See Massachusetts’s main highlights while learning about its whale-related history. Travel inland to the beautiful Berkshires where Moby Dick author Herman Melville lived, and learn about the legacy of the rightly abandoned whaling industry. You can spot whales on boat trips, and maybe even from the shore.

Self-drive
9 nights
Boston, Falmouth, Stockbridge, Gloucester
Self-Drive

Itinerary overview

Boston

Freedom city

Soak up the city’s heritage and sights on the famous Freedom Trail.

Falmouth

To the Cape

Relax in one of Cape Cod’s best seaside towns.

Stockbridge

The Berkshires

See picturesque backdrops in this small town in the Berkshires.

Gloucester

Maritime heritage

See lighthouses and discover fascinating fishing history in this coastal town on Cape Ann.

Boston

Freedom city

Soak up the city’s heritage and sights on the famous Freedom Trail.

Falmouth

To the Cape

Relax in one of Cape Cod’s best seaside towns.

Stockbridge

The Berkshires

See picturesque backdrops in this small town in the Berkshires.

Gloucester

Maritime heritage

See lighthouses and discover fascinating fishing history in this coastal town on Cape Ann.

Personalise your trip

We'll help plan your holiday in store, or from the comfort of your own home

01306 744 988

Available until 8pm