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Winthrop

Winthrop, MA, USA

Winthrop

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Winthrop

Venture to Winthrop, a cozy coastal town just a hop, skip, and a jump away from Boston. Stroll along the scenic shores, indulge in fresh seafood delights, and soak up the laid-back seaside vibes. Don't forget to snap a selfie with the iconic Winthrop Water Tower! Pack your bags and get ready for a wicked good time in Winthrop, MA, USA.

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Recommendations

Outdoor4.8/5

Deer Island

Come visit Deer Island for stunning views of Boston Harbor and the city skyline. Explore the walking trails, enjoy a picnic at the beach, or learn about the island's history at the visitor center. Don't forget to snap a selfie with the iconic water treatment facility in the background!

Landmark4.7/5

Winthrop Center

Welcome to Winthrop Center, a dazzling gem in Boston's skyline! Standing tall at 691 feet, it's the second tallest building in the city. Marvel at its sleek glass façade, then explore the vibrant surroundings brimming with shops and eateries. Don't miss the observation deck for breathtaking views! Perfect for city adventurers and urban photographers alike!

Outdoor4.8/5

Pleasure Bay

Welcome to Pleasure Bay, where sun, sand, and surf collide in perfect harmony. Located in South Boston, this hidden gem offers stunning views of the Boston skyline, a beautiful beach, and plenty of opportunities for kayaking, paddleboarding, and relaxing in the sun. Don't forget your sunscreen and swimsuit for a day of pure enjoyment!

Eat$$$4.4/5

Belle Isle Seafood

Tucked away on Main Street, Belle Isle Seafood is a treasure for seafood lovers! This charming spot offers fresh catch delights from clam rolls to lobster sandwiches, all with stunning views of the water. Grab a picnic table outside, indulge in mouthwatering bites, and soak up the coastal vibes. A must-stop gem for any Winthrop adventure! 🦞🌊✨

Outdoor4.5/5

Belle Isle Marsh Reservation

Nestled within Boston's lush coastal charm, Belle Isle Marsh Reservation is a nature lover's paradise! With serene trails winding through marshes, vibrant birdlife, and stunning shoreline views, it’s perfect for leisurely strolls or picnics. Keep your eyes peeled for fascinating wildlife! This hidden gem offers a refreshing escape from the city buzz—just grab your camera and let the adventure begin!

Eat$$4.4/5

Blackstrap BBQ

Eat$$4.6/5

La Siesta Restaurante

Cafe4.3/5

Cafe Delite

Cafe$$$4.3/5

Caffè Paradiso

Caffè Paradiso, nestled in the heart of Boston's Hanover Street, is a traveler's oasis. With its cozy atmosphere and aromatic coffee, this gem offers a little taste of Italy without the jet lag. Indulge in their delectable pastries and people-watch to your heart's content. A must-visit spot for caffeine enthusiasts seeking a delightful escape in the bustling city.

Eat$$4.3/5

Ferrante's

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.

Eat4.4/5

Winthrop Market Place Inc

Stays

Stay4.2/5

Winthrop Beach Inn and Suites

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

Salem Witch Trials, Ghosts and History Walking Tour

Walk Salem's most haunted streets and uncover the fascinating true story of the 1692 witch trials — told the way only a lifelong local of old Salem can tell it. Named one of the best Salem walking tours by TripAdvisor in the Top 10 Salem Walking Tours of 2026. Enjoy Hocus Pocus stops, thrilling ghost stories - then be surprised along the way by Salem's lesser known history, and the question nobody thinks to ask: Why are there no Sheriffs in Salem anymore? Enter Salem's stunning McIntire District with Revolutionary War, maritime, and pirate tales woven throughout. This is a historical tour enriched with some beloved ghost stories. Tours end with dining, shopping and exploring recommendations on request. Perfect for families, couples, day trips from Boston, solo travelers, haunted history tours, friends, bachelorette parties, bridal parties, and curious kids. Meeting point: East India Fountain, 158 Essex St, Salem MA 01970. About 2 hrs. Outdoors only, no entry. See you in Salem!

$28.00
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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

Salem Merchants and Mansions Guided Architecture Walking Tour

All ages Spring/summer only Merchants & Mansions Architecture Tour Salem has one of the most naturally varied collections of historic structures in the country, spanning nearly 400 years. Come learn about how the inhabitants of Salem have kept their city comfortable, livable, and beautiful for centuries! From First Period to Georgian, Federal to Brutalist, Salem has some of everything. Your guide will wind you through the cobblestoned streets, discovering hidden gems, and viewing dozens of historic buildings and structures, as well as learning the fascinating stories behind them, from Salem's days as the wealthiest city in the country in the 18th century, to the great fire that nearly destroyed it all! Tours run RAIN or SHINE. We do NOT cancel for weather. For a full refund, you must cancel 24 hours prior.

$36.00
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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

Salem & North Shore Full Day Private Tour from Boston

Take a break from your Boston city break with this scenic private tour. There's lots of ocean views, rocky coastline, a bit of shopping and even some witch history. We keep this full day itinerary flexible to let you customize the tour but here's a feel for what we'll see. Pick up in Downtown Boston, taking the 60 minute highway drive to Manchester-by-the-Sea, where we pick up the scenic back roads. We'll take a picturesque country road to Gloucester, where we stop to walk along the waters edge to the Fisherman's memorial statue. We'll continue the scenic drive to Rockport, where there's a great collection of cute stores to browse and views to admire. Then drive to Salem, where we have time for a short walking tour around the main sites and historic spots. To finish out the day we'll squeeze in a few more ocean views on our drive back to Boston. We'll stop along the way for lunch (not included in price of tour).

$995.00
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5/5
4 h

Salem half day private tour from Boston

If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour consists of: - Downtown Boston pick up, ~45 minute drive to Salem - Stories of what happened before, during & after the Salem Witch trials - Walking tour of movie scenes, sites and fun facts of Salem - Go into one of the main Salem attractions (entry fee not included, and availability not guaranteed) - 45 minute drive back to Boston If you'd rather skip going into any of the sites, we use that time to take you to Marblehead for some amazing ocean views. The return journey and tour is 4 hours, we're happy to customize it to accomplish the things you're most interested in.

$695.00
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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

Salem Through a New Lens: Anniversary of Joseph White Murder

A walking tour and photography workshop in one! Experience a fascinating, in-depth exploration of Salem’s most notorious murder with a local guide. Along the way, a local photographer will help you get some great images of the beautiful historic sites you visit. Join our professional photographer and experienced tour guide Rebecca for a fascinating exploration of Salem’s most notorious murder. The death of aged sea Captain Joseph White was not just a personal tragedy to the families involved. It was a sign of the times that Salem’s identity as a wealthy and successful seaport was sinking into the horizon. The story of the murder became an international sensation and influenced authors Edgar Allen Poe and Nathaniel Hawthorne. **Bring your DSLR camera or Cell phone with extra batteries for this tour! Dive deep into the details of a true crime murder mystery. Take a walk with us!

$36.00
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