15 days in Eastern Shore Itinerary

15 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore trip builder

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Make it your trip
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Assateague Island
— 2 nights
Unknown
2
Chesapeake City
— 2 nights
Drive
3
Ocean City
— 6 nights
Drive
4
Crisfield
— 1 night
Drive
5
St. Michaels
— 3 nights
Fly

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Assateague Island

— 2 nights
On the 16th (Sun), stroll through Assateague Island National Seashore.

To find more things to do, reviews, and other tourist information, you can read our Assateague Island day trip planning app.

Miami to Assateague Island is an approximately 16.5-hour travel. Prepare for little chillier weather when traveling from Miami in August: high temperatures in Assateague Island hover around 82°F and lows are around 67°F. On the 17th (Mon), you're off to Chesapeake City.

Things to do in Assateague Island

Parks · Nature · Wildlife
Highlights from your trip

Chesapeake City

— 2 nights
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. Start off your visit on the 18th (Tue): get engrossed in the history at C&D Canal Museum, stroll through Painted Sky Alpaca Farm & Fiber Mill, then contemplate the waterfront views at Bohemia RIver, and finally awaken your taste buds at M/V Bay Breeze of Chesapeake City. Keep things going the next day: immerse yourself in nature at Elk Neck State Park, then look for gifts at Book Plate, and then head outdoors with Schooner Sultana.

For more things to do, photos, traveler tips, and other tourist information, read Chesapeake City trip planner.

Use the Route module to find suitable travel options from Assateague Island to Chesapeake City. In August, daily temperatures in Chesapeake City can reach 84°F, while at night they dip to 66°F. Finish your sightseeing early on the 19th (Wed) to allow enough time to travel to Ocean City.

Things to do in Chesapeake City

Parks · Outdoors · Nature · Wineries

Side Trips

Ocean City

— 6 nights

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.
Explore Ocean City's surroundings by going to Salisbury (Ward Museum of Wildfowl Art, Salisbury Zoo, &more). And it doesn't end there: take a leisurely stroll along Ocean City Boardwalk, stroll around Northside Park, get outside with Outdoor Activities, and kick back and relax at Ocean City Beach.

For maps, traveler tips, ratings, and other tourist information, read Ocean City planner.

You can drive from Chesapeake City to Ocean City in 2.5 hours. In August, daytime highs in Ocean City are 82°F, while nighttime lows are 67°F. Finish your sightseeing early on the 25th (Tue) to allow enough time to drive to Crisfield.

Things to do in Ocean City

Outdoors · Theme Parks · Parks · Tours

Side Trips

Crisfield

— 1 night
Crisfield is a city in Somerset County, Maryland, United States, located on the Tangier Sound, an arm of the Chesapeake Bay. Kick off your visit on the 26th (Wed): examine the collection at Crisfield Heritage Foundation, go on a hair-raising tour with Chesapeake Ghost Walks, and then immerse yourself in nature at Janes Island State Park.

For where to stay, photos, more things to do, and other tourist information, read Crisfield road trip planning website.

Traveling by car from Ocean City to Crisfield takes 1.5 hours. In August, daily temperatures in Crisfield can reach 84°F, while at night they dip to 68°F. Cap off your sightseeing on the 26th (Wed) early enough to go by car to St. Michaels.

Things to do in Crisfield

Parks · Nature · Museums · Tours

Side Trip

St. Michaels

— 3 nights
Explore the numerous day-trip ideas around St. Michaels: Cambridge (Choptank Charlie's Emporium, Blackwater National Wildlife Refuge, &more).

For more things to do, traveler tips, where to stay, and other tourist information, you can read our St. Michaels trip builder.

Drive from Crisfield to St. Michaels in 2 hours. August in St. Michaels sees daily highs of 84°F and lows of 67°F at night. Wrap up your sightseeing on the 29th (Sat) early enough to fly back home.

Things to do in St. Michaels

Parks · Wildlife · Tours · Museums

Side Trips