18 days in Eastern Shore Itinerary

18 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore holiday builder

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Route & dates

18 days in Eastern Shore Itinerary

Start: Tel Aviv
Fly:  17​h 45​min
1
St. Michaels
— 2 nights
Drive:  2​h
2
Crisfield
— 2 nights
Drive:  1​h 15​min
3
Ocean City
— 8 nights
Travel:  2​h 45​min
4
Assateague Island
— 1 night
Fly:  4​h 30​min
5
Elkton
— 2 nights
Fly:  17​h 30​min
End: Tel Aviv

2
nights
St. Michaels

St. Michaels ©
Get out of town with these interesting St. Michaels side-trips: Cambridge (Blackwater National Wildlife Refuge & Harriet Tubman Museum and Educational Center).

To find more things to do, ratings, and tourist information, read our St. Michaels trip itinerary builder .

Tel Aviv, Israel to St. Michaels is an approximately 18-hour flight. The time zone difference when traveling from Tel Aviv to St. Michaels is minus 7 hours. In September, St. Michaels is little chillier than Tel Aviv - with highs of 31°C and lows of 19°C. Wrap up your sightseeing on the 21st (Sat) to allow time to drive to Crisfield.

Things to do in St. Michaels

Parks Museums Wildlife

Side Trips

Cambridge, Phillips Wharf Environmental Center, Academy Art Museum
Highlights from your plan
Blackwater National Wildlife Refuge ©
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Lyon Distilling Company ©
Lyon Distilling Company

2
nights
Crisfield

Crisfield ©
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 22nd (Sun): examine the collection at Crisfield Heritage Foundation, then do a tasting at Bordeleau Winery, and then head off the coast to Smith Island. Get ready for a full day of sightseeing on the 23rd (Mon): admire the majestic nature at Janes Island State Park and then take in the waterfront activity at Somers Cove Marina.

To find more things to do, reviews, photos, and tourist information, go to the Crisfield road trip planning website .

Traveling by car from St. Michaels to Crisfield takes 2 hours. In September in Crisfield, expect temperatures between 31°C during the day and 20°C at night. Finish up your sightseeing early on the 23rd (Mon) so you can go by car to Ocean City.

Things to do in Crisfield

Parks Nature Museums

Side Trip

Bordeleau Winery
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Somers Cove Marina ©
Somers Cove Marina
Bordeleau Winery ©
Bordeleau Winery

8
nights
Ocean City

Ocean City ©
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.
Change things up with a short trip to Salisbury Zoo in Salisbury (about 40 minutes away). And it doesn't end there: tour the pleasant surroundings at Ocean City Beach, take a memorable tour with Tours, find something for the whole family at Jolly Roger Amusement Park, and immerse yourself in nature at Assateague State Park.

Discover how to plan a Ocean City trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Crisfield to Ocean City takes 1.5 hours. In September, plan for daily highs up to 30°C, and evening lows to 20°C. Wrap up your sightseeing on the 1st (Tue) to allow time to travel to Assateague Island.

Things to do in Ocean City

Outdoors Theme Parks Tours

Side Trips

Berlin, Salisbury Zoo
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Jolly Roger Amusement Park ©
Jolly Roger Amusement Park

1
night
Assateague Island

Assateague Island ©
On the 2nd (Wed), explore the striking landscape of Assateague Island National Seashore.

To see photos, reviews, maps, and other tourist information, read Assateague Island road trip tool .

The Route module can help you plan travel from Ocean City to Assateague Island. In October, daytime highs in Assateague Island are 24°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 2nd (Wed) early enough to travel to Elkton.

Things to do in Assateague Island

Wildlife Nature Parks
Highlights from your plan
Assateague Island National Seashore ©

2
nights
Elkton

Elkton ©
The town of Elkton is the county seat of Cecil County, Maryland, United States. On the 3rd (Thu), make a trip to Historical Society of Cecil County, stroll through Plumpton Park Zoo, and then admire the majestic nature at Elk Neck State Park. Get ready for a full day of sightseeing on the 4th (Fri): explore the activities along Bohemia RIver, then make a trip to Mount Harmon Plantation, then get engrossed in the history at C&D Canal Museum, and finally explore and take pictures at Milburn Orchards.

To find photos, traveler tips, more things to do, and more tourist information, use the Elkton driving holiday planner.

Explore your travel options from Assateague Island to Elkton with the Route module. Expect a daytime high around 24°C in October, and nighttime lows around 11°C. Finish your sightseeing early on the 4th (Fri) to allow enough time to travel back home.

Things to do in Elkton

Parks Nature Zoos & Aquariums

Side Trips

Chesapeake City, Mount Harmon Plantation, Elk Neck State Park, Plumpton Park Zoo
Highlights from your plan
Elk Neck State Park ©
Elk Neck State Park
Milburn Orchards ©
Milburn Orchards
Mount Harmon Plantation ©
Mount Harmon Plantation