Top Boston Holidays in 2026

There are lots of ways to follow in the footsteps of the founding fathers in Boston, but not many tours allow you to do so while drinking in historic pubs and taverns. On this small-group combination pub crawl and walking tour, visit a range of New England drinking establishments while listening to facts about the country’s formation.

Relive one of the most important events leading up to the American Revolution and learn about a side of the story most tourists miss on this guided tour of the Boston Tea Party Ships and Museum. Explore authentically restored tea ships with the help of a guide as you get their insights into this pivotal event, and throw some of your own tea into Boston Harbor. It's an ideal experience for American history buffs, tourists, and locals alike.

Hop into a duck boat—s renovated World War II amphibious vehicle—for a comprehensive city sightseeing tour of Boston. Pass Boston Common, Quincy Market, the Celtics' home turf at TD Garden, and much more. Then splashdown into the Charles River for a view of the city by boat. Learn all about Boston's history and landmarks as you go.

Combine horror stories and booze on this haunted small-group pub crawl through Boston. Hear stories about spooky occasions and haunted history in Boston’s past from your guide and hop from pub to pub along the way. Take time to learn about Boston’s architecture and explore four different local bars in the city.

Eat your way through Boston’s North End and learn about its history with this group tour. Explore the neighborhood’s Italian heritage in the company of a guide and stroll through the area’s scenic streets. Enjoy a local lunch at a North End eatery featuring arancini, pizza, Italian meats and cheeses, a pasta course, cannoli, and more, and hear stories about the neighborhood’s past.

Ready to mix spirits with… well, spirits? Join Boston’s premier haunted pub crawl, where the drinks are strong and the ghost stories are even stronger. Grab your bravest drinking buddies and stumble (responsibly!) through Beantown’s booziest and most bone-chilling history—from haunted pubs and ghost-filled restaurants to the eerie cemeteries where Boston’s past refuses to stay buried. You’ll hear tales of restless Founding Fathers, scandalous secrets, and blood-stained streets that might just send a chill up your spine—or maybe that’s just the whiskey. So pour yourself a Boston Lager, toast to the dearly departed, and see just how much haunted history you can handle. With Ghost City Tours, it’s all fun and fright until someone sees a ghost... and then it’s even better. *Entry into establishments is subject to operating hours and availability. Drinks not included. Only for guests ages 21+.

Save time—and money—and pair your Boston sightseeing with a frothy brew or two on this combination history tour and tavern crawl. Meet your guide and set off with just a small group for company. Wander along the city’s Freedom Trail, and see several key Boston attractions—all while your guide shares the stories and history behind the sights. As you go, stop for refreshing beers in several centuries-old taverns.

It can be tough for visitors to know the best venues to experience Boston’s rich Italian culinary culture. On this guided food tour, head to the North End of Boston and learn about the region’s Italian immigrant history, which is kept alive today through the eateries serving pizza, pasta, arancini, meats, cheeses, cannoli, espresso, and more. Visit both historic institutions and under-the-radar spots to meet the people and traditions behind the food.

Discover the best of Boston’s hops and history on a small-group pub crawl along the Freedom Trail. Offered at three separate times, you can easily start at a time that fits with your schedule. Purchase drinks as you please as you visit some of the city’s top pubs with your guide while passing iconic historical sites and learning about Boston's colonial and revolutionary past.

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore the world-famous Boston Harbor and see the city’s historic sites while listening to live commentary on board, from tales of the Revolutionary War to local legends. While you cruise, enjoy views of the city skyline as well as the Boston Harbor Islands, USS Constitution (“Old Ironsides”), and the Bunker Hill Monument.

Combine two attractions Boston has to offer—delicious food and rich history—on this walking tour that starts in the popular North End and continues along the Freedom Trail. Taste fresh bread, pizza, and a classic Italian deli sandwich at local stops in this historic Italian neighborhood. Then, walk the Freedom Trail to learn about the American Revolution, all while enjoying scenic views of Boston Harbor and the Rose Kennedy Greenway. Explore the charming architecture of Beacon Hill and experience the city's blend of old and new.

