14 days in Boston, Cambridge & Gloucester Itinerary

14 days in Boston, Cambridge & Gloucester Itinerary

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Route & dates

14 days in Boston, Cambridge & Gloucester Itinerary

Start: Boston
1
Boston
— 7 nights
Drive:  30​min
2
Cambridge
— 3 nights
Drive:  1​h
3
Gloucester
— 3 nights
Drive:  1​h
End: Boston

7
nights
Boston

Boston ©
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.
Your day-by-day itinerary now includes Free Tours by Foot - Boston Tours, Fenway Park and Bully Boy Distillers. Explore Boston's surroundings by going to Marginal Way Walkway (in Ogunquit), Newport (The Breakers & Cliff Walk) and Dolphin & Whale Watching (in Gloucester). There's much more to do: appreciate the extensive heritage of Freedom Trail, examine the collection at Heritage Museums & Gardens, admire the masterpieces at Museum of Fine Arts, and get engrossed in the history at John F. Kennedy Presidential Museum & Library.

For maps, ratings, traveler tips, and other tourist information, you can read our Boston road trip planning tool .

If you are flying in from Israel, the closest major airports are General Edward Lawrence Logan International Airport, Portsmouth International at Pease Airport and Bradley International Airport. In July, daily temperatures in Boston can reach 33°C, while at night they dip to 22°C. Finish up your sightseeing early on the 31st (Wed) so you can go by car to Cambridge.

Things to do in Boston

Museums Parks Historic Sites

Side Trips

Provincetown, Newport, Heritage Museums & Gardens, Marginal Way Walkway, The House of the Seven Gables
Highlights from your plan
Freedom Trail ©
Freedom Trail
Fenway Park ©
Fenway Park
Boston Public Garden ©
Boston Public Garden

3
nights
Cambridge

Cambridge ©
Best known as the location of two internationally renowned universities, Cambridge sits just across the Charles River from Boston.
Cambridge Historical Tours has been added to your itinerary. Start off your visit on the 1st (Thu): get thoroughly spooked out with Cambridge Historical Tours, explore the different monuments and memorials at Old Burying Point Cemetery, and then cool off at Canobie Lake Park. Keep things going the next day: take in the local highlights with Walking tours, learn more about the world around you at Harvard Museum of Natural History, then take in the architecture and design of Harvard University, and finally stop by Brookline Booksmith.

To see where to stay, more things to do, ratings, and other tourist information, use the Cambridge day trip planning website .

Cambridge is just a short distance from Boston. In July, daytime highs in Cambridge are 33°C, while nighttime lows are 22°C. Wrap up your sightseeing by early afternoon on the 3rd (Sat) to allow time for the car ride back home.

Things to do in Cambridge

Historic Sites Theme Parks Tours

Side Trips

Salem, Canobie Lake Park, Brookline Booksmith
Highlights from your plan
Harvard University ©
Harvard University
Cambridge Historical Tours ©
Cambridge Historical Tours
Harvard Museum of Natural History ©
Harvard Museum of Natural History

3
nights
Gloucester

Gloucester ©
The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Your day-by-day itinerary now includes 7 Seas Whale Watch. Take a break from Gloucester with a short trip to Hampton Beach State Park in Hampton, about 44 minutes away. There's still lots to do: admire the majestic nature at Halibut Point State Park, get great views at Bearskin Neck, kick back and relax at Good Harbor Beach, and don't miss a visit to Rockport Breakwater.

For ratings, photos, traveler tips, and other tourist information, go to the Gloucester trip app .

Traveling by car from Cambridge to Gloucester takes an hour. Alternatively, you can take a train. In August, plan for daily highs up to 31°C, and evening lows to 19°C. You will leave for home on the 6th (Tue).

Things to do in Gloucester

Parks Outdoors Wildlife

Side Trips

Rockport, Hampton Beach State Park
Highlights from your plan
Good Harbor Beach ©
Good Harbor Beach
7 Seas Whale Watch ©
7 Seas Whale Watch
Hampton Beach State Park ©
Hampton Beach State Park

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