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Brookline

Brookline, MA, USA

Brookline

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Brookline

Welcome to Brookline, a charming town just outside of Boston, MA! With tree-lined streets, quaint shops, and delicious eateries, Brookline is the perfect blend of city and suburb. Explore the historical sites, like the birthplace of JFK, or enjoy a leisurely stroll through the beautiful parks. Don't miss out on this hidden gem!

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Recommendations

Outdoor4.7/5

Larz Anderson Park

Nestled in the heart of Brookline, Larz Anderson Park is a lush oasis perfect for picnics or a game of frisbee. With sweeping views of the Boston skyline and a charming vintage automobile collection in the nearby museum, this park is the ideal spot for a relaxing day out. Don't forget your camera!

Landmark4.7/5

The Country Club

Landmark4.6/5

John Fitzgerald Kennedy National Historic Site

John Fitzgerald Kennedy National Historic Site is the childhood home of the 35th U.S. president, offering visitors a glimpse into his early life and the idealism that shaped a generation.

Shop4.8/5

Brookline Booksmith

Nestled in the heart of Brookline, Brookline Booksmith is a literary treasure trove! This charming indie bookstore invites you to lose yourself among its cozy shelves filled with new releases, quirky gifts, and an impressive selection of used books. Don’t miss their delightful café for a caffeine fix! Perfect for bookworms and casual readers alike—happy browsing!

Shop4.4/5

The Street

The Street at 33 Boylston St in Chestnut Hill, MA, is a vibrant destination featuring a unique blend of upscale shopping, diverse dining, and lively community events, making it an iconic spot for both relaxation and entertainment.

Landmark4.6/5

Brookline Farmers' Market

Attention all foodies and farmers market enthusiasts! Get ready to explore the vibrant Brookline Farmers' Market at Centre Street West Parking Lot. Indulge in fresh produce, tasty treats, and local crafts while soaking up the bustling atmosphere. Don't forget to chat with the friendly vendors and sample some mouthwatering goodies. Happy shopping!

Self Care4.3/5

Oak Square YMCA

Unleash your inner kid at Oak Square YMCA in Brighton, MA! This vibrant hub boasts a fantastic pool, spacious gym, and fun fitness classes to keep you moving. Enjoy family-friendly events or just relax in their cozy community vibes. Whether you're a fitness fanatic or just looking for a good time, Oak Square is your perfect pit stop!

Eat$$$4/5

Hamilton Restaurant & Bar

Step into Hamilton Restaurant & Bar for a taste of local charm and delicious fare. Located in Brookline, MA, this cozy spot offers a diverse menu of American cuisine with a creative twist. Sip on craft cocktails while enjoying the lively atmosphere. Don't miss out on their famous brunch offerings!

Eat$$$4.4/5

Blossom Bar at Sichuan Garden

Step into Blossom Bar at Sichuan Garden, a vibrant gem in Brookline! Delight in spicy Sichuan dishes that dance on your palate, paired with exotic cocktails and a cozy atmosphere. Whether you're sharing a lazy brunch or an electrifying dinner with friends, this bar beckons for a flavor adventure. Don't miss their iconic chili oil—it's a culinary must-try!

Outdoor4.8/5

Chestnut Hill Reservoir

Nestled in the scenic Chestnut Hill neighborhood, the Chestnut Hill Reservoir is a must-visit gem! Perfect for a leisurely stroll or a brisk jog, this sparkling oasis offers stunning views of the Boston skyline and lush green surroundings. Pack a picnic, grab your bike, and soak in the charm of this urban retreat—your adventure awaits!

Eat$$$4.5/5

Bakey | Brookline

Located in Brookline, MA, Bakey on Harvard St is a cozy café perfect for breakfast or a quick snack. The menu boasts tasty pastries, delicious coffee, and a warm atmosphere that will make you feel right at home. With friendly staff and a convenient location, Bakey is a must-visit for any traveler exploring the area.

