2 days in Cape Ann Itinerary

2 days in Cape Ann Itinerary

Created using Inspirock Cape Ann trip itinerary builder

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Route & dates

1
Manchester-by-the-Sea
— 1 day
2
Gloucester
— 1 night

1
day
Manchester-by-the-Sea

Manchester-by-the-Sea ©
Manchester-by-the-Sea is a town on Cape Ann, in Essex County, Massachusetts, in the United States. Your day-by-day itinerary now includes Frayed Knot Sailing Charters. Kick off your visit on the 14th (Tue): contemplate the long history of Castle Hill on the Crane Estate, kick back and relax at Singing Beach, and then take a tour by water with Frayed Knot Sailing Charters.

For more things to do, maps, ratings, and more tourist information, you can read our Manchester-by-the-Sea vacation planner.

Boston to Manchester-by-the-Sea is an approximately 1-hour car ride. In July in Manchester-by-the-Sea, expect temperatures between °F during the day and °F at night. Finish your sightseeing early on the 14th (Tue) to allow enough time to drive to Gloucester.

Things to do in Manchester-by-the-Sea

Outdoors Beaches Tours

Side Trip

Castle Hill on the Crane Estate
Find places to stay Jul 14 — 15:
Highlights from your plan
Frayed Knot Sailing Charters ©
Frayed Knot Sailing Charters
Castle Hill on the Crane Estate ©
Castle Hill on the Crane Estate
Singing Beach ©
Singing Beach

1
night
Gloucester

The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Kick off your visit on the 15th (Wed): take in the pleasant sights at Rockport Breakwater, enjoy the sand and surf at Good Harbor Beach, and then get up close to creatures of the deep with a dolphin and whale watching tour.

To see traveler tips, maps, other places to visit, and tourist information, use the Gloucester holiday planner.

Gloucester is just a stone's throw from Manchester-by-the-Sea. In July, daily temperatures in Gloucester can reach °F, while at night they dip to °F. Finish your sightseeing early on the 15th (Wed) to allow enough time to drive back home.

Things to do in Gloucester

Outdoors Tours Wildlife

Side Trip

Rockport Breakwater
Find places to stay Jul 14 — 15:
Highlights from your plan
Dolphin & Whale Watching
Good Harbor Beach ©
Good Harbor Beach