Gloucester trip planner

Create a fully customized
day by day itinerary for free

Build your own package

+ Add destination
2 adults
- +
- +
- +
Trip Planner USA  /  Massachusetts  /  Cape Ann  /  Gloucester


Dolphin & Whale Watching · Beaches · Monuments
Sandy Bay
The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town. This rich culture has a foundation that reaches back to pre-revolutionary settlement. Some of the architecture of this period sits perched atop one large hill that overlooks the town, while a few houses down the hill in the city center are preserved from the 18th and 19th centuries. These wooden structures sport red and white paint and house cozy restaurants and shops. Many of these sell food and items that reflect the rich fishing culture that the town is known for. Take a look at our United States sightseeing planner to refine the details of your trip to Gloucester.
Create a full itinerary — for free!
  • Build a trip
    Tell us where and when you
    want to go, we will build
    the best sightseeing itinerary
  • Refine it
    You have complete flexibility on your destinations and itinerary
  • Book as a package
    Use our travel agents to get
    package savings and hassle free booking
  • Enjoy your trip!
    Enjoy our 24x7
    on-trip assistance

Places to visit with Gloucester

BostonTrip planner BEST FOR: Historic Walking Area, History Museum, Art Museum ProvincetownTrip planner BEST FOR: Beach, Dolphin / Whale Watching, Landmark ChathamTrip planner BEST FOR: Pier / Boardwalk, Beach, Lighthouse FalmouthTrip planner BEST FOR: Biking Trail, Lighthouse, Aquarium NantucketTrip planner BEST FOR: Specialty Museum, Beach, Lighthouse