26 days in Cape Ann Itinerary

26 days in Cape Ann Itinerary

Created using Inspirock Cape Ann Trip Planner

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Route & dates

26 days in Cape Ann Itinerary

Start: Boston
Drive:  1​h
— 25 nights
Drive:  1​h
End: Boston


The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
When in Gloucester, make a side trip to see Front Beach in Rockport, approximately 42 minutes away. The adventure continues: get up close to creatures of the deep with a dolphin and whale watching tour, pause for some photo ops at Fishermen's Memorial Monument, immerse yourself in nature at Halibut Point State Park, and contemplate the long history of Cogswell's Grant.

To find photos, maps, ratings, and other tourist information, read Gloucester itinerary maker.

Boston to Gloucester is an approximately 1-hour car ride. You can also take a train. Traveling from Boston in July, you can expect nighttime temperatures to be little chillier in Gloucester, with lows of 62°F. You'll set off for home on the 26th (Wed).

Things to do in Gloucester

Parks Outdoors Beaches

Side Trips

Rockport, Essex, Manchester-by-the-Sea
Highlights from your plan
Dolphin & Whale Watching
Good Harbor Beach ©
Good Harbor Beach
Fishermen's Memorial Monument ©
Fishermen's Memorial Monument