7-Nights Boston, Cape Cod & The Islands - Small Group from $4,946

Insight Vacations

OFFER ID 1556433

Treasures Of 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)

Choice Highlights

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.

Authentic Dining

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.

Insight Choice

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.

Insight Experiences

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.

Make Travel Matter

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 artifacts and possessions carried on the Mayflower as you explore the personal stories behind early Plymouth Colony. Your visit directly supports United Nations Sustainable Development Goal 4: Quality Education.

Top Rated Highlights

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, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here.

7 nights from $4,946 per person

Itinerary

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Itinerary Details

Insight Vacations: Treasures of 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 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
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. 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.
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 centuries. 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

Featured Destinations

Sandwich

Martha's Vineyard

Newport, OR

Boston

The history and bricklaid beauty of Boston is easy to enjoy. Follow the Freedom Trail past Old North Church, Paul Revere Park, Fanieul Hall, the Commons, Old Ironsides and more landmarks of America's birth. Across the Charles River is Cambridge and Harvard. Venture to Marblehead and Salem to the south, or Lexington and Concord to the north. Back in town, have clam chowder at the warf or great Italian food in North End.

Excursions

Boston: Private North End Italian Food Tasting Walking Tour - 3 Hours

Boston: Private Sunset Boston Harbor Cruise with Cocktails and Hors d'oeuvres - 2 Hours

Boston: Private VIP Boston Yacht Experience With Cocktails & Hors d’oeuvres - 2 Hours

Boston: Boston Private Cycle Boat Charter - 4 Hours

Boston: Discover Boston Private Sightseeing Program - 4 Hours

Boston: Private Historic Boston Pub Crawl - 4 Hours

Boston: Freedom Trail Private Walking Tour - 1.5 Hours

Boston: Private Harvard Campus Tour - 1.5 Hours

Vacation Details

Valid Date Ranges

05/08/2026 - 05/15/2026

from $5,216 per person

08/21/2026 - 08/28/2026

from $4,946 per person

* 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.

Prices Start At

from $4,946 per person

Length

7 Nights

Air City

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Vacation Rating

Deluxe

Remarks

Trip prices are per person, land only, based on double occupancy and reflect applicable discounts. Trip prices and discounts are subject to change. Airfare is additional. Tour prices, dates and itineraries are correct at the time of the website going live, however are subject to confirmation at the time of booking. Other restrictions may apply.

All fares are quoted in US Dollars.

OFFER ID

1556433

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