Eat$$$4.4/5

Life Alive Organic Cafe Brookline

Step into Life Alive Organic Cafe in Brookline for a vibrant feast of flavors! This cozy haven serves up wholesome, plant-based dishes that are as colorful as they are delicious. From smoothie bowls to hearty grain bowls, each bite is a celebration of life! Perfect for health-conscious foodies, it’s a delightful pit stop on your Boston adventure!

Eat$$$4.5/5

Michael's Deli

Dive into Michael's Deli, a savory gem at 256 Harvard St, Brookline! This cozy spot serves up mouthwatering sandwiches and classic deli delights, perfect for hungry explorers. With friendly staff and a vibrant atmosphere, you'll feel right at home. Whether you're grabbing a brisket or a bagel, this deli is a must-stop on your culinary adventure!

Cafe$$4.1/5

Temptations Cafe

Come get tempted at Temptations Cafe in Brookline! This cozy spot on Beacon St serves up delicious breakfast and lunch options, perfect for fueling up before a day of exploring. Don't miss their famous avocado toast or homemade pastries. With friendly service and a welcoming atmosphere, Temptations Cafe is a must-visit for any hungry traveler.

Attraction4.4/5

Paradise Rock Club

Welcome to Paradise Rock Club, a gem nestled in Boston! This lively venue boasts an intimate atmosphere perfect for catching up-and-coming bands and indie rock legends. With a capacity of 1,000, enjoy unforgettable nights filled with electrifying performances, stellar acoustics, and delicious refreshments. Don’t miss the chance to groove in this iconic hotspot at 967 Commonwealth Ave!

Eat$$4.5/5

Barcelona Wine Bar

Eat$$4.6/5

The Abbey

Cafe$$$4.6/5

Cutty's

Cutty's, a beloved Brookline gem, is known for its mouthwatering sandwiches and vibrant atmosphere, making it a must-visit spot for food lovers seeking a unique local dining experience.

Eat$$4.2/5

Pavement Coffeehouse - BU

Get ready to fuel up at Pavement Coffeehouse - BU! Located at 736 Commonwealth Ave, this cozy spot in Brookline, MA offers a trendy atmosphere perfect for studying or catching up with friends. Enjoy a delicious cup of coffee and tasty pastries while soaking in the local college vibe. Don't miss out on this must-visit caffeine haven!

Stays

Stay4.45/5

Courtyard by Marriott Boston Brookline

Welcome to the Courtyard Boston Brookline! Nestled in the vibrant cool neighborhood of Brookline, this hotel offers comfort and convenience just minutes away from Fenway Park and downtown Boston. Enjoy modern amenities, spacious rooms, and a cozy courtyard perfect for sipping your morning coffee. Whether you're here for a Red Sox game or a city adventure, this hotel has you covered!

Stay4/5

Samuel Sewall Inn

Nestled in Brookline, the Samuel Sewall Inn captivates with its charming Victorian architecture and personalized service, offering a cozy retreat that reflects the area’s rich heritage and vibrant local culture.

Stay4/5

Longwood Inn

Welcome to Longwood Inn! This charming bed and breakfast on Longwood Ave in Brookline, MA offers cozy rooms, delicious breakfast options, and friendly staff. Just a short drive away from Fenway Park and the Museum of Fine Arts, this is the perfect spot for a relaxing stay in the heart of Boston.

Stay3.95/5

Coolidge Corner Guest House

Nestled in the heart of Brookline, Coolidge Corner Guest House offers charming accommodations and a warm, inviting atmosphere, making it a perfect getaway for visitors looking to explore the vibrant local culture and historic charm.

Stay3.45/5

Beacon Inn

Welcome to Beacon Inn, a cozy and charming guesthouse located at 1750 Beacon St in Brookline, MA. Just a short drive away from downtown Boston, this historic inn offers comfortable rooms, complimentary breakfast, and a friendly staff ready to make your stay unforgettable. Come relax and explore the sights of beautiful Brookline!

