8 days in Chesapeake City & Gatlinburg Itinerary

8 days in Chesapeake City & Gatlinburg Itinerary

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Route & dates

8 days in Chesapeake City & Gatlinburg Itinerary

Start: New York City
Drive:  3​h 15​min
1
Chesapeake City
— 3 nights
Drive:  8​h 45​min
2
Gatlinburg
— 3 nights
+2
taxi + Fly + bus:  5​h
End: New York City

3
nights
Chesapeake City

Chesapeake City ©
Chesapeake City is a town in Cecil County, Maryland, USA. Get in touch with nature at Valley Forge National Historical Park and Bohemia RIver. Cape May Lighthouse and Historic Cold Spring Village are good opportunities to explore the local culture. Venture out of the city with trips to World War II Lookout Tower (in Cape May), Air Mobility Command Museum (in Dover) and Wilmington (Hagley Museum and Library & Nemours Estate). It doesn't end there: enjoy the sand and surf at Cape Henlopen State Park.

For more things to do, photos, other places to visit, and more tourist information, read our Chesapeake City itinerary planner .

New York City to Chesapeake City is an approximately 2.5-hour car ride. Traveling from New York City in September, Chesapeake City is a bit cooler at night with lows of 60°F. Wrap up your sightseeing on the 17th (Tue) early enough to travel to Gatlinburg.

Things to do in Chesapeake City

Parks Historic Sites Museums

Side Trips

Cape May, Wilmington, Cape Henlopen State Park, Air Mobility Command Museum, Valley Forge National Historical Park
Highlights from your plan
Cape May Lighthouse ©
Cape May Lighthouse
Valley Forge National Historical Park ©
Cape Henlopen State Park ©
Cape Henlopen State Park

3
nights
Gatlinburg

Gatlinburg ©
Nestled in the lush, wooded forests of the Great Smoky Mountains National Park, Gatlinburg is Tennessee’s premier mountain resort destination.
You'll discover tucked-away gems like The North Carolina Arboretum and Zipline. Escape the urban bustle at Tuckaleechee Caverns and Gatlinburg Scenic Overlook. Explore Gatlinburg's surroundings by going to Asheville (Basilica of Saint Lawrence & Thomas Wolfe Memorial). The adventure continues: learn about winemaking at Sugarland Cellars, have some family-friendly fun at Mysterious Mansion, get in on the family fun at 7D Dark Ride Adventure, and see the interesting displays at Christ in the Smokies Museum & Gardens.

To see reviews, maps, photos, and tourist information, you can read our Gatlinburg travel planning site .

You can drive from Chesapeake City to Gatlinburg in 9.5 hours. Another option is to do a combination of car and flight. In September, daytime highs in Gatlinburg are 83°F, while nighttime lows are 62°F. Finish your sightseeing early on the 21st (Sat) to allow enough time to travel back home.

Things to do in Gatlinburg

Parks Outdoors Museums

Side Trips

Asheville, Tuckaleechee Caverns, Rainbow Falls Trail, Zipline
Highlights from your plan
Sugarland Cellars ©
Sugarland Cellars
Basilica of Saint Lawrence ©
Basilica of Saint Lawrence
The North Carolina Arboretum ©
The North Carolina Arboretum

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