Boston Cape Cod and The Islands

8 Days
From $3,834 Was $4,260
Best Rate
Guarantee
Trip Type
Group Tour
Activity Level
Easy

Rating


(20 reviews)

Experience Overview

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.

Highlights

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.Your experience advances UN Global Goals 10 & 11: Reduced Inequalities & Sustainable Cities and Communities.

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.

Trip Details

Product CodeProduct Code: 1447

Tour TypeTour Type: Group Tour

AccommodationAccommodation: Deluxe

TransportTransport: Private

Guide LanguageGuide Language: English

Travel StylesTravel Styles: Family, 55+, Luxury

Supplier CodeSupplier Code: 19.1097A

StartStarts: Boston (MA), United States Of America

FinishFinishes: Boston (MA), United States Of America

DurationDuration: 8 days

DeparturesDepartures: Not Guaranteed

Physical RatingPhysical rating: Easy

Includes

Price

Price per person: (Double Occupancy) $3,834 ($479 /day)

Itinerary

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 with Wine

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, with Insight Choice 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 with Wine

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, Martha's Vineyard
Meals: Breakfast, Dinner with Wine

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 influenced 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: 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: Viking, Newport
Meals: Breakfast, Dinner with Wine

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

Tour Operator

Insight Vacations (US)

As a global leader in premium escorted travel, Insight Vacations® has been crafting magical journeys for 40 years that embody The Art of Traveling in Style. Through meticulous planning, detailed preparation and boundless passion, Insight’s collection of award-winning itineraries showcases the most outstanding destinations in Europe and North America. Guided by a highly-skilled Travel Director, guests can look forward to traveling in smaller groups, savoring authentic dining and enjoying a range of immersive Insight Experiences.

In Business Since 1978

Reviews

 

George T Byers   -  Traveled, July 2024

Hotel in Sandwich was poor and not up to standards. VERY DISSAPOINTED in not getting to Nantucket, The day was a looser. Not your fault but we all should get a refund. I certainly expect one. The driver and guide were good . Some hotels are not up to standards ie Sandwich Very disappointed Ferry was down and did not get to Nantucket . The day was a disaster even though they tried. I am due a refund because the tour was one day less than indicated. Not your fault but we suffered and your costs were less Also suggest 2 nights on Martha's Vineyard. The tour of Boston Harbour should be dropped

Source: Tour operator   Submitted: 07/15/2024

 

Christopher Mcdermott   -  Traveled, July 2024

Terrible. Left on our own way to often and tour director was not very knowledgeable of the area.

Source: Tour operator   Submitted: 07/10/2024

 

Anonymous   -  Traveled, July 2024

Great itinerary. Good choice of hotels except the hotel in Sandwich . Very old , and smelly. Very poor service . Also you should improve the breakfast menu . More variety and we didn’t even have bread in one of the hotels. It was not up to the insight vacation standards. Very disappointed.

Source: Tour operator   Submitted: 07/10/2024

 

Anonymous   -  Traveled, July 2024

I have had excellent experiences in the past with the exception of this last tour. lot of repetition. Would like to have seen the aquatic research center in Woods Hole. Have more access to to beaches.

Source: Tour operator   Submitted: 07/10/2024

 

Donald Puliz   -  Traveled, July 2024

This trip was overpriced by far. Some marginal hotels and dinners. Several travelers voiced concerns about the fast pace of walking tours. Me included. Maybe removing a little from the itinerary to slow down the pace. Maybe viewing one lighthouse is enough. Museums aren't a favorite for me. Loved seeing the camp cottages, loved the boat ride, the glass blowing, the Vanderbilt "cottage". The breakfast and dinners were all very well done. (even the one who had the fire stepped up quite well, Bless their hearts.) Accommodations were very nice. Manuel did a wonderful job (even handling the mishaps of the week). Loved his music and trivia. Erwin was superb, I felt very safe with him at the wheel. Our "coach" was wonderful. Thanks for the experience. One of the few areas I've never visited and have always wanted to. I would recommend Insight for certain.

Source: Tour operator   Submitted: 07/10/2024

 

Anonymous   -  Traveled, July 2024

Well organised and flowed well. All the places we visited were interesting though we didn’t like Provincetown and could have had less time there. The organised tours and docents were very good On a tour it’s always limited in time spent at various places but on the whole the timings were good.

Source: Tour operator   Submitted: 07/10/2024

 

Anonymous   -  Traveled, July 2024

Itinerary was educational, fun and satisfying The hotels, meals and sights were above average

Source: Tour operator   Submitted: 07/10/2024

 

Anonymous   -  Traveled, June 2024

It was more or less what I expected. I didn't like the way the Tour Director and Coach driver praised each other to encourage us to give large tip. Present itinerary too long, for example, on one day there was more travel time than actual time spent at destination. Would have liked more time in Boston.

Source: Tour operator   Submitted: 06/10/2024

 

Anonymous   -  Traveled, June 2024

The service was excellent. Our tour director, Scott Smiley, was absolutely wonderful. We have been on many tours over the years & Smiley is leaps & bounds over all tour directors. He is knowledgeable, humorous, extremely organized & detailed & a friendly warm person. He and Arden, our Coach Driver make a great team. Together, they made the tour excellent. The itinerary was good overall, however I think the trip to Martha’s Vineyard should be altered. It should be a 2 night stay or eliminated entirely. Our time there was so short, we basically just went there for dinner & sleep, then left early the next morning.

