5 days in Pennsylvania, Virginia & Maryland Itinerary

5 days in Pennsylvania, Virginia & Maryland Itinerary

Created using Inspirock United States itinerary planner

Plan created by another user. Make it yours
Fly
1
Gettysburg
— 1 night
Drive
2
Chincoteague Island
— 1 night
Drive
3
Ocean City
— 1 night
Drive
4
Philadelphia
— 1 night
Fly

S M T W T F S
12
13
14
15
16
17
18
19
20
21
22
23
24
25

1
night
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.
Start off your visit on the 16th (Thu): pause for some photo ops at State of Pennsylvania Monument, witness the site of a historic battle at Gettysburg National Military Park, then explore the different monuments and memorials at Gettysburg National Cemetery, then see the interesting displays at Rupp House, and finally take in the history at Abraham Lincoln Statue.

To see maps, photos, and other tourist information, you can read our Gettysburg trip planner.

Denver to Gettysburg is an approximately 8.5-hour flight. You can also fly; or drive; or do a combination of train and bus. The time zone difference when traveling from Denver to Gettysburg is 2 hours. Traveling from Denver in July, Gettysburg is somewhat warmer at night with lows of 66°F. Wrap up your sightseeing on the 16th (Thu) to allow time to drive to Chincoteague Island.

Things to do in Gettysburg

Historic Sites · Museums · Parks

1
night
Chincoteague Island

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Kick off your visit on the 17th (Fri): enjoy the sea views from Assateague Lighthouse, get engrossed in the history at Museum of Chincoteague, and then get a dose of the wild on a nature and wildlife tour.

To see ratings, traveler tips, other places to visit, and more tourist information, you can read our Chincoteague Island trip itinerary planning website.

You can drive from Gettysburg to Chincoteague Island in 5 hours. Alternatively, you can do a combination of flight, bus, and taxi; or do a combination of bus and train. Traveling from Gettysburg in July, Chincoteague Island is a bit warmer at night with lows of 72°F. Finish your sightseeing early on the 17th (Fri) to allow enough time to drive to Ocean City.

Things to do in Chincoteague Island

Museums · Historic Sites · Wildlife · Outdoors

Side Trip

1
night
Ocean City

The White Marlin Capital of the World

One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
On the 18th (Sat), glide through the air with a parasailing or paragliding tour, then admire the majestic nature at Assateague State Park, then see the interesting displays at Ocean City Life-Saving Station Museum, and finally walk around Northside Park.

For maps, traveler tips, ratings, and other tourist information, refer to the Ocean City route site.

You can drive from Chincoteague Island to Ocean City in 1.5 hours. Another option is to do a combination of taxi and bus. In July, plan for daily highs up to 84°F, and evening lows to 70°F. Wrap up your sightseeing on the 18th (Sat) to allow time to drive to Philadelphia.

Things to do in Ocean City

Parks · Outdoors · Nature · Tours

Side Trip

1
night
Philadelphia

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Kick off your visit on the 19th (Sun): take an in-depth tour of Eastern State Penitentiary, explore the world behind art at Philadelphia Museum of Art, pause for some photo ops at Liberty Bell Center, then get a sense of history and politics at Independence Hall, and finally steep yourself in history at Washington Square Park.

For more things to do, photos, where to stay, and more tourist information, go to the Philadelphia trip planner.

Getting from Ocean City to Philadelphia by car takes about 3 hours. Other options: fly; or do a combination of bus and train. In July, plan for daily highs up to 88°F, and evening lows to 72°F. Cap off your sightseeing on the 19th (Sun) early enough to travel back home.

Things to do in Philadelphia

Museums · Historic Sites · Parks

Pennsylvania travel guide

4.3
Specialty Museums · Casinos · History Museums
The Keystone State
One of the country's 13 original founding states, Pennsylvania contains a balance of modern cities and fertile fields. A rich and varied state with a colorful history dating back to colonial times, it remains a worthy holiday destination with its well-preserved 19th-century battle sites and memorial parks. This diverse land is home to pristine forests and rugged mountain regions. For an urban experience, visit the state's university cities, offering numerous tourist attractions as well as thriving music, performance, art, and culinary scenes. The region's Amish country provides a weekend getaway in a picturesque setting of quaint towns surrounded by rolling hills and fertile farmland.

Virginia travel guide

4.6
Historic Sites · Wineries & Vineyards · Specialty Museums
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.

Maryland travel guide

4.1
Casinos · Specialty Museums · Aquariums
The Old Line State
Perhaps best known as the birthplace of religious and political freedom in the United States, Maryland retains the spirit of colonial America, with stately 18th-century villages and historical landmarks. Although it's one of the nation's smallest states, there is no shortage of things to do here and you may find your itinerary fills up quickly. Make time in your vacation to tour Maryland's diverse landscape, which includes mountain peaks, picturesque Atlantic coastline, and the bustling city of Baltimore. Military buffs will enjoy touring the state's four Civil War Trails, where you can follow the footsteps of U.S. soldiers, or visiting the port city of Annapolis, home to the United States Naval Academy.