Boston, Cape Cod & The Islands - Small Group

Boston, Cape Cod & The Islands - Small Group

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8 Days From

$5253

$4774

Boston, Cape Cod & The Islands - Small Group

8 Days Starting and ending in Boston, USA

Visiting: Boston, Plymouth, Cape Cod, Martha's Vineyard, Nantucket Island, Newport

Tour operator:

Insight Vacations

Tour code:

SACAPZN20

Specialist Group:

Family/Kids

Guide Type:

Fully Guided

Group size:

12 - 24

Physical rating:

Low

Age range:

5-99

Special diets catered:

Vegetarians

Tour operated in:

English

Trip Styles:

Sailing, Small Group

Activities:

Sightseeing

From: $5253 $4774 Operator discount: -$479

NB: Prices correct on 16-Sep-2024 but subject to change.

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

Tour Overview

Embark on an unforgettable journey through Boston, Cape Cod, and the Islands with this small group tour. Begin in historic Boston, exploring iconic sites like Fenway Park and the Freedom Trail. Discover the Pilgrim heritage in Plymouth and the charming coastal town of Sandwich. Experience the natural beauty and rich history of Cape Cod, including an optional sand dune adventure. Sail to Martha's Vineyard, known for its picturesque cottages and presidential visits, and enjoy a Sea-to-Table Highlight Dinner. Visit the exclusive Nantucket Island and the elegant town of Newport, with its Gilded Age mansions and scenic schooner cruise. Conclude your adventure back in Boston, with options to extend your stay or continue on a Canada & New England Discovery cruise.

Highlights

  • Step through the hallowed gates and enter Fenway Park, the oldest baseball stadium in America.

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

  • Explore the great city of Boston, following part of the red-brick Freedom Trail and visiting historically significant sights.

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

  • Experience the techniques of the English and Irish glassmakers at the Sandwich Glass Museum.

  • Board a ferry to Martha's Vineyard and visit Oak Bluffs, known for its rainbow-colored, gingerbread-like cottages.

  • Jump onboard the Adirondack II, an 80-foot schooner, and cruise around Newport's coastline, learning about the region's exciting history.

  • Visit the Breakers, the grandest of Newport's summer cottages and former home of the Vanderbilt family.

Itinerary

Expand All

Day 1: Boston, The Cradle Of Liberty

Location: Boston

Accommodation Name: Hyatt Regency Boston

Meals Included: Dinner

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 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: Plymouth

Accommodation Name: Inn in Sandwich

Meals Included: Breakfast, Dinner

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: Cape Cod

Accommodation Name: Inn in 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: Martha's Vineyard

Accommodation Name: Hotel in 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: Nantucket Island

Accommodation Name: Hotel in Martha's Vineyard

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 Name: Boutique hotel in Newport

Meals Included: Breakfast, Dinner

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

Accommodation Name: Hyatt Regency 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

  • Meals

    The tour includes 3 dinners with wine, 1 dinner, and 7 breakfasts.

  • Guided Tours

    Enjoy guided tours of Fenway Park, the John F. Kennedy Presidential Library and Museum, and the Pilgrim Hall Museum.

  • Welcome Dinner

    Join your Travel Director for a Welcome Dinner with wine on the first day.

  • Sea-to-Table Highlight Dinner

    Experience a Sea-to-Table Highlight Dinner at Menemsha Room with fresh offerings from local farms, fishing boats, foragers, and markets.

  • Celebration Dinner

    Enjoy a seafood Celebration Dinner with wine in Newport.

  • Accommodation

    Stay at the Hyatt Regency Boston and other luxurious hotels throughout the tour.

  • Transportation

    Board a ferry to Martha's Vineyard and a high-speed catamaran to Nantucket Island.

  • Cruise

    Cruise around the coastline on the Adirondack II schooner in Newport.

  • Transfers

    Complimentary transfers to Boston Logan International Airport on the last day.

What's Not Included

  • Optional Activities

    Optional experiences such as the Sand Dunes of the National Seashore are not included.

  • Personal Expenses

    Personal expenses such as souvenirs, additional meals, and drinks are not included.

  • Travel Insurance

    Travel insurance is not included and should be purchased separately.

  • Gratuities

    Gratuities for guides, drivers, and hotel staff are not included.

  • Flights

    International and domestic flights to and from Boston are not included.

Mode of Transport

Travel in style with a mix of guided tours, ferry rides to Martha's Vineyard and Nantucket, and a high-speed catamaran. Enjoy a scenic cruise on the Adirondack II schooner in Newport and comfortable coach transfers throughout the tour.

Accommodation

Stay at the Hyatt Regency Boston, conveniently located near Boston's top attractions, and enjoy charming inns and luxurious hotels in Sandwich, Martha's Vineyard, and Newport, each offering unique local experiences and comfort.

Check out our Q&As

  • What kind of activities can I choose from in Boston?

    In Boston, you can choose between visiting Fenway Park, America's oldest baseball stadium and home of the Boston Red Sox, or touring The John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation's thirty-fifth president.

  • What unique experience is offered in Plymouth?

    In Plymouth, you will visit the Pilgrim Hall Museum, the oldest continuously operating public museum in the country, and the Plimoth Patuxet Museum, which is dedicated to preserving the histories of the Native and English inhabitants of the region. You will also meet a direct descendant of the Mayflower party and hear their family stories.

  • What can I expect during the visit to Martha's Vineyard?

    During your visit to Martha's Vineyard, you will board a ferry to the island, explore the port neighborhood of Oak Bluffs known for its rainbow-colored, gingerbread-like cottages, and see the oldest operating platform carousel in America. In the evening, you will enjoy a Sea-to-Table Highlight Dinner at Menemsha Room with fresh offerings from local farms, fishing boats, foragers, and markets.

  • What is special about the visit to Newport?

    In Newport, you will visit the Breakers, the grandest of Newport's summer cottages and a symbol of the Vanderbilt family's social and financial pre-eminence. You will also sail on the Adirondack II, an 80-foot schooner, and cruise around the coastline, passing nearby islands, historical buildings, and homes of the rich and famous while learning about the region's exciting history, including its pirate activity. In the evening, you will enjoy a Celebration Dinner at La Forge Casino restaurant.

  • What historical insights will I gain from the tour in Boston?

    In Boston, you will follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. You will visit sights such as Boston Common, the Old Corner Bookstore, and the Bunker Hill Monument in Charlestown. You will also explore the colorful neighborhoods of Back Bay and the historic North End, known as Boston's Little Italy.

  • What is the significance of the Sandwich Glass Museum?

    At the Sandwich Glass Museum, you will learn about the techniques of English and Irish glassmakers developed during the early 19th century. The museum showcases the skilled craftsmanship and history of glassmaking in the region.

  • What can I expect from the Nantucket Island visit?

    On Nantucket Island, you will experience the charm of a bygone era with antique cobblestone streets, high-end boutiques, and breathtaking architecture. The island is known for its simple homes dating back to its whaling days, which influenced much of the local culture. You will return to the mainland in the late afternoon to relax at your luxurious hotel.

  • 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?

    Yes

  • 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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Oct 10, 2025 - Oct 17, 2025
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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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