trolly tours of boston

Old Town Trolley Tours of Boston

Hop aboard the city’s most enthralling Boston sightseeing excursion! The orange and green trolleys have been providing guests with Transportainment for more than 40 years. Old Town Trolley is the best way to relive history and see all our country’s Cradle of Liberty has to offer.

Boston's Original Storyteller

Join us in honoring our 40-year legacy, welcome to boston.

While on board Old Town Trolley Tours of Boston, you’ll feel as if you’ve journeyed back in time to the era of the first colonists. Imagine how Paul Revere felt when he made his historic “midnight ride”; hear tales of how he and other famous settlers fought for freedom. As the Old Town Trolley makes its way throughout the city, you’ll have the freedom to get off and back on as often as you wish; and there’s always another trolley coming along soon. Boston tours aboard the trolley are the best way to see the sights in the city.

See ancient burial grounds, national historic landmarks like the Old North Church and the Old State House and many of the moving monuments in Boston like Bunker Hill and the site of the Boston Massacre. Experience the magnitude of what our forefathers suffered through as you walk along the Freedom Trail. Boston’s critical place in the history of our country is evident in the many sights you’ll see on the Old Town Trolley Tour.

Hop On and Off

You can also hop off the trolley to visit chic shops, museums, fine restaurants and the famous pub that the TV show “Cheers” was fashioned after. There’s so much to do and see in Boston and we’ll help you discover it all in a comfortable, relaxing, informative tour. Our expert conductors make the ride even more enjoyable as they delight guests with humorous stories and historical facts about the many points of interest along the way.

The Past and Present

One of the most important places in the USA’s past and present, Boston is steeped in history and culture, offering an array of exciting activities and intriguing attractions. And on board Old Town Trolley Tours, you’ll get an up close and in-depth look at it all. So when you’re ready to see everything from Faneuil Hall to the Boston Harbor and everything in between, take your seat on one of our orange and green trolleys.

Did You Know?

Boston is home to the nation's first public park (the boston common 1634), the first public library (1653) and the first subway (1897)..

Here are just a few reasons why Old Town Trolley is the best sightseeing tour:

• Unlimited hop-on & hop-off as often as you like all day long
• 50% off Historic Harbor Cruise*
• $10 off Ghosts & Gravestones Tour*
• $6 off admission to Boston Tea Party Ships & Museum*
• $5 off Boston Summer Nights Tour & Charles River Cruise* (May 24 – Sept. 2, 2024)
• 50% off admission at The Sports Museum*
• All our tours are 100% live in real time
• The finest, most highly-trained and knowledgeable guides
• Ride up high without worrying about the weather
• Best view! State-of-the-art stadium trolleys
• All-weather trolleys – rain or shine!
• Comfortable padded seats for a pleasant tour

*Applies to standard trolley pass. Pass is non-transferable. Other restrictions may apply. Pass discounts have no cash value and are not refundable and non-transferable. Historic Harbor Cruise and Boston Summer Nights Tour & Charles River Cruise operate seasonally. Sports Museum: Must be redeemed within 48 hours from the day your Old Town Trolley Tour was taken. Please present your Trolley receipt at Sports Museum Information Desk. No need to book in advance. Check hours of operations and tour times. May not be combined with any other promos, offers or discounts. 5% city fee charged at time of purchase.

Old Town Trolley Tours of Boston

Highlights:

1 day of free unlimited reboarding, hop on & off at 14 old town trolley stops, 100% live narration (no pre-recorded tours), discount at the booth for boston tea party ships & museum, 100% satisfaction guarantee, operating times:, reservation notes:, number of stops:, booth location:, nearest intersection:, age requirements:, you may also be interested in these.

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The best Boston trolley tours

See the city while giving your feet a rest with these fun and informative trolley tours around Boston

If you don’t feel like hoofing it on one of the best walking tours in Boston , there are plenty of alternatives for a guided tour around the city. Trolley tours are a great option if you’re looking for something in a smaller group setting. These trolleys are actually on wheels, not tracks, and will take you around to see all the Boston highlights. Hop-on hop-off tours offer a chance to see the greatest hits at your own pace, while other tours will reveal a different side of Boston. For even more tour options, check out our guide to the best tours in Boston . And once you ’ ve finished a tour, keep the fun going by knocking off the  best Boston attractions ,   best free things to do in Boston , and   best museums in Boston .

RECOMMENDED: Full guide to the  best   things to do   in Boston

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Best Boston trolley tours

1.  Boston Old Town Trolley Tours

• Things to do
• Walks and tours
• Quincy Market

Look for the bright orange and green trolleys to see the city on your own schedule with this hop-on-hop-off tour featuring 18 stops. The tour covers all the major neighborhoods and sights, including four exclusive stops: the historic North End, North Station, Boston Convention & Exposition Center, and the Seaport District. Guides are knowledgeable and entertaining. Choose a two-day ticket to have even more time to explore. One- and two-day tickets include free admission to the Old State House and discounts on other admissions.

