Top Boston Day Trips

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 ocean walks, charming seaside towns, and authentic working harbors. Highlights include a full walk along the Marginal Way, time to explore Kennebunkport, lunch and free time in Portland’s historic Old Port, and a visit to Portland Head Light, one of the most photographed lighthouses in the country. With dramatic coastal views, fresh seafood options, and thoughtfully paced stops, this trip captures the essence of southern Maine in a single, effortless day!

Explore Newport in a single day without planning or driving from Boston. This small-group tour includes pre-booked mansion admissions, guided transport with hotel pickup, and free time in the historic waterfront district to help you use your time efficiently. Visit iconic mansions, enjoy a scenic coastal walk, and discover additional historic landmarks along the way. With logistics handled in advance, you can focus on architecture, scenery, and independent exploring.

Join us on a journey from the vibrant city of Boston to the historic town of Salem, Massachusetts. Our expert guides will take you on a fascinating tour through time, starting with the famous Salem Witch Trials. Learn about the panic and hysteria that engulfed the town during that fateful period, as well as the solemn reminders of the innocents whose lives were forever changed. As we explore the narrow streets and charming architecture, you will catch glimpses of the colonial past that still resonate throughout the town. Hear tales of the city's maritime heritage, with trade and seafaring shaping Salem's development into a bustling port. Delve into the captivating past of this enchanting town, an epitome of New England charm infused with a rich tapestry of stories waiting to be unraveled. Our tour of Salem's history is sure to leave you with a deeper appreciation for the intricate layers of its past and the enduring legacy it holds in American history.

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.

Spend a full day exploring Manhattan from Boston with ease on this group tour. Depart early from Boston in a comfortable vehicle with a driver-guide and make your way down to New York City. Take time to visit One World Trade Center, the Statue of Liberty, and Times Square before returning to Boston.

Take a deep dive into the history of the American Revolution on this walking tour of Boston. Your historian guide will focus on the years between 1760 and 1775, a tumultuous time with plenty to talk about. Stroll the Freedom Trail and ask your guide questions along the way to learn things most tourists miss.

Discover a whole new side of baseball history with the help of a guide on this tour of Fenway Park, one of baseball’s most beloved stadiums. Revisit the careers of Red Sox greats like Ted Williams, Babe Ruth, and Carl Yastrzemski, celebrate the club’s numerous World Series titles, and tour famous stadium locales like the ‘Green Monster,’ ‘Pesky’s Pole,’ and the Fenway Park Living Museum. It’s ideal for baseball fans, be they locals or tourists.

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.

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.

While a guided tour is a great way to get to know a city, many try to fit in as many participants as possible. On this small-group tour of Boston, one-on-one time with your guide is guaranteed. Explore the interior of Old Ironsides, the battlegrounds and museum at Bunker Hill, Harvard, and much more on this full-day driving tour dedicated to sharing the hidden history even Bostonians don’t know.

Make exploring beyond Boston city limits seamless—and discover the history and highlights of Newport, Rhode Island, long a summer retreat for the city's upper crust—on this full-day tour from Boston. Visit the Breakers Mansion (owned by the Vanderbilts) and the Marble House (a "Great Gatsby" filming location), and go for a bus tour of Newport's other highlights before enjoying free time for some independent sightseeing.

Experience the Black Heritage Trail and get to know more about Civil War-era Boston on this small-group walking tour. In the company of a guide, head out into Beacon Hill and hear stories about the Underground Railroad, Boston Brahmins, and other historical facts. Enjoy a focus particularly on the Civil War years.

New England is renowned for having some of the most beautiful fall foliage in the country—and this seamless, full-day tour from Boston makes it easy to discover the region’s vibrant scenery. Following morning pickup from your Boston hotel, travel to New Hampshire’s White Mountains, and stop for photography breaks along the Kancamagus Highway. Following lunch in charming North Conway (own expense), continue the seasonal sightseeing as you journey to the storied Mount Washington Hotel. At the end of the day, return to your Boston hotel.

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.

Discover the rugged beauty of the Maine coast on a full-day trip from Boston to Portland. Visit Fort Williams Park and see the legendary Portland Head Light, one of the most photographed lighthouses in the country, set against sweeping Atlantic Ocean views. Continue to Portland’s historic Old Port for free time to explore cobblestone streets, waterfront shops, and acclaimed seafood restaurants. A stop at Lobsterman Park highlights the city’s deep maritime roots. With curated stops and ample free time, this tour delivers a classic New England coastal experience without the hassle of planning.

Discover the New Hampshire and Maine coasts, plus the highlights of Kennebunkport, all in one day: this private, full-day tour from Boston makes exploring easy. Meet your guide in the morning at your departure point, and hop aboard your private van. You'll stop in the historic town of Portsmouth, will discover the Cape Neddick Nubble Lighthouse, can tour the President Bush Compound at Kennebunkport, and upgrade to add on a lobster tour.

Salem and Boston have been home to such a diverse range of historical events that it can be tough to take it all in on your own. On this full-day private tour, join your guide and discover the region’s Puritan history, learn about the 17th-century witch hunt hysteria, hunt for ghosts at several historical local landmarks, and much more.

Discover the best of historic Plymouth in just one day—and enjoy a hassle-free way to explore—on this full-day trip from Boston. Check off several key Plymouth sights, including Plymouth Rock, the Mayflower II, and Plimoth Patuxet Museums, all while benefitting from skip-the-line admission tickets. Plus, have bonus free time to explore the 400-year-old town's harbor, enjoy lunch (own expense), and sightsee at your own pace.

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.

Plymouth Colony comes to life in our recreation of early Plymouth, complete with timber-framed houses furnished with reproductions of the types of objects that the Pilgrims owned, aromatic kitchen gardens, and heritage breeds livestock. At The Patuxet Homesite, learn about the Indigenous heritage of the 17th-century lifeways of a culture that continues to thrive today. At the Craft Center, located in close proximity to the 17th-Century English Village, you will learn from a variety of skilled artisans and museum historians. Mayflower is an iconic symbol of freedom. Of the hundreds of ships that made the transatlantic crossing in the 1600s, she is the ship we remember. At our reproduction of the Plymouth Colonists’ original 1636 grain mill on Town Brook, take a fascinating look at the mill’s history and workings, from the 200-year-old millstones grinding corn to the ecology of the brook that has powered mills throughout the centuries.

Take a semi-private day trip you'll never forget! Start the day with a pickup at your door, then ride up the North Shore to Hammond Castle, located on the ocean cliffs of Gloucester. Take a guided tour of the castle, learning about the history of the eccentric millionaire inventor who built it. Enjoy free time to explore the castle and gardens with plenty of opportunities for stunning photos. Drive to Salem, where you will have free time for lunch. Choose from a wide variety of dining options in the historic downtown. After lunch, your guide will take you on a tour of Salem. Learn about the infamous witch trials of 1692, see the real places where the victims were hanged. Learn the story of the "Corwin Curse" as you take a picture in front of the historic Witch House. See the locations where Hocus Pocus was filmed. Take a drive through one of the most beautiful streets in North America, lined with mansions built on the city's maritime fortune.

Walk the Freedom Trail with a guide in historic costume on a tour from Boston Common to Faneuil Hall, a 1.2-mile route that covers important sites in the heart of Boston. This tour's shorter distance lets you follow in the footsteps of the founding fathers and American revolutionaries without making the more strenuous trek all the way across the Charles River, finishing in a spot that’s convenient to top Boston attractions.

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed boat in Boston that gets to and from the whales in the least amount of time possible. Look out for humpback and fin whales, plus Atlantic white-sided dolphins, with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.