Boston, Cape Cod & The Islands - Small Group

Boston, Cape Cod & The Islands - Small Group

8 Days From



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:


Specialist Group:


Guide Type:

Fully Guided

Group size:

12 - 24

Physical rating:


Age range:


Special diets catered:


Tour operated in:



Cultural, History

From: $5253 $4624 Operator discount: -$479 Mid-Year Mayhem Discount: -$150 -12%

NB: Prices correct on 15-Jul-2024 but subject to change.

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.


  • Boston: Explore Fenway Park, the oldest baseball stadium in America, with an in-depth guided tour including the press box and the 'Green Monster' seats.

  • Choose to visit the John F. Kennedy Presidential Library and Museum in Boston or explore Newport's grand mansions like the Breakers or the Elms, or the Tennis Hall of Fame.

  • Enjoy a Sea-to-Table Highlight Dinner at Martha's Vineyard, featuring the season's freshest offerings from local farms and fishing boats.

  • Sail around Newport's coastline on the Adirondack II, an 80-foot schooner, learning about the region's history and viewing homes of the rich and famous.

  • Visit Pilgrim Hall Museum in Plymouth, the oldest continuously operating public museum in the country, and hear stories from a direct descendant of the Mayflower party.

  • Explore the living history museum of Plimoth Patuxet in Plymouth, dedicated to the Pilgrim Fathers and their interactions with the Wampanoag People.

  • Discover the Sandwich Glass Museum in Sandwich, learning about the glass-making techniques developed in the early 19th century.

  • Experience the natural wonder and human history of Cape Cod's National Seashore, including a visit to the port neighborhood of Oak Bluffs on Martha's Vineyard, known for its gingerbread-like cottages and the oldest operating platform carousel in America.


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Day 1: Boston, The Cradle Of Liberty

Location: Boston

Accommodation: Hyatt Regency Boston

Accommodation Name: 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

Location: Boston

Accommodation: Hyatt Regency Boston

Accommodation Name: 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

Accommodation Name: Dan'l Webster Inn and Spa

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

Accommodation Name: Dan'l Webster Inn and Spa

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

Accommodation Name: Harbor View Hotel

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

Accommodation Name: 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

Location: Newport

Accommodation: Hotel Viking Newport

Accommodation Name: 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

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.

What's Included

  • Welcome Dinner with Wine in Boston

    Kick off your journey with a special dinner accompanied by wine, allowing you to meet your fellow travelers.

  • Guided Tours

    Enjoy guided tours of historic and cultural sites, including Fenway Park, Pilgrim Hall Museum, and the Freedom Trail in Boston.

  • Exclusive Experiences

    Participate in unique experiences such as a visit to the Sandwich Glass Museum, a sail on the Adirondack II schooner, and a Sea-to-Table Highlight Dinner at Martha's Vineyard.

  • Hotel Accommodations

    Stay in comfortable and well-located hotels throughout your journey, including the Hyatt Regency Boston and the Harbor View Hotel on Martha's Vineyard.

  • Meals

    Enjoy 7 breakfasts, 3 dinners with wine, and 1 dinner, providing a taste of the local cuisine.

  • Transportation

    Travel comfortably with all transportation provided during the tour, including ferry rides to Martha's Vineyard and Nantucket.

  • Expert Travel Director

    Benefit from the knowledge and insights of an expert Travel Director who will accompany you throughout your journey.

What's Not Included

  • Travel Insurance

    Travel insurance is not included and is recommended for all travelers.

  • Some Meals

    Not all meals are covered.

    Guests are responsible for some lunches and dinners throughout the tour.

  • Optional Experiences

    Some experiences and excursions may require an additional fee and are not included in the tour package.

  • Personal Expenses

    Items of a personal nature, including souvenirs, laundry, and tips, are not included.

  • Airport Transfers

    Airport transfers at the beginning and end of the tour are not included, except for guests on the final day returning to Boston Logan International Airport.

Check out our Q&As

  • How many meals are included in the tour?

    The tour includes 3 Dinners with Wine, 1 Dinner, and 7 Breakfasts.

  • What are the highlights of the Boston, Cape Cod & The Islands tour?

    The highlights of the tour include a guided tour of Fenway Park, the choice between visiting the John F. Kennedy Presidential Library and Museum or other selected activities, a visit to the Breakers or the Elms in Newport, a Welcome Dinner in Boston, a Sea-to-Table Highlight Dinner at Menemsha Room in Martha's Vineyard, a seafood Celebration Dinner in Newport, a cruise on the Adirondack II schooner, visits to Pilgrim Hall Museum and Plimoth Patuxet Musem in Plymouth, exploring Boston with a Travel Director, learning glass-making techniques at the Sandwich Glass Museum, experiencing Cape Cod's National Seashore, and visiting the gingerbread-like cottages in Oak Bluffs on Martha's Vineyard.

  • What type of activities are included in the tour?

    Activities included in the tour are guided tours of historical sites like Fenway Park and Pilgrim Hall Museum, a choice between visiting the John F. Kennedy Presidential Library and Museum or other selected activities, a cruise on the Adirondack II schooner, exploring Cape Cod's National Seashore, and experiencing glass-making at the Sandwich Glass Museum.

  • What is the starting and ending location of the tour?

    The tour starts and ends in Boston (MA).

  • What are the accommodation options during the tour?

    Accommodation options during the tour include the Hyatt Regency Boston, Dan'l Webster Inn and Spa in Sandwich, Harbor View Hotel on Martha's Vineyard, and Hotel Viking Newport.

  • What is the pick-up and drop-off time for the tour?

    The pick-up time for the tour is at 18:00, and the drop-off time is at 12:00.

  • 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

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Friday - Friday

Oct 10, 2025 - Oct 17, 2025
$5253 $4624

Operator discount: -$479

Mid-Year Mayhem Discount: -$150

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May 08, 2026 - May 15, 2026
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Mid-Year Mayhem Discount: -$152

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Aug 21, 2026 - Aug 28, 2026
$4815 $4663

Mid-Year Mayhem Discount: -$152

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.

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