7-Nights Treasures of Cape Cod & the Islands from $5,325

Insight Vacations

OFFER ID 1708123

Treasures Of Cape Cod & The Islands
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, visit Oak Bluffs, an idyllic town with gingerbread-like cottages, and overnight at an iconic historic hotel overlooking the harbor. Indulge in a sea-to-table feast filled with fish caught by local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board a 24 m (80 ft) 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

  • 4 Dinner (D)
  • 7 Breakfast (B)
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: Dine at Bettini, the signature restaurant of the historic Harbor View Hotel in Edgartown, where Martha’s Vineyard’s culinary traditions take center stage. Savor locally caught seafood, seasonal produce and ingredients sourced from island fishermen and farmers. Named for the Bettini family, longtime island residents with strong maritime connections, the restaurant also reflects the Vineyard’s enduring relationship with the sea.
  • 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.
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: Journey through Cape Cod National Seashore, nearly 40 miles of protected coastline shaped by beaches, dunes and lighthouses. At the Salt Pond Visitor Center, take in views across Salt Pond and Nauset Marsh before exploring exhibits on Wampanoag heritage, maritime history, fishing, lifesaving stations and the evolution of tourism on Cape Cod and its enduring relationship with the Atlantic coast.
  • 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.
Insight Experiences
  • Provincetown: At the tip of Cape Cod, Provincetown combines maritime history with one of America’s most distinctive arts communities. The Pilgrims first landed here in 1620 before continuing to Plymouth, while the Pilgrim Monument still marks that story today. Explore Commercial Street, where galleries, independent shops and cafes reflect a town long shaped by fishing, creativity, tourism and the sea today.
  • Martha's Vineyard: Discover Oak Bluffs, where Ocean Park faces a working harbor filled with ferries, fishing boats and sailboats. See the Flying Horses Carousel, the oldest continuously operating carousel in the U.S., with its original hand-carved horses, and explore streets lined with Victorian inns, independent shops and cafes that reveal the town’s long history as a summer resort.
  • Explore the Martha’s Vineyard Camp Meeting Association with your Local Expert and discover more than 300 colorful Victorian cottages. What began in 1835 as a Methodist summer gathering of worshippers living in tents evolved into an extraordinary collection of Carpenter Gothic homes, known for their intricate ‘gingerbread’ woodwork, decorative porches and brightly painted facades surrounding the historic Tabernacle.
  • Newport: Meet your captain and jump onboard the Madeline, a 72-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.
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 desi


7 nights from $5,325 per person

Itinerary

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

Featured Destinations
Martha's Vineyard
Newport, RI
Sandwich
Boston

Vacation Details

Valid Date Ranges
05/12/2028 - 05/19/2028
from $5,395 per person
05/26/2028 - 06/02/2028
from $5,625 per person
06/09/2028 - 06/16/2028
from $5,675 per person
06/23/2028 - 06/30/2028
from $5,325 per person
07/06/2028 - 07/13/2028
from $5,495 per person
08/18/2028 - 08/25/2028
from $5,650 per person
09/01/2028 - 09/08/2028
from $5,825 per person
09/08/2028 - 09/15/2028
from $5,825 per person
09/15/2028 - 09/22/2028
from $5,650 per person
09/22/2028 - 09/29/2028
from $5,625 per person
09/29/2028 - 10/06/2028
from $5,495 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 $5,325 per person
Length
7 Nights
Air City
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Vacation Rating
Deluxe
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.
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. 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
1708123

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Uniglobe Five Star Travel

3355 Lenox Rd. Suite 750
Atlanta, GA 30326
USA

404-231-8747
1 800 486-5257