Cape Ann trip planner

Create a fully customized day-by-day itinerary for free
Itinerary planner
+ Add destination
2 adults
- +
- +
- +
Trip Planner USA  /  Massachusetts  /  Cape Ann

Cape Ann

Dolphin & Whale Watching · Beaches · Monuments
Cape Ann is a collection of coastal towns interspersed with rocky coastline. The towns represent some of the earliest settlements along the East Coast. Captain John Smith was the first to chart the area in the 17th century. Travelers come to visit tide pools and more than a dozen beaches and take part in water activities like whale watching, sailing, and fishing. The community supports the arts, designating four regional cultural districts that showcase everything from art galleries and studios to museums, music, and performing art venues. East of the Annisquam River is referred to as "The Island" where "old families" exhibit a fiercely independent culture that is true to the cape's early roots. Plan your visit to Cape Ann and other destinations in United States using our United States trip planner.
Create a full itinerary — for free!

Plan your trip to Cape Ann

  • Get a personalized trip
    A full day by day itinerary based on your preferences
  • Customize it
    Refine your trip. We'll find the
    best routes and schedules
  • Manage it
    Everything in one place. Everyone on the same page.