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7-Nights Boston, Cape Cod & The Islands - Small Group from $4,725
Insight Vacations
OFFER ID 1556433
Boston, Cape Cod & The Islands - Small Group
This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Plymouth, a coastal town famous for its rich history as the landing site of the Pilgrims in 1620; visit the living history museum at Plimoth Patuxet. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous - and learn about the area’s past as a pirates’ haven.
Dining Summary
- 3 Dinner (D)
- 7 Breakfast (B)
- 1 Dinner with Wine (DW)
- Choose between two carefully selected activities
- Newport: A striking destination for design lovers and motoring enthusiasts alike, this museum reimagines the automobile as a canvas for innovation. Housed in a repurposed missile plant, its collection features over 100 cars, from the sculpted lines of mid-century Cadillacs to performance icons like the Ford GT, Porsche 911 and Corvette Stingray. Each car is selected for its impact on design, engineering and culture.
- Newport: Established in 1872, this is America’s oldest topiary garden, where horticultural craftsmanship meets imaginative design. Set on seven coastal acres, the collection includes more than 80 sculpted shrubs, from giraffes and elephants to intricate geometric forms. Maintained by generations of gardeners, it remains a living work of art on Rhode Island’s historic shoreline.
- Boston: At 18:00, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
- Martha's Vineyard: Indulge in a locally sourced dinner in a private dining space in Bettini Restaurant.
- Newport: Meet your new friends in the evening for a seafood dinner with wine, where you can share the highlights of your trip while savoring a freshly prepared meal.
- Newport: A striking destination for design lovers and motoring enthusiasts alike, this museum reimagines the automobile as a canvas for innovation. Housed in a repurposed missile plant, its collection features over 100 cars, from the sculpted lines of mid-century Cadillacs to performance icons like the Ford GT, Porsche 911 and Corvette Stingray. Each car is selected for its impact on design, engineering and culture.
- Newport: Established in 1872, this is America’s oldest topiary garden, where horticultural craftsmanship meets imaginative design. Set on seven coastal acres, the collection includes more than 80 sculpted shrubs, from giraffes and elephants to intricate geometric forms. Maintained by generations of gardeners, it remains a living work of art on Rhode Island’s historic shoreline.
- Newport: Meet your captain and jump onboard the Adirondack II, an 80-foot schooner sailing ship and cruise around the coastline. You’ll sail out and pass nearby islands, old historical buildings and homes of the rich and famous, as you learn about the region’s exciting history, including its pirate activity.
- Newport: Enjoy a visit to one of Newport's renowned landmarks, The Vanderbilt's Breakers Mansion.
- Plymouth: Led by a Mayflower descendant, enjoy a guided visit to Pilgrim Hall Museum, the oldest continuously operating public museum in the United States. View original 17th-century artefacts and possessions carried on the Mayflower as you explore the personal stories behind early Plymouth Colony. This MAKE TRAVEL MATTER® Experience supports United Nations Sustainable Development Goal 4: Quality Education through inclusive programming, extensive historical resources and its mission to deepen public understanding of America’s colonial beginnings. Your Experiences advances United Nations Sustainable Development Goals 4: Quality Education
- Plymouth: Visit detailed reconstructions of a 1600s English village and a Wampanoag homesite. As you walk through the open-air exhibits, see timber-framed houses, dugout canoes and heritage crops, and observe traditional skills in practice. This museum offers a clear, research-based insight into the lives of early colonists and Indigenous communities in what was once Patuxet.
- Boston: Trace America’s path to independence with your Travel Director as you stroll past Boston’s iconic sites. See Boston Common, the oldest public park in the United States; the red-bricked Granary Burying Ground where Samuel Adams rests; and the evocative Old State House, the spark site of the Boston Massacre.
- Cape Cod: Experience the natural wonder and human history emphasizing the cultural themes represented on Cape Cod, including the First People--the Wampanoag; European settlement culture; fishing, life-saving, and lighthouses; communication technology of Cape Cod's National Seashore.
- Nantucket: Walk through historic downtown Nantucket and discover the unique history of the island. Journey through Nantucket’s past and hear about the rise and the fall of the whaling industry, the rise of tourism, and the impacts the island’s economy has had on social and racial development on Nantucket.
- Martha's Vineyard: After disembarking from your ferry ride, visit the port neighborhood of Oak Bluffs and be transported to a different era. Known for its rainbow-colored, gingerbread-like cottages with Gothic storybook decorations, hig
7 nights from $4,725 per person
Special Promotion: Save up to 15% on September 2025 tours or up to 15% on tours departing in the next 4 months
Valid for new bookings deposited March 24, 2025 – May 29, 2025 for travel from September 1 – September 30, 2025 (or) on select tours departing in the next 4 months.
*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply.
Insight Vacations: Boston, Cape Cod & The Islands - Small 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
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 artefacts 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
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
Vacation Details
* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.
Fine dining, on-site bars or lounges and room service with extended hours are characteristic of deluxe establishments. Guest services usually include valet parking, concierge services, baggage assistance and laundry services. Other on-site facilities often include shops and boutiques, full service spas, full fitness facilities with pools and tennis courts. Business amenities may include available up-to-date technology and support staffs available for services. Attention to detail is apparent in the guestrooms which typically have stylish furnishings, quality bedding and bath products and often provide an evening turn down service.
All fares are quoted in US Dollars.
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Windsor Travel Corp.
2121 Sage Road Suite 111
Houston, TX 77056
USA
(713) 627-0111