Top New England Architecture Tours

Skip the line and journey through 5,000 years of art at Boston’s Museum of Fine Arts. See masterpieces by Van Gogh, Monet, and ancient treasures from Egypt to Asia. Discover one of America’s finest museums, rich in history, beauty, and culture. Highlights: • Visit the renowned Museum of Fine Arts with a 5-Star Licensed Private Guide • Skip the queue with our exclusive skip-the-line tickets to this iconic museum • Discover hidden gems and masterpieces tailored to your artistic interests • Learn fascinating stories behind American art, Impressionism, and ancient Egypt • Explore at your own pace with a fully personalized and interactive experience Step into a world of artistic brilliance with Rosotravel on a Private Tour of Boston’s iconic Museum of Fine Arts. With Skip-the-Line Tickets and a Licensed Guide at your side, enjoy a personalized journey through one of the most prestigious art collections in the U.S. Discover the wonders of Boston with us today!

Hear the true stories that inspired the HBO show The Gilded Age on a self-guided walking tour down Bellevue Avenue, from Rough Point Mansion to The Breakers on Ochre Point Avenue. Along the way, I’ll share the juicy details behind Newport’s palatial ”summer cottages” as you gaze at their impressive designs. You’ll find out about the owners of these homes, many of them New York’s most elite families including the Vanderbilts and Astors. I’ll also introduce you to the architects who designed them and the staff that kept these homes running despite harsh working conditions and low pay. You’ll hear about the impact that the sinking of Titanic had on the owners of the Miramar Mansion, and how it took 36 staff members to look after Mable House, a holiday home used for only eight weeks of the year. This hour-long stroll takes you behind the scenes to discover the personalities that built today’s Newport.

Explore the best of Boston's Freedom Trail—and get more out of the visit than you could if exploring on your own—on this guided walking tour that covers many of the city's most important sights. Wander cobblestone streets, check out the historic architecture, and learn about the colorful past of this dynamic destination. Stops include Faneuil Hall, King's Chapel, Boston Common, and more.

Explore elegant neighborhoods, historic streets, and American landmarks on a Boston walking tour from the Back Bay to Beacon Hill and downtown portions of the Freedom Trail. Learn about Boston’s history and culture as you stroll brownstone-lined avenues and walk the shady paths of the Boston Public Garden. Step into Boston’s Revolutionary history in the churches, cemeteries, and battlegrounds of the American struggle for independence.

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.

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.

Vermont’s blend of history, craftsmanship, and beauty is best experienced on a scenic drive through its most charming towns. On this self-guided driving tour, you'll journey along picture-perfect roads, over historic covered bridges, and into the heart of the region’s artistic culture. The tour starts in Woodstock, in what’s often called one of the most beautiful small towns in America. You’ll set off towards Quechee, passing through Taftsville to see its striking red covered bridge, one of the most attractive in Vermont. From there, you’ll have a chance to browse a bounty of antiques, vintage finds, and fine art at Vermont Antique Mall and BF Southgate & Company. You’ll follow a historic route to Windsor that parallels the Connecticut River, affectionately known as the “Birthplace of Vermont.“ I’ll show you the Cornish-Windsor Covered Bridge, the longest wooden covered bridge in the United States, before you make your way back to Woodstock via West Windsor and South Woodstock.

Embark on a privately guided journey through Truro’s soul, where history, culture, and breathtaking landscapes converge. This tour weaves together three iconic Cape Cod landmarks: The Highland House Museum, Highland Links Golf Course, and the historic Highland Light. Begin at Highland Light, Cape Cod’s oldest lighthouse (1797). Ascend 69 steps to the lantern room for panoramic Atlantic Ocean views and hear the thrilling tale of its 1996 relocation. Next, step into the Highland House Museum, a 1907 farmhouse-turned-hotel-turned-cultural gem. Once a haven for literary giant Henry David Thoreau, who penned parts of Cape Cod here. Explore rooms inspired by Edward and Josephine Hopper’s artistry. Stroll along the Highland Links Golf Course, America’s first 9-hole links course. Nestled amid rolling dunes and windswept grasses. Available June-September only.

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of Oak Bluffs. Starting in Ocean Park, you’ll follow the coast to Inkwell Beach before heading into the heart of the town. Along the way, you’ll hear its history and find out what makes this island paradise so alluring to everyone from the rich and famous, to curious Cape Cod vacationers that come for a day. Around Trinity Park, you’ll see Martha’s Vineyard Camp Meeting Association, its cottage museum, and the Tabernacle in Oak Bluffs which is a place of worship. After heading down Circuit Avenue, where I’ll show you the town’s famous Flying Horses Carousel, our tour will come to an end at the harbor. Whether you’re on the island for only a day, or calling Martha’s Vineyard home for the season, this tour is for anyone who wants to dig into Oak Bluffs’ past and enjoy its present.

Step into the grandeur of New England’s past with a visit to Castle Hill on the Crane Estate, a breathtaking National Historic Landmark overlooking the Atlantic Ocean. This immersive day trip from Boston includes round-trip rail transportation and a private shuttle, making it an effortless way to explore one of Massachusetts’ most stunning estates. What to Expect: Round-Trip Commuter Rail Ticket from Boston- we provide detailed, step by step instructions on how to get to North Statin in Boston an what train to take. Private Shuttle to the Crane Estate – We will pick you up from the Ipswich MBTA station and take you to the estate and back Enjoy the Guest of the Cranes Guided Tour – Step inside this magnificent 1920s mansion, where expert guides will transport you back to the era of lavish parties, grand architecture, and breathtaking seaside views. Free Time to Explore the Estate Grounds Return Shuttle & Train to Boston

Uncover the hidden stories of Boston’s Jewish community, from immigrant roots at Vilna Shul to powerful reflection at the New England Holocaust Memorial. Walk through history, faith, and resilience in the heart of one of America’s oldest cities. Highlights: • Visit Boston’s Jewish landmarks with a 5-Star Private Guide fluent in your language • Discover stories of resilience and heritage that shaped Boston’s Jewish community • Explore historic synagogues, moving memorials, and striking architecture • Learn local insights and get personalized tips to enrich your Boston journey • Enjoy a private walking tour tailored to your pace and interests in the city This powerful walking tour through Boston’s historic Jewish Quarter offers a unique lens on the city’s past. With a Licensed Private Guide, uncover forgotten stories of resilience and faith from Boston’s Jewish community. Discover hidden gems and iconic landmarks. Book with Rosotravel today!

Explore Boston's iconic Back Bay while honing your sketching skills. This lesson includes visits to 3-4 notable locations, where you'll receive all necessary materials to create your own sketches. Participants will leave with both initial sketches and a more developed final artwork. Additionally, the session will cover some of the rich history of the area's architecture and highlight key figures who shaped it.