Boston, Cape Cod & The Islands - Small Group

Boston, Cape Cod & The Islands - Small Group

8 Days



Boston, Cape Cod & The Islands - Small Group

8 Days Starting and ending in Boston (MA)

Visiting: Boston, Plymouth, Sandwich, Cape Cod National Seashore, Martha's Vineyard, Nantucket, Newport

Tour operator:

Insight Vacations

Tour code:



Cultural, History

$4024 (USD) Operator discount: $1057 The Big ADVENTURE Sale: $114 -23%

This tour is no longer available, please see similar tours below or send an enquiry

Tour 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.


  • 3 Dinner with Wine (DW)

  • 7 Breakfast (B)

  • 1 Dinner (D)

  • 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.

  • : The John F. Kennedy Presidential Library and Museum dedicated to the memory of thenation's thirty-fifth president.

  • Choose between two carefully selected activities

  • Newport: Choose to visit the Breakers, the grandest of Newport's summer cottages and former home of the Vanderbilt family. Alternatively, choose to visit the Elms and its mid-18th century French inspired interior. Another option is to visit the Tennis Hall of Fame.

  • Boston: At 18:00, join your Travel Director for a Welcome Dinner with wine and an opportunity to mingle with fellow guests.

  • Martha's Vineyard: Tonight's Sea-to-Table Highlight Dinner at Menemsha Room is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.

  • Newport: Meet your new friends in the evening for a seafood Celebration Dinner with wine, where you can share the highlights of your trip while savouring a freshly prepared meal.

Show all


Expand All
Day 1: Boston, The Cradle Of Liberty
Location: Boston
Accommodation: Hyatt Regency Boston
Meals Included: Dinner with Wine

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.

Day 2: Historic Boston Relaxed Start
Location: Boston
Accommodation: Hyatt Regency Boston
Meals Included: Breakfast

Explore the city with your Travel Director and learn about the city's transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Sights include Boston Common, the Old Corner Bookstore and the Bunker Hill Monument in Charlestown. View the colourful neighbourhoods of Back Bay and historic North End, otherwise known as Boston’s Little Italy. Make sure you try the neighbourhood's famous cannoli and grab yourself some of the best espresso in town. Later, choose to visit Fenway Park, America's oldest baseball stadium and home of the Boston red Sox or tour The John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation's thirty-fifth president. The rest of the day is free to pursue your own interests.

Day 3: Pilgrim Heritage And On To Sandwich
Location: Boston, Plymouth, Sandwich
Accommodation: Dan'l Webster Inn and Spa Sandwich
Meals Included: Breakfast, Dinner, with Wine

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. Experience the techniques of the English and Irish glassmakers at the Sandwich Glass Museum. Relax at your charming inn tonight and indulge in a Dinner with wine.

Day 4: Sandwich, Oldest Town On The Cape
Location: Sandwich, Cape Cod National Seashore
Accommodation: Dan'l Webster Inn and Spa, Sandwich
Meals Included: Breakfast

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.

Day 5: Martha's Vineyard, A Presidential Paradise
Location: Sandwich, Martha's Vineyard
Accommodation: Harbor View Hotel, Martha's Vineyard
Meals Included: Breakfast, Dinner

Board a ferry this morning to Martha's Vineyard. Home to pristine sandy beaches, outdoor attractions and heavenly harbour 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-coloured, 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 Sea-to-Table Highlight Dinner at Menemsha Room is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.

Day 6: Nantucket Island
Location: Martha's Vineyard, Nantucket
Accommodation: Hotel Viking Newport
Meals Included: Breakfast

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. The simple 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 late afternoon to relax at your luxurious hotel.

Day 7: Newport, The Queen Of Summer Resorts Relaxed Start
Location: Newport
Accommodation: Hotel Viking Newport
Meals Included: Breakfast, Dinner with Wine

The elegant town of Newport is lined with the Gilded Age mansions of America's wealthiest families. Visit the Breakers, the grandest of Newport's summer cottages and a symbol of the Vanderbilt family's social and financial pre-eminence during the late 19th century. The seaside city is also famous for being the home of the America's Cup for more than 50 years and is known as the Sailing Capital of the World. Explore in nautical style onboard the Adirondack II, an 80-foot (24 metre) schooner, as you cruise around the coastline. You’ll sail out and pass some of the 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. In the evening, enjoy a Celebration Dinner at La Forge Casino restaurant, known for local fare, fresh seafood and many New England favourites. Afterwards you'll head back to your boutique hotel, registered with the Historic Hotels of America.

