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5 Unique Date Ideas in Williamburg, VA: Beyond the Basics

Content may contain affiliate links. When you shop the links, we receive a small commission at no cost to you.


Looking for a unique and exciting date night? Williamsburg, Virginia has it all! From historical adventures to adrenaline-pumping activities, there’s something for every couple. Here are our top 5 must-do experiences, complete with locations and hours:

1. Sail into Sunset on the Jamestown Discovery Cruise

Location: Jamestown Settlement, 100 Visitor Center Dr, Jamestown, VA 23134 Hours: Daily, 10 AM – 5 PM (Sunset cruises depart at specific times, check the website for details)

Set the mood for a romantic evening with a sunset cruise on the Jamestown Discovery. Enjoy stunning views of the river, listen to great music, and test your knowledge with trivia. Even on a rainy day, this is a must-do experience. The owner and captain was so into the history and making sure we all have a fun trip.

2. Be Amazed by the Wagsters Magic Theatre

Location: The Wagsters Magic Theatre: 5535 Olde Towne Rd, Williamsburg, VA 23188, Hours: Wednesday & Saturdays (may change)

This family-friendly show is perfect for couples looking for a touch of magic. With mind-blowing tricks and a charming atmosphere, the Wagsters will leave you in awe. You can feel their love for each other coming off the stage which makes this a perfect place for a date because their love is contagious. 

3. Explore Yorktown on a Segway or E-Bike

Location: Patriot Tours and Provisions, 110 N Boundary St, Yorktown, VA 23690 Hours: Daily, 10 AM – 5 PM

Get active and explore the historic town of Yorktown on a Segway or E-Bike. Enjoy stunning views of the water, visit historical sites, and experience the charm of this coastal town. Don’t miss the Rhythm on the Riverwalk event for a night of dancing under the stars (during warmer months)

4. Challenge Your Partner at VR64

Location: 1010 High St, Williamsburg, VA 23185 Hours: Monday-Thursday: 12 PM – 10 PM, Friday-Saturday: 12 PM – 11 PM, Sunday: 12 PM – 9 PM

Have a blast with your partner at VR64, a virtual reality arcade with over 200 games to choose from. Compete against each other in thrilling simulations and create unforgettable memories. The owner was so nice and welcoming that it makes you want to visit again and again. Perfect for a rainy or hot date to stay dry and cool off!

5. Unleash Your Inner Child at Go Karts Plus

Location: 1200 High St, Williamsburg, VA 23185 Hours: Daily, 10 AM – 10 PM

Get your heart racing at Go Karts Plus, where you can enjoy go-kart racing, mini golf, arcade games, and even pool bumper boats. This is the perfect spot for a fun and competitive date night.

Bonus: Stay at the Wedmore Hotel Location:

1000 Winery Ln, Williamsburg, VA 23185 Hours: 24/7

For a truly romantic experience, stay at the Wedmore Hotel, a French-style mansion located on the grounds of Williamsburg Winery. Enjoy a luxurious bath, a delicious breakfast, and a cozy atmosphere.


No matter what your interests are, Williamsburg has something to offer. So grab your partner, explore this charming city, and create unforgettable memories together!

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