19 days in United States Itinerary

19 days in United States Itinerary

Created using Inspirock United States attractions planner

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Route & dates

19 days in United States Itinerary

Start: Boston
Drive:  6​h
1
Philadelphia
— 1 night
Drive:  7​h 30​min
2
Orangeburg
— Few hours
Drive:  12​h
3
Miami
— 2 nights
Drive:  4​h
4
Orlando
— 3 nights
Drive:  12​h 45​min
5
Williamsburg
— 1 night
Drive:  5​h 15​min
6
Philadelphia
— 2 nights
Drive:  5​h 30​min
7
Derry
— 6 nights
Drive + Fly:  15​h 15​min
End: Lima

1
night
Philadelphia

Philadelphia
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
To see other places to visit, reviews, photos, and tourist information, read Philadelphia trip builder .

Boston to Philadelphia is an approximately 3.5-hour flight. You can also do a combination of flight and train; or drive. In August, daytime highs in Philadelphia are 85°F, while nighttime lows are 69°F. You will leave for Orangeburg on the 29th (Thu).

Things to do in Philadelphia

Parks Nightlife Outdoors

few
hours
Orangeburg

Orangeburg
Orangeburg, also known as The Garden City, is the principal city in and the county seat of Orangeburg County, South Carolina, United States. For maps, other places to visit, where to stay, and tourist information, you can read our Orangeburg day trip planning website .

Use the Route module to find suitable travel options from Philadelphia to Orangeburg. In August, daytime highs in Orangeburg are 90°F, while nighttime lows are 71°F. You'll set off for Miami on the 29th (Thu).

Things to do in Orangeburg

Parks Nature Museums

2
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
On the 31st (Sat), you'll have a packed day of sightseeing: examine the collection at Vizcaya Museum and Gardens, see the interesting displays at Lock & Load Museum, then wander the streets of Lincoln Road, and finally enjoy the sand and surf at South Beach.

To see traveler tips, where to stay, other places to visit, and other tourist information, you can read our Miami trip planner.

The Route module can help you plan travel from Orangeburg to Miami. Expect a bit warmer evenings in Miami when traveling from Orangeburg in August, with lows around 78°F. Cap off your sightseeing on the 1st (Sun) early enough to travel to Orlando.

Things to do in Miami

Parks Museums Historic Sites

Side Trip

Miami Beach
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

3
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Head to The Mall at Millenia and Disney Springsfor some retail therapy. Your inner history buff will appreciate Stetson Mansion and City Hall. Pack the 2nd (Mon) with family-friendly diversions at Discovery Cove. Have a day of magic on the 1st (Sun) at Walt Disney World Resort. And it doesn't end there: admire the masterpieces at Charles Hosmer Morse Museum of American Art, discover the magic at Happily Ever After Fireworks, and test your problem-solving skills at The Escape Game Orlando.

To see reviews, where to stay, other places to visit, and tourist information, read Orlando trip itinerary builder .

Traveling by flight from Miami to Orlando takes 3.5 hours. Alternatively, you can drive; or do a combination of train and flight. In September, daytime highs in Orlando are 89°F, while nighttime lows are 74°F. Finish your sightseeing early on the 4th (Wed) so you can travel to Williamsburg.

Things to do in Orlando

Theme Parks Parks Beaches

Side Trips

Stetson Mansion, Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Stetson Mansion ©
Stetson Mansion

1
night
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
Kick off your visit on the 5th (Thu): look for gifts at Yankee Candle Company, steep yourself in history at Colonial Williamsburg, steep yourself in history at George Wythe House, then pause for some serene contemplation at Bruton Parish Episcopal Church, and finally view the masterpieces at Williamsburg Art Gallery.

To see maps, more things to do, other places to visit, and other tourist information, refer to the Williamsburg online trip itinerary planner .

Do a combination of flight and bus from Orlando to Williamsburg in 6.5 hours. Alternatively, you can do a combination of flight and train; or drive. Plan for little chillier temperatures traveling from Orlando in September, with highs in Williamsburg at 84°F and lows at 66°F. Cap off your sightseeing on the 6th (Fri) early enough to travel to Philadelphia.

Things to do in Williamsburg

Historic Sites Museums Shopping
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Bruton Parish Episcopal Church ©
Bruton Parish Episcopal Church
George Wythe House ©
George Wythe House

2
nights
Philadelphia

Philadelphia ©
Start off your visit on the 6th (Fri): admire the masterpieces at Barnes Foundation and then get to know the fascinating history of Independence National Historical Park. Here are some ideas for day two: get engrossed in the history at Eastern State Penitentiary, then stop by Kitchen Kettle Village, and then contemplate the long history of Valley Forge National Historical Park.

To find where to stay, maps, and other tourist information, go to the Philadelphia trip site .

Getting from Williamsburg to Philadelphia by flight takes about 4.5 hours. Other options: do a combination of bus and flight; or drive. Finish up your sightseeing early on the 8th (Sun) so you can travel to Derry.

Things to do in Philadelphia

Parks Historic Sites Museums

Side Trips

Longwood Gardens, Kitchen Kettle Village, Valley Forge National Historical Park
Highlights from your plan
Barnes Foundation ©
Barnes Foundation
Eastern State Penitentiary ©
Eastern State Penitentiary

6
nights
Derry

Derry ©
Derry is a town in Rockingham County, New Hampshire, United States. Popular historic sites such as Searles Castle and Robert Frost Farm State Historic Site are in your itinerary. Change things up with these side-trips from Derry: Kingston State Park (in Kingston) and Four Oaks Golf Course (in Dracut). The adventure continues: tour the pleasant surroundings at Massabesic Audubon Center, do a tasting at Sweet Baby Vineyard, tee off at Windham Country Club, and have some family-friendly fun at Pinball Wizard Arcade.

For where to stay, more things to do, ratings, and tourist information, read our Derry travel route app .

Use the Route module to find suitable travel options from Philadelphia to Derry. Expect little chillier evenings in Derry when traveling from Philadelphia in September, with lows around 55°F. On the 14th (Sat), you'll travel back home.

Things to do in Derry

Outdoors Golf Parks

Side Trips

Windham, Kingston State Park, Plaistow Town Forest, Zorvino Vineyards, Pinball Wizard Arcade
Highlights from your plan
Plaistow Town Forest ©
Plaistow Town Forest
Searles Castle ©
Searles Castle
Robert Frost Farm State Historic Site ©

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