Train access works, but a car adds coastal flexibility.
Cape Ann
Rockport, Gloucester, working harbors, art history, and rocky coastal scenery within reach of Boston.
1–3 nightsSuggested stay
Reviewed by 4Boston travel editors · Updated July 26, 2026WHERE TO STAY
Choose the location before the hotel
Gloucester for services; Rockport for small-town atmosphere.
Weather changes boat plans.
Do not reduce working harbors to scenery.
Add a memorable day to the trip.
Browse current tours and activities, review the full details here, and continue to the supplier only when you are ready to choose dates and book.
Browse bookable experiences →