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Chestnut Hill

Get ready for a delightful romp through Chestnut Hill, Newton, MA! Picture charming streets lined with lush trees and stunning architecture. Stroll along the serene Chestnut Hill Reservoir, catch a game at Boston College, and savor artisanal delights at the local shops. This charming village bursts with small-town warmth and vibrant culture, making every visit a cherished adventure!

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Recommendations

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.

Shop4.3/5

The Shops at Chestnut Hill

The Shops at Chestnut Hill offers a luxurious shopping experience with high-end retailers, exquisite dining options, and stylish architecture, making it a vibrant destination for both locals and visitors seeking sophistication and leisure.

Outdoor5/5

Newton Reservoir

Nestled in Newton, MA, Newton Reservoir offers stunning views and serene walking trails, making it a perfect escape for nature lovers and a picturesque spot for relaxation amid the urban landscape.

Outdoor4.7/5

Hammond Pond Reservation

Nestled in the heart of Newton, Hammond Pond Reservation offers serene walking trails, scenic views of the picturesque pond, and a vibrant array of wildlife, making it an ideal escape for nature lovers and outdoor enthusiasts.

Culture4.2/5

Mary Baker Eddy Historic House

The Mary Baker Eddy Historic House in Chestnut Hill offers a glimpse into the life of the founder of Christian Science, featuring original furnishings and an inspiring atmosphere that captivates visitors seeking spiritual insight and historical significance.

Shop4.7/5

Allandale Farm

Nestled in Chestnut Hill, Allandale Farm impresses with its picturesque landscapes and commitment to sustainable farming, offering visitors a charming retreat complete with fresh produce, nature trails, and seasonal events that celebrate local agriculture.

Landmark4.6/5

Boston College

Outdoor4.8/5

Houghton Garden

Houghton Garden enchants visitors with its lush landscapes, serene pond, and winding trails, making it a hidden gem in Chestnut Hill, perfect for tranquil strolls and nature-inspired moments.

Shop4.7/5

Polkadog Bakery

At Polkadog Bakery in Chestnut Hill, indulge your pup with artisanal treats crafted from wholesome ingredients, making it a beloved destination for dog lovers seeking quality and creativity in every bite.

Shop4/5

Onyx Boutique

Shop4.1/5

Bloomingdale's

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$$$$4.2/5

Davio's Northern Italian Steakhouse

Eat$$$$4.2/5

Legal Sea Foods - Chestnut Hill

Eat$$$4.2/5

Tatte Bakery & Cafe | Newton Centre

Eat$$$3.9/5

Shake Shack Chestnut Hill

Cafe$$$3.9/5

Blue Bottle Coffee

Eat4.7/5

Van Leeuwen Ice Cream

Eat$$$4.3/5

Frank Pepe Pizzeria Napoletana

Eat$$$4.1/5

The Cheesecake Factory

Stays

Stay4.65/5

The Verb Hotel

Nestled between Fenway Park and the Boston Symphony Orchestra, The Verb Hotel is a vibrant homage to rock ‘n’ roll! With retro-style rooms and killer vinyl soundtracks, it’s a music lover's dream. Enjoy a splash in the pool, grab a bite at the on-site diner, and soak in the electrifying atmosphere. Your Boston adventure starts here! 🎸✨

Stay4.6/5

The Langham, Boston

Nestled in the heart of Boston, The Langham is a chic blend of history and luxury. With its stunning architecture, sumptuous rooms, and a fabulous pub, it’s the perfect base for exploring. Don’t miss the renowned afternoon tea! Plus, the nearby Rose Kennedy Greenway invites leisurely strolls. Get ready for a delightful stay in Beantown!

Stay4.55/5

Boston Harbor Hotel

Welcome to the Boston Harbor Hotel, where luxury meets charm! Nestled on Rowes Wharf, this waterfront gem boasts stunning harbor views, lavish rooms, and top-notch dining. Sip a cocktail by the pool or stroll along the scenic wharf. With easy access to the city’s attractions, it’s the perfect launchpad for your Boston adventures. Ahoy, luxury!

Stay4.5/5

Hotel Commonwealth

Welcome to Hotel Commonwealth, where Boston charm meets modern flair! Nestled in the bustling Kenmore Square, this vibrant hotel offers plush rooms, a rooftop terrace with stunning views, and quick access to Fenway Park. Savor delicious bites at NHL star–owned restaurants and explore local hotspots. Your unforgettable Boston adventure starts here—pack your bags and get ready for fun!

