16 days in Hamilton, Pennsylvania & New York City Itinerary

16 days in Hamilton, Pennsylvania & New York City Itinerary

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Route & dates

16 days in Hamilton, Pennsylvania & New York City Itinerary

Start: George Town, Grand Cayman
Fly + Drive:  9​h 30​min
1
Hamilton
— 3 nights
Drive:  4​h 30​min
2
Pittsburgh
— 1 night
Fly + taxi:  3​h 45​min
3
Gettysburg
— 2 nights
Drive:  2​h 30​min
4
Philadelphia
— 4 nights
train:  1​h 45​min
5
New York City
— 5 nights
foot + Fly:  4​h 45​min
End: George Town, Grand Cayman

3
nights
Hamilton

Hamilton ©
Hamilton is a city in and the county seat of Butler County, Ohio, United States, in the state's southwestern corner. Explore Hamilton's surroundings by going to Clifton Gorge State Nature Preserve (in Yellow Springs), Dayton (National Museum of the US Air Force, Esther Price Fine Chocolates, & more) and Cincinnati (Cathedral Basilica of the Assumption, Houdini's Room Escape, & more). Next up on the itinerary: take a peaceful walk through Cincinnati Nature Center and don't miss a visit to Butler County Courthouse.

To see traveler tips, other places to visit, photos, and more tourist information, use the Hamilton holiday planner .

George Town, Cayman Islands to Hamilton is an approximately 9.5-hour combination of flight and car. Plan for cooler temperatures traveling from George Town in December, with highs in Hamilton at 7°C and lows at -2°C. Wrap up your sightseeing on the 23rd (Mon) early enough to travel to Pittsburgh.

Things to do in Hamilton

Wildlife Parks Historic Sites

Side Trips

Cincinnati, Dayton, Clifton Gorge State Nature Preserve, Cincinnati Nature Center
Highlights from your plan
Houdini's Room Escape ©
Houdini's Room Escape
National Museum of the US Air Force ©
Spring Grove Cemetery & Arboretum ©
Spring Grove Cemetery & Arboretum

1
night
Pittsburgh

Pittsburgh ©
Known primarily for its steel-related heritage and 446 bridges, Pittsburgh sits at the confluence of the Monongahela and Allegheny Rivers, which meet to form the Ohio River.
On the 24th (Tue), take in nature's colorful creations at Phipps Conservatory and Botanical Gardens, see the interesting displays at Bicycle Heaven, and then get your game on at LumberjAxes.

For other places to visit, traveler tips, photos, and more tourist information, read Pittsburgh road trip planning site .

Traveling by car from Hamilton to Pittsburgh takes 5 hours. Alternatively, you can do a combination of car and flight. December in Pittsburgh sees daily highs of 6°C and lows of -1°C at night. Finish your sightseeing early on the 24th (Tue) so you can travel to Gettysburg.

Things to do in Pittsburgh

Fun & Games Museums Parks

Side Trip

LumberjAxes
Highlights from your plan
Bicycle Heaven ©
Bicycle Heaven

2
nights
Gettysburg

Gettysburg ©
Located near the memorial park marking the site of one of the largest Civil War battles, the town of Gettysburg sits in a landscape of rolling green hills with views of the Blue Ridge Mountains in the distance.
On the 25th (Wed), take in the dramatic natural features at Devils Den, steep yourself in history at Little Round Top, pause for some photo ops at Equestrian Monument to Major General John Sedgwick, then witness the site of a historic battle at Gettysburg National Military Park, and finally stroll the grounds of Gettysburg National Cemetery. Get ready for a full day of sightseeing on the 26th (Thu): pause for some photo ops at State of Pennsylvania Monument, get answers to all your questions at Gettysburg National Military Park Museum & Visitor Center, then get your game on at Victorian Photography Studio, and finally admire the masterpieces at Gibson's Photographic Gallery.

To plan Gettysburg vacation without wasting time, ask Inspirock to design an itinerary.

Getting from Pittsburgh to Gettysburg by combination of flight and taxi takes about 4 hours. Other options: drive; or do a combination of flight and car. December in Gettysburg sees daily highs of 8°C and lows of 0°C at night. Finish your sightseeing early on the 26th (Thu) to allow enough time to drive to Philadelphia.

Things to do in Gettysburg

Museums Historic Sites Parks
Highlights from your plan
Gettysburg National Military Park ©
Gettysburg National Military Park
Little Round Top ©
Little Round Top
Devils Den ©
Devils Den

4
nights
Philadelphia

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Change things up with these side-trips from Philadelphia: Longwood Gardens (in Kennett Square) and Sandy Hollow (in West Chester). There's much more to do: walk around Wissahickon Valley Park, deepen your understanding at Fairmount Water Works Interpretive Education Center, have some family-friendly fun at Urban Axes Philadelphia, and explore the world behind art at Philadelphia Museum of Art.

To see other places to visit, more things to do, where to stay, and tourist information, go to the Philadelphia trip itinerary planning website .

Getting from Gettysburg to Philadelphia by car takes about 2.5 hours. Other options: do a combination of taxi, flight, and train; or do a combination of bus and train. In December, plan for daily highs up to 10°C, and evening lows to 1°C. Finish your sightseeing early on the 30th (Mon) so you can take a train to New York City.

Things to do in Philadelphia

Museums Parks Fun & Games

Side Trips

Sandy Hollow, Bury The Hatchet Cherry Hill - Axe Throwing, Longwood Gardens
Highlights from your plan
Urban Axes Philadelphia ©
Urban Axes Philadelphia
Longwood Gardens ©
Longwood Gardens
Wissahickon Valley Park ©
Wissahickon Valley Park

5
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, appreciate the history behind 9/11 Memorial, make a trip to Rockefeller Center, and take in panoramic vistas at Top of the Rock.

For where to stay, other places to visit, ratings, and other tourist information, read New York City road trip planning tool .

You can take a train from Philadelphia to New York City in 2 hours. Alternatively, you can drive; or take a bus. In December, plan for daily highs up to 10°C, and evening lows to 2°C. Wrap up your sightseeing on the 4th (Sat) to allow time to travel back home.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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