14 days in New England, Philadelphia & Yorktown Itinerary

14 days in New England, Philadelphia & Yorktown Itinerary

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Route & dates

14 days in New England, Philadelphia & Yorktown Itinerary

Start: Chicago
Fly:  4​h
1
Boston
— 2 nights
ferry:  1​h 30​min
2
Provincetown
— 2 nights
Drive:  1​h 30​min
3
Plymouth
— 1 night
Drive:  45​min
4
Falmouth
— 1 night
Drive:  1​h 30​min
5
Newport
— 1 night
Fly:  4​h 45​min
6
Philadelphia
— 3 nights
Fly:  2​h 45​min
7
Yorktown
— 3 nights
taxi + Fly:  4​h 30​min
End: Chicago

2
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.
Get some historical perspective at Freedom Trail and North Bridge. Do some cultural sightseeing at Museum of Fine Arts and Granary Burying Ground. Explore the numerous day-trip ideas around Boston: Dolphin & Whale Watching (in Gloucester) and Marginal Way Walkway (in Ogunquit). There's still lots to do: steep yourself in history at Louisa May Alcott's Orchard House.

To find maps, more things to do, where to stay, and more tourist information, read Boston trip itinerary planning website .

Chicago to Boston is an approximately 4-hour flight. You can also do a combination of flight and bus; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Boston. May in Boston sees daily highs of 67°F and lows of 50°F at night. Finish your sightseeing early on the 2nd (Tue) so you can ride a ferry to Provincetown.

Things to do in Boston

Historic Sites Wildlife Tours

Side Trips

Concord, Dolphin & Whale Watching, Marginal Way Walkway
Highlights from your plan
Freedom Trail ©
Freedom Trail
Marginal Way Walkway ©
Marginal Way Walkway
Museum of Fine Arts ©
Museum of Fine Arts

2
nights
Provincetown

Provincetown ©
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.
Kick off your visit on the 3rd (Wed): appreciate the history behind Pilgrim Monument & Provincetown Museum and then stroll through Cape Cod National Seashore. On the 4th (Thu), you'll have a packed day of sightseeing: steep yourself in history at Captain Penniman House, then kick back and relax at Nauset Beach, and then enjoy the sand and surf at Race Point Beach.

To see other places to visit, traveler tips, where to stay, and more tourist information, use the Provincetown road trip planning app .

You can ride a ferry from Boston to Provincetown in 1.5 hours. Other options are to fly; or drive. In June, daily temperatures in Provincetown can reach 72°F, while at night they dip to 56°F. Wrap up your sightseeing on the 4th (Thu) to allow time to drive to Plymouth.

Things to do in Provincetown

Outdoors Beaches Parks

Side Trips

Nauset Beach, Cape Cod National Seashore, Captain Penniman House
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Nauset Beach ©
Nauset Beach
Race Point Beach ©
Race Point Beach

1
night
Plymouth

Plymouth ©
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Start off your visit on the 5th (Fri): engage your brain at Sandwich Glass Museum, see the interesting displays at Heritage Museums & Gardens, contemplate the waterfront views at Cape Cod Canal, admire the majestic nature at National Monument to the Forefathers, then make a trip to Mayflower II, and finally pause for some photo ops at Plymouth Rock.

To see more things to do, maps, ratings, and other tourist information, go to the Plymouth trip itinerary builder website .

You can drive from Provincetown to Plymouth in 1.5 hours. Alternatively, you can take a bus; or do a combination of ferry and bus. In June, daytime highs in Plymouth are 76°F, while nighttime lows are 56°F. Finish your sightseeing early on the 5th (Fri) to allow enough time to drive to Falmouth.

Things to do in Plymouth

Museums Historic Sites Childrens Museums

Side Trips

Sandwich, Cape Cod Canal
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum
Plymouth Rock ©
Plymouth Rock

1
night
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Kick off your visit on the 6th (Sat): explore the world behind art at Highfield Hall & Gardens, get to know the fascinating history of Cornelia Carey Sanctuary (The Knob), then grab your bike and head to Shining Sea Bikeway, and finally enjoy the sand and surf at Old Silver Beach.

