Tour Description

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 Plymouth, a coastal town famous for its rich history as the landing site of the Pilgrims in 1620; visit the living history museum at Plimoth Patuxet. 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.

Priced From:

$ 8708pp ^*

From: 2026-05-08

To: 2026-10-09

Start Location: Boston (MA), United States Of America

End Location: Boston (MA), United States Of America

Trip Type: Eastern USA & Canada

Tour Advisors

Tiffany McCrea-Lennon

Managing Director

Russell Mein

Travel Specialist

Caitlin Lennon

Travel Coordinator

Michelle Baldwin

Travel Specialist

Gaylyn Murdoch

Administration Manager

Holly Skene

Travel Co-ordinator

Kim Thomas

Broker

Itinerary

Welcome to Boston

Day 1

Duration: 1

Accommodation: Hyatt Regency, Boston

Boston, often described as America’s most European city, is a captivating blend of history, art, and culinary delights. Upon your arrival at the Hyatt Regency, nestled in the heart of downtown, you're just moments from sights such as the historic Faneuil Hall and the fashionable Newbury Street. Take a leisurely stroll through the charming South End or along the picturesque Charles River Esplanade. This evening, meet your Travel Director and fellow guests for a delightful dinner, marking the beginning of your unforgettable journey.

Exploring Plymouth's Past

Day 2

Duration: 1

Accommodation: Dan'l Webster Inn and Spa, Sandwich

Join your Travel Director for an enriching exploration of Boston’s storied past. Walk along the famous Freedom Trail, where each step brings the American Revolution to life. Visit landmarks like Boston Common, the Old Corner Bookstore, and the Old State House. Continue your historic exploration at the Pilgrim Hall Museum in Plymouth, hosted by a Mayflower descendant, offering personal stories tied to the museum’s fascinating collection of 17th-century artefacts. At the Plimoth Patuxet Museum, immerse yourself in the stories of early English settlers and the Wampanoag Indigenous community during a MAKE TRAVEL MATTER® Experience. From the replica Mayflower II to the recreated homesites, your visit contributes to preserving this vital heritage, supporting pre-industrial crafts, trades, and maritime traditions.

The Wonders of Cape Cod

Day 3

Duration: 1

Accommodation: Dan'l Webster Inn and Spa, Sandwich

The windswept shores and pristine landscapes of Cape Cod await as you embark on a journey through the heart of New England’s maritime history. The Cape’s rolling sand dunes, historic lighthouses, and timeless fishing villages set the stage for a day rich in cultural discovery. Explore Cape Cod’s National Seashore, where the stories of the Wampanoag people and European settlers converge against a backdrop of stunning coastal beauty. Enjoy a relaxed evening in the historic charm of Sandwich.

Nautical History in Nantucket

Day 4

Duration: 1

Accommodation: Dan'l Webster Inn and Spa, Sandwich

Set sail from Hyannis to the island of Nantucket, where cobblestone streets and preserved historic homes tell the story of a bygone whaling era. Stroll through the charming downtown, learning how the rise and fall of the whaling industry shaped Nantucket’s social fabric and economy. As you uncover tales of seafaring adventures, witness the island’s transformation into a beloved destination for visitors from across the globe. After a day steeped in maritime history, return to Hyannis by ferry for an evening at leisure.

The Charms of Martha’s Vineyard – An Island Escape

Day 5

Duration: 1

Accommodation: Harbor View, Martha's Vineyard

Board a morning ferry to Martha’s Vineyard, an island known for its pristine beaches, charming harbour towns, and storied visitors, including U.S. presidents. Explore Oak Bluffs with its gingerbread cottages, visit the Flying Horses Carousel and see State Beach, made famous by the film Jaws. Discover the island’s colourful past, from whaling to modern-day tourism, as you gain insights into the history of Edgartown harbor lighthouse. Later, enjoy island hospitality with seasonal offerings from local farms, fishing boats and foragers during a dining experience at Bettini, located in your elegant hotel.

