31 days in Philadelphia, Boston & Waterbury Itinerary

31 days in Philadelphia, Boston & Waterbury Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
Fly
1
Philadelphia
— 11 nights
Fly
2
Boston
— 13 nights
Drive
3
Waterbury
— 5 nights
Drive to Plattsburgh International Airport, Fly to Eleftherios Venizelos International Airport

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Philadelphia

— 11 nights

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S. democracy, as it was once the meeting place for the country's Founding Fathers.
Venture out of the city with trips to Penns Woods Winery (in Chadds Ford), Winterthur Museum, Garden & Library (in Winterthur) and Longwood Gardens (in Kennett Square). There's still lots to do: steep yourself in history at Independence Hall, examine the collection at The Franklin Institute, engage your brain at Mutter Museum, and get up close and personal with brilliant marine life at National Aquarium.

To see traveler tips, maps, photos, and more tourist information, go to the Philadelphia trip itinerary planning tool.

Athens, Greece to Philadelphia is an approximately 14-hour flight. Due to the time zone difference, you'll gain 7 hours traveling from Athens to Philadelphia. In December, Philadelphia is little chillier than Athens - with highs of 10°C and lows of 1°C. Wrap up your sightseeing by early afternoon on the 12th (Sat) to allow time for travel to Boston.

Things to do in Philadelphia

Museums · Parks · Historic Sites · Zoos & Aquariums

Side Trips

Boston

— 13 nights

Beantown

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.
Venture out of the city with trips to Marginal Way Walkway (in Ogunquit), Newport (Cliff Walk & The Elms) and Nubble Lighthouse (in York). There's lots more to do: admire the masterpieces at Museum of Fine Arts, take an in-depth tour of Boston Tea Party Ships & Museum, get to know the fascinating history of Freedom Trail, and take in nature's colorful creations at Isabella Stewart Gardner Museum.

To see other places to visit, where to stay, photos, and other tourist information, use the Boston day trip site.

Getting from Philadelphia to Boston by flight takes about 4 hours. Other options: drive; or take a train. Traveling from Philadelphia in December, expect nights in Boston to be about the same, around 0°C, while days are slightly colder, around 7°C. Finish up your sightseeing early on the 25th (Fri) so you can go by car to Waterbury.

Things to do in Boston

Historic Sites · Museums · Parks · Shopping

Side Trips

Waterbury

— 5 nights
Waterbury is a town in Washington County in central Vermont, United States. Venture out of the city with trips to Boyden Valley Winery & Spirits (in Cambridge), Joseph Smith Birthplace Memorial (in South Royalton) and Ole's Cross Country Center (in Warren). Next up on the itinerary: indulge your thirst for a good beer at Woodchuck Cider House, identify plant and animal life at Birds of Vermont Museum, ski along the peaceful trails at Rikert Nordic Center, and relax in the rural setting at Hartshorn Organic Farm.

For where to stay, reviews, other places to visit, and other tourist information, read Waterbury holiday planning website.

You can drive from Boston to Waterbury in 3.5 hours. Alternatively, you can take a bus; or do a combination of flight and car. Plan for a bit cooler temperatures traveling from Boston in December, with highs in Waterbury at 0°C and lows at -9°C. Finish your sightseeing early on the 30th (Wed) to allow enough time to travel back home.

Things to do in Waterbury

Outdoors · Parks · Winter Sports · Nature

Side Trips