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Boston, Cape Cod & The Islands - Small Group

Days
8
From
USD $5,325
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Dates & Prices

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From
Friday,
Oct 10, 2025
To
Friday,
Oct 17, 2025
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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.

Itinerary

Tour Itinerary

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 Sandwich, a coastal town famous for its glassmakers; here, visit the Sandwich Glass Museum, where you can learn tricks of the trade. 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.

Countries Visited

United States

  1. Day 1
    Boston, the Cradle of Liberty
    Welcome to Boston, described by many as the most European city in the U.S., you can expect a thriving art scene, delicious variety of seafood delicacies and plenty of charm. Arrive to the Hyatt Regency Boston, just steps from Boston's most desirable area-attractions such as the Boston Common, Faneuil Hall, and Boston's famous shopping destination, Newbury Street. A 10-to-15 minute walk will bring you to the South End, Back Bay or the Charles River Esplanade. At 18:00, join your Travel Director for a Welcome Dinner with wine and an opportunity to mingle with fellow guests.Accommodation: Hyatt Regency, Boston
    Meals:   Dinner
  2. Day 2
    Historic Boston
    Explore the city 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. See Bunker Hill Monument, Boston Common, Boston Public Garden, Trinity Church and Copley Square. Later, choose to visit the John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation's thirty-fifth president, or tour Boston's oldest and largest Museum of Fine Arts, which is home to over 500,000 works of art, making it one of the largest art collections in the Americas. The rest of the day is at leisure.Accommodation: Hyatt Regency, Boston
    Meals:   Breakfast
  3. Day 3
    Pilgrim Heritage and on to Sandwich
    This morning, discover Plymouth's history at the first Pilgrim settlement. Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Join a MAKE TRAVEL MATTER® Experience as you visit the Plimoth Patuxet museum. This living memorial is dedicated to preserving the histories of the Native and English inhabitants of this region and educating the public on early settlers and the Wampanoag People in an immersive and engaging environment. Later you'll get to know the Cape more intimately as you make your way to the coastal haven of Sandwich. This afternoon, discover the art and science of glass making at Sandwich Glass Museum where you can watch glassblowers in action and explore exhibits spanning over three centuries. Enjoy a dinner back at your hotel later this evening featuring local favorites.Accommodation: Dan'l Webster Inn and Spa, Sandwich
    Meals:   Breakfast   Dinner
  4. Day 4
    Explore Cape Cod
    Head out to Salt Pond on Cape Cod's National Seashore and learn about the natural wonder and human history represented on the Cape, from its First People and European settlement to modern lifestyles and communication technology. An optional experience on the Sand Dunes of the National Seashore may present itself later today. Roll through the Dune Shacks of Peaked Hill Bars Historic District, catching sight of Pilgrim Lake and the famed artists’ dune shacks while Local Experts share the history and ecology of these striking and inspiring dunes.Accommodation: Dan'l Webster Inn and Spa, Sandwich
    Meals:   Breakfast
  5. Day 5
    Martha's Vineyard, a Presidential Paradise
    Board a ferry this morning to Martha's Vineyard (seasonal). Home to pristine sandy beaches, outdoor attractions and heavenly harbor towns, this summer hangout is no stranger to presidential visits. The island has hosted the Clintons and the Obamas, while the former U.S. First Lady, Jacqueline Kennedy Onassis, maintained a home here. After disembarking, make your way to Oak Bluffs, 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. Get acquainted with the island, before reaching your hotel. Tonight's dinner is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.Accommodation: Harbor View Hotel Martha's Vineyard
    Meals:   Breakfast   Dinner
  6. Day 6
    Nantucket Island
    Depart Martha's Vineyard in style on a high-speed catamaran for the picturesque island of Nantucket. Not only has it retained the charm of a bygone era, it is one of the most exclusive coastal communities in the U.S. During your visit, take in the beauty of the antique cobblestone streets, lined with high- end boutiques and breathtaking architecture during a guided walking tour. The homes date back to its whaling days which also in?uenced much of the culture on the island. In the past, the style of home directly correlated to a whaler's ranking. Return to the mainland in the evening to relax at your luxurious hotel.Accommodation: Hotel Viking, Newport
    Meals:   Breakfast
  7. Day 7
    Newport, the Queen of Summer Resorts Relaxed Start
    This morning, you'll enjoy a visit to The Breakers, a Gilded Age mansion and summer residence of Cornelius Vanderbilt II. The 70-room estate is the grandest of Newport's summer cottages. Today, it is a National Historic Landmark that serves as a symbol of the Vanderbilt family's social and financial pre-eminence in the Gilded Age. This afternoon, sail around Newport Harbor aboard the Rum Runner II cruising by Newport mansions and former speakeasies, lighthouses, islands, and many other points of interest along the waterfront. Our journey through New England is almost at its end, but not before you join your fellow travelers for a Celebration Dinner at La Forge Casino Restaurant originally established in 1880.Accommodation: Hotel Viking, Newport
    Meals:   Breakfast   Dinner
  8. Day 8
    Back to Boston Relaxed Start
    It's time to say goodbye to your fellow travelers as you return to Boston. For those heading home there will be complimentary transfers to Boston Logan International Airport, arriving at 12:00. Alternatively, you may return to the Hyatt Regency Boston if you wish to extend your stay.
    Meals:   Breakfast

