trips planned today
out of 5
Trustscore rating

Gloucester trip planner

Create a fully customized day-by-day itinerary for free
Itinerary planner
+ Add destination
2 adults
- +
- +
- +
You have 2 trips in progress.   See all
Trip PlannerUSA  /  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. Explore the family-friendly attractions of Gloucester and add them to your vacation plans using our United States online journey planner.
Create a full itinerary — for free!

Plan your trip to Gloucester

  • Get a personalized trip
    A full day by day itinerary based on your preferences
  • Customize it
    Refine your trip. We'll find the
    best routes and schedules
  • Book it
    Choose from the best hotels and activities. Up to 50% off
  • Manage it
    Everything in one place. Everyone on the same page.

Where to stay in Gloucester

The town prides itself on maintaining a quaint New England charm. Many inns and rental properties offer views, or accommodation in historical red-brick buildings. Some accommodations have only a few rooms, so book ahead to ensure you get the room of your choice.
20 million rooms are at your fingertips!
2 adults
Adults (12 +)
- +
Children (2-11)
- +
Infants (Under 2)
- +

Places to visit with Gloucester

BostonTrip planner Best for: Historic Walking Area, History Museum, Garden ProvincetownTrip planner Best for: Beach, Dolphin / Whale Watching, Landmark SalemTrip planner Best for: Nightlife, Gift & Specialty Shop, Specialty Museum SandwichTrip planner Best for: Specialty Museum, Science Museum, Pier / Boardwalk FalmouthTrip planner Best for: Biking Trail, Lighthouse, Aquarium