16 days in Eastern Shore Itinerary

16 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore trip itinerary planner
Make it your trip
Fly
1
St. Michaels
— 4 nights
Drive
2
Crisfield
— 2 nights
Unknown
3
Assateague Island
— 1 night
Unknown
4
Ocean City
— 7 nights
Drive
5
Chesapeake City
— 1 night
Drive

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St. Michaels — 4 nights

Your inner history buff will appreciate 1879 Hooper Strait Lighthouse and The Third Haven Friends Meeting House. You'll discover tucked-away gems like St. Michaels Museum and Lyon Rum Distillery. You'll find plenty of places to visit near St. Michaels: Cambridge (Long Wharf Park & Choptank River Lighthouse).

To see ratings, reviews, more things to do, and tourist information, go to the St. Michaels tour itinerary planner.

New York City to St. Michaels is an approximately 3-hour flight. You can also drive; or do a combination of train, bus, and taxi. June in St. Michaels sees daily highs of 84°F and lows of 66°F at night. Finish your sightseeing early on the 13th (Mon) so you can drive to Crisfield.
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Museums · Historic Sites · Breweries & Distilleries · Parks
Side Trips

Crisfield — 2 nights

Crisfield is a city in Somerset County, Maryland, United States, located on the Tangier Sound, an arm of the Chesapeake Bay. On the 14th (Tue), take in the waterfront activity at Somers Cove Marina and then immerse yourself in nature at Janes Island State Park. Keep things going the next day: see the interesting displays at Crisfield Heritage Foundation and then do a tasting at Bordeleau Vineyards & Winery.

To see other places to visit, maps, where to stay, and more tourist information, read Crisfield journey maker website.

Traveling by car from St. Michaels to Crisfield takes 2 hours. In June, plan for daily highs up to 82°F, and evening lows to 66°F. Finish up your sightseeing early on the 15th (Wed) so you can travel to Assateague Island.
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Parks · Nature · Museums · Wineries
Side Trip

Assateague Island — 1 night

On the 16th (Thu), explore the wealth of natural beauty at Assateague Island National Seashore.

For traveler tips, other places to visit, photos, and tourist information, go to the Assateague Island planning tool.

Use the Route module to find suitable travel options from Crisfield to Assateague Island. June in Assateague Island sees daily highs of 79°F and lows of 65°F at night. Finish your sightseeing early on the 16th (Thu) so you can travel to Ocean City.
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Nature · Wildlife · Parks
Highlights from your trip

Ocean City — 7 nights

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.
Satisfy your inner culture vulture at Art League of Ocean City and Ward Museum of Wildfowl Art. You'll explore the less-touristy side of things at The Kite Loft and Globe Theater. Step out of Ocean City to go to Salisbury and see Pemberton Historical Park, which is approximately 52 minutes away. There's still lots to do: tour the pleasant surroundings at Ocean City Beach, immerse yourself in nature at Assateague State Park, find something for the whole family at Jolly Roger Amusement Park, and stroll around Northside Park.

To see reviews, where to stay, other places to visit, and tourist information, you can read our Ocean City trip planner.

Explore your travel options from Assateague Island to Ocean City with the Route module. In June in Ocean City, expect temperatures between 79°F during the day and 65°F at night. Finish up your sightseeing early on the 23rd (Thu) so you can travel to Chesapeake City.
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Parks · Outdoors · Museums · Shopping
Side Trips

Chesapeake City — 1 night

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. Start off your visit on the 24th (Fri): take an in-depth tour of C&D Canal Museum and then awaken your taste buds at M/V Bay Breeze of Chesapeake City.

For photos, maps, reviews, and other tourist information, go to the Chesapeake City online tour builder.

Traveling by car from Ocean City to Chesapeake City takes 2.5 hours. In June in Chesapeake City, expect temperatures between 82°F during the day and 63°F at night. Finish your sightseeing early on the 24th (Fri) so you can travel back home.
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Museums · Outdoors · Tours · Wineries