Stay2.9/5

The Farrington Inn

Nestled in the vibrant Boston neighborhood of Allston, The Farrington Inn is your cozy home base for adventures! Offering charming rooms and a friendly atmosphere, it’s perfect for budget travelers. Explore trendy cafes, quirky shops, and nearby parks, all while being just a T ride away from downtown. Affordable and welcoming, it’s the perfect spot for your Boston escapade!

Things To Do
Provided byViator

5/5
3 h

Boston Private 3-Hour Tour by Car

This private car tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On this tour we'll take you into all the city neighborhoods and along the sites of the Freedom Trail. We'll share the history and legends of the city, keep it topical with current day fun facts and light hearted stories. All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles.

$550.00
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5/5
2 h 30 mins

Boston: Votes for Women History Tour of Back Bay

Boston’s leading role in the American fight for women’s suffrage is found on the tree-lined streets of its elegant Back Bay neighborhood. This masterpiece of Victorian-era architecture is best experienced on foot, in a small group, with a local guide! Your 2.5-hour tour travels from Boston Common into historic Back Bay, visiting must-see landmarks such as the Public Garden, Newbury Street, and iconic Copley Square. Our walking tour delves deeply into the years 1870 to 1920, tumultuous decades culminating in women earning the right to vote in the United States. Walk in the footsteps of prolific activists and financiers, visiting the political battleground for pro- and anti-suffrage groups. With a captivating storytelling approach, Hub Town Tours provides the perfect introduction to Boston's role in the advancement of women’s rights. As we travel past key landmarks and historic homes, your guide shares captivating stories of the Bostonians who assembled the Women’s Suffrage Movement.

$35.00
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5/5

Harvard Square's Sweetest Food Tour: Donuts, Sweet Treats & More

Our tour begins at the Charles Hotel to make sure you get your morning fix before we quickly head over to our first stop, Union Square Donuts. Union Square is featured on both our Harvard Square tour as well as our downtown Boston tour - that’s how good they are! After we get our first fill of donuts, we’re off for a quick walk through Harvard Square and through the university itself. We’ll give you a brief history of Harvard Square, the surrounding area and Harvard University itself. After a short walk through the picturesque campus, we’ll stop at our second shop in the campus center for some unique donut flavors. We can’t tell you what the flavors will be as they change seasonally and we want your input on which ones we pick. All of them are good, we guarantee it. Our last and final stop will be Saloniki, a local Greek restaurant that serves some amazing loukoumades. What are loukoumades you ask? Well, it’s a unique greek twist on donuts. You’re going to love it.

$70.00
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5/5
3 h

A Taste of the Freedom Trail: Boston's Iconic Food History Tour

Experience Boston's iconic Freedom Trail through its most legendary dishes. Savor generous tastings of New England classics, including creamy clam chowder, a classic lobster roll, slow-cooked Boston baked beans, and the city's famous Boston Cream Pie at the very hotel where it was first created in the 1850s. Follow your local guide through Boston's historic streets, uncovering the fascinating stories behind each dish—from Native American influences and colonial traditions to the flavors that continue to define Boston's culinary heritage. Unlike many food tours, most of our tastings are enjoyed while comfortably seated inside the restaurants with individually plated portions, giving you time to relax, savor each stop, and soak in the atmosphere. With small groups, leisurely walking, and insider recommendations, you'll experience Boston like a local and discover its most famous landmarks tell a richer story when experienced through the food that has defined the city for generations.