For traveler tips, ratings, other places to visit, and more tourist information, read Falmouth trip itinerary planning app .

Drive from Plymouth to Falmouth in an hour. Alternatively, you can take a bus; or take a bus. In June, daytime highs in Falmouth are 73°F, while nighttime lows are 55°F. Finish up your sightseeing early on the 6th (Sat) so you can go by car to Newport.

Things to do in Falmouth

Parks Outdoors Beaches
Highlights from your plan
Shining Sea Bikeway ©
Shining Sea Bikeway
Cornelia Carey Sanctuary (The Knob) ©
Highfield Hall & Gardens ©
Highfield Hall & Gardens

1
night
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
On the 7th (Sun), make a trip to Cliff Walk, then take a memorable drive along Ocean Drive Historic District, and then visit a coastal fixture at Beavertail Lighthouse and Park.

To see photos, other places to visit, maps, and other tourist information, read our Newport visit planner.

Drive from Falmouth to Newport in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In June, plan for daily highs up to 73°F, and evening lows to 58°F. Finish your sightseeing early on the 7th (Sun) so you can travel to Philadelphia.

Things to do in Newport

Historic Sites Outdoors Parks

Side Trip

Beavertail Lighthouse and Park
Highlights from your plan
Beavertail Lighthouse and Park ©
Beavertail Lighthouse and Park
Ocean Drive Historic District ©
Ocean Drive Historic District

3
nights
Philadelphia

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Get outdoors at Valley Forge National Historical Park and Schuylkill River Trail. Get some historical perspective at Independence Hall and Liberty Bell Center. Step out of Philadelphia with an excursion to Tyler State Park in Newtown--about 40 minutes away. And it doesn't end there: explore the world behind art at Philadelphia Museum of Art, hike along Kelly Drive, stroll the grounds of Christ Church, and get to know the fascinating history of Independence National Historical Park.

For more things to do, maps, and tourist information, read Philadelphia itinerary builder website .

Fly from Newport to Philadelphia in 5 hours. Alternatively, you can drive; or do a combination of flight and train. Expect somewhat warmer temperatures when traveling from Newport in June; daily highs in Philadelphia reach 84°F and lows reach 65°F. Wrap up your sightseeing on the 10th (Wed) early enough to travel to Yorktown.

Things to do in Philadelphia

Parks Historic Sites Nature

Side Trips

Tyler State Park, Valley Forge National Historical Park
Highlights from your plan
Valley Forge National Historical Park ©
Independence Hall ©
Independence Hall
Philadelphia Museum of Art ©
Philadelphia Museum of Art

3
nights
Yorktown

Yorktown ©
Yorktown is a census-designated place (CDP) in York County, Virginia, United States. Popular historic sites such as Colonial Williamsburg and Historic Jamestowne are in your itinerary. Your cultural itinerary includes sights like St. Luke's Historic Church & Museum and Jamestown Settlement. Step out of Yorktown to go to Williamsburg and see Historic Jamestowne, which is approximately 32 minutes away. There's still lots to do: trek along The Noland Trail, pause for some serene contemplation at Bruton Parish Episcopal Church, and explore and take pictures at Colonial National Historical Park.

For photos, other places to visit, ratings, and other tourist information, read our Yorktown trip itinerary site .

Traveling by flight from Philadelphia to Yorktown takes 3 hours. Alternatively, you can do a combination of flight and taxi; or drive. In June, plan for daily highs up to 86°F, and evening lows to 68°F. Wrap up your sightseeing on the 13th (Sat) early enough to travel back home.

Things to do in Yorktown

Historic Sites Museums Parks

Side Trips

Williamsburg, The Noland Trail, St. Luke's Historic Church & Museum
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
St. Luke's Historic Church & Museum ©

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