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Inclusions

Dining Summary

  • 4 Dinner with Wine (DW)
  • 7 Breakfast (B)

Choice Highlights

  • Boston: Step through the hallowed gates and enter Fenway Park. Home to the nine-time World Series winning Boston Red Sox since 1912, Fenway is the oldest baseball stadium in America. Enjoy an in depth one-hour guided tour of the legendary sports history that has taken place here, with a chance to visit the press box, view memorabilia, and sit in the fabled ‘Green Monster’ overlooking left field. You will be sure to feel the electric energy of the stadium that represents America’s favorite pastime.
  • Boston: Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.

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

  • Boston: Step through the hallowed gates and enter Fenway Park. Home to the nine-time World Series winning Boston Red Sox since 1912, Fenway is the oldest baseball stadium in America. Enjoy an in depth one-hour guided tour of the legendary sports history that has taken place here, with a chance to visit the press box, view memorabilia, and sit in the fabled ‘Green Monster’ overlooking left field. You will be sure to feel the electric energy of the stadium that represents America’s favorite pastime.
  • Boston: Visit the Museum of Fine Arts, renowned for its Impressionist paintings, Asian and Egyptian collections and early American art.

Insight Experiences

  • Newport: 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.

Top Rated Highlights

  • 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 Bunker Hill Monument in Charlestown. View the colorful neighborhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy.
  • 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.
  • Sandwich: View through the lens of the skilled craftsmen at the Sandwich Glass Museum, where you will learn the techniques of the English and Irish glass-makers developed during the early 19th century.
  • 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.
  • 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.
  • 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.

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Questions & Answers

Question: How many suitcases can I take with me on my trip?

Each person is allowed one "check-in," and one "carry-on." Remember to take all valuables with you as "carry-on", because electronic equipment, cameras, laptops, jewelry, business documents and money are not covered by the airlines' liability, so always carry them aboard with you.

Question: Is Airfare Included in the Price?

Airfare from your point of origin to and from the trip is not included in the land price.

Insight Vacations Tours Customer Reviews

Overall Rating
4.1
Accommodations
3.9
Itinerary
4.3
Professional Staff
4.5
Repeat with Operator
4.1
Value for Money
3.9

Ratings based off 2313 reviews about Insight Vacations Tours - currently showing 15 reviews with comments only

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!

This was a perfect vacation!! We loved being on a boat and having one room to return to each night no packing and unpacking or hauling belongings from place to place. We were surprised how roomy and very comfortable our room on board was. Even the bathroom gave us plenty of room to move around in. And the boat itself was spacious, clean, and laid out with lots of thought put into the needs of guests. The staff onboard was phenomenal. They went above and beyond, always smiling, helpful, and spoiling us. Everything was clean, the food excellent and plentiful, and planned stops included keeping passengers safe at all times. I would highly recommend this trip to anyone who wants to relax and enjoy the Adriatic! Thank you Affordable Tours.

I have been on 4 trips with Insight and will continue to use them. They are a wonderful company

This was our 2nd tour with Insight Vacations and it was a wonderful experience. Michael, our tour director, was excellent!

The Tour Director and Driver were excellent! Very enjoyable.

Insight took care of everything! Great hotels and excursions!

Insight not only provides an educational and cultural experience, but they also lessen the stress that can come with traveling as they provide airport pick ups and drop offs, and just tell us when to have our luggage outside our hotel door. We would definitely travel with Insight again.

Got my money's worth! This was a fabulous trip! American the Beautiful has a deeper meaning after seeing unimaginable beauty every mile of the way. The Tour Guide and Wellness Coordinator were fabulous, and you just can't find a better bus driver. The extra legroom available on Insight Tours makes all the difference when you are on a bus for 10 glorious days.

This trip was one of my best. The itinerary was just right. Everything went to perfection

This was my third trip with Insight Tours. It was a very good tour. I chose Insight because of their itinerary for this particular tour.

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