My boyfriend and I are planning a trip to Williamsburg (and maybe Jamestown) in late June. Will the weather be unbearable? It's the only time we're both able to go. Also, how long would it take us to drive from Williamsburg to the Shenandoah National Park? I've heard that's a beautiful area, but I'm not sure we can fit it in (we'll only have 5 - 6 days). How many days will we need in Williamsburg & Jamestown? If only 2 or 3, then (if it's not too far), maybe we could drive to the park for another 2 or 3 days. I don't want to overschedule, but I would like to do as much as we can in the time we have. Thanks!

Where are you returning to after Shenandoah NP? The northern entrance to Skyline Drive and the park is in Front Royal off I-66 176 miles, 3:15 hours from Wmsbg. The southern end of the drive is in Waynesborro, 143 miles, 2:25 hours from Wmsbg. off I-64.

I assume you are talking about the humidity. June will be a LOT better than July and if we end up with "dog days" in August the month of June will seem ideal.

You can use Google Maps for road distances but at least you can get to the Shenandoah or at least part of it by using I-64 West from Williamsburg and then onward.

I cannot help you with the "time needed" part but there will be others who can. I may be a faster traveler than you are..I like Williamsburg but a couple days would be more than enough for me; you might want to spend a whole week in the so-called 'historic triangle' and then there's the BEACH!!!!

have a great trip

We're flying into Richmond, so we'd have to return there on the last day.

What beach is nearby, Dukey? I hadn't given the beaches any real thought.

Virginia Beach is nearby. Shenandoah National Park is beautiful & you don't have to stay on the entire Skyline Drive. You can get off whenever your schedule permits. We stayed at Big Meadows Lodge about 10 years ago. Personally, I think you only need one day at Williamsburg; then perhaps one day for both Jamestown and Yorktown. Are you interested in Busch Gardens? One option would be to spend your entire 5-6 days in the historic triangle, as Dukey suggests, which would include Colonial Williamsburg, Jamestown, Yorktown, Busch Gardens & Virginia Beach. I think there is also a water park near Busch Gardens if that interests you.

OR your other doable option would be 2 days at Williamsburg, Jamestown & Yorktown, then drive to Shenandoah.

I think June is fine. We have spent many vacations in DC & Virginia during June, July & August. June would be better than July or August. The heat is tolerable.

We did a similar vacation to what you're describing last Fall.
We spent two days/nights at Williamsburg (stayed at the Lodge and really enjoyed it). Got up early, drove west to Charlottesville and visited Michie Tavern and another Presidential home. Stayed the night at The Inn at Monticello (very relaxing/close to Monticello). Visited Monticello the next morning, left around noon, drove Skyline Drive to our next stop at Skyline Lodge (one of two lodges available in park). We had plenty time to arrive in time for dinner. On our trip the next day we turned off the Parkway and continued to Fredricksburg, where we spent the day at Civil War battlefields. We stayed the evening at The Kenmore Inn (historical B&B) - VERY relaxing, with one of the best seafood meals we have had in awhile! (Restaurant on-site).
The next morning we browsed antique shops before going back to Richmond - stayed the night at the new Hyatt Place near the airport for the next morning's early flight out.
We were looking for a relaxing driving trip - it was very nice and we didn't feel rushed - but there is more than enough to see/do in the Williamsburg/Yorktown area alone.
It all depends on what your interests are.