Top Boston Seasonal & Special Occasions - page 2

Enjoy an alternative night out in Boston on a dinner cruise on Boston Harbor, with an all-you-can-eat buffet meal with live entertainment and dancing. Watch the sunset, then admire the view of the illuminated Boston skyline at night or head to the dance floor for music and fun inside the ship’s nightclub. Bring that special someone or a whole group of friends for a night to remember.

Explore Boston after dark on a guided walking tour focused on true crime, urban legends, and lesser-known historical events. Led by a local guide, the experience emphasizes storytelling and discussion rather than scripted narration. The small-group format creates an engaging evening experience that presents a different perspective on the city’s past beyond standard daytime tours.

Home of the famous Samuel Adams and Lamplighter breweries, Boston has a thriving culture of microbreweries, distilleries, and cider houses. A brewery tour is one of the best ways to experience Boston’s beer scene, and on this half-day excursion you can taste award-winning beer and cider, learn about the history of each brewery, and explore the brewing process.

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

Exclusive transportation by local driver. Complimentary Cold Coca Cola, Coke Zero, Saratoga Springs Water, Polar Orange Dry.

BUT FIRST, DESSERT! Do dessert before dinner when you join us for Cocktails & Cannoli, an all inclusive walking food tour of Boston’s North End. Skip the infamous lines to taste delicious drinks and classic cannoli, and sample the best sweets the North End has to offer. Not to mention the Paul Revere House and Old North Church along the way! To top it all off, our local tour guides will sprinkle in fascinating historic knowledge, fun cultural facts, and culinary tidbits.

Embark on an enchanting evening in Boston with our comprehensive tour featuring a narrated city drive and a memorable sunset cruise. Begin your journey with a guided drive through the city, where you'll pass by iconic landmarks such as the Boston Common, Beacon Hill, and the historic North End. Learn about Boston's rich history, from the American Revolution to its modern-day significance, and vibrant culture from our knowledgeable guide as you soak in the city's lively atmosphere. Next, unwind aboard a relaxing sunset cruise along Boston Harbor. Admire panoramic views of the city's glittering skyline and waterfront attractions, including the Boston Tea Party Ships and Museum, as the sun sets. Feel the cool harbor breeze and capture stunning photos of the twilight sky reflecting on the water. This tour is perfect for those seeking a blend of informative sightseeing and serene evening relaxation, offering an unforgettable perspective of Boston under the enchanting glow of twilight.

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes. Learn more about the art of styling your body features and take a figurative soft tour outside your comfort zone as your stylist pulls pieces for you to explore and try. Think of it as a mini style consultation followed by recommendations and a hands-on practice session during the shopping tour where you can ask any fashion and style-related questions. Throughout your shopping circuit and neighborhood's discovery, listen to fashion stories as told by your fashion savvy guide, and get a unique insight into the industry. Prior to your shopping tour, you will be sent a little shopping form to help personalize your experience. And following your fashion escapade, you will be sent a personal style summary of recommendations received by your stylist as well as some tour souvenir photos.

Boston offers spectacular shots that outdo any selfie on this private photoshoot. Join a local photographer for a relaxed tour around some of Boston’s famous landmarks, many dating back to Revolutionary times. Smile and pose with yourself, your partner, or your family at popular monuments and hidden spots tourists may not know about. This shoot leaves you with photos and memories to cherish.

Make this holiday season one to remember with this cocoa and carols holiday cruise on Boston Harbor. With dates offered throughout December, you can add a magical touch to your holiday, and easily find a date that works for you. Plus, you’ll cruise the harbor aboard a classic yacht with live music as you take in beautiful views of Boston.

Enjoy the beauty of Boston illuminated on this 1-hour evening cruise. Coast past sights like the Old North Church, Independence Wharf, the U.S.S. Constitution, the New England Aquarium, and more. Choose between open-air seating on the top deck, with blankets available, or stay cozy in the interior cabin. Alcohol, water, soda, and snacks are available for sale.

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!

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.

Ready for a night that’s equal parts laughter, creativity and cocktails? Join this hands-on paint and sip class in Boston, hosted through Classpop!, and rediscover how fun it feels to just make something. Your local instructor keeps it light and easy while you sip, swirl and paint your way to a surprisingly awesome masterpiece — even if you swear you can’t draw a stick figure. Everything’s included (canvas, brushes, paint, apron), and every class takes place in a cool local spot like a brewery or bar. Whether it’s a casual date, a team hangout or your solo night of self-care, this experience guarantees good vibes, great drinks and a painting you’ll actually want to show off.

Travel back in time to colonial New England on a historic walking tour. Your costumed and in-character guide gives you an immersive understanding of life during America’s infancy. Hear exclusive stories about the country’s Founding Fathers and discover iconic historical sites on this tour that covers approximately 1.2 miles (two kilometers).

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure! "

Watching the Boston Celtics live at TD Garden offers an unmatched atmosphere that immerses you in the legacy of one of the NBA’s most storied franchises. The atmosphere in TD Garden is electric, when Jayson Tatum hits a clutch shot, the energy from Celtics fans is unmatched - it’s more than just a game for Celtics fans, it's a way of life. The Celtics are one of the league’s top contenders, and watching them play in person reveals the speed, strategy, and physicality that TV just can’t capture. Whether you're a die hard Celtics fan or just a lover of great basketball, seeing the Celtics live at TD Garden is a thrilling and memorable experience, not to be missed. Located in the heart of Boston, TD Garden is accessible by public transit and surrounded by great food, pubs, and iconic landmarks. Whether you’re grabbing a bite in the North End or walking along the Freedom Trail pregame, attending a Celtics game can easily become part of a full day exploring the city!

Travel back in time, to the early years of the United States of America, during this guided walking tour of Boston’s Freedom Trail and beyond. Relive the events of the American Revolution as you pass Faneuil Hall, see the Old and New State Houses, and visit the setting of the infamous Boston Massacre. Then head downtown past Boston Common and the modern John Hancock Tower, finishing in Copley Square.

Discover Boston’s fall beauty on this guided, 4-hour, small-group bike tour around the North End of the city. Explore the historic Emerald Necklace, a 1,100-acre chain of parks linked by parkways and waterways in Boston and Brookline. Visit the shaded boulevard on Commonwealth Avenue, the shores of Jamaica Pond, and the popular, winding paths of the Arnold Arboretum of Harvard University. Also, see the Rose Kennedy Greenway, Boston’s newest public park; the famous Charles River Esplanade; the Boston Common and Public Garden and much more.

This is a one of a kind opportunity to visit Boston's Living Music Museum and Hall of Fame. Explore the featured exhibit that changes quarterly (Fall 2025 - This Wheel's Still on Fire). Watch interviews with music legends. See personal artifacts from private collections.

The Untold History of Boston Walking Tour steps off the beaten path and explores the captivating stories that lie just beyond the Freedom Trail. This small group tour by a lifelong local will take you through the city's lesser-known but equally fascinating sites, where remarkable events have shaped Boston's vibrant history. Get ready to immerse yourself in tales of disaster, transformation, resilience, and deception as we visit these intriguing locations.