Top Massachusetts Private Sightseeing Tours - page 3

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.

Experience Boston Harbor on a sunset cruise aboard a historic tall ship. Depart from Fan Pier Marina on the 67-foot Liberty Star enjoy views of the outer harbor, Fort Independence, East Boston, the Charlestown Navy Yard, and beyond. Relax and let the crew handle the sails or jump in the action and a grab a line on this fun and affordable outing.

Taste your way through Boston with a private food-focused tour. Meet your guide for a half-day city stroll that includes popular landmarks such as Boston Common, the Paul Revere House, and the Bunker Hill Monument. Sample several traditional flavors of Boston including Boston clam chowder and Boston cream pie. Learn about local history and culture from your private guide.

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.

See the landmarks and highlights of Boston from the water on this sightseeing cruise in Boston Harbor aboard a 1920s-style yacht. Snap photos and enjoy a unique perspective of the harbor, very different than a typical walking or driving tour through Boston. Highlights include the USS Constitution, Bunker Hill Monument, Old North Church, and the USS Cassin Young.

Don’t waste time looking for the ideal place to eat as you walk the cobblestone streets of Boston’s North End. Join other passionate foodies to snack your way through the neighborhood’s hidden gems. Your guide directs you to a hidden Italian bakery, an authentic Italian salumeria, and a family-run pastry shop. Visit the Old North Church (or equivalent alternative) and enjoy a rich cappuccino or bold espresso with a pastry.

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.

Download GuideAlong’s self-guided audio walking tour of Salem and uncover America’s most infamous witch hunt, the Salem Witch Trials. Step into Salem’s intriguing past and visit iconic sites like the Old Burying Point Cemetery, the Salem Witch Trials Memorial, the House of the Seven Gables, and more. Along the way, hear the true stories of the 1692 witch trials, Salem’s colonial past, and its literary legacy play automatically as you walk through Salem’s historic cobblestone streets. 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 Like having a personal guide by your side on every step

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.

Explore Boston’s history, culture, and culinary heritage on this private tour. Delve into the city’s pivotal role in America’s founding, stroll historic neighborhoods, and hear stories that tie past and present together. The private format ensures your day is paced to your interests while minimizing logistical hassles, giving you a meaningful and personalized overview of Boston.

Discover a history of resistance among Beacon Hill’s cobblestone streets with a self-guided smartphone tour of underground railroad sites. Vivid audio narration brings to life the stories behind landmarks from the Charles Street Meeting House to Boston’s first integrated school. You won’t be limited by a guided tour’s fixed schedule, so you can pause for photos, take breaks, and enjoy the experience at your own pace.

Get a comprehensive overview of Boston’s key landmarks during this half-day tour of the city. Combine a walking tour with a driving tour to cover more ground than you would if you just did one. See important sights like the USS Constitution, Old North Church, and the Paul Revere House and learn about the city’s history from your tour guide.

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.

Enjoy an alternative night out in Boston on a dinner cruise on Boston Harbor, with an all-you-can-eat buffet meal with live entertainment and dancing. Watch the sunset, then admire the view of the illuminated Boston skyline at night or head to the dance floor for music and fun inside the ship’s nightclub. Bring that special someone or a whole group of friends for a night to remember.

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.

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 stories behind historic Boston sites on a self-guided tour of downtown, and enjoy the flexibility to experience the city on your own schedule. Booking this tour means access to audio guides that never expire, so you can explore as much—or as little—as you want at a time. The included GPS-enabled app gives turn-by-turn directions as expert tour guides narrate revolutionary history and more.

Explore Boston in a way that interests you on a private walking tour that can be customized to your preferences. You'll follow a flexible itinerary tailored to include attractions that you want to see, such as Boston Common, Freedom Trail, or Copley Square. If you don't have specific interests, you can leave the itinerary up to your guide. Either way, this is a chance to enjoy Boston's history and charm with a guide all to yourself.

Join Your guide Cathy and embark on a captivating journey through Provincetown’s West End, where the sands of time meet the tides of history. This unique walking tour weaves together the stories of ancient homes, weathered wharves, and steadfast lighthouses, all nestled along the shimmering edge of Provincetown Harbor. Designed to feel like a step into a living museum, this tour blends maritime grit, pilgrim lore, and bohemian charm, offering a soulful exploration of Cape Cod’s northernmost tip. This 90 minute walking tour covers about .5 mile along the West End of Commercial Street. Each stop pulses with Provincetown’s unique blend of history, art, and seafaring spirit, making this tour a love letter to a town that’s both timeless and ever-evolving. After the tour, opt for a Pedi-cab back to the center of town!

Cover the highlights of the Freedom Trail on this walking tour of Downtown Boston. A shorter route leading between Boston Common and Faneuil Hall Marketplace is ideal for travelers who don’t have the time or inclination to cover the full extended route. A costumed guide adds a theatrical touch to the experience.

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.

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.

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.

Explore Boston’s Mafia past and learn the story behind North End’s immigrants with this interactive outdoor exploration game. Taking the role of an investigative reporter, solve a series of challenges on your phone that will lead you around the neighborhood, including to Rose Kennedy Rose Garden, North Street Park, North Square, and hidden gems.