Stay4.3/5

Kimpton Marlowe Hotel

Nestled along the scenic Charles River, the Kimpton Marlowe Hotel is a playful mix of chic comfort and local flair! Enjoy vibrant décor, pet-friendly perks, and delightful dining options, all just a hop away from Cambridge's hottest spots. Unwind in the cozy lobby bar or take a splash in the indoor pool—adventure awaits around every corner!

Stay4.3/5

Omni Parker House

The Omni Parker House, a historic hotel in Boston, is renowned for its classic ambiance, delicious Boston cream pie, and rich literary heritage, making it a must-visit for history and culture enthusiasts.

Stay4.25/5

Homewood Suites by Hilton Boston Brookline-Longwood Medical

Homewood Suites by Hilton Boston Brookline-Longwood Medical offers spacious, stylish accommodations with a complimentary breakfast and easy access to Boston's medical district, making it the perfect blend of comfort and convenience for both leisure and business travelers.

Stay4.2/5

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!

Stay4.15/5

AC Hotel Boston Cleveland Circle

Get ready to live the Bostonian dream at AC Hotel by Marriott Boston Cleveland Circle! Nestled in the vibrant heart of Beantown, this trendy hotel promises sleek, modern design with a touch of European flair. Unwind in spacious rooms, fuel up with delectable breakfast options, and explore the charming Cleveland Circle neighborhood just steps away. AC Hotel guarantees an unforgettable and Instagram-worthy stay in Boston!

Stay4.15/5

Hilton Boston Back Bay

Stay4/5

The Liberty, a Luxury Collection Hotel, Boston

Welcome to The Liberty, where history meets luxury in the heart of Boston! Housed in a former jail, this one-of-a-kind hotel provides an unforgettable experience. Explore historic Beacon Hill, indulge in delectable cuisine at our award-winning restaurants, or enjoy a cocktail in our iconic Alibi bar. With stylish rooms and top-notch amenities, this is the perfect spot for a memorable getaway.

Stay3.95/5

The Inn At Longwood Medical

Stay3.95/5

Four Points by Sheraton Boston Newton

Nestled in a charming suburb, Four Points by Sheraton Boston Newton offers a perfect blend of modern comfort and classic New England charm, making it an ideal retreat for both business and leisure travelers.

Things To Do
Provided by

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

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

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

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

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

5/5

4 h

Private 4-Hour Driving & Walking 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

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

5/5

1 h 30 mins

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 90 minute/1.5 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

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

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

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

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

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

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

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

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

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

5/5

3 h

Boston North End Food and History Tour Stories Behind the Bites

Discover Boston's oldest neighborhood on a food tour that's equal parts delicious and "mostly" accurate. Join a local guide as you wander the cobblestone streets of the historic North End, stopping at handpicked restaurants to sample iconic local favorites. Along the way, you'll uncover fascinating stories, colorful legends, and the rich history that shaped one of America's oldest cities. Perfect for food lovers, history buffs, and curious travelers, this relaxed walking tour combines incredible local flavors with unforgettable storytelling for an experience that's as entertaining as it is delicious. Tour Highlights * Enjoy six generous tastings, including handmade ravioli, brick-oven pizza, a classic Italian sandwich, seasonal New England treats, fresh cannoli, and a Boston lobster roll. * Explore Boston's oldest neighborhood with a local guide. * Discover fascinating history, local legends, and Mostly Accurate stories. * All food and 20% gratuity for each stop is included.

$99.00

5/5

2 h 30 mins

Stroll, Sip and Savor: Boston Evening Food & Cocktail Experience

Local Foods, Libations & Lots of Fun! Visit the local eateries Boston's South End residents call home. Walk to 4 different locations, where each visit includes an alcoholic beverage paired with your food tasting. Food Tastings are representative of the diverse food scene in Boston's South End neighborhood and may include visits to a Creole / Asian Fusian hotspot, French-Cambodian restaurant, a beloved Wine and Cheese shop, and a Mexican lounge. When it comes to food - and cocktails - Boston's South End is not to be missed! Available exclusively on Wednesdays and Fridays at 4:30pm.

$135.45

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).