2.  Ghosts and Gravestones

If you’ve had your fill of history, explore the spooky side of Boston with Ghosts and Gravestones. On the 90-minute Trolley of the Doomed tour, you’ll hear tales of the Boston Strangler, murders and executions that took place on the Boston Common, and paranormal activity at the Omni Parker House. Most of the tour is aboard the trolley, but you’ll also walk through two of the oldest burial grounds in the city and visit the site of a notorious grave-robbing scandal. It’s not for little kiddies or the easily spooked. 

3.  CityView Trolley Tour

Another hop-on-hop-off option, the CityView Trolley Tour features nine stops, including the New England Aquarium, Faneuil Hall, Quincy Market, Boston Common, and South Station. Drivers narrate along the way. Stops are convenient for shopping or grabbing a bite to eat. Seasonally, you can add a harbor cruise for a small additional fee. 

4.  Boston Beantown Trolley Tour

Stay off your feet and enjoy a three hour guided tour with the Beantown Trolley. Informative guides narrate the tour as you pass the highlights, including Beacon Hill, Boston Common, the Freedom Trail, Quincy Market, Faneuil Hall, and the New England Aquarium. There are three stops for photos along the way, at Copley Square, Fenway Park, and the USS Constitution. (A harbor cruise tour can be added for an additional fee.) 

5.  Mobsters and Lobsters Trolley Tour

This unique trolley tour explores Boston’s historic underworld. You’ll learn about heists, mobster hangouts, infamous thieves, sinister local lore, and general Boston mayhem. More entertaining than scary, it’s a fun tour for groups of friends and family. After touring around in the shadows, you’ll enjoy a traditional New England lobster dinner at a waterfront restaurant. 

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Stops & Attractions

Hours of Operation 2024 Season

Opening day: April 10, 2024 Last Day: November 30 2024 Open: 9:30 am to 4:30 pm

Board CityView Trolley at : Atlantic Avenue side of the 255 State Street Building Boston ,  MA   02109   617.363.7899

Pickup Locations: Frequent Departures!

• Main Depot Stop #1 - Atlantic Ave alongside the 255 State St building
• Faneuil Hall
• Quincy Market
• Boston Common
• South Station

Comedy Trolley Tours of Boston

The funniest shows in boston are now... all over boston, improv asylum has created boston’s best trolley tour.

Get ready to laugh your way through Boston’s iconic landmarks and neighborhoods by hopping on board trolley tours of Boston unlike any other!

Our guides, who happen to be some of Boston’s funniest comedians, cannabis-users, and drag performers, lead our private charter bus tours. They take you on a journey through Boston’s rich history and culture, mixing in clever fiction to keep your group guessing. But don’t worry, the facts are mostly  true!

Our guides will keep you entertained with their bits on bits on bits, so you’ll never be bored with a typical tour guide droning on and on and on.

All our tours start and finish at the  Asylum CoLab  in Boston’s historic  Faneuil Hall .

In addition to getting one of the best tours of the city, everyone on the tour is offered complimentary tickets to an Improv Asylum show (that’s a $35 value!), as well as complimentary pizza and champagne or beer, courtesy of Sam Adams .

Our tours are not only fun and engaging, but also educational ( sort of ). Learn about Boston’s history and culture, while having an absolute blast.

Planning a fun team outing, bachelorette party, birthday weekend, or maybe even a divorce celebration? Book a private Comedy Trolley Tour! With the Massholes Comedy Tour, the Bliss Bus, and the Dragtacular Trolley all available for private charter, grab your crew and treat them to an INCREDIBLE private event!  

SOUTH SHORE SIGHTS AND LIGHTS HOLIDAY TROLLEY TOURS

Hop on board the South Shore Sights and Lights Holiday Trolley Tour at 6PM and 7PM for a boozy, adults-only adventure exploring the amazing lights!

• Our knowledgeable guide of sharing interesting facts and stories.
• Perfect way to experience the magic of the season with friends.
• You will be treated to a stunning display of holiday decorations.
• Making the tour not only visually stunning but also educational.
• Bringing your own beverages (BYOB) to sip on during the tour and raising a toast to the holiday spirit.

Join us for a festive evening of holiday cheer on our South Shore Sights and Lights Holiday Trolley Tour! This adults-only event is the perfect way to experience the magic of the season with friends. Hop aboard our trolley at Wollaston Station and get ready to be dazzled by the sparkling lights and enchanting sights of the South Shore. As we cruise through the neighborhood, you’ll be treated to a stunning display of holiday decorations, including beautifully lit houses and festive landscapes. Bring your own beverages (BYOB) to sip on during the tour and raise a toast to the holiday spirit.

