7 days in Boston, Salem & Gloucester Itinerary

7 days in Boston, Salem & Gloucester Itinerary

Created using Inspirock Massachusetts trip planner
Make it your trip
Fly
1
Boston
— 1 night
Drive
2
Salem
— 2 nights
Drive
3
Gloucester
— 2 nights
Drive
4
Boston
— 1 night
Fly

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Boston — 1 night

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
On the 11th (Mon), ponder the world of politics at Old State House, then stroll around Boston Common, then examine the collection at The Mapparium, and finally steep yourself in history at John F. Kennedy National Historic Site.

For more things to do, photos, where to stay, and more tourist information, go to the Boston road trip site.

Knoxville to Boston is an approximately 4-hour flight. You can also drive; or take a bus. Traveling from Knoxville in October, you will find days in Boston are little chillier (64°F), and nights are about the same (50°F). Wrap up your sightseeing on the 12th (Tue) early enough to drive to Salem.
Historic Sites · Museums · Parks
Side Trip
Find places to stay Oct 11 — 12:

Salem — 2 nights

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Your day by day itinerary now includes Old Burying Point Cemetery as well as Salem Witch Museum. On the 12th (Tue), get engrossed in the history at Salem Witch Museum, stroll the grounds of Old Burying Point Cemetery, get to know the fascinating history of Pickering Wharf, then get engrossed in the history at Gallows Hill Museum/Theatre, and finally take an in-depth tour of Witch House. Keep things going the next day: enjoy the sea views from Chandler Hovey Park, contemplate the long history of The Custom House, and then get engrossed in the history at The House of the Seven Gables.

To see ratings, reviews, more things to do, and other tourist information, refer to the Salem planner.

Getting from Boston to Salem by car takes about an hour. Other options: take a train; or take a bus. Traveling from Boston in October, you can expect nighttime temperatures to be a bit cooler in Salem, with lows of 45°F. Finish your sightseeing early on the 14th (Thu) so you can drive to Gloucester.
Historic Sites · Museums · Parks
Side Trip
Find places to stay Oct 12 — 14:

Gloucester — 2 nights

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 14th (Thu): explore the historical opulence of Hammond Castle Museum and then get outside with Outdoor Activities. Keep things going the next day: examine the collection at Beauport, the Sleeper-McCann House and then admire the majestic nature at Halibut Point State Park.

For ratings, maps, where to stay, and other tourist information, you can read our Gloucester day trip planning app.

Gloucester is just a short distance from Salem. In October, plan for daily highs up to 64°F, and evening lows to 45°F. Finish your sightseeing early on the 16th (Sat) so you can drive to Boston.
Wildlife · Museums · Outdoors · Tours
Side Trip
Find places to stay Oct 14 — 16:

Boston — 1 night

Kick off your visit on the 16th (Sat): contemplate the waterfront views at Walden Pond State Reservation, then take an in-depth tour of Louisa May Alcott's Orchard House, then steep yourself in history at The Old North Bridge, and finally explore the different monuments and memorials at Sleepy Hollow Cemetery. Get ready for a full day of sightseeing on the 17th (Sun): contemplate the long history of Hancock-Clarke House, then learn more about the world around you at The Harvard Museum of Natural History, then contemplate the long history of Longfellow House Washington's Headquarters National Historic Site, and finally take in the architecture and atmosphere at Trinity Church.

To see ratings, reviews, maps, and other tourist information, refer to the Boston trip maker tool.

Drive from Gloucester to Boston in an hour. Alternatively, you can do a combination of bus and train; or take a bus. Wrap up your sightseeing on the 17th (Sun) early enough to fly back home.
Historic Sites · Museums · Nature · Parks
Side Trips
Find places to stay Oct 16 — 17: