17 days in Gloucester & Portland Itinerary

17 days in Gloucester & Portland Itinerary

Created using Inspirock United States tour planner

©
Make it your trip
1
Gloucester
— 2 nights
Drive
2
Portland
— 14 nights

S M T W T F S
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4

Gloucester

— 2 nights

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.
Start off your visit on the 15th (Sun): explore the world behind art at Peabody Essex Museum, then contemplate the long history of The House of the Seven Gables, and then kick back and relax at Good Harbor Beach. Get ready for a full day of sightseeing on the 16th (Mon): examine the collection at Salem Witch Museum, then pause for some photo ops at Fishermen's Memorial Monument, and then get up close to creatures of the deep with a dolphin and whale watching tour.

For more things to do, photos, and other tourist information, use the Gloucester trip itinerary builder tool.

The Route module shows you all the different ways you can get to Gloucester. In August in Gloucester, expect temperatures between 80°F during the day and 61°F at night. Cap off your sightseeing on the 17th (Tue) early enough to go by car to Portland.

Things to do in Gloucester

Outdoors · Museums · Wildlife · Tours

Side Trip

Portland

— 14 nights

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Venture out of the city with trips to Ogunquit (Perkins Cove, Marginal Way Walkway, &more), Mt. Washington Auto Road (in Gorham) and Veteran's Park (in Lewiston). The adventure continues: catch all the local highlights with The Maine Brew Bus, get outside with Red Claws Basketball, visit a coastal fixture at Portland Head Light, and wander the streets of Old Port.

To find where to stay, reviews, traveler tips, and tourist information, read Portland vacation maker site.

You can drive from Gloucester to Portland in 2 hours. Alternatively, you can take a train; or do a combination of train and bus. In August, daytime highs in Portland are 79°F, while nighttime lows are 59°F.

Things to do in Portland

Parks · Outdoors · Nature · Historic Sites

Side Trips