This history-driven pub crawl combines Revolutionary Boston with four wildly different bars, drinks, and stories. Over two hours, you’ll discover what connects Sam Adams Brewery, the tropical Tiki Cove, the legendary Green Dragon Tavern, and Modern Underground, a hidden cocktail bar tucked beneath a famous pastry shop. Along the way, your local guide will explore Boston’s history from the colonial era through the Revolution and into the modern day, with stories of smoky taverns, the Boston Tea Party, Caribbean influences, colorful characters, and some of the city’s stranger myths and legends. This isn’t four stops that feel the same, or a history lecture with a bar at the end. Expect beer, rum, cocktails, trivia, gangsters, and plenty of laughs as we separate historical fact from Boston folklore. Your guide may even challenge you to a game of 2 Truths and a Lie! It’s history, drinking, and storytelling with a distinctly Boston sense of humor. Some of it might even be true!

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.

End a day in Boston the right way with a sunset sightseeing cruise on Boston Harbor. See all of the harbor’s historic attractions as well as the city’s modern skyline, and witness the USS Constitution’s traditional sunset ritual: a ceremonial firing of the cannon of the oldest commissioned sailing ship in the US, and a lowering of her flag, signaling the end of the day.

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!!

See Boston from a whole new angle aboard a Boston Harbor evening cruise. Watch the sunset from the water, and glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, the USS Cassin Young, and more. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night, and sip a cocktail (own expense) from the onboard bar as you relax and enjoy the views.

Combine an indulgent brunch with a sightseeing boat tour on this two-in-one festive outing. Meet at Rowes Wharf, and hop aboard the *Northern Lights*, 1920s-style yacht. Over the course of several hours, you’ll see landmarks ranging from the Bunker Hill Monument and USS Constitution at Charlestown Navy Yard to Castle Island and beyond. You’ll also enjoy a holiday buffet brunch onboard.

From seals and sea lions to sea turtles, seadragons, and stingrays, the New England Aquarium is the place to discover hundreds of different marine animals under one roof—or in one big tank. Check out the four-story Giant Ocean Tank, featuring a brand new coral reef, underwater communications system and hundreds of Caribbean reef animals. Grab an admission ticket and have an unforgettable aquarium adventure.

Learn about the Boston Tea Party and Boston’s revolutionary history at your own pace with this private self-guided audio walking tour. Download the app to your phone and use it whenever you like, even offline. Follow the route and hear stories about Boston’s history and the sites along the way.

Discover Boston’s top attractions on this comprehensive guided bike tour around the city. See the unique character and charm of each community up close, like the beautiful brownstones in Back Bay and the South End. Visit Boston’s historic North End and pedal past Copley Square and Fenway Park. Cross the Freedom Trail, passing significant locations to United States history.

Your holiday tour begins in the Financial District at Kane’s Donuts where we’ll sample several of their daily flavors. After which, we’ll take a leisurely stroll along the waterfront on the way over to Boston’s Public Market. While there, we’ll try some delicious donuts and apple cider. You’ll also learn some history around the market and have a moment to check out other vendors. On to the third stop, we’ll walk through Boston’s North End neighborhood. It’s also the home to the Old North Church, which was the starting point for Paul Revere’s famous ride during the Revolutionary War. In the North End, we’ll stop at one of the oldest bakeries in the neighborhood. We’ll have a uniquely Boston treat while we’re here. Lastly, we’ll walk back through the North End to end the tour back at the Public Market where we’ll finish with Union Square Donuts. We’re so excited to share this experience and the amazing donuts of Boston. We hope you can join us very soon!

Skip the crowded holiday tours during the Christmas season, and instead choose this Boston Self-Guided Christmas Tour that shows you all the best spots in Boston without the hassle of going at a group’s pace. See the Boston Christmas Tree, as well as parts of Beacon Hill and other areas all decorated for the holidays at your own pace using an easy-to-download app.