Our services

While our normal specialty is corporate events and company outings in Boston, we didn’t want the rest of the world to miss out on the fun. You have probably seen the party trolleys around the city, our beautiful blue trolleys in the South Boston St.Patrick’s Day parade, tailgating at the Patriots games or partying at The Xfinity Center or Gillette Stadium for a concert. We know that tradition calls for white wedding trolleys, but we’re all about switching it up. There’s nothing more beautiful than a white wedding dress and a gorgeous wedding party with our blue in the background. Ditch the boring and traditional mentality and book your wedding with us instead.

We provide the best trolley service in Boston, and we are ready to give your bachelor party, birthday party, wedding, concert, night out or special gathering the ultimate classy trolley experience you deserve. This is going to set a completely different mood and enhance the entertainment factor to ensure that your group is able to enjoy interacting with each other as you travel to your destination or just cruise around town.

Our trolleys are custom built to carry 40 passengers with leather seats. Specially designed to give you extra leg room than a normal trolley. We have open air concepts for the nice weather, and clear windows that roll down with ease to not restrict any visibility! We are fully equipped to operate all year, with plenty of heat for those cold times of year.

Custom audio with drop down video monitors, fully installed interior lighting with the option to utilize our color changing LED lights enhance your experience. Design your own playlists and sync your phone or device to our Bluetooth enabled speakers so you are in control of the music while on board.

Your concerns as far as health and general safety are more than logical, and we invest time and capital to ensure that we can keep up with your expectations. This is the way the world works now and we consider taking proper safety measures to be extremely important. Anytime you have a special day in the way, we are aiming to be there in order to make it extra special. Our trolley is one of a kind and it goes beyond the features available in other similar services. The trolley includes custom leather seats with extra leg space, drop-down video monitors, and Bluetooth speakers. You can come on board with your favorite playlist, and we’ll make sure your songs are played without a hitch.

Our staff goes above and beyond to ensure that you are both comfortable and satisfied with the service that we provide.

We take safety very seriously and our trolleys are kept in the most impeccable conditions by sanitizing the interior and exterior before any of our clients book them for use. This is something that we consider to be an essential step in the process of giving our clients optimal results for their event needs.

We are offering the best packages with rates that start at 4 hours of use and we can handle between 5 and 40 people for any event. This means that we can provide the best trolley experience for a small group and a larger group of people. Our trolley service is going to be extremely useful for all kinds of events, and it will give your group more time to focus on having fun and making the experience truly unforgettable.

Boston Trolley Company is New England’s Premier Trolley Experience, brought to you by Mobsters and Lobsters, LLC

Email: [email protected]

Phone: 781-964-2472, copyright 2023 © all rights reserved. boston trolley company.

Photo Credit: Capture by Caitlin / Web Designer: Peter O.

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Tour Boston sights covers all the major areas including Downtown, Beacon Hill, Back Bay, the Theater District, and the Waterfront District. Stand on the very ground where Samuel Adams and other revolutionary leaders urged their fellow colonials to fight for liberty in Faneuil Hall.

Tour Key West sights – The island of Key West is full of fun and exciting things to do and see. From the Southernmost Point to the quaint streets of Old Town, our tour takes you to all the major areas and attractions.

Tour Nashville sights – From the hunter-gatherers making their home along the Cumberland to the first musician to step off a bus onto Broadway with nothing but a guitar and dream. Nashville has been the hook on which the brave and entrepreneurial have hung their hopes and aspirations.

San Antonio

Tour San Antonio sights – Embark on a captivating journey through the heart of San Antonio aboard the Old Town Trolley. Our expert guides breathe life into the city’s history, offering a unique blend of entertainment and education.

Tour San Diego sights – Explore the Old Town San Diego State Historic Park and experience Mexican and early American life in the 19th century, tour the Midway Aircraft Carrier Museum, enjoy the shopping, dining, and entertainment at Seaport Village and the historic Gaslamp Quarter.

Tour Savannah sights – Known for its impressive 18th and 19th century architecture, travel back to the Civil War era as you visit the Green-Meldrim House , the Andrew Low House, home to the founder of Girl Scouts USA, Juliette Gordon Low, and the Flannery O’Connor House.

St. Augustine

Tour St. Augustine sights – Relive the story of the first settlement in North America as you visit Castillo de San Marcos , visit the world famous Fountain of Youth, experience early St. Augustine as you tour old St. Augustine Village, featuring houses from the 18th and 19th centuries.

Washington DC

Tour Washington DC sights – Visit our Union Station, the most visited destination in DC. See the Capitol building, the Supreme Court and Library of Congress . Visit the Smithsonian, the National Gallery, and the Museum of Natural History.

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