Looking for an incredible itinerary for a fun-filled, scenic Virginia weekend getaway?
I have the perfect weekend getaway itinerary for you – full of cave explorations, American history, gorgeous views and delicious wine!
So if any, or all of this sounds like your cup of tea (or glass of wine) then check out this perfect two-day itinerary!
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Day One
Visit Skyline Caverns
Beginning our itinerary in Front Royal, Virginia, you’ll find Skyline Caverns.
Skyline Caverns is, you guessed it, located on Skyline Drive in the Shenandoah National Park.
Discovered in 1937 by geologist Walter S. Amos, the caverns are millions of years old.
They are home to the oldest known examples of anthodites in the world. The largest known anthodite known as The Chandelier, measures 18″ long.
If you’re a geologist you may find that incredibly interesting. I’m not, but I did find the caverns to be beautiful all the same.
The kids enjoyed the tour as well and the caverns ended up being one of the top 5 things they enjoyed most on our trip.
We chose to visit Skyline Caverns over the more touristy Luray Caverns on the basis of other internet reviews that said the Skyline Caverns are more interesting, less crowded, less commercialized, and have a more authentic feel with its no-frills approach.
Allow about an hour to explore the caverns via a guided tour and also be sure to bring a light jacket or sweatshirt as it’s a relatively cool 54 degrees inside.
Tickets for the tour can be purchased at the caverns and you’ll find a coupon for $2 off per adult on their website here.
If you enjoy exploring underground caverns, consider visiting Carlsbad Caverns in New Mexico. Find out more about these beautiful caves in my Southwestern National Park Road Trip Itinerary here.
Drive Along Skyline Drive in Shenandoah National Park
Upon leaving Skyline Caverns, take the opportunity to explore Skyline Drive, the absolutely gorgeous road that takes you through the heart of Shenandoah National Park.
The two-lane road follows the mountaintops along the Blue Ridge Mountains and was made a National Scenic Byway in 2005.
Skyline Drive begins in Front Royal and extends 105 miles south to Rockfish Gap.
The drive itself takes about 3 hours with a maximum speed limit of only 35mph.
There are 75 overlooks that give you plenty of opportunity to pull over and enjoy the views. So be sure to take lots of pictures!
For more information on experiencing Shenandoah National Park, check out Six Ways to Explore Shenandoah National Park here.
If you’re visiting in the summer months, consider staying the night in one of Shenandoah’s three park lodges. You can make reservations and find out more here.
The park lodges are closed from November to April so if you’re visiting during that timeframe, consider staying the night in one of Charlottesville’s many beautiful hotels. Check out your options here.
Charlottesville is only about a thirty minute drive east from where Skyline Drive meets Interstate 64, making it a great option for both dining and accommodations.
Day Two
Visit Thomas Jefferson’s Monticello
For day two of this incredible itinerary for an epic Virginia weekend getaway, start off by visiting Thomas Jefferson’s Monticello estate.
Park at the visitor’s center (it’s free) and either make the 1/2 mile trek up to the main house, or take the shuttle that runs every couple of minutes.
You do need to make reservations and these can be made online here.
There are a variety of tour passes available depending on what you want to see.
We chose the self-guided tour through the grounds and the first floor of the house.
I would have loved to visit the upstairs, but time and cost prevented it this trip.
However, if you are a huge history buff, I would definitely recommend booking the Behind the Scenes Day Pass that gives you guided tour access to the second and third stories of the house.
When you’re done with the tour, make sure to stop in the souvenir shop at the visitor center.
They have tons of great items and we thought the prices were very reasonable. They also have a great selection of local wines available as well!
Helpful Tips:
1. Make sure you visit the covered tent at the main house for your pre-house tour introduction. We discovered that you must be part of a group formed at the tent area in order to gain access to your house tour time.
2. Make sure your phone is well-charged before entering the house as each room has a Q-code placard you can scan with your phone that will tell you everything you need to know about what you are seeing in each room. As the self-guided tour is just that, self-guided, this brings what you are seeing to life and makes the tour that much more informative.
3. You are encouraged to take all the photos and videos you like (just no flash) and there are also volunteers stationed in each room if you have questions.
Visit James Monroe’s Highland Estate
Just down the road from Monticello you’ll find another home of a past American president.
Thomas Jefferson convinced his close friend James Monroe to purchase acreage next to his Monticello estate.
Monroe ended up purchasing about 3,500 acres for the estate he named Highland where he, his wife Elizabeth and their two daughters resided for the greater part of twenty-five years.
Today, the estate encompasses about 500 acres and both self-guided and private tours of the house and grounds are available.
Check here for times and ticket prices.
While a much smaller estate than Monticello, it is nonetheless beautiful and worth a visit if you have the time.
End the Day Relaxing at Trump Winery
Ten minutes from James Monroe’s Highland is one of the most beautiful wineries along the Monticello Wine Trail.
Trump Winery is one of 23 wineries on the MWT and also the largest in Virginia.
Follow the long, winding drive up to the Tasting Room where you’ll find great wine and delicious dining options.
The prices are reasonable and we particularly enjoyed the wine flights, a cheese charcuterie board, and even some delicious caviar!
The winery has produced some outstanding wines that have subsequently won several prestigious awards.
The views of the Blue Ridge Mountains from the Tasting Room are gorgeous and we found the the staff to be very friendly, helpful and informative.
If you want to pamper yourself, consider spending the night at the luxurious Albemarle Estate at Trump Winery, a beautiful 26,000 sq. ft. mansion on the property guaranteed to take your breath away.
Enjoying a glass (or two!) of delicious wine accompanied by amazing appetizers was a great way to wind down after a long day of sightseeing and exploring.
Who wouldn’t want to relax while enjoying views like this?
This incredible itinerary for a Virginia weekend getaway is a great way to experience some of the best sights Virginia has to offer.
From the rainbow lit Skyline Caverns to the amazing views along Skyline Drive and the Shenandoah National Park to the historic Monticello and Highland estates and ending at Trump Winery, there’s something for everyone to enjoy.
So get out there and travel! Experience life and embrace your inner dragonfly!
Looking for other unique road trip ideas? Check out these 5 Best Things To Do In Massachusetts.
And if you enjoy hunting or want to try it, Virginia is a great place to do so. Check out my Reasons for Hunting and Why You Should Hunt Too here.
