3 days in Cape Ann Itinerary

3 days in Cape Ann Itinerary

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Route & dates

3 days in Cape Ann Itinerary

Start: Cleveland
Fly:  6​h
— 2 nights
Fly:  6​h
End: Cleveland


The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
On the 13th (Mon), pause for some photo ops at Fishermen's Memorial Monument. On the 14th (Tue), you'll have a packed day of sightseeing: take in the pleasant sights at Rockport Breakwater, then get great views at Bearskin Neck, and then identify plant and animal life at Halibut Point State Park.

To find traveler tips, where to stay, reviews, and tourist information, read our Gloucester trip builder .

Cleveland to Gloucester is an approximately 6-hour combination of flight, bus, and train. You can also drive; or take a train. Expect little chillier evenings in Gloucester when traveling from Cleveland in August, with lows around 61°F. Wrap up your sightseeing on the 15th (Wed) to allow time to travel back home.

Things to do in Gloucester

Wildlife Parks Nature

Side Trip

Highlights from your plan
Dolphin & Whale Watching
Halibut Point State Park ©
Halibut Point State Park
Fishermen's Memorial Monument ©
Fishermen's Memorial Monument