The 25 Best Romantic Things To Do In Charlottesville, Virginia

Right in the heart of Virginia, Charlottesville is this perfect mix of history, nature, and charming vibes. If you’re a local looking to spice things up or a couple just checking out the scene, Charlottesville has a bunch of romantic things to do for every taste. 

My husband and I grew up an hour from Charlottesville and spent many weekends traveling to the city for its fantastic views and endless things to do.

We even tied the knot in Charlottesville due to its stunning views of the Blue Ridge Mountains, central location, and abundance of unique experiences you can embark on throughout the city. 

So, in this guide, I’m going to pinpoint the ultimate romantic things to do in Charlottesville, VA each one a chance to make your own unforgettable moments against the backdrop of this awesome city.

1. Take A Ride Down Skyline Drive

Taking a drive down Skyline Drive isn’t just a scenic road trip, it’s a romantic adventure where you discover breathtaking views at every turn. 

The calm beauty of the Blue Ridge Mountains sets the stage for intimate moments, making it a perfect getaway for couples wanting to connect with nature and each other.

We love going on scenic road trips and Skyline Drive is one of the best in Virginia thanks to its fantastic mountain views.

2. Appreciate A Tasting At Trump Winery

Enjoying a wine tasting at Trump Winery is a classy experience crafted for couples who enjoy a touch of sophistication. 

Surrounded by scenic vineyards, explore a variety of exquisite wines, turning each sip into a shared memory. The pleasant atmosphere and top-notch wine quality make this tasting a delightful outing for those who appreciate life’s finer pleasures.

I’ve attended multiple weddings for family and friends at Trump Winery, making it a sought-after venue in central Virginia, primarily due to its romantic atmosphere. 

If you’re searching for a lovely spot to enjoy wines, I highly recommend this winery for its delightful beverages and unforgettable setting.

3. Go For A Hike

Taking a hike to explore the natural wonders around Charlottesville is a romantic activity for outdoorsy folks. 

Whether you’re walking the trails at Carter Mountain Orchard or catching the sunset at Walnut Creek Park, it turns into a shared adventure that brings you closer together while appreciating the beauty of Virginia’s landscapes.

Going on a hike is a go-to date for Sam and me. We hiked on our very first date and again when Sam popped the question. It’s the perfect way to step outside, soak in nature, and have both fun and meaningful conversations along the way.

4. Visit Carter Mountain Orchard

Carter Mountain Orchard is more than just a place to pick fruit; it’s a romantic spot where couples can soak in the orchard’s charm, savor seasonal treats, and enjoy the scenic groves.

Sam and I enjoyed a couple of hours at Carter Mountain Orchard in the fall, picking apples to bake a homemade apple pie. It stands out as one of our favorite dates in Charlottesville because it was a unique and memorable experience.

If you are looking for romantic things to do in Charlottesville VA and want something that is a bit more special and not so common, don’t hesitate to make your way to the orchard for a fun time.

5. Spend An Afternoon At Pippin Hill Farm & Vineyards

Pippin Hill Farm & Vineyards is a lovely countryside retreat. Couples can enjoy a relaxed afternoon with beautiful views, delicious wines, and farm-to-table food. The rolling hills and charming atmosphere make it a perfect spot for a romantic date. 

We’ve been there multiple times and even had our rehearsal dinner there, making it a special place for us.

6. Enjoy A Hot Air Balloon Ride

A hot air balloon ride over Charlottesville elevates romance to new heights, literally. Soaring above the city and countryside, couples can share the thrill of adventure and take in panoramic views, creating an unforgettable memory etched against the backdrop of the Virginia sky.

A hot air balloon ride might not be the most budget-friendly choice, making it perfect for special occasions like birthdays, anniversaries, or perhaps even a proposal. However, if you’re in the mood for an extravagant date on any ordinary day, this is still an excellent option. 

Being whisked away in a hot air balloon is a rare experience, and the gorgeous Charlottesville scenery adds a touch of magic to the whole adventure.

7. Stroll Through The Downtown Mall

Charlottesville’s Downtown Mall turns into a delightful spot for romantic moments. Couples can wander through historic streets, check out unique shops, and soak in the lively atmosphere with street performers and cafes. It’s a perfect setting for a casual and intimate date.

8. Walk Around James Monroe’s Highland

Formerly owned by James Monroe, a Founding Father and the 5th President of the United States, this stunning estate offers a beautiful setting to explore and enjoy the views. 

It’s an excellent opportunity to delve into history. If you’re on the lookout for romantic activities in Charlottesville VA, with a touch of history on your date, this is the perfect choice.

9. Take A Guided Tour Of Monticello

Monticello, once home to Thomas Jefferson, gives you a captivating peek into history. Taking a guided tour turns into a romantic journey through time, letting couples explore the impressive architecture and discover the legacy of one of America’s Founding Fathers.

10. Go On A Picnic

A simple yet classic romantic idea, a picnic in Charlottesville’s scenic parks or vineyards lets couples enjoy tasty bites, share conversations, and soak in the natural beauty around them.

11. Spend Time At The Lovingston Winery Tasting Room

The Lovingston Winery Tasting Room invites wine enthusiasts for a refined tasting experience. Tucked in Virginia’s wine country, it’s a cozy spot for couples to appreciate great wines and each other’s company.