$135.45
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5/5
1 h 30 mins

Tour Boston's Rock and Roll Past, Present, and Future

Guided by a local musician, explore Boston’s rock and roll past, present (and future), on a walking tour through Boston’s Fenway neighborhood. Visit the sites of legendary venues like the Rat, Storyville, and the Boston Tea Party- The Velvet Underground’s favorite place to play in the whole country! Learn how pioneering DJs, producers, and educators sparked a revolution in how music was transmitted, recorded and taught. And trace Boston’s impact on the careers of iconic artists like B.B King, Joan Baez, Bob Dylan, Springsteen, Tracy Chapman, New Edition, Nirvana, Aimee Mann, Pixies, Radiohead, Peter Wolf, Bonnie Raitt, Van Morrison, Jonathan Richman and more. Scroll below to learn more….

$40.00
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5/5
4 h

Private 4-Hour Walking and Driving City Tour

Private tours are priced per GROUP, not per person. This amazing tour is for those who want more than a driving tour but not a ton of walking.(aprox. 90 minute walk) Stroll through the historic North End. Have a snack from a famous North End pastry shop. Go inside the Old North Church and see Paul Revere's house, Explore Copp's Hill Burial Ground and learn about the "Spite House", the "Brink's Job" robbery. and the Great Molasses Flood. Visit the USS Constitution, and go up Bunker Hill where the first organized battle of the Revolutionary war took place. Learn how the Colonists lost that battle but won at the same time. Ride through Downtown, up Beacon Hill, The Back Bay, Fenway and over to Cambridge to see Harvard & MIT. You will see the entire city in half a day. ​Learn all about our history as well as what makes Boston such a great 21st century city. We can confirm tour start time after booking is complete. Weekday tours during the school year tours can only start after 2:30PM

$550.00
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5/5
3 h 30 mins

Private North End Neighborhood Tour

Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original food tours. Our North End Neighborhood Tour offers a view of Boston's Little Italy from the perspective of our founder, a native Bostonian, with topics ranging from best eats to history to crime to movies, and personal stories that you can't Google! We've included some surprises, too, including FOUR sites that aren't what they appear to be, and two hidden gems in a very unexpected place. And, if you're lucky, you might meet a neighbor or two!

$135.00
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5/5
2 h

Boston After Dark Walking Tour

Meet Boston, after dark. The real Boston. The Boston of terrifying serial killers, infamous gangsters, urban legends, bizarre industrial accidents, unsolved crimes, ghost stories, and other extraordinary tales. Led by a Boston local, this is Boston like you've never seen it. Our tour is capped to 15 guests so you are part of a conversation, not a lecture! This 2 hour/1.7 mile walking tour takes you through two of Boston's most notorious neighborhoods; the North End and the West End. Please wear comfortable walking shoes. This is not a kid-friendly tour. Children under 13 are not allowed, and parental discretion is advised for those 13 and up. This tour contains foul language, and discussions of death and violence. Children must be accompanied by an adult. Adults are responsible for their own and their children's behavior. This tour will run in light rain. We will cancel for unsafe or unpleasant weather conditions. Tour requires at least two guests to operate.

$35.00
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5/5
6 h

Full-Day Minivan Tour of Revolutionary Boston, Lexington and Concord

Immerse yourself in our colonial history! On this six-hour driving tour, you will see the sights and hear the stories of Boston's colonial past narrated by a professional historian and experienced guide with ample opportunities for taking pictures. This is an excellent tour for seasoned historians and students alike. A meal break will be taken in Concord or elsewhere as directed.

$975.00
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5/5
2 h 30 mins

Freedom Trail Walking Tour in Boston in French

It's a perfect tour to see the essentials of Boston. We'll delve into the fascinating history of Boston's founding. You'll discover the Freedom Trail's 16 iconic sites and learn about Boston's role in the American Revolution, among other topics. Plus, you'll hear interesting facts about the city's construction, its architecture, notable figures, abolition, American education, immigration and even contemporary daily life. Along the way, you'll see modern Boston sculptures, including "The Embrace," a recent sculpture, and the poignant Holocaust Memorial and many others. At the end of the tour, you will have a thorough understanding of downtown Boston, often described as an open-air museum, and leave with unforgettable memories and fantastic photos. Your guide will be a passionate French speaker ready to share captivating and original anecdotes with you.

