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

Route & dates

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

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

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

Side Trip

Chesapeake Ghost Walks
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Smith Island ©
Smith Island
Somers Cove Marina ©
Somers Cove Marina

9
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 outdoors at Ocean City Beach and Rum Pointe Seaside Golf Links. 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). Next up on the itinerary: take in the waterfront at Ocean City Boardwalk, cool off at West OC Watersports, take the plunge with Skydive OC, and sample the fine beverages at Seacrets Distilling Company.

To see ratings, reviews, where to stay, and tourist information, read our Ocean City planning website.

Getting from Crisfield to Ocean City by car takes about 1.5 hours. In August in Ocean City, expect temperatures between 82°F during the day and 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 · Theme Parks · Parks

Side Trips

Berlin, Salisbury
Highlights from your plan
OC Massage ©
OC Massage
Ayers Creek Adventures ©
Ayers Creek Adventures
Rum Pointe Seaside Golf Links ©
Rum Pointe Seaside Golf Links

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 Chesapeake Bay Environmental Center. You'll find plenty of places to visit near St. Michaels: Adkins Arboretum (in Ridgely) and Eastern Neck National Wildlife Refuge (in Rock Hall).

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 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 travel to Stevensville.

Things to do in St. Michaels

Parks · Wildlife · Museums

Side Trips

Tilghman, Choptank River Lighthouse, Adkins Arboretum, Chesapeake Bay Environmental Center, Eastern Neck National Wildlife Refuge
Highlights from your plan
Lyon Rum Distillery & Tasting Room ©
Lyon Rum Distillery & Tasting Room
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse
Phillips Wharf Environmental Center ©
Phillips Wharf Environmental Center

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 Matapeake Clubhouse and Beach. Get in touch with nature at Chesapeake Bay Charter Services and Casey Michelle Charters. It doesn't end there: sample the fine beverages at Blackwater Distilling & Tavern and head outdoors with Lead Dog Charters.

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

Travel 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 travel to Chesapeake City.

Things to do in Stevensville

Outdoors · Parks · Wildlife
Highlights from your plan
Chesapeake Bay Charter Services ©
Chesapeake Bay Charter Services
Blackwater Distilling & Tavern ©
Blackwater Distilling & Tavern

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 journey 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

Side Trips

Elk Neck State Park, Painted Sky Alpaca Farm & Fiber Mill, Schooner Sultana
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