Boston, often described as America’s most European city, is a captivating blend of history, art, and culinary delights. Upon your arrival at the Hyatt Regency, nestled in the heart of downtown, you're just moments from sights such as the historic Faneuil Hall and the fashionable Newbury Street. Take a leisurely stroll through the charming South End or along the picturesque Charles River Esplanade. This evening, meet your Travel Director and fellow guests for a delightful dinner, marking the beginning of your unforgettable journey. 

Trace the footsteps of America’s founding history on a guided walk along Boston’s Freedom Trail, exploring landmarks that shaped the nation’s earliest days. In Plymouth, step aboard the Mayflower II, a full-scale replica of the ship that carried the Pilgrims across the Atlantic. At Plimoth Patuxet, enjoy a Taste of Two Cultures lunch featuring traditional English fare and indigenous dishes. Afterwards, delve into the daily lives and evolving relationships of the early settlers and Wampanoag people on a guided tour. Your day concludes with a MAKE TRAVEL MATTER® Experience at Pilgrim Hall Museum, where you’ll gain insight into the vital roles of women in the Plymouth colony and how their contributions shaped the settlement’s survival and legacy. 

Awaken to the rugged beauty of Cape Cod National Seashore, where history and landscape intertwine. From the ancestral lands of the Wampanoag to the maritime traditions of early European settlers, the shoreline speaks to generations of seafarers, lighthouse keepers, and fishermen. Opt for a guided excursion through the windswept Peaked Hill Bars Historic District dunes, where a Local Expert reveals the area’s unique ecology and the artists it has inspired. Enjoy a relaxed evening in the historic charm of Sandwich. 

Your day begins with a ferry ride from Hyannis to the enchanting island of Nantucket, aboard Hy-Line Cruises. On arrival, set out on the “Notable Nantucket Women” walking tour, guided by a Local Expert from the Nantucket Historical Association. Stroll through the island’s storied downtown, uncovering tales of the women who influenced the rise and fall of the whaling industry and shaped the island’s domestic life. Following lunch, enjoy some unhurried time to explore Nantucket’s quaint streets at your own pace before sailing back to Hyannis, carrying with you the unique heritage and remarkable stories of the women of Nantucket.

Board a morning ferry to Martha’s Vineyard, an island known for its pristine beaches, charming harbour towns, and storied visitors, including U.S. presidents. Explore Oak Bluffs with its gingerbread cottages, visit the Flying Horses Carousel and see State Beach, made famous by the film Jaws. Discover the island’s colourful past, from whaling to modern-day tourism, as you gain insights into the history of Edgartown Harbor Lighthouse. Later, enjoy island hospitality with seasonal offerings from local farms, fishing boats and foragers during a dining experience at Bettini, located in your elegant hotel. 

Arrive in Newport, where over 95 years of hospitality and charm characterise the historic Hotel Viking. Set in the heart of this coastal city, your boutique accommodation offers luxurious rooms and stunning views. Personalise your afternoon with Insight Choice. Opt to visit the Newport Car Museum, where over 100 vehicles highlight milestones in design and performance of cars throughout the 19th and 20th century. Or explore Green Animals Topiary Garden at the Brayton House, the oldest of its kind in the United States, where sculpted shrubs have been meticulously shaped since 1872. This evening, take a leisurely stroll through Newport’s vibrant streets, where every corner reveals another piece of its storied past. 

Your day begins with Newport’s famed Ten Mile Drive, a scenic route that hugs the coastline, showcasing public parks, historic landmarks and breathtaking ocean views. Afterwards, explore the grandeur of Newport’s "summer cottages" as you visit the Breakers, the grandest of them all. A symbol of the Vanderbilt family’s wealth and prominence, this opulent mansion offers a glimpse into the lavish lifestyle of America’s Gilded Age elite. Cap off the day with a sunset sail aboard the Adirondack II, gliding along Newport Harbor and Narragansett Bay.

As your tour comes to a close, bid farewell to your fellow travellers and transfer to Logan International Airport for your onward journey. With memories of Boston’s historic charm, the beauty of Cape Cod, and the elegance of Newport, you leave with a deeper appreciation for this unique corner of New England.