Top Massachusetts Day Trips

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.

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.

Visit Martha's Vineyard highlights on this half-day, small-group tour from Oak Bluffs. Make the most of your time on the island as you check out Oak Bluffs, Edgartown, and the Aquinnah Cliffs, learning stories about island history and cultures along the way. This Martha’s Vineyard tour is limited to 14 people for personal service from the local guide, and it includes a 15-minute break to explore the Aquinnah Cliffs.

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.

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.

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.

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.

Discover Boston’s most iconic sights in one perfectly planned day. Walk through the world-famous campuses of Harvard and MIT, where history, innovation, and genius collide. Enjoy free time at the lively Quincy Market for lunch and local flavors before boarding a scenic Boston Harbor cruise included with your tour during the summer or a classic New England Lobster Lunch at Quincy Market during the winter. This experience blends academic legends, historic charm, and waterfront views into a complete, effortless Boston adventure built to impress.

This is an action packed private day tour of the sites, history and events of the Revolutionary War era in Boston, Cambridge Lexington & Concord. We drive the Freedom Trail with stories of the city's 400 year history, the events, people and sites which led up to the war. In the oldest neighborhoods of the city, we'll give context to historic events like the Boston Tea Party, Boston Massacre and Battle of Bunker Hill. We'll take a quick walking tour of Harvard, explain the role it played in the start of the war and where George Washington himself spent time. A 10 mile drive gets us to Lexington Green where we take in the significance of the site and the story of what happened that night in April 1775. Next the picturesque town of Concord, to the Old North Bridge and how the second battle of the war took the British by surprise. Pick up and drop off in Downtown Boston, a stop for lunch along the way (not included in price of tour) and as light or heavy on history as you'd like.

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.

Take a break from your Boston city break with this scenic private tour. There's lots of ocean views, rocky coastline, a bit of shopping and even some witch history. We keep this full day itinerary flexible to let you customize the tour but here's a feel for what we'll see. Pick up in Downtown Boston, taking the 60 minute highway drive to Manchester-by-the-Sea, where we pick up the scenic back roads. We'll take a picturesque country road to Gloucester, where we stop to walk along the waters edge to the Fisherman's memorial statue. We'll continue the scenic drive to Rockport, where there's a great collection of cute stores to browse and views to admire. Then drive to Salem, where we have time for a short walking tour around the main sites and historic spots. To finish out the day we'll squeeze in a few more ocean views on our drive back to Boston. We'll stop along the way for lunch (not included in price of tour).

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.

I know the secrets that no one else knows. You will go on a small private tour where you will learn the amazing origins of everyday things. Enjoy the stories of the great places where liberty was born, told by an amazing guide and driver who really knows his stuff. I will lead you through the interior of Old Ironsides, the battleground and museum at The Battle of Bunker Hill and the incredible history of Harvard while amazing you with information about Boston that most Bostonians don't even know. We provide better service because unlike big chains, we are local and depend on our guests' satisfaction.

See all Boston's most important sights in a six hours, private, guided city tour, in a comfortable vehicle. If you value, time, privacy, comfort and would like to have a good overview of the city of Boston, Lexington and Concord at your own convenience and pace, we are the right choice for you. We will drive by or stop and wait at the sights you are most interested in. Our tour is totally customizable and our priority is to please you, not keep a schedule.

Discover the Concord of writers including Thoreau, Emerson, Hawthorne, and Alcott on a private tour focused on literary history. From Louisa May Alcott’s Orchard House to Walden Pond, you’ll find the real-world places behind stories you love. Offering the option to meet your guide in Concord or at a central location in Boston, this tour can adapt to your schedule and preferences, without the fixed itinerary of a group excursion.

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.

Discover Boston's highlights on a full-day private tour with hotel pickup and drop-off. Travel comfortably in a private vehicle with a dedicated driver and official tour guide. See top attractions like the Freedom Trail, Faneuil Hall, Boston Common, Beacon Hill, and several famous universities, or customize the itinerary to your interests.

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.

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.

Step into the world of film and television on this immersive, full-day tour through Boston and the North Shore. Begin at the Boston Public Garden, where Good Will Hunting fans can sit at the famous bench from Robin Williams and Matt Damon's emotional lakeside scene. Nearby, retrace Ted’s playful antics on the garden’s lawns and capture photos by the iconic swan boats. Next, visit Cheers Beacon Hill, the real-life bar behind the beloved sitcom. Snap a photo at its recognizable staircase and enjoy a themed drink where "everybody knows your name." In the afternoon, head to Cape Ann to explore CODA’s heartfelt story. At Rockport Wharf, see the real fishing boat “Angela Rose,” symbolizing Ruby’s family and her dream to sing beyond the horizon. Then, follow the Gloucester coastline to Manchester by the Sea’s filming spots. The sweeping ocean views and quiet streets echo the film’s grief, healing, and resilience. From laughter to legacy, every stop brings the screen to life.

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.

This private car tour is comprehensive enough for any history buff, but as interesting in other ways for non history nerds. It's a unique combination of the Revolutionary War sites in Boston and Cambridge that you won't have seen. Then onto Lexington and Concord to see the towns where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant, and lesser known sites along the way giving a detailed account of events in April 1775. For those less interested in the details of the battles, there's the option to visit the home of Louisa May Alcott or just take some time to enjoy the pretty main street of Concord. The itinerary gives the list of sites we'll visit, but timings are flexible to let us spend time at the places you're most interested in. We'll also stop for lunch (not included in price of tour) and there's plenty of photo opportunities.

Uncover the hidden corners and rich history of Nantucket on this self-guided driving or biking tour (does not include rental). From lighthouses and historic homes to pristine beaches and iconic vistas, this tour offers a comprehensive exploration of the island's unique character. Learn about Nantucket’s culture and history as you ride (or drive) across the island, from Madaket to Sconset. We’ll point out several points of interest along the way as you explore Nantucket from coast to coast. Need a bike? We recommend Young's Bike Shop (on Broad St.) or Cook's Cycles (on S Beach St.). You will need to contact them directly to arrange your own rentals separately.