15 days in Eastern Shore Itinerary

15 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore journey planner

©
Plan created by another user. Make it yours

Route & dates

1
Ocean City
— 6 nights
2
Crisfield
— 1 night
3
St. Michaels
— 3 nights
4
Stevensville, Kent Island
— 2 nights
5
Rising Sun
— 2 nights

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.
You'll explore the less-touristy side of things at Ocean City Screams Haunted House and Oceancity Watersports. Explore the numerous day-trip ideas around Ocean City: Salisbury (Salisbury Zoo, Ward Museum of Wildfowl Art, &more). Next up on the itinerary: stop by The Kite Loft, enjoy the sand and surf at Ocean City Beach, play a few rounds at Lost Treasure Golf, and examine the collection at Ocean City Life-Saving Station Museum.

To see reviews, more things to do, traveler tips, and more tourist information, read Ocean City trip planning tool.

Prague, Czech Republic to Ocean City is an approximately 18.5-hour combination of flight and car. Traveling from Prague to Ocean City, you'll gain 6 hours due to the time zone difference. Traveling from Prague in June, expect Ocean City to be a bit warmer, temps between °C and °C. Finish your sightseeing early on the 15th (Mon) so you can drive to Crisfield.

Things to do in Ocean City

Parks Theme Parks Outdoors

Side Trips

Salisbury, Berlin
Highlights from your plan
Ocean City Boardwalk ©
Ocean City Boardwalk
Ocean City Screams Haunted House ©
Ocean City Screams Haunted House
The Kite Loft ©
The Kite Loft

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 16th (Tue): examine the collection at Crisfield Heritage Foundation, thenimmerse yourself in nature at Janes Island State Park, and then take in the waterfront activity at Somers Cove Marina.

To see maps, reviews, more things to do, and more tourist information, refer to the Crisfield trip maker site.

Traveling by car from Ocean City to Crisfield takes 1.5 hours. June in Crisfield sees daily highs of °C and lows of °C at night. Wrap up your sightseeing on the 16th (Tue) to allow time to drive to St. Michaels.

Things to do in Crisfield

Parks Nature Museums
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Somers Cove Marina ©
Somers Cove Marina
Crisfield Heritage Foundation ©
Crisfield Heritage Foundation

3
nights
St. Michaels

St. Michaels ©
You'll discover tucked-away gems like 1879 Hooper Strait Lighthouse and Olivins. Explore St. Michaels' surroundings by going to Historical Society of Kent County (in Chestertown) and Cambridge (Choptank River Lighthouse & Blackwater National Wildlife Refuge).

To find traveler tips, ratings, and more tourist information, use the St. Michaels trip itinerary app.

Traveling by car from Crisfield to St. Michaels takes 2 hours. In June, daytime highs in St. Michaels are °C, while nighttime lows are °C. Wrap up your sightseeing on the 19th (Fri) early enough to travel to Stevensville.

Things to do in St. Michaels

Museums Breweries & Distilleries Tours

Side Trips

Cambridge, Historical Society of Kent County, Academy Art Museum, Boat Tours & Water Sports, The Oxford Museum
Highlights from your plan
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse
Lyon Rum Distillery & Tasting Room ©
Lyon Rum Distillery & Tasting Room
Choptank River Lighthouse ©
Choptank River Lighthouse

2
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. Kick off your visit on the 20th (Sat): enjoy the sand and surf at Matapeake Clubhouse and Beach, do a tasting at Mark Cascia Vineyards, thenbrush up on your knowledge of spirits at Blackwater Distilling & Tavern, and finally tour the pleasant surroundings at Terrapin Beach Park. Get ready for a full day of sightseeing on the next day: get outside with Lead Dog Charters, thenget outside with Casey Michelle Charters, and then head outdoors with Breezin' Thru Charters.

To see ratings, where to stay, maps, and tourist information, refer to the Stevensville travel route planning tool.

Travel from St. Michaels to Stevensville in an hour. In June, daytime highs in Stevensville are °C, while nighttime lows are °C. Wrap up your sightseeing on the 21st (Sun) early enough to travel to Rising Sun.

Things to do in Stevensville

Outdoors Parks Trails
Highlights from your plan
Mark Cascia Vineyards ©
Mark Cascia Vineyards
Blackwater Distilling & Tavern ©
Blackwater Distilling & Tavern

2
nights
Rising Sun

Rising Sun ©
Rising Sun is a town in Cecil County, Maryland, United States. On the 22nd (Mon), try to win big at Hollywood Casino, get to know the resident critters at Plumpton Park Zoo, and then learn about winemaking at Dove Valley Winery.

To see ratings, maps, and tourist information, you can read our Rising Sun visit website.

Travel from Stevensville to Rising Sun in 2 hours. In June, daily temperatures in Rising Sun can reach °C, while at night they dip to °C. Finish your sightseeing early on the 23rd (Tue) so you can travel back home.

Things to do in Rising Sun

Casinos Wineries Parks

Side Trip

Hollywood Casino
Highlights from your plan
Hollywood Casino ©
Hollywood Casino
Plumpton Park Zoo ©
Plumpton Park Zoo
Dove Valley Winery ©
Dove Valley Winery