a clearly marked, easy to follow trail that could be walked from end to end without the chance of getting rerouted or lost. There was also the idea that the Freedom Trail would’ve been a typical path to walk for the average colonist back in the day, further enhancing the sensation of traveling back in time.

Boston Harbor Cruises

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!