5 days in Coastal Virginia - Eastern Shore & Rockford Itinerary

Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.

On the 21st (Fri), visit a coastal fixture at Cape Henry Lighthouse, then stroll through Virginia Beach, and then take a leisurely stroll along Virginia Beach Boardwalk.

To find traveler tips, photos, and other tourist information, read Virginia Beach trip planner.

New York City to Virginia Beach is an approximately 4.5-hour flight. You can also drive; or take a bus. Expect a bit warmer weather when traveling from New York City in May: highs in Virginia Beach hover around 77°F, while lows dip to 60°F. Finish up your sightseeing early on the 21st (Fri) so you can go by car to 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.

Kids will appreciate attractions like Busch Gardens Williamsburg and Colonial Williamsburg. Next up on the itinerary: take an in-depth tour of Historic Jamestowne, stop by Whitley's Peanut Factory, and contemplate the long history of Jamestown Settlement.

To find more things to do, reviews, ratings, and other tourist information, refer to the Williamsburg road trip planning tool.

You can drive from Virginia Beach to Williamsburg in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, daytime highs in Williamsburg are 79°F, while nighttime lows are 59°F. Wrap up your sightseeing on the 24th (Mon) to allow time to travel to Rockford.

Rockford is the third largest city in the U.S. Kick off your visit on the 25th (Tue): explore the engaging exhibits at Discovery Center Museum and then admire the natural beauty at Anderson Japanese Gardens.

To see where to stay, more things to do, photos, and tourist information, refer to the Rockford vacation planner.

You can fly from Williamsburg to Rockford in 7.5 hours. Alternatively, you can drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 1 hour traveling from Williamsburg to Rockford. In May, Rockford is slightly colder than Williamsburg - with highs of 72°F and lows of 50°F. Finish up your sightseeing early on the 25th (Tue) so you can travel back home.