$45.00
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5/5
2 h

Boston Strong Sports Walking Tour

Journey from the Boston Marathon finish line to the Red Sox home at Fenway Park and walk in the footsteps of sports legends! Come discover how Boston sports make Boston Strong! Back Bay is home to the iconic Boston Marathon and Red Sox. Learn how the hallowed grounds of the Boston Marathon and Fenway Park developed, the strong connection between the two, and the rich history of those who have graced these playing fields since the late 1800s. Discover how the strength of the Boston community carried Sox fans through an 86-year winning drought and held the city together in the wake of the 2013 marathon bombing. Dig into the inspiration and complexities between the city's diverse populations and these sports that fill their hearts. Journey to Fenway Park via historic Copley Square and the Boston Marathon Finish Line - following the last mile of the marathon route and circling the ballpark - all while uncovering famous and hidden sports spots and iconic historic stories along the way.

$35.00
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5/5
1 h 30 mins

Private Boston Freedom Trail Walking Tour

Hire a private tour guide for your 90-minute walking tour of the Freedom Trail. Take your time, and ask any questions you want! We cover the first 11 historic sites starting in Boston Common at the Visitor Information Center, and end at Faneuil Hall. Ask your guide to give you local's recommendations for spots to go after your tour! Entertaining and educational, this tour is centered on American history with a focus on the Revolutionary War. You'll learn patriotic, fascinating stories of America's founding by great patriots in Boston. Great for school groups, work outings, and families ranging all ages! A highlight of many people's visit here. A must-do. Any start time can be arranged for your convenience.

$450.00
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5/5
6 h

Boston, Cambridge, Lexington and Concord Private Car Tour

This is an action packed private day tour of the sites, history and events of the Revolutionary War era in Boston, Cambridge Lexington & Concord. We drive the Freedom Trail with stories of the city's 400 year history, the events, people and sites which led up to the war. In the oldest neighborhoods of the city, we'll give context to historic events like the Boston Tea Party, Boston Massacre and Battle of Bunker Hill. We'll take a quick walking tour of Harvard, explain the role it played in the start of the war and where George Washington himself spent time. A 10 mile drive gets us to Lexington Green where we take in the significance of the site and the story of what happened that night in April 1775. Next the picturesque town of Concord, to the Old North Bridge and how the second battle of the war took the British by surprise. Pick up and drop off in Downtown Boston, a stop for lunch along the way (not included in price of tour) and as light or heavy on history as you'd like.

$995.00
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5/5
6 h

Boston, Lexington and Concord Revolutionary War Car Tour

This private car tour is comprehensive enough for any history buff, but as interesting in other ways for non history nerds. It's a unique combination of the Revolutionary War sites in Boston and Cambridge that you won't have seen. Then onto Lexington and Concord to see the towns where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant, and lesser known sites along the way giving a detailed account of events in April 1775. For those less interested in the details of the battles, there's the option to visit the home of Louisa May Alcott or just take some time to enjoy the pretty main street of Concord. The itinerary gives the list of sites we'll visit, but timings are flexible to let us spend time at the places you're most interested in. We'll also stop for lunch (not included in price of tour) and there's plenty of photo opportunities.

$995.00
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5/5
2 h

Pizza Beer and Paul Revere Tour

There’s tons of options for things to do in this city, and tons of Tour Guides…while you’re here, come hang out with the most colorful one in town, on the Pizza, Beer, and Paul Revere Tour! I’m Jimbo the Tye Dyed Tour Guide, and I strive to have these tours feel like you’re just hanging out with an old friend, in a new city... grabbing a bite and a beer while checking out some history. Super casual, not overwhelming with dates and facts…just enjoying a couple slices and a beer in a pre-revolutionary Boston. See tiny back alleys ways from the 1700's as we walk down cobblestones the forefathers walked on, on our way to grab two slices of the best pizza you've ever had!! Also, i take a really neat little video of our tour, which i post to my social media pages like instagrem, feel free to find me there and see past videos of people having a wicked good time under: TyeDyedTourGuide!!

$75.00
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5/5
1 h 30 mins

Private Boston Movie Mile Guided Walking Tour

Tour the Boston Common and Beacon Hill areas and visit more than 30 movie locations on this captivating private movie and TV walking tour! This tour is a must for film buffs, and is also a great way to explore Boston and its many attractions. On this Boston walking tour, your guide, a local actor, will provide a unique sightseeing tour with an entertaining twist!

$68.75
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5/5

Boston Tour from New York

We will leave New York for Boston, a historic city with European architecture and renowned for its scientific development.Your first stop will be in Copley Square, where we will admire the Boston Public Library, the Trinity Church, the Old Church of the South, the Fairmont Copley Plaza, the endpoint of the Boston Marathon and the Prudential and John Hancock Towers. Continue to Christ the Scientist Church and walk along Commonwealth Avenue, where the monument to Dominic Faustino Sarmiento is located. Then we visit Fenway Park, home of the Red Sox. At Cambridge, we're stopping at MIT and Harvard University. Back in Boston we will tour Beacon Hill, Boston Common, Public Garden and the Massachusetts State House. We’ll finish at Quincy Market, with free time to have lunch and photograph iconic landmarks like Old State House, Faneuil Hall and The Freedom Trail, before heading back to New York.

$130.00
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5/5
5 h 30 mins

Boston Food and History Private Tour

Start the day in Little Italy, with traditional cannoli and espresso at the oldest Italian café in Boston. Proceed through the historic "Little Italy" neighborhood to learn about Boston's history! Listen to stories about the neighborhood's ties to the American Revolution such as the ride of Paul Revere. Try traditional sandwiches from an Italian Salumeria. Drive through Boston's historical downtown while learning about the city's colorful past. Walk through Beacon Hill, Boston's most prestigious neighborhood. Visit Boston Common, the oldest public park in America. Stop at a local seafood chain for lobster rolls and New England clam chowder. Take a drive through Back Bay, Boston's man-made neighborhood lined with 19th century Victorian houses. Take a quick drive through Cambridge for stunning views of Boston and MIT. End the tour with seeing the stunning Copley Library! Be sure to come hungry! The tour includes pick-up and drop-off anywhere in the Boston area (up to 6 people).

$487.00
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5/5

Freedom Trail Experience

Let a costumed colonial dressed expert Guide show you Samuel Adams Boston, Sam Adams was a key figure in many of Boston's key Revolutionary events The Boston Massacre, The Boston Tea Party and more... At The Tour of The Freedom Trail, our Mission is to provide family-friendly experiences that guide guests as they discover Boston's history on walking tours to the historic locations along Boston's Freedom Trail. Join us on a 1 hour and 45 minute walking tour and learn about the inspiring history of Boston on The Tour of The Freedom Trail. Traverse through the graveyards and sites of the Boston's history including the Tea Party and The Boston Massacre with a costumed historical interpreter.

$35.00
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5/5
6 h

Boston and Cambridge walking and driving private tour

This private day tour is the perfect way to get to know Boston & Cambridge at a leisurely pace. It's a combination of walking and driving (although can be driving only if you prefer). We start with a walking tour of parts of the Freedom Trail, stopping at some of the city's most significant sites. We'll then drive in and out of the other city neighborhoods, Beacon Hill, Back Bay and Seaport and finish out the Freedom Trail with a stop at Bunker Hill. Then it's across the Charles River to Cambridge, where we drive around the MIT campus, and onto Harvard for a walking tour of the oldest college in the country. We'll share lots of history and legends but also keep it topical with current day fun facts and light hearted stories. After the walk you'll need some lunch and we know some great spots (not included in price of tour). All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles.

$995.00
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