Day 8: Back To Boston Relaxed Start
Location: Boston
Meals Included: Breakfast

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. For those embarking on the Canada & New England Discovery cruise, you'll stay in Boston and transfer on your own to the port the following morning to board the MS Zaandam.

Check out our Q&As

  • Can I join the tour once it has departed?

    We regret that no refunds can be made for absences from a tour, including experiences such as missed meals or sightseeing.

  • How long has the tour company been trading?

    Since 1978.

  • What Ethical Travel credentials does the tour company have?

    Insight Vacations is a founding member of the TreadRight Foundation, a joint initiative created by the brands within The Travel Corporation (TTC) almost 15 years ago to ensure our impact through tourism is positive. Our ethos to #MakeTravelMatter guides our decision-making at every level of our business.

  • Will the accommodation included meet local health and safety regulations?


  • Do you operate a “single share” option and how does it work?

    You have two options as a solo traveller. Either choose to be matched with a same sex partner for a room share - at no extra cost. Or choose a room of your own with a reduced or even free private room upgrade on select tours.

  • What policies are in place for Covid-19?

    Please contact us for latest COVID-19 policies

Reviews of this Operator

Peggy Lindenborn  

Country Roads of Southern Italy and Sicily


Country Roads of Southern Italy and Sicily is a delightful trip and our travel guides and driver, Enzo, Chris and Greg were amazing and made the trip very memorable. We saw so many places and had great experiences along the way! Thanks to them for such a wonderful vacation.!

Feefo Trusted Reviews
Trusted Customer  

Best of Spain & Portugal


Great itinerary, good pace, tour director was friendly and very knowledgeable and organised. Bus was very spacious and driver was great. Yes would recommend insight to friends and families

Feefo Trusted Reviews
Jacqueline Thornberry  

Scenic Iceland and the Northern Lights


The number is our group was small which meant we got to know each other. Our tour guide, Laura Spiers, was excellent as was our driver. The food was good, and of course everything we saw in Iceland was beautiful and educational.

Feefo Trusted Reviews
Kathryn Ronca  

Enchanting Canyonlands


The trip was fantastic. Everything was well planned and exceeded my expectations. All insight personal were courteous helpful and professional Ann Manual and Kevin were a topnotch team There was attention to every detail and at all times felt safe and always a personal touch to the trip. The motor coach was clean and roomy and there was multiple wipe downs during the day All hotels were top notch and all staff at the hotels and restaurants were helpful and courteous I would recommend this trip as it gave you a fantastic view of the natural wonders of the the West.

Feefo Trusted Reviews
Patrick Ong  

Italian Intermezzo


This trip is absolutely amazing! Worth every Penny! Our Tour guide did not Disappoint.

Feefo Trusted Reviews

Dates & Availability

tourhub Discount Available - Sign In

Instant Booking Available

Friday - Friday

Oct 04, 2024 - Oct 11, 2024
$5195 $4024 (USD)

Operator discount: $1057 (USD)

The Big ADVENTURE Sale: $114 (USD)

Instant Booking Available

Friday - Friday

Oct 10, 2025 - Oct 17, 2025
$4963 $4827 (USD)

The Big ADVENTURE Sale: $136 (USD)

Book with Confidence

  • Low Deposit

    Insight Vacations requires a minimum deposit of 350 USD per person or the full booking value, whichever is less, with the final balance not due until 90 days before departure.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of insight vacations charges.

    Up to 91 days before tour starts: Forfeit 100% of deposit.

    At 90 days before tour starts: Forfeit 50% of booking price.

    At 29 days before tour starts: Forfeit 80% of booking price.

    At 1 days before tour starts: Forfeit 100% of booking price.

Why book with tourhub?

Safe & Secure

Your money is protected in an external trust until you travel.

pts logo

100% Guaranteed Refunds if your trip is cancelled.

The safest way to make overseas, multi-currency payments.

Guaranteed Best Value

Industry leading discounts, we won't be beaten on price.

No cancellation or amendment fees from tourhub.

(Operator terms may apply)

Expert Knowledge

Reliable & unbiased advice from travel experts.

Direct contact with the tour operator via our messaging service.

Inspiration & advice from a community of 6000+ real travellers, influencers & content creators.

Trusted Service

Official partners & licensed agents of 1000+ tour operators worldwide.

Don't just take our word for it...

"Tourhub: Friendliness, Professionalism & Integrity I would happily give tourhub a 6* review if I could..."

Similar Tours

Travel Guru Features

Our Reviews