Top Massachusetts Day Trips

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.

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.

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.

Download GuideAlong's Cape Cod audio tour to discover what “summer” really means. Drive the iconic “bent arm” between Barnstable and Provincetown, with side trips to striped lighthouses, sandy beaches, and historic Pilgrim landmarks. Along this 60-mile route down Route 6, we’ll detour to discover everything from quaint coastal towns, gorgeous salt marsh hikes, and hidden histories. Don’t miss the highlights: Nauset Light, which once guided ships past the treacherous Cape shores, Pilgrim Monument, with its gorgeous ocean views, and the thrilling rocky causeway at the very end of Provincetown. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. Stories, tips, and directions play automatically based on your location Travel at your own pace Tour offline using GPS. No cell service or WiFi is needed Suggested itineraries for half, full, or multi-day use No time limits or expiry, and free updates

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.

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.

Discover some of Boston’s deepest, darkest secrets that lots of tourists miss out on by joining this “frightseeing” tour aboard the Trolley of the Doomed, which roams around the haunted streets and burial grounds of Boston. Your costumed host provides illuminating insights into the history of the city's spookiest sights, such as Copp’s Hill Burying Ground.

Experience the best of Nantucket with this 2-in-1 bundle — two complete self-guided tours available together at a discounted price. Begin your adventure with a walking tour through the heart of downtown Nantucket, learning about the whaling trade, and discovering landmarks like the Atheneum and Hadwen House. Next, embark on the Nantucket Coast to Coast drive or bike tour, stretching from Madaket to Sconset. Follow a scenic route past windswept beaches, historic lighthouses, and classic shingle cottages that reveal the island’s more tranquil side. Each tour is available separately, but when purchased together, they offer a flexible and memorable way to explore the entire island at a discounted rate. - Two complete self-guided tours at a discounted bundle price - Walking tour through downtown Nantucket’s historic sites - Scenic drive or bike tour from Madaket to Sconset - GPS-triggered audio works offline - Discover hidden gems and learn about the island’s maritime heritage

Explore Nantucket from coast to coast on a self-guided audio tour designed for driving or biking. Follow the route from historic Nantucket Town to Madaket, Sconset, Sankaty Head Lighthouse, and other scenic corners of the island while GPS-triggered narration plays automatically along the way. Discover beaches, historic homes, cranberry bogs, lighthouses, and stories from Nantucket’s past as you travel at your own pace. Stop whenever you like for photos, sightseeing, food, or a break, then continue when you’re ready. Download the tour in advance and use it offline. Bike or vehicle rental is not included. - Explore Nantucket from Madaket to Sconset - GPS-triggered narration plays automatically - Designed for either driving or biking - Works offline after download - Stop and explore whenever you like

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.

Visit historic sites in Lexington and Concord. Focus on sites related to the start of the War of Independence, early years of the towns, and authors of 19th Century Concord. Experience scenic countryside, town centers and Walden Pond Reservation. We can customize this tour to specific interests and to other locations in Lexington and Concord. Your guide is licensed by the town of Concord.

Experience the best of Boston and Cambridge with ease on this private full-day tour. Depart from your hotel in a private vehicle and learn about the two cities from your guide. Explore at your own pace and stop by the sights along the Freedom Trail, Bunker Hill, Harvard University, MIT, and more.

Welcome to Martha's Vineyard, the storied island off Cape Cod that has captivated visitors for generations with its windswept beaches and fiercely independent spirit. This self-guided tour takes you across the island's six unique towns, each with its own character. Begin in bustling Vineyard Haven, where ferries have delivered travelers since the whaling era, then explore Oak Bluffs and its fantastical Victorian gingerbread cottages painted in every color. Drive to elegant Edgartown, where sea captains' houses line streets unchanged since the 1800s. Journey west to witness the dramatic clay cliffs of Aquinnah, sacred to the Wampanoag people who have called this island home for over ten thousand years. Discover quiet fishing villages, pristine wildlife sanctuaries, and the rolling farmland that gives the Vineyard its bucolic countryside charm. From presidents and literary legends to fishermen and farmers, this island attracts those who value beauty, solitude, and community.

Enjoy the beauty of New England’s coastal towns on a private day trip from Boston, driving along the North Shore to Cape Ann, including Manchester-by-the-Sea, Gloucester, Salem and Rockport. Spend a day immersing yourself along Massachusetts’s coastline marked with idyllic towns and dotted with lighthouses.

Explore the beauty of Martha's Vineyard on an electric bike tour designed just for you. It offers unique experiences tailored to your interests: secluded beaches, historic farms, the iconic Gingerbread Houses, and more. Let us take you there. Choose 4-6 hour private tour, where every detail is curated to ensure you see a few of the island's gems: lighthouses, Downtown Edgartown, Oak Bluffs, Chappaquiddick. Or call us and inquire about our 3-day Tour De L'ile for an in-depth adventure across the island's six towns. All tours include e-bike use, helmet, water, snacks, and admission to select attractions. - Explore top attractions like the Campground Cottages in Oak Bluffs and Chappaquiddick Island. - Private tours available for groups up to six riders, ensuring a personalized experience. If you have more riders, give us call a week in advance and we will try to accommodate you.

While there are many areas within Boston where you can experience the city’s revolutionary history, to get a more complete picture, history lovers can visit the real locations where the American Revolution began. On this full-day private tour, head to Lexington and Concord to walk the Battle Road Trail, see where the Minutemen bested the Redcoats, and much more.

Exclusively available during the Halloween season! Discover the spooky, historic city of Salem on this full-day tour from Boston, where the infamous witch trials of 1692 left a profound legacy. Begin with a pickup at your hotel before exploring Salem's haunting landmarks including the Witch Trials Memorial and the Witch House, the residence of a judge from the trials. Experience the prosperity of Salem during the Old China Trade, and enjoy 1.5 hours of free time for lunch and shopping at local eateries and unique shops. Your journey back to Boston is just as comfortable, making it convenient and enriching for history enthusiasts and curious travelers alike. - Full-day semiprivate tour with pickup from Boston - Visit key sites like the Witch Trials Memorial and the Witch House - 1.5 hours of free time for lunch and shopping in Salem - Comfortable transportation in a van with a small group size of 1 to 9

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.

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.

History enthusiasts will love this private tour of American Revolution sights around Boston, Cambridge, Lexington, and Concord. See where the revolution began on a tour that will bring to life the places and characters you learned about in school. Save yourself the hassle of catching public transport or walking by touring with a private driver and car.

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.

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.