22 days in Eastern Shore Itinerary

22 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore trip itinerary planner

©
Plan created by another user. Make it yours
1
Assateague Island
— 1 night
2
Crisfield
— 2 nights
3
Ocean City
— 9 nights
4
St. Michaels
— 4 nights
5
Stevensville, Kent Island
— 3 nights
6
Chesapeake City
— 2 nights

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1
night
Assateague Island

Assateague Island ©
On the 23rd (Sun), explore the wealth of natural beauty at Assateague Island National Seashore.

For where to stay, reviews, maps, and tourist information, refer to the Assateague Island driving holiday planner.

Orlando to Assateague Island is an approximately 13.5-hour combination of flight and car. In August, Assateague Island is slightly colder than Orlando - with highs of 82°F and lows of 67°F. Wrap up your sightseeing on the 23rd (Sun) early enough to travel to Crisfield.

Things to do in Assateague Island

Nature · Wildlife · Parks
Highlights from your trip

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 24th (Mon): go for a stroll along the water at Somers Cove Marina, then immerse yourself in nature at Janes Island State Park, and then get thoroughly spooked out with Chesapeake Ghost Walks. Keep things going the next day: see the interesting displays at Crisfield Heritage Foundation and then head off the coast to Smith Island.

To find more things to do, ratings, reviews, and other tourist information, you can read our Crisfield visit app.

The Route module can help you plan travel from Assateague Island to Crisfield. In August, plan for daily highs up to 84°F, and evening lows to 68°F. Finish your sightseeing early on the 25th (Tue) to allow enough time to drive to Ocean City.

Things to do in Crisfield

Parks · Nature · Museums · Tours

Side Trip

Highlights from your trip
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Island
Smith Island
2.3

9
nights
Ocean City

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.
Get outdoors at Ocean City Beach and Lost Treasure Golf. Get some historical perspective at Main Street Berlin and Pemberton Historical Park. Change things up with a short trip to Ward Museum of Wildfowl Art in Salisbury (about 48 minutes away). There's still lots to do: surround yourself with nature on Ayers Creek Adventures, examine the collection at Ocean City Life-Saving Station Museum, cross one thing off your bucket list with Skydive OC, and tee off at Rum Pointe Seaside Golf Links.

To see photos, maps, ratings, and more tourist information, read Ocean City tour itinerary maker site.

Drive from Crisfield to Ocean City in 1.5 hours. August in Ocean City sees daily highs of 82°F and lows of 67°F at night. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to St. Michaels.

Things to do in Ocean City

Outdoors · Parks · Tours · Golf

Side Trips

Highlights from your trip

4
nights
St. Michaels

St. Michaels ©
Deepen your sense of the past at sights like 1879 Hooper Strait Lighthouse and Choptank River Lighthouse. Escape the urban bustle at Boat Tours & Water Sports and Adkins Arboretum. Step out of St. Michaels with an excursion to Eastern Neck National Wildlife Refuge in Rock Hall--about 1 hour away.

To plan St. Michaels vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by car from Ocean City to St. Michaels takes 2 hours. Alternatively, you can do a combination of shuttle and taxi; or do a combination of bus and taxi. In September, daytime highs in St. Michaels are 80°F, while nighttime lows are 62°F. Finish your sightseeing early on the 7th (Mon) so you can drive to Stevensville.

Things to do in St. Michaels

Wildlife · Parks · Museums · Outdoors

Side Trips

Highlights from your trip

3
nights
Stevensville, Kent Island

Stevensville ©
Stevensville is a census-designated place (CDP) in Queen Anne's County, Maryland, and is the county's most populous place among both CDPs and municipalities. Explore hidden gems such as Terrapin Beach Park and Blackwater Distilling & Tavern. Get in touch with nature at Matapeake Clubhouse and Beach and Lead Dog Charters. It doesn't end there: cast your line with Chesapeake Bay Charter Services and get outside with Casey Michelle Charters.

Ask Inspirock to suggest an itinerary and make planning a trip to Stevensville fast, fun, and easy.

You can drive from St. Michaels to Stevensville in an hour. In September, plan for daily highs up to 78°F, and evening lows to 64°F. Finish your sightseeing early on the 10th (Thu) so you can drive to Chesapeake City.

Things to do in Stevensville

Outdoors · Parks · Wildlife · Tours
Highlights from your trip
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Fishing Charter / Tour
Chesapeake Bay Charter Services
4.9

2
nights
Chesapeake City

Chesapeake City ©
Chesapeake City is a town in Cecil County, Maryland, USA. Kick off your visit on the 11th (Fri): immerse yourself in nature at Elk Neck State Park, then take an in-depth tour of C&D Canal Museum, and then awaken your taste buds at M/V Bay Breeze of Chesapeake City. On your second day here, get outside with Schooner Sultana and then identify plant and animal life at Painted Sky Alpaca Farm & Fiber Mill.

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

Traveling by car from Stevensville to Chesapeake City takes 1.5 hours. In September, daytime highs in Chesapeake City are 80°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 12th (Sat) early enough to travel back home.

Things to do in Chesapeake City

Outdoors · Parks · Nature · Wineries

Side Trips

Highlights from your trip