Top Boston Outdoor Activities - page 2

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

Escape Boston for a full day along the southern Maine coast, blending scenic seaside walks, historic harbor towns, and iconic lighthouse views. Begin at Marginal Way in Ogunquit, a cliffside coastal path that winds along the Atlantic with uninterrupted ocean views and classic New England scenery. Continue to Kennebunkport, a postcard-perfect harbor town known for its historic homes, local boutiques, and working waterfront. Arrive in Portland in time for lunch in the Old Port district, where cobblestone streets, 19th-century brick buildings, and fishing piers set the scene for some of Maine's best seafood — this is the spot to try fresh, locally caught lobster on your own. Finish at Portland Head Light, Maine's oldest and most iconic lighthouse, perched dramatically above the rocky shoreline within Fort Williams Park, with sweeping Atlantic views to close out the day.

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.

We'll see the sights on Boston's Freedom Trail and get a closer look by leaving the car and walking inside some locations (depends on day and hours of operation for some sites). We'll have time to go aboard the USS Constitution (closed Mondays). A close-up experience in the oldest neighborhoods of the North End, Beacon Hill, School Street, and Charlestown. Look at places of events and the people from different periods of the settlement of Boston, and the American Revolution. If weather isn't favorable, we can revise the walking portions according to your wishes. A favorite stop is Faneuil Hall, the Great Hall Meeting Room and the Ancient and Honorable Artillery Company Museum (hours vary).

SEA the skyline twinkle at night as you cruise around the harbor. Whether you’re ending your evening onboard or starting your night out, come Sea Boston with Mass Bay Lines. Sit back, relax and enjoy the city views from the water. The sea breeze and smooth cruise will relax you after a busy day about town. Just add water!

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.

See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Snap photos of Boston's coast from the water and feel free to ask the captain or crew questions about the passing landmarks.

An immersive clue-solving adventure around Boston's North End. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll never forget! Reschedule anytime with no fees. It's a scavenger hunt, escape room, and urban crawl all-in-one. Follow the storyline around town as you find clues and use them to crack codes. Then enter solutions on the app to find out where to go next. Clues can be anywhere - murals, statues, landmarks, and more! Plan on about two hours of playtime, depending on your experience level and how much time you spend exploring along the way. Difficulty level is adjustable - take as many or as few hints as you’d like! PLEASE NOTE: Bookings made less than 7 days before your play date will be scheduled for local pickup. For bookings made 7+ days in advance, our team will contact you to arrange shipping.

Escape Boston for a full day in New Hampshire's White Mountains. During the summer route, explore the caves, waterfalls, bridges, and forest paths of Lost River Gorge; during the fall foliage period, travel the scenic Kancamagus Highway instead. Both routes continue to Flume Gorge for a walk through its dramatic granite walls and woodland scenery.

Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic ferry crossing, historic seaside villages, and the laid-back charm of island life. Board the Island Queen ferry in Falmouth and cruise across Nantucket Sound to Oak Bluffs, where colorful gingerbread cottages surround the historic Tabernacle at the Martha's Vineyard Camp Meeting Association. Enjoy time to explore the island's most iconic spots, with an optional sightseeing bus tour covering the Flying Horses Carousel, the refined harbor town of Edgartown, Gay Head Light atop the dramatic Aquinnah cliffs, and Nobska Point Lighthouse. Return via the Steamship Authority ferry from Woods Hole, rounding out a full day of coastal views, ocean breezes, and authentic New England island character.

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).

See more of Boston for one low price by purchasing the Boston Explorer Pass by Go City. Enjoy great savings off regular prices as you get admission to your choice of two, three, four, or five Boston attractions, picking among top city highlights like a Boston sightseeing cruise, a hop-on hop-off trolley tour, and much more. An included digital guide helps design the perfect itinerary.

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.

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.

Boston CityPASS® — Planning a trip to Boston? Save 45% on admission to four must-see attractions. Experience Boston’s must-see tourist attractions — and enjoy considerable savings — on this exciting Boston CityPASS. Choose four admissions between the following seven attractions: New England Aquarium, Museum of Science, Boston Harbor City Cruises, View Boston Observation Deck, Franklin Park Zoo, or Harvard Museum of Natural History This Boston CityPASS is valid for 9 consecutive days from date of first use. Convenient mobile tickets are valid for 1 year from the date of purchase. Transportation to and from the attractions is not included.

Take a leisurely ride through Boston on the on this 2.5-hour cycling tour. Take in the Boston skyline, ride along the banks of the Charles River, and learn about Cambridge and Boston's history through your guide's commentary. Suitable for families with young children, this tour includes use of bike and helmet.

Enjoy a gourmet brunch on this scenic cruise of the Boston Harbor. Set sail aboard the Northern Lights at Rowes Wharf and settle in for a buffet filled with eggs, bacon, fresh fruit, and more. View popular Boston highlights such as Bunker Hill Monument, the USS Constitution, Old North Church, and Sea Castle Island. This brunch cruise offers a great overview of Boston and a lovely morning on the water.

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.

Celebrate a special occasion or just enjoy the company of your family and friends on this leaf-peeping Boston Harbor brunch cruise. On board a 1920s-style yacht, the Northern Lights, you’ll sail through Boston Harbor, cruise past the Harbor Islands, and spot landmarks and beautiful fall scenery along the way. Indulge in a fresh, gourmet brunch prepared by the onboard chef as you take in the waterfront views.

Spend a day away from Boston and experience southern Maine's picture-perfect coastline without transportation headaches and the benefit of a guide to provide insights and history on the region you'd miss otherwise. Drink in the ocean views as you head north to the Nubble Light lighthouse and Ogunquit's Marginal Way before visiting idyllic Kennebunkport. Here, enjoy a narrated trolley tour and time to shop and eat (own expense) before your return trip. Hotel pickup and drop-off are included for ease.

Check off many of the Boston area’s top sights and experiences in a single day, all on this hassle-free, small-group tour. Following pickup at your chosen location, travel by comfortable vehicle to highlights such as Harvard University, MIT, and Quincy Market, where you have time to explore the sights on foot. Bonus seasonal perks are also available, including a Boston Harbor cruise in summer and a lobster and chowder lunch in winter.

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.

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.

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.