Top Boston Outdoor Activities - page 3

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this public sail is a perfect outing for family and friends. All ticket proceeds contribute to the World Ocean School's educational programs, ensuring a meaningful experience on the water. Enjoy an enriching day while supporting maritime and experiential education.

Traverse your own 'Mini Boston Marathon' - warm up from the Common to Kenmore and then run the last mile of the marathon route across the finish line, all while learning the race’s rich history with a local Boston Marathoner. Learn how the Boston Marathon's revered path and elite status developed and the rich history of those who have graced these hallowed streets since the late 1800s. Discover the Boston Marathon's many historical 'firsts,' why Marathon Monday is the best day of the year (every year!), and how the strength of Boston held the community together in the wake of the 2013 marathon bombing. Run through the Boston Common & Garden, down tree-lined Commonwealth Avenue, to the iconic CITGO Sign - then turn around to follow the last mile of the Boston Marathon route home to the finish line! End in historic Copley Square at the Boston Marathon monument, all while uncovering famous, hidden, and iconic marathon stories along the way.

Visit Martha’s Vineyard on a day trip from Boston to experience the island beauty without the hassle of booking ground and ferry transport. From hotel pickup and drop-off to included ferry tickets, snacks, water, and sightseeing maps, this Martha’s Vineyard excursion is designed for maximum time exploring, with the option to upgrade and include a guided tour of the entire island aboard a high-top, small-group van and explore all six towns on the island, indulge in lunch, and spend more time learning about scenic New England.

Discover Boston's revolutionary spirit and rich heritage through an immersive audio experience that puts you in complete control of your journey. Unlike crowded group tours that rush you through attractions, this self-guided adventure allows you to pause at monuments that captivate you, delve deeper into stories that intrigue you, and explore hidden corners that traditional tours overlook. Our expertly crafted narration reveals exclusive insider stories, untold historical secrets, and fascinating details that even many locals don't know, all delivered through crystal-clear audio by professional storytellers whose engaging voices bring Boston's past to life. You'll gain authentic insights into the city's revolutionary roots, architectural marvels, and cultural treasures while enjoying the freedom to customize your route, spend extra time at your favorite sites, and discover Boston at a pace that suits your schedule and interests perfectly.

Beat the Boston heat and get out on the water on this dog-friendly harbor cruise. With your group and your canine companion, board the cruise boat and set sail. Learn about Boston's history and sights including the Seaport District, Castle Island, USS Constitution, and North End from live narration onboard, and relax during Boston’s long summer days in the company of your dog.

Discover New Hampshire’s most striking natural wonders on a full-day escape from Boston. This curated tour brings you deep into the White Mountains for a choice between two unforgettable experiences: the adventurous Lost River Gorge or the scenic, nationally acclaimed Kancamagus Highway. Continue to the iconic Flume Gorge, where towering granite walls, waterfalls, and lush forest create a one-of-a-kind landscape. With plenty of time to explore, walk, and capture incredible photos, this tour delivers the perfect blend of nature, fresh air, and adventure—all in a single day.

Immerse yourself in the autumn season while exploring beautiful Boston Harbor on a relaxing sightseeing cruise. Step aboard the Northern Lights vessel and catch spectacular views of colorful seasonal foliage on the Boston Harbor Islands. Then, enjoy a delicious gourmet lunch and sip a hot cider.

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.

Enjoy lunch on the waters of Boston Harbor during this cruise aboard the "Odyssey Boston." You'll have the chance to admire views of the city skyline and seaport from the boat decks, plus listen to live music. The 3-course lunch includes a starter, main course, and dessert. This is a relaxing way to see the city from another perspective.

Explore Boston's rich sports history on foot! Dynasty beginnings to banner nights—experience the legacies that make this town shimmer! Come discover why Boston gets its Title Town reputation with a walk through the Celtics, Bruins, and Patriots' storied histories. Learn the powerful beginnings of each team and how they rose to elite prominence, giving Boston unforgettable record-setting title runs. Follow the Freedom Trail to TD Garden and learn about how America's earliest values overlay with this Title Town's sports legacy and discover the inspirational and complex connections between the city's diverse populations and their accomplished sports teams. Journey from Government Center to TD Garden - along the Champion's Parade Route, through Boston's historic West End via the Freedom Trail, and on to the 'Hub on Causeway' at TD Garden - all while discovering iconic monuments, hidden sports spots, and rich sports history along the way.

Experience the charms of Cambridge on this bicycle tour. Sometimes referred to as “Boston’s Left Bank,” Cambridge is a celebrated hub for academia, technology, and culture. Ride across the gleaming waters of the Charles River and visit Harvard Square, MIT, the Stata Center designed by Frank Gehry, and more. Over the course of 2.5 to 3 hours, you’ll cover 11-13 miles in this bike-friendly area.

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.

This self-guided tour of Boston’s historic Back Bay neighborhood turns exploring into a scavenger hunt with more than 20 challenges, games, and puzzles to solve. Instead of the fixed schedule of a traditional tour, you’ll have the flexibility to walk at your own pace. Along the way, experience some of Boston’s top landmarks and unearth their offbeat backstories.

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.

Explore Boston’s cultural landmarks on this private scavenger hunt. Download the app and play the game at your own pace and time. Learn about Boston’s history and cultural heritage as you and your teammates take on different interactive roles. Answer trivia questions and solve puzzles while visiting Copley Square, the Boston Opera House, and more.

Stroll Boston’s Freedom Trail independently and learn about the history of the city with this self-guided walking tour app. Download and use the app offline and let the GPS guide you from historic location to historic location. Explore at your own pace and use it any day and time that suits your schedule.

Explore Boston independently through a zombie-themed scavenger hunt game with this app. With your team, solve puzzles and find items that will help you survive the zombie apocalypse of the game. In the course of playing, see Boston on a self-guided walking tour and reach out to a remote host if you have any questions.

Independently explore central Boston with a scavenger hunt. Learn about Boston’s history, architecture, and cinematic heritage with challenges that take you past the Old City Hall, the New England Aquarium, the Boston Common, the Massachusetts State House, and Faneuil Hall, among other places. Solve each challenge to move onto the next location, including 5 film locations around Boston's civic center.

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.

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.

Explore Boston’s North End neighborhood on this scavenger hunt. Solve challenges to discover your next destination. At each step, learn some history as well as interesting facts about your surroundings. This is a self-guided walking tour you complete using your mobile device. Go from Long Wharf to Bunker Hill Bridge through Quincy Market to Paul Revere Mall.

Solve a murder mystery while exploring Boston’s streets Enjoy a mix of storytelling, puzzles, and real-world exploration Play at your own pace—pause, resume, or replay anytime A fun outdoor activity for couples, families, or groups of friends

"Dive into adventure, 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, the 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! Every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s go and make every day an adventure!"

Set out for the colonial streets of Boston with this 24-hour bike rental and explore the city’s winding neighborhoods at your own pace. Select among a variety of comfortable hybrid bikes and pedal past the North End, Boston’s picturesque wharfs, historical Fenway Park, the dignified brownstones of Beacon Hill, and the downtown public park of Boston Common within minutes.