12. Enjoy A Sunset At Walnut Creek Park

As the day winds down, Walnut Creek Park offers a serene setting for couples to take in a breathtaking sunset. The calm waters and peaceful atmosphere make it a perfect spot for a romantic date in Charlottesville. 

As two people who love breathtaking sunsets, we can attest to how amazing it is to enjoy a beautiful and enjoyable date by watching the sun go down.

13. Appreciate A Sunset Tasting At Jefferson Vineyards

Jefferson Vineyards, with its lovely setting, welcomes couples to enjoy a sunset wine tasting. The beautiful colors of the setting sun, combined with exceptional wines, set a romantic atmosphere for a delightful evening of shared enjoyment.

14. Go On A Brewery Tour

For couples who love craft brews, a brewery tour in Charlottesville offers a laid-back and enjoyable experience. Exploring local breweries, trying unique flavors, and soaking in the casual atmosphere make it a delightful and relaxed date option.

Sam and I are big fans of craft beer and have enjoyed a brewery tour together. We can definitely say it’s a fun date idea. 

While a group beer tour might not scream romance initially, it’s a unique way to try something different with your significant other, turning the whole experience into a memorable and enjoyable time.

15. Spend Time At The Charlottesville Opera

Dive into Charlottesville’s cultural scene by catching a show at the Charlottesville Opera. The beautiful melodies and captivating performances create an atmosphere of refined romance, making it an ideal date night for those who love the arts.

16. Relax At Keswick Hall During A Spa Day

Keswick Hall offers a luxurious retreat for couples seeking relaxation and rejuvenation. A spa day at this luxurious venue provides a peaceful escape, allowing couples to unwind in a chill environment. 

This is the perfect opportunity to get pampered together and it brings out a sense of connection as you both relax.  Sam and I have tried out a couple of spas, and every time, we walk away feeling more relaxed and less tense. 

It’s also a great chance to have some uninterrupted conversations, away from distractions like work, phones, and other people.

17. Go Stargazing At Ivy Creek Natural Area

For a romantic night under the stars, Ivy Creek Natural Area is a perfect spot for stargazing. 

The open skies and peaceful surroundings make it a magical setting for couples. It’s one of the top romantic things to do in Charlottesville VA, if you want to escape the city lights and hustle and bustle. 

18. Spend Time At A Bed & Breakfast

Opting for a stay at one of Charlottesville’s charming bed and breakfasts adds a cozy touch to your romantic getaway. 

The intimate atmosphere and personalized service create a home away from home, enhancing the overall experience of your time together.

19. Attend The Sunset Series At Carter Mountain Orchard

The Sunset Series at Carter Mountain Orchard turns evenings into magical moments. Live music, tasty treats, and the setting sun provide an enchanting vibe for couples to enjoy each other’s company in a lively yet romantic setting.

20. Enjoy A Movie At The Virginia Film Festival

For film-loving couples, the Virginia Film Festival offers a unique cinematic experience. Attending screenings and discussions together provides an opportunity to share in the excitement of the arts and create lasting memories surrounded by fellow film fans.

21. Attend A Sporting Event At The University Of Virginia

If you enjoy the thrill of sports, attending a sporting event at the University of Virginia becomes a spirited date option. 

The energetic atmosphere of a game or match adds a dynamic element to your time together, creating shared memories filled with excitement. As avid sports fans, we can vouch for what a fun date attending a live sporting event is. 

22. Go Horseback Riding

Go on a romantic adventure by riding horses in the scenic countryside. Many local stables give couples the chance to enjoy a relaxed trail ride, fostering a connection with nature and each other.

Sam and I went horseback riding on our honeymoon and it remains one of our favorite dates and memories. There’s something so unique about the whole experience and the views are truly remarkable as you make your way around scenic landscapes while riding on the back of a horse.

23. Appreciate Art At The C’Ville Arts Cooperative Gallery

Couples with an appreciation for the arts can explore the vibrant local art scene at the C’Ville Arts Cooperative Gallery. The diverse artworks created by talented local artists are always impressive to see. 

The atmosphere provides an opportunity for a  unique and romantic date option. Plus, it’s a great way to support local businesses. 

24. Take A Date Night Cooking Class

Spice up your culinary skills together by taking a date night cooking class. The Happy Cook offers an opportunity for couples to bond over the art of cooking, creating a delicious meal under the guidance of experienced chefs.

It’s one of the most romantic things to do in Charlottesville VA and sure to make a memorable date.

25. Grab A Bite To Eat At The Melting Pot

Finish off your romantic outing at The Melting Pot, offering a cozy and intimate setting for a delightful meal. Enjoy a fondue experience, savoring various flavors in a warm and inviting atmosphere, the perfect way to wrap up a day of shared experiences.

Although the Melting Pot is a chain restaurant, it’s one of my very favorites. I love going to the Melting Pot for a fun date night or birthday celebration. It’s not your typical steakhouse, or Italian restaurant, it’s more of an experience and it’s a fun way to end an exciting day.

What’s Your Favorite Romantic Thing To Do In Charlottesville VA?

Tell us all about it in the comments!