14 days in Eastern Shore Itinerary

14 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore journey planner
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Make it your trip
Fly to Philadelphia International Airport, Drive to Chesapeake City
1
Chesapeake City
— 1 day
Drive
2
Ocean City
— 7 nights
Unknown
3
Assateague Island
— 1 night
Unknown
4
St. Michaels
— 5 nights
Fly

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Chesapeake City — 1 day

Chesapeake City is a town in Cecil County, Maryland, USA. The population was 673 at the 2010 census.The town was originally named by Bohemian colonist Augustine Herman the Village of Bohemia — or Bohemia Manor — but the name was changed in 1839 when the Chesapeake and Delaware Canal (C&D Canal) was built. Kick off your visit on the 1st (Wed): get engrossed in the history at C&D Canal Museum and then see the top attractions with M/V Bay Breeze of Chesapeake City.

Take the guesswork out of planning a Chesapeake City vacation by using our trip itinerary maker.

Atlanta to Chesapeake City is an approximately 5.5-hour combination of flight and car. You can also drive. Traveling from Atlanta in June, expect Chesapeake City to be a bit cooler, temps between 82°F and 63°F. Finish your sightseeing early on the 1st (Wed) to allow enough time to travel to Ocean City.
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Museums · Outdoors · Wineries · Tours

Ocean City — 7 nights

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.
Appreciate the collections at Ocean City Life-Saving Station Museum and Calvin B. Taylor House Museum. Deepen your sense of the past at sights like Main Street Berlin and Pemberton Historical Park. There's lots more to do: enjoy the sand and surf at Ocean City Beach, admire the majestic nature at Assateague State Park, look for gifts at The Kite Loft, and get a new perspective on things with Boat Tours & Water Sports.

To see ratings, where to stay, more things to do, and more tourist information, go to the Ocean City trip maker site.

Traveling by car from Chesapeake City to Ocean City takes 2.5 hours. Expect a daytime high around 79°F in June, and nighttime lows around 65°F. Wrap up your sightseeing on the 8th (Wed) to allow time to travel to Assateague Island.
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Museums · Parks · Shopping · Outdoors
Side Trips

Assateague Island — 1 night

On the 9th (Thu), stroll through Assateague Island National Seashore.

To find reviews, maps, and other tourist information, read Assateague Island trip itinerary planning site.

Explore your travel options from Ocean City to Assateague Island with the Route module. Expect a daytime high around 79°F in June, and nighttime lows around 65°F. Cap off your sightseeing on the 9th (Thu) early enough to travel to St. Michaels.
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Wildlife · Nature · Parks
Highlights from your trip

St. Michaels — 5 nights

Chesapeake Bay Maritime Museum and Hopkins Original Art are good opportunities to explore the local culture. For shopping fun, head to Olivins or Queenstown Premium Outlets. Explore St. Michaels' surroundings by going to Queenstown Harbor Golf (in Queenstown) and Cambridge (Harriet Tubman Museum and Educational Center, Choptank River Lighthouse, &more).

To find more things to do, traveler tips, ratings, and other tourist information, use the St. Michaels online trip itinerary builder.

The Route module can help you plan travel from Assateague Island to St. Michaels. Expect a daytime high around 84°F in June, and nighttime lows around 66°F. Finish up your sightseeing early on the 14th (Tue) so you can catch the flight back home.
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Museums · Historic Sites · Shopping · Outdoors
Side Trips