22 days in Eastern Shore Itinerary

22 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore trip itinerary planner

Make it your trip
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Assateague Island
— 1 night
Unknown
2
Crisfield
— 2 nights
Drive
3
Ocean City
— 9 nights
Drive
4
St. Michaels
— 4 nights
Drive
5
Stevensville, Kent Island
— 3 nights
Drive
6
Chesapeake City
— 2 nights
Drive to Philadelphia International Airport, Fly to Orlando

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Assateague Island

— 1 night
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 14.5-hour travel. 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

Parks · Wildlife · Nature
Highlights from your trip

Crisfield

— 2 nights
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

Ocean City

— 9 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.
Get outdoors at Ocean City Beach and Ayers Creek Adventures. Get some historical perspective at Pemberton Historical Park and Main Street Berlin. 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: play a few rounds at Eagle's Landing Golf Course, take a leisurely stroll along Oceanic Fishing Pier, sample the fine beverages at Seacrets Distilling Company, and indulge in some personalized pampering at OC Massage.

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 · Historic Sites

Side Trips

St. Michaels

— 4 nights
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 Eastern Neck National Wildlife Refuge. Step out of St. Michaels with an excursion to Adkins Arboretum in Ridgely--about 38 minutes 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

Parks · Wildlife · Museums · Outdoors

Side Trips

Stevensville, Kent Island

— 3 nights
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 Nature Park and Chesapeake Bay Charter Services. Get in touch with nature at Matapeake Clubhouse and Beach and Breezin' Thru Charters. It doesn't end there: sample the fine beverages at Blackwater Distilling & Tavern and head outdoors with Casey Michelle Charters.

For reviews, where to stay, traveler tips, and other tourist information, use the Stevensville online trip planner.

Drive from St. Michaels to Stevensville in an hour. In September, daily temperatures in Stevensville can reach 78°F, while at night they dip to 64°F. Cap off your sightseeing on the 10th (Thu) early enough to go by car to Chesapeake City.

Things to do in Stevensville

Outdoors · Wildlife · Parks · Tours

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. 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 tour the pleasant surroundings 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 · Wildlife

Side Trips