30 days in Eastern Shore Itinerary

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. Take a break from the city and head to Boat Tours & Water Sports and Painted Sky Alpaca Farm & Fiber Mill. Do some cultural sightseeing at C&D Canal Museum and Upper Bay Museum. Take a break from Chesapeake City with a short trip to Hollywood Casino in Perryville, about 32 minutes away. And it doesn't end there: do a tasting at Chateau Bu-De, explore the activities along Bohemia RIver, don't miss a visit to Mount Harmon Plantation, and immerse yourself in nature at Elk Neck State Park.

To find traveler tips, photos, where to stay, and other tourist information, you can read our Chesapeake City trip itinerary maker site.

Vancouver, Canada to Chesapeake City is an approximately 12-hour combination of flight and car. You can also drive. Traveling from Vancouver to Chesapeake City, you'll lose 3 hours due to the time zone difference. Prepare for somewhat warmer weather when traveling from Vancouver in September: high temperatures in Chesapeake City hover around 31°C and lows are around 18°C. You'll set off for Stevensville on the 5th (Tue).

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. Discover out-of-the-way places like Terrapin Nature Park and Matapeake Clubhouse and Beach. Visiting Fishing Charters & Tours and Lead Dog Charters will get you outdoors. There's still lots to do: learn about winemaking at Mark Cascia Vineyards, sample the fine beverages at Blackwater Distilling & Tavern, and get outside with Casey Michelle Charters.

For ratings, traveler tips, photos, and more tourist information, read Stevensville day trip app.

Drive from Chesapeake City to Stevensville in 1.5 hours. Expect a daytime high around 30°C in September, and nighttime lows around 20°C. Cap off your sightseeing on the 9th (Sat) early enough to go by car to St. Michaels.

Your cultural itinerary includes sights like Chesapeake Bay Maritime Museum and Saint Michaels Winery. Explore hidden gems such as Tilghman Island and Lyon Rum Distillery. Venture out of the city with trips to Eastern Neck National Wildlife Refuge (in Rock Hall) and Choptank River Lighthouse (in Cambridge).

To see photos, ratings, more things to do, and other tourist information, you can read our St. Michaels holiday planner.

Traveling by car from Stevensville to St. Michaels takes an hour. September in St. Michaels sees daily highs of 31°C and lows of 19°C at night. Finish your sightseeing early on the 14th (Thu) to allow enough time to drive to Crisfield.

Crisfield is a city in Somerset County, Maryland, United States, located on the Tangier Sound, an arm of the Chesapeake Bay. Take a break from the city and head to Janes Island State Park and Smith Island. Bordeleau Vineyards & Winery and Crisfield Heritage Foundation are good opportunities to explore the local culture. There's still lots to do: go for a stroll along the water at Somers Cove Marina and stop by The Bay Gift Vault.

To find maps, traveler tips, reviews, and more tourist information, you can read our Crisfield attractions planning site.

You can drive from St. Michaels to Crisfield in 2 hours. In September, daytime highs in Crisfield are 31°C, while nighttime lows are 20°C. You will leave for Assateague Island on the 17th (Sun).

Spend the 18th (Mon) exploring nature at Assateague Island National Seashore.

To find photos and tourist information, you can read our Assateague Island travel route planner.

Use the Route module to find suitable travel options from Crisfield to Assateague Island. In September, daily temperatures in Assateague Island can reach 30°C, while at night they dip to 20°C. You will leave for Ocean City on the 20th (Wed).

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.

Step off the beaten path and head to Rum Pointe Seaside Golf Links and Art League of Ocean City. Get in touch with nature at Ocean City Beach and Ayers Creek Adventures. You'll find plenty of places to visit near Ocean City: Salisbury (Salisbury Zoo, Ward Museum of Wildfowl Art, &more). And it doesn't end there: brush up on your knowledge of spirits at Seacrets Distilling Company, tee off at Eagle's Landing Golf Course, relax and rejuvenate at some of the best spas, and see the interesting displays at Ocean City Life-Saving Station Museum.

For ratings, traveler tips, more things to do, and tourist information, read our Ocean City sightseeing planner.

The Route module can help you plan travel from Assateague Island to Ocean City. In September, daily temperatures in Ocean City can reach 30°C, while at night they dip to 20°C. Wrap up your sightseeing by early afternoon on the 30th (Sat) to allow enough time to travel back home.