5 days in New England Itinerary

5 days in New England Itinerary

Created using Inspirock New England planner
©
Make it your trip
Fly
1
Gloucester
— 1 day
Drive
2
Hyannis
— 2 nights
Drive
3
Provincetown
— 2 nights
Fly

S M T W T F S
4
5
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7
8
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11
12
13
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17

Gloucester — 1 day

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 9th (Fri), enjoy the sand and surf at Good Harbor Beach and then see majestic marine mammals with a dolphin and whale watching tour.

To find other places to visit, ratings, maps, and tourist information, you can read our Gloucester trip itinerary planning tool.

Chicago to Gloucester is an approximately 4-hour flight. You can also drive; or do a combination of bus and train. The time zone difference when traveling from Chicago to Gloucester is 1 hour. Traveling from Chicago in September, Gloucester is a bit cooler at night with lows of 54°F. Finish your sightseeing early on the 9th (Fri) so you can drive to Hyannis.
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Outdoors · Wildlife · Tours · Beaches

Hyannis — 2 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Start off your visit on the 10th (Sat): admire the masterpieces at Atwood Museum, enjoy the sand and surf at Chatham Lighthouse Beach, and then kick back and relax at Nauset Beach. Get ready for a full day of sightseeing on the 11th (Sun): kick back and relax at Craigville Beach, then see majestic marine mammals with Hyannis Whale Watcher Cruises, and then contemplate the long history of Captain Bangs Hallet House Museum.

To see reviews, other places to visit, more things to do, and more tourist information, read Hyannis online visit planner.

You can drive from Gloucester to Hyannis in 2.5 hours. Alternatively, you can fly; or do a combination of train and bus. In September, daily temperatures in Hyannis can reach 73°F, while at night they dip to 57°F. Finish up your sightseeing early on the 11th (Sun) so you can go by car to Provincetown.
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Outdoors · Beaches · Parks · Wildlife
Side Trips

Provincetown — 2 nights

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Start off your visit on the 12th (Mon): appreciate the history behind Pilgrim Monument & Provincetown Museum and then explore the wealth of natural beauty at Cape Cod National Seashore. Get ready for a full day of sightseeing on the 13th (Tue): tour the pleasant surroundings at Coast Guard Beach, enjoy the sand and surf at Nauset Light Beach, and then take a leisurely stroll along MacMillan Wharf.

To see other places to visit, ratings, traveler tips, and more tourist information, you can read our Provincetown driving holiday planner.

Drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. In September in Provincetown, expect temperatures between 71°F during the day and 57°F at night. Finish your sightseeing early on the 13th (Tue) so you can fly back home.
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Beaches · Outdoors · Parks · Nature
Side Trips