Itinerary Details
Insight Vacations: Boston, Cape Cod & The Islands - Classic Group
Day 1 - Welcome to Boston
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.
Accommodations: Hyatt Regency, Boston
Meals: Dinner with Wine
Day 2 - Exploring Plymouth's Past
Join your Travel Director for an enriching exploration of Boston’s storied past. Walk along the famous Freedom Trail, where each step brings the American Revolution to life. Visit landmarks like Boston Common, the Old Corner Bookstore, and the Old State House. Continue your historic exploration at the Pilgrim Hall Museum in Plymouth, hosted by a Mayflower descendant, offering personal stories tied to the museum’s fascinating collection of 17th-century artefacts. At the Plimoth Patuxet Museum, immerse yourself in the stories of early English settlers and the Wampanoag Indigenous community during a MAKE TRAVEL MATTER® Experience. From the replica Mayflower II to the recreated homesites, your visit contributes to preserving this vital heritage, supporting pre-industrial crafts, trades, and maritime traditions.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast
Day 3 - The Wonders of Cape Cod
The windswept shores and pristine landscapes of Cape Cod await as you embark on a journey through the heart of New England’s maritime history. The Cape’s rolling sand dunes, historic lighthouses, and timeless fishing villages set the stage for a day rich in cultural discovery. Explore Cape Cod’s National Seashore, where the stories of the Wampanoag people and European settlers converge against a backdrop of stunning coastal beauty. Enjoy a relaxed evening in the historic charm of Sandwich.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast, Dinner
Day 4 - Nautical History in Nantucket
Set sail from Hyannis to the island of Nantucket, where cobblestone streets and preserved historic homes tell the story of a bygone whaling era. Stroll through the charming downtown, learning how the rise and fall of the whaling industry shaped Nantucket’s social fabric and economy. As you uncover tales of seafaring adventures, witness the island’s transformation into a beloved destination for visitors from across the globe. After a day steeped in maritime history, return to Hyannis by ferry for an evening at leisure.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast
Day 5 - The Charms of Martha’s Vineyard – An Island Escape
Board a morning ferry to Martha’s Vineyard, an island known for its pristine beaches, charming harbor 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 colorful 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.
Accommodations: Harbor View, Martha's Vineyard
Meals: Breakfast, Dinner with Wine
Day 6 - The Timeless Elegance of Newport Relaxed Start
Arrive in Newport, where over 95 years of hospitality and charm characterize the historic Hotel Viking. Set in the heart of this coastal city, your boutique accommodation offers luxurious rooms and stunning views. Personalize 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.
Accommodations: Viking, Newport
Meals: Breakfast
Day 7 - Newport, the Queen of Summer Resorts Relaxed Start
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.
Accommodations: Viking, Newport
Meals: Breakfast, Dinner
Day 8 - Farewell to Boston Relaxed Start
As your tour comes to a close, bid farewell to your fellow travelers 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.
Meals: Breakfast
