15 days in Eastern Shore Itinerary

15 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore trip builder

©
Plan created by another user. Make it yours

Route & dates

1
Assateague Island
— 2 nights
2
Chesapeake City
— 2 nights
3
Ocean City
— 6 nights
4
Crisfield
— 1 night
5
St. Michaels
— 3 nights

2
nights
Assateague Island

Assateague Island ©
On the 16th (Sun), look for all kinds of wild species at 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 14-hour combination of flight and car. Prepare for little chillier weather when traveling from Miami in August: high temperatures in Assateague Island hover around °F and lows are around °F. On the 17th (Mon), you're off to Chesapeake City.

Things to do in Assateague Island

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

2
nights
Chesapeake City

Chesapeake City ©
Chesapeake City is a town in Cecil County, Maryland, USA. Start off your visit on the 18th (Tue): get engrossed in the history at C&D Canal Museum, look for all kinds of wild species at Painted Sky Alpaca Farm & Fiber Mill, thencontemplate 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, thenlook 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 °F, while at night they dip to °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

Side Trips

Chestertown, Painted Sky Alpaca Farm & Fiber Mill, Elk Neck State Park
Highlights from your plan
Elk Neck State Park ©
Elk Neck State Park
M/V Bay Breeze of Chesapeake City ©
M/V Bay Breeze of Chesapeake City
Painted Sky Alpaca Farm & Fiber Mill ©
Painted Sky Alpaca Farm & Fiber Mill

6
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.
Get out of town with these interesting Ocean City side-trips: Salisbury (Ward Museum of Wildfowl Art, Salisbury Zoo, &more). There's lots more to do: take a leisurely stroll along Ocean City Boardwalk, find something for the whole family at Frontier Town, stroll around Northside Park, and catch all the local highlights with Ayers Creek Adventures.

For other places to visit, ratings, traveler tips, and more tourist information, read Ocean City driving holiday planner.

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

Things to do in Ocean City

Outdoors Parks Theme Parks

Side Trips

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

1
night
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 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 °F, while at night they dip to °F. Cap off your sightseeing on the 26th (Wed) early enough to go by car to St. Michaels.

Things to do in Crisfield

Nature Museums Parks

Side Trip

Chesapeake Ghost Walks
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Chesapeake Ghost Walks ©
Chesapeake Ghost Walks
Crisfield Heritage Foundation ©
Crisfield Heritage Foundation

3
nights
St. Michaels

St. Michaels ©
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 °F and lows of °F at night. Wrap up your sightseeing on the 29th (Sat) early enough to travel back home.

Things to do in St. Michaels

Parks Tours Wildlife

Side Trips

Cambridge, The Oxford Museum, Eastern Shore Food Tours - Eating Easton, Phillips Wharf Environmental Center
Highlights from your plan
Blackwater National Wildlife Refuge ©
Blackwater National Wildlife Refuge
Boat Tours & Water Sports
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum