6 days in Williamsburg, Gwynn & Chesapeake Bay Itinerary

6 days in Williamsburg, Gwynn & Chesapeake Bay Itinerary

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Route & dates

6 days in Williamsburg, Gwynn & Chesapeake Bay Itinerary

Start: Mobile
Fly:  6​h 45​min
1
Williamsburg
— 1 night
Drive:  1​h
2
Gwynn
— 1 night
Drive:  45​min
3
Gloucester
— 3 nights
Drive + Fly:  7​h 30​min
End: Mobile

1
night
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
Your day-by-day itinerary now includes Colonial Williamsburg. Start off your visit on the 22nd (Fri): step aboard Jamestown Settlement, then steep yourself in history at Colonial Williamsburg, then pause for some serene contemplation at Bruton Parish Episcopal Church, and finally have some family-friendly fun at Bounce House & Laser Tag. Get ready for a full day of sightseeing on the 23rd (Sat): witness the site of a historic battle at Yorktown Battlefield and then make a splash at Water Country USA.

To find more things to do, where to stay, and more tourist information, refer to the Williamsburg trip itinerary planning tool .

Mobile to Williamsburg is an approximately 7-hour flight. You can also do a combination of car and flight; or drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Plan for little chillier nights when traveling from Mobile in May since evenings lows in Williamsburg dip to 59°F. Finish your sightseeing early on the 23rd (Sat) to allow enough time to travel to Gwynn.

Things to do in Williamsburg

Historic Sites Theme Parks Museums

Side Trip

Yorktown Battlefield
Highlights from your plan
Water Country USA ©
Water Country USA
Jamestown Settlement ©
Jamestown Settlement
Bounce House & Laser Tag ©
Bounce House & Laser Tag

1
night
Gwynn

Gwynn ©
Chesapeake Bay has been added to your itinerary. Start off your visit on the 24th (Sun): see the interesting displays at Gwynn's Island Musuem and then explore the activities along Chesapeake Bay.

To see reviews, photos, ratings, and other tourist information, read our Gwynn online holiday planner .

Traveling by car from Williamsburg to Gwynn takes 1.5 hours. In May in Gwynn, expect temperatures between 77°F during the day and 57°F at night. Wrap up your sightseeing on the 24th (Sun) early enough to travel to Gloucester.

Things to do in Gwynn

Nature Parks Museums

Side Trip

Chesapeake Bay
Highlights from your plan
Chesapeake Bay ©
Chesapeake Bay
Gwynn's Island Musuem ©
Gwynn's Island Musuem

3
nights
Gloucester

Gloucester ©
Gloucester Courthouse is a census-designated place (CDP) in and the county seat of Gloucester County, Virginia, United States. Explore the numerous day-trip ideas around Gloucester: Colonial Beach (George Washington Birthplace National Monument & Westmoreland State Park) and Stratford Hall (in Stratford). There's lots more to do: trek along Beaverdam Park, make a trip to Riverwalk Landing, steep yourself in history at Rosewell Ruins, and explore the wealth of natural beauty at Colonial National Historical Park.

To see photos, traveler tips, where to stay, and tourist information, go to the Gloucester trip builder website .

Gloucester is just a stone's throw from Gwynn. In May, plan for daily highs up to 77°F, and evening lows to 57°F. Finish up your sightseeing early on the 27th (Wed) so you can travel back home.

Things to do in Gloucester

Parks Nature Historic Sites

Side Trips

Colonial Beach, Yorktown, Stratford Hall
Highlights from your plan
Westmoreland State Park ©
Westmoreland State Park
Colonial National Historical Park ©
Colonial National Historical Park
Beaverdam Park ©
Beaverdam Park