Boston, Cape Cod & The Islands - Classic Group
ACAPN26-19-1
Boston, MA
Boston, MA
First Class
8 days
5+ Years Old
40 people
Dates & Prices
| Start Date | End Date | Offers | Brochure Land Price | Quote |
|---|---|---|---|---|
| Friday, May 15, 2026 | Friday, May 22, 2026 | Get Lower Price | Get Quote | |
| Friday, May 29, 2026 | Friday, Jun 05, 2026 | Get Lower Price | Get Quote | |
| Friday, Jun 12, 2026 | Friday, Jun 19, 2026 | Get Lower Price | Get Quote | |
| Friday, Jun 26, 2026 | Friday, Jul 03, 2026 | Get Lower Price | Get Quote | |
| Thursday, Jul 09, 2026 | Thursday, Jul 16, 2026 | Get Lower Price | Get Quote | |
| Friday, Sep 04, 2026 | Friday, Sep 11, 2026 | Get Lower Price | Get Quote | |
| Friday, Sep 11, 2026 | Friday, Sep 18, 2026 | Get Lower Price | Get Quote | |
| Friday, Sep 18, 2026 | Friday, Sep 25, 2026 | Get Lower Price | Get Quote | |
| Friday, Sep 25, 2026 | Friday, Oct 02, 2026 | Get Lower Price | Get Quote | |
| Friday, Oct 02, 2026 | Friday, Oct 09, 2026 | Get Lower Price | Get Quote | |
| Friday, Oct 09, 2026 | Friday, Oct 16, 2026 | Get Lower Price | Get Quote |
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Promotion Details
Offer does not apply to all vacations, contact your travel consultant for applicable vacations. There is a no-smoking policy in all shared rooms. Does not apply to additional accommodation, stopovers, airfare or flight supplements, Independent City Breaks, Israel, Jordan, Eastern Mediterranean trips with included cruises or cruise extensions. Exceptions apply.
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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.
Boston, MA Cape Cod, MA Nantucket, MA Newport, RI Sandwich, MA
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Day 1
Welcome to BostonBoston, 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.Accommodation: Hyatt Regency, Boston
Meals: Dinner -
Day 2
Exploring Plymouth's PastJoin 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.Accommodation: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast -
Day 3
The Wonders of Cape CodThe 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.Accommodation: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast Dinner -
Day 4
Nautical History in NantucketSet 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.Accommodation: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast -
Day 5
The Charms of Martha’s Vineyard – An Island EscapeBoard 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.Accommodation: Harbor View, Martha's Vineyard
Meals: Breakfast Dinner -
Day 6
The Timeless Elegance of Newport Relaxed StartArrive 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. Enjoy complimentary bike rentals or relax in the hotel’s spa, pool, or café. This evening, take a leisurely stroll through Newport’s vibrant streets, where every corner reveals another piece of its storied past.Accommodation: Viking, Newport
Meals: Breakfast -
Day 7
Newport, the Queen of Summer Resorts Relaxed StartYour 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.Accommodation: Viking, Newport
Meals: Breakfast Dinner -
Day 8
Farewell to Boston Relaxed StartAs 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
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Dining Summary
- 2 Dinner with Wine (DW)
- 7 Breakfast (B)
- 2 Dinner (D)
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 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: Visit the Plimoth Patuxet (Puh – tux- it) Museum – which is really more like a living memorial dedicated to the lifestyle of the first English settlers and the Wampanoag Indigenous community. Enjoy a guided journey to the early homesite of the Wompanoag people, a living version of the early English settlement village and a full scale replica of the Mayflower 2 – the ship that made the initial voyage in 1620. By visiting, we’re helping the museum preserve the histories and stories of the early inhabitants and the revitalization of pre-industrial crafts, trades, domestic skills, horticulture, and maritime arts.Your experience advances UN Global Goals 10 & 11: Reduced Inequalities & Sustainable Cities and Communities.
Top Rated Highlights
- Plymouth: Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Meet a direct descendant of the Mayflower party that landed on America's shores in 1620 and hear their family stories.
- Boston: Explore the great city of Boston, with your Travel Director and learn about its transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Journeying to other historically significant sights that include the Boston Common, the Old Corner Bookstore and the The Old State House.
- 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.
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Questions & Answers Ask A Question
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The trip was not exhausting and full of new things and places to explore. The tour guides presented the history of the different places and held my attention most times. It was a fun and a educational experience.
Judith Surjit, our guide, was #1, very informative, so well organized on our day to day itinerary. I would highly recommend her with Insight vacations. Her personality, knowledge of history of areas we visited was wonderful. Local guides were great also. Our driver, Greg, was great also, always felt safe with him driving, whether rain, sleet or snow. Just a great tour, learned so much about the different cultures. I hadn’t been to these countries.
Wonders of Egypt was an absolute amazing experience. Everything from the beginning to end was like clockwork. I felt safe and taken care of at all times.
Robbie Joyce was wonderful and the driver was excellent
The tour guide, Remi Gosselin, was superb and Enzo, our driver, was incredible. They were professional, knowledgeable, accommodating, and very thoughtful. For instance, when we did the gondola ride in Venice, Remi arranged for us to be serenaded. The musicians sang popular songs we recognized and it turned into a sing-along. The locals may not have enjoyed us but we had a great time. I still marvel at Enzo's driving. I would never have attempted to get a bus in some of the places he negotiated with seeming ease. And never once did he make a wrong turn.
It is my sixth trip with Insight. Need I say more?! Thank you to our Travel Consultant. I am looking forward for new opportunities.
This was my seventh Insight vacation and can’t wait to book my next one!
Insight continues to deliver high-quality services and experiences. This was our 4th tour with them, and we will definitely book our next one with them.
Insight Vacations is a reputable company with a great formula for success. This is our fifth trip with them. We know what to expect and we are always very pleased with our trips.
Insight Vacations consistently provides excellent tours, services, drivers and tour directors.
This is my 5th Insight Tour in 5 years...they are great at what they do; their staff, the tour bus and the great optional excursions. I am ready to book my tour for next year.
Insight is a wonderful company and offered an amazing experience traveling throughout Europe. We would highly recommend it!
Toured with Insight before and have never been disappointed! Understand, you are on the go and walk a lot. But, that is what we wanted and paid for!
I have been on 4 trips with Insight and will continue to use them. They are a wonderful company
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Operator: GlobusStarts
Rapid City, SDEnds
Salt Lake City, UTDays
10From
$4179
Call Us 1-800-935-2620
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Lovely trip; will use Insight again