Discover the charm, the culture, and the captivating experiences that await in Charlottesville. Charlottesville holds the charm of a small Town but offers both city experiences and countryside activities. Here at Charlottesville Insider we’ve curated a list of our most enjoyable experiences for both visitors and residents alike. Whether you are seeking adventure, relaxation, historical tours, experiences the culture and arts or something new we’ve got you covered. Book with us today and let us guide you through the enchanting tapestry of Charlottesville, ensuring you create memories that will last a lifetime.

Wine Tour: The Sprinter Shuttle

Chauffeured private 5 hour wine/brewery tour for Group up to 14 Passengers (ability to add additional hours)

Day Tickets to the Looking Glass

Virginia’s first Immersive art space featuring a whimsical enchanted forest and kaleidoscopic cave. Experience the wonderland for yourself.

The Glass Palette

Come and experience this interactive glass art studio. Pick your desired art piece before you get to work cutting and placing the glass as you see fit. The owners are extremely helpful and ready assist.

River Tubing with the Rivanna River Co.

A fun, easy float down the Rivanna River is a great way to cool off on a hot summer day. Explore calm waters and rapids, riverside beaches and scenic views.

Vehicle Rental: 2023 Jeep Wrangler w/ Soft Top

This 2023 4 Door Jeep Wrangler is a robust and stylish vehicle perfect for adventure-seekers and daily commuters alike.

Helicopter Tours

With Skyline Heli, you can experience Charlottesville like never before! Take a helicopter ride and witness breathtaking views of local attractions that include historic sites, Virginia's vineyards, and the Blue Ridge Mountains. Operations are conducted at the Charlottesville- Albemarle Airport.

Vehicle Rental: Chevrolet Tahoe LT

Drive in comfort and style with the 2022 Chevrolet Diesel Tahoe 4x4 with Panoramic Sunroof.

Wine Tour: Mercedes Sprinter Van - 14 Passenger

Chauffeured private 5 hour wine/brewery tour for group up to 14 Passengers (ability to add additional hours)

Wine Tour: Mercedes Sprinter Van - 11 Passenger

Chauffeured private 5 hour wine/brewery tour for Group up to 11 Passengers (ability to add additional hours)

Vehicle Rental: 2024 Mercedes GLE 450

The 2024 GLE 450 4MATIC is a comfortable and luxurious SUV that offers a smooth and quiet ride.

Wine Tour: Luxury Suburban w/ Panoramic Sunroof

Chauffeured private 5 hour wine/brewery tour for Group up to 6 Passengers (ability to add additional hours)

Meridian Air Group

Meridian Air Group is a full-service aviation company dedicated to providing a professional and personal travel experience second to none. Based in Charlottesville, Virginia, they are able to serve Central and Northern Virginia, along with the Greater DC area.

The Fralin Museum

The Fralin Museum at UVA features diverse, compelling exhibitions from around the world, along with community programs and events. Admission is always free; donations are welcome.

Sunrise flight

Enjoy a memorable early morning balloon ride followed by the traditional toast. The ultimate way to begin a day to remember.

Private flight

A more intimate experience, the guaranteed flight for two (plus the pilot of course!) is a natural choice. A wonderful way to celebrate your anniversary or special occasion.

River Cruise

Begin by traveling upriver hearing the story of the batteau and batteaumen’s legacy in Virginia. At the halfway point the signature charcuterie boards are served and swimming is optional. Book to celebrate the long history of community on the James River.

Arts Festival at the Ix Park. May 25th & 26th 2024

Enjoy fine and visual arts, immersive art experiences and interactive artist demonstrations and workshops.

Farm to Batteau

A collaboration with local Chef Sarah Rennie of Two Fire Table and the James River Batteau Co. Get ready for an open fire, family-style, farm to table dinner out on America’s Founding River. This experience showcases the agricultural and historical richness of the local area, against the backdrop of the golden hour on the James River.

Romance Package

The ultimate all-inclusive experience for two (plus pilot). Perfect for a proposal or showing your loved one how special they are to you.

The Kluge-Ruhe Aboriginal Art Collection of the University of Virginia

The Kluge-Ruhe Aboriginal Art Collection of the University of Virginia is the only museum outside of Australia dedicated to the exhibition and study of indigenous Australian art. Complimentary 30 tours are offered, pre-registration required.

Paddling Trips with Rivanna River Co.

Enjoy the great outdoors by canoe or kayak. There are multiple beautiful location around Charlottesville for you to explore.

Sunset Cruise

Prior to dusk travel upriver listening to tales from the bygone era of batteaux. At the halfway point anchor to begin food and music, celebrate a time honored river tradition. As the last of the daylight fades the float back to shore begins.

The Virginia Discovery Museum

The Virginia Discovery Museum is a small, nonprofit children's museum for families with infants to kids age 8. VDM seeks to foster intellectual curiosity and development for all children in our community through hands-on educational, exploratory, and imaginative play across 6,000 square feet of exhibit space.