Source: Tour operator   Submitted: 06/10/2024

 

Samson Aristotel Usagani   -  Traveled, July 2024

Insight tours offer a hassle-free travel experience, taking care of planning and booking in advance. To ensure a smooth tour for everyone, it's important to be punctual. If you're short on time or resources for trip planning, Insight Vacations is a great option. It also eliminates decision-making conflicts with travel companions, allowing everyone to simply relax and enjoy the journey. It offers a lot of history on the process of how America became a great nation. It is suitable for tourists of all ages.

Source: Tour operator   Submitted: 07/10/2024

 

Michael Waldo   -  Traveled, July 2024

I thought the Tour Director’s pace was good. We saw a lot during the week. The Tour Director tried to be sensitive to those with mobility issues without holding others back. He and the driver showed grace under pressure as they navigated curve balls throughout the week such as difficult Boston traffic due to the Celtics parade on 6/21, a hotel kitchen fire that made meals in Sandwich challenging as well as accommodating guests who required/demanded more of the director's attention. I saw some of the other negative comments on this specific week. While everyone is entitled to their opinion, shaped by their own experiences of the week, it is obvious to me that group tours are not for everyone. Some people just do not play well with others and folks should be honest with themselves before booking such a trip. People need to be cognizant that there are other travelers in the group and not monopolize the time of the Director. The itinerary is set for a reason - it is not a jumping off point to start negotiations with the director and driver. When things go wrong as they sometimes will, show some grace. If you have issues, keep your comments to yourself and do not vent to other travelers who you met 10 minutes ago who are just trying to have a good time. I’ve done Trafalgar and Contiki in the past. This was my first Insight tour. I would definitely do Insight again. Great itinerary. Covered everything I wanted. Enough time in Boston with an option to add time at the beginning and end of my trip which I did. This trip also included the Breakers in Newport which was a bucket list item for me. Plenty of time on my own which I value.

Source: Tour operator   Submitted: 07/10/2024

 

Anonymous   -  Traveled, July 2024

The scenery was great as well as all the tours we took. Weather really worked out for us with mid 80's and lows in the high 60's. Didn't get any rain except for the first day when we arrived. The problems we had were with one of our hotels that had a fire 3 days prior to our arrival in their kitchen. It smelled like smoke everywhere and everything had to be catered in with all plastic utensils, plates and glasses. When we got our food, the steak was cold and a very small salad. Didn't seem like the tour guide didn't know some of the key information from some of the areas we visited. Even some of the local tour guides were reading information from index cards. We spent a lot of money for this trip and didn't seem to measure up to that.

Source: Tour operator   Submitted: 07/10/2024

 

David Coad   -  Traveled, July 2024

Knowledgeable and helpful staff with a good knowledge of the area. Some guests tend to monopolise their time. Fascinating history and good mix of indigenous and early European settlement. The day to day itinerary would be improved by tweeking the islands visit to make better use of time. Otherwise a well put together tour

Source: Tour operator   Submitted: 07/10/2024

 

Anonymous   -  Traveled, June 2024

Service was excellent Thoroughly enjoyed.. even though it was raining..!! There was a rather circuitous route to get there.. (due to off season) but interesting none the less

Source: Tour operator   Submitted: 06/10/2024

 

Anonymous   -  Traveled, June 2024

This tour gives so much knowledge and land coverage for the Cape Cod area

Source: Tour operator   Submitted: 06/10/2024

 

Anonymous   -  Traveled, June 2024

The service on our tour was outstanding! Our tour director, Scott Smiley was amazing. His attention to detail, organization, knowledge, humor & warmth are beyond excellent. We have been on many Insight & Trafalgar tours (as well as others over the years) and have never encountered a Tour Director of Smiley’s caliber. He has definitely set the “bar” very high. Our Coach Driver, Andre, was also wonderful . He was an excellent driver of course, which is pretty much the norm we have come to expect. However, Andre was also humorous & knowledgeable. He shared details & stories about the places & sites, and was friendly & pleasant to be with. He & Smiley make an outstanding team. R It was a very nice itinerary, however, I would suggest Martha’s Vineyard be a two night stay, or skip it entirely. We weren’t even there for 24 hours. it seemed as if we just went there for dinner & to sleep.

Source: Tour operator   Submitted: 06/10/2024

 

Richard Tenbarge   -  Traveled, May 2024

Best to go when not prime tourist season we went early in May and was best time to go

Source: Tour operator   Submitted: 05/10/2024

 

Anonymous   -  Traveled, May 2024

The travel director and driver were both well prepared for anything and could entertain us constantly. It was nice to have three 2-night stays at hotels. This is very relaxing.

Source: Tour operator   Submitted: 05/10/2024

 

Anonymous   -  Traveled, May 2024

vary good carefully arranged excellent communication . all information given was clear understandable and very useful . Very pleased with how all arrangements carried out hotels good, timing excellent. pleased that not every day up early to get going. Good selection of activities for those who were more able to get around or those persons less mobile could stay in one location . Good idea to move people about on seat location on coach. You mix people up and so get to know each other more, swap holiday location stories, and share details of home location some from outside USA . Pleased to find you use different types of transport . All hotels very good. some variation in breakfasts were better than others, those who had main evening meals were excellent.

Source: Tour operator   Submitted: 05/10/2024

 

Mark Lemenager   -  Traveled, May 2024

They took care of everything. Had a wonderful time on this tour. Lots of great scenery and interesting places to visit. Only negative was the Nantucket day. 10 hours travel for 2 hours on the island. Great group of travelers and outstanding tour director and driver.

Source: Tour operator   Submitted: 05/10/2024

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