Bespoke Cape Cod and Islands Holidays 2026 & 2027

Cape Cod View Holidays

From JFK to movie stars, Cape Cod and Martha’s Vineyard have long attracted celebrities and tourists alike to enjoy miles of beaches, idyllic islands, charming towns, delicious seafood and unforgettable whale-watching.

View Holidays

Cape Cod is a delightful summer playground for affluent New Englanders, drawn to some 40 miles of protected shoreline on the Cape Cod National Seashore. The peninsula is peppered with beautiful historic towns that combine fishing and tourism, supplying North America with clams, oysters and mussels. Cape Cod is also one of the USA’s premier destinations for whale-watching in Stellwagen Bank with large populations of humpback and finback whales.

Start with Chatham, one of the most popular destinations in the region with its whitewashed old town, lighthouses and beaches, visitors will also find maritime history at the local Old Atwood House Museum, and a haven for birdwatching at the nearby Monomoy National Wildlife Refuge.

Then head to Provincetown at the very tip of Cape Cod peninsula, with its thriving artistic community and lively downtown nightlife. The town is dominated by the impressive 75-metre granite Pilgrim Monument, and two picturesque lighthouses that look out over the Atlantic.

A New England holiday isn’t complete without a visit to the iconic island of Martha’s Vineyard. Located seven miles south of Cape Cod, it is where the movie Jaws was filmed, but fortunately real life on the island is nothing like fiction. Martha’s northern beaches are more sheltered for bathing while the southern beaches are better for surfing. The island has six towns, each with their own charms – from the lighthouses of Edgartown to the gingerbread cottages of Oak Bluffs.

Offering a slower pace than the rest of Cape Cod, and still very much worth the journey, is the island of Nantucket which boasts more than 800 pre-Civil War buildings, in addition to several art galleries and museums. Explore the island’s fascinating whaling history in the Nantucket Whaling Museum, which features a 47-foot sperm whale skeleton.

Read More

Holidays in Cape Cod and Islands

Our Private Journeys seamlessly bring together the most unmissable experiences that Cape Cod and Islands has to offer. Carefully crafted by our travel experts, these holidays distil the most iconic sights and stunning landscapes of the destination.

Portland Maine
New England Classic New England:
15 days from £4,180pp
Click me

15 days from £4,180pp

(based on two people sharing & excluding flights)

The holiday price excludes international flights. We are happy to quote flights separately based on your dates of travel and preferences.

Contact us Close
Nantuckett
New England Boston, Cape Cod and The Islands:
10 days from £4,140pp
Click me

10 days from £4,140pp

(based on two people sharing & excluding flights)

The holiday price excludes international flights. We are happy to quote flights separately based on your dates of travel and preferences.

Contact us Close
View all holidays

Things to do in Cape Cod and Islands

Explore a wide range of activities, excursions and one-of-a-kind experiences in Cape Cod and Islands, tried and tested personally by our travel experts.

Whale-watching off the coast of Boston, in the Stellwagen Banks National Marine Sanctuary
Whale-watching off Boston’s Coast
View all

Places to Stay in Cape Cod and Islands

Browse our unrivalled portfolio of accommodation in Cape Cod and Islands. Every option has been carefully chosen by our team of travel experts.

USA_Massachussets_The Coonamessett_Exterior
Cape Cod and Islands
The Coonamessett
Hotel as seen from above
Cape Cod and Islands
Nobnocket Boutique Inn
Exterior of Hotel
Cape Cod and Islands
Jared Coffin House
Resort pool
Cape Cod and Islands
InnSeason Resorts, Captain’s Quarters
View all
Grand Canyon
About Us

Brought to you by Journey Latin America, the team behind the UK's No.1 Specialist in travel to Central and South America, Journeyscape is a collection of inspiring, authentic and extraordinary journeys delivered with exceptional customer service across the USA and Canada.

Learn more
Rocky Mountaineer train in Canada
Holiday Styles

Centred around Canada and the USA's most unforgettable experiences and unique activities, our holiday styles cater to every interest.

Learn more
How we travel in North America
How we travel

Journeyscape crafts unforgettable holidays designed around your specific preferences, delivering personalised travel experiences every time.

Learn more

Inspire

Your edit for North America inspiration

Inspired by the landscapes, culture, wildlife and cuisine of Canada and the USA, explore our entertaining range of articles, travel tips, destination guides, recipes and much more.

View Extraordinary Inspiration
Whales Swimming and Jumping in Cape Cod

Wildlife and Nature

Best Whale Watching Spots in New England

Learn more
Dinner table at dusk

Destination Guides

The World’s Best Destinations for Dining at Dusk

Learn more
Perkins Cove is a small tidal harbor at the southern end of Ogunquit, connected to the Atlantic and shaped by both nature and human digging

Destination Guides

The Best Coastal Towns in New England

Learn more
Deer in National Park in Alberta Canada
Destination Guides
A Beginner’s guide to Alberta: Where to Go, What to See & Travel Tips Read more
Summer in Canmore Alberta
Destination Guides
Alberta in Summer: Must-See Landscapes and Experiences Read more
Kootenay Rockies

Meet Our Team

Real North America Travel Experts

Rob Holmes at Elvis Presley Birth Place in Tupelo
Rob Holmes - Travel Expert

Rob has been travelling to both the USA & Canada for nearly 20 years and in that time, has been lucky enough to visit 38 (and counting) of the 50 States, plus extensive travels through Canada.

Stuart
Stuart Whittington - Head of Product

Stuart is the Head of Product at Journeyscape and our sister brand, Journey Latin America. He is passionate about new adventures, venturing off the beaten path, and firmly believes that travel, when planned well, can be a force for good for all people and places involved.

Travel Expert Tom Chamberlain at Joshua Tree National Park
Tom Chamberlain - Travel Expert

Tom is a North America specialist with extensive first-hand experience across 28 states and provinces, known for his passion for the USA’s most iconic landscapes and diverse travel styles. With a personal connection to the destination and a love for exploration, he creates tailored journeys designed to deliver truly memorable experiences.

IMG-20241012-WA0011
Ben Line - Head of Sales

Ben Line is the Head of Sales at Journeyscape and our sister brand Journey Latin America, having lived abroad and travelled extensively over the years.

Dominique
Dominique Kotsias - Product Manager

Dominique caught the North America travel bug when she was in her late teens and has travelled extensively throughout the USA and Canada, particularly drawn to the countries' outstanding natural beauty and wildlife. With over 10 years of product and marketing experience in North America, Dominique’s passion for the destination is infectious.

Why Journeyscape?

We love north america

  • Up-to-the-minute knowledge underpinned by 40 years experience
  • All of our Travel Experts have personal knowledge of the destination
  • A passion for the region runs through all we do

Travel with Confidence

  • Fully bonded and licensed
  • ATOL-protected
  • Book with confidence, knowing every penny is secure
  • 24 hour help available at every step of your journey

The Real North America

  • Our insider knowledge helps you go beyond the guidebooks
  • We hand-pick hotels both for their character and services
  • We'll give you authentic experiences based on your personal preferences

Journeyscape brought to you from the award-winning experts at Journey Latin America

Explore Journey Latin America