The Timeless Elegance of Newport Relaxed Start

Day 6

Duration: 1

Accommodation: Viking, Newport

Arrive in Newport, where over 95 years of hospitality and charm characterise the historic Hotel Viking. Set in the heart of this coastal city, your boutique accommodation offers luxurious rooms and stunning views. Personalise your afternoon with Insight Choice. Opt to visit the Newport Car Museum, where over 100 vehicles highlight milestones in design and performance of cars throughout the 19th and 20th century. Or explore Green Animals Topiary Garden at the Brayton House, the oldest of its kind in the United States, where sculpted shrubs have been meticulously shaped since 1872. This evening, take a leisurely stroll through Newport’s vibrant streets, where every corner reveals another piece of its storied past.

Newport, the Queen of Summer Resorts Relaxed Start

Day 7

Duration: 1

Accommodation: Viking, Newport

Your day begins with Newport’s famed Ten Mile Drive, a scenic route that hugs the coastline, showcasing public parks, historic landmarks and breathtaking ocean views. Afterwards, explore the grandeur of Newport’s "summer cottages" as you visit the Breakers, the grandest of them all. A symbol of the Vanderbilt family’s wealth and prominence, this opulent mansion offers a glimpse into the lavish lifestyle of America’s Gilded Age elite. Cap off the day with a sunset sail aboard the Adirondack II, gliding along Newport Harbour and Narragansett Bay.

Farewell to Boston Relaxed Start

Day 8

Duration: 1

As your tour comes to a close, bid farewell to your fellow travellers and transfer to Logan International Airport for your onward journey. With memories of Boston’s historic charm, the beauty of Cape Cod, and the elegance of Newport, you leave with a deeper appreciation for this unique corner of New England.

Dates & prices

Start Date: 2026-05-15

End Date: 2026-05-22

twin

Child Price: 8527

Adult Price: 9475

triple

Child Price: 7760

Adult Price: 8708

single

Child Price:

Adult Price: 12004

Start Date: 2026-05-29

End Date: 2026-06-05

twin

Child Price: 8995

Adult Price: 9995

triple

Child Price: 8113

Adult Price: 9113

single

Child Price:

Adult Price: 12905

Start Date: 2026-06-12

End Date: 2026-06-19

twin

Child Price: 8995

Adult Price: 9995

triple

Child Price: 8113

Adult Price: 9113

single

Child Price:

Adult Price: 12905

Start Date: 2026-06-26

End Date: 2026-07-03

twin

Child Price: 8815

Adult Price: 9795

triple

Child Price: 7980

Adult Price: 8960

single

Child Price:

Adult Price: 12551

Start Date: 2026-07-09

End Date: 2026-07-16

twin

Child Price: 8932

Adult Price: 9925

triple

Child Price: 8069

Adult Price: 9062

single

Child Price:

Adult Price: 12771

Start Date: 2026-09-04

End Date: 2026-09-11

twin

Child Price: 8725

Adult Price: 9695

triple

Child Price: 7909

Adult Price: 8879

single

Child Price:

Adult Price: 12387

Start Date: 2026-09-11

End Date: 2026-09-18

twin

Child Price: 8725

Adult Price: 9695

triple

Child Price: 7909

Adult Price: 8879

single

Child Price:

Adult Price: 12387

Start Date: 2026-09-18

End Date: 2026-09-25

twin

Child Price: 8725

Adult Price: 9695

triple

Child Price: 7909

Adult Price: 8879

single

Child Price:

Adult Price: 12387

Start Date: 2026-09-25

End Date: 2026-10-02

twin

Child Price: 8725

Adult Price: 9695

triple

Child Price: 7909

Adult Price: 8879

single

Child Price:

Adult Price: 12387

Start Date: 2026-10-02

End Date: 2026-10-09

twin

Child Price: 8725

Adult Price: 9695

triple

Child Price: 7909

Adult Price: 8879

single

Child Price:

Adult Price: 12387

Start Date: 2026-10-09

End Date: 2026-10-16

twin

Child Price: 8725

Adult Price: 9695

triple

Child Price: 7909

Adult Price: 8879

single

Child Price:

Adult Price: 12387

Boston, Cape Cod & The Islands – Classic Group

Tour Advisors

Itinerary

Dates & prices