Itinerary Details
Insight Vacations: Treasures of Cape Cod & the Islands
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
Day 2 - Exploring Plymouth's Past
Trace the path of American independence along Boston’s Freedom Trail. See the nation’s oldest public park, Boston Common, the Old State House and the Granary Burying Ground, final resting place of revolutionaries. Then travel to Plymouth and step aboard the Mayflower II, a full-scale replica of the 1620 ship. At Pilgrim Hall Museum, explore an extraordinary collection of 17th-century artifacts with a Mayflower descendant on a MAKE TRAVEL MATTER® Experience, gaining powerful insight into the founding stories of early Plymouth Colony. Finally, walk through recreated homesites at Plimoth Patuxet Museums, where you’ll witness traditional practices and lifeways of both the Wampanoag and English communities.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast
Day 3 - The Wonders of Cape Cod
Travel through Cape Cod National Seashore, where nearly 40 miles of beaches, dunes and lighthouses define the Outer Cape. At Salt Pond Visitor Center, look across Nauset Marsh and discover exhibits on Wampanoag heritage, maritime history and Cape Cod’s lifesaving stations. Continue to Provincetown, where colorful Commercial Street reflects a community shaped by fishing, art and the Pilgrims’ first landing in 1620. After lunch, enjoy time to explore at your own pace or join an Optional Experience through the surrounding dunes. After a day exploring Cape Cod’s natural and cultural history, gather at your hotel for dinner.
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 long favored for its natural beauty and notable visitors. Begin at the Gingerbread Cottage Museum in Oak Bluffs, where your Local Expert reveals the origins of this colorful 19th-century neighborhood. Enjoy free time to explore at your own pace, perhaps visiting the Flying Horses Carousel, the oldest of its kind in America. Later, gain a broader perspective during an orientation of the island, passing coastal landmarks including State Beach, made famous by the film Jaws. Spend the night on Martha’s Vineyard, giving you more time to experience the island’s distinctive character. This evening, savor island hospitality at Bettini, located in your elegant hotel, with a seasonal menu shaped by local farms, fishing boats and foragers.
Accommodations: Harbor View, Martha's Vineyard
Meals: Breakfast, Dinner
Day 6 - The Timeless Elegance of Newport
Wake on Martha’s Vineyard before taking the ferry back to Cape Cod and continuing to Newport, Rhode Island, where more than 95 years of hospitality characterize your hotel. Personalize your afternoon with Insight Choice. Visit the Newport Car Museum, where more than 100 vehicles trace milestones in automotive design and performance, or explore Green Animals Topiary Garden at Brayton House, the oldest of its kind in the United States, where sculpted shrubs have been shaped since 1872. This evening, take a leisurely stroll through Newport’s streets and uncover more of its storied past.
Accommodations: Viking, Newport
Meals: Breakfast
Day 7 - Newport, the Queen of Summer Resorts
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" with a visit to 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. Later, take to the water aboard the Madeline, gliding through Newport Harbor and Narragansett Bay. This evening, gather at La Forge for dinner overlooking the International Tennis Hall of Fame — a fitting finale in the heart of this elegant seaside city.
Accommodations: Viking, Newport
Meals: Breakfast, Dinner
Day 8 - Farewell to Boston
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
