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Date Night Ideas in Williamsburg, VA

Romantic Dinner at Fat Canary

Enjoy a delicious dinner at Fat Canary, one of Williamsburg’s most popular fine dining restaurants. Indulge in gourmet dishes and a curated wine selection in an intimate and romantic setting. After dinner, take a stroll through the historic streets of Williamsburg, hand in hand.

Alternative options: Second Street Bistro, Blue Talon Bistro

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Wine Tasting at Williamsburg Winery

Sip on award-winning wines at Williamsburg Winery, located just a short drive from the city center. Take a tour of the vineyards and enjoy a tasting of their signature wines. Relax on the picturesque grounds and soak in the peaceful atmosphere.

Alternative options: Saude Creek Vineyards, New Kent Winery

Ghost Tour in Colonial Williamsburg

Embark on a spooky ghost tour in Colonial Williamsburg and learn about the city’s haunted history. Walk through the historic streets by lantern light and listen to chilling tales of ghosts and paranormal activity. This thrilling experience is sure to keep you on the edge of your seat.

Alternative options: Spooks and Legends Haunted Tours, Williamsburg Colonial Ghost Tours

Kayaking on the James River

Rent a kayak and explore the scenic James River with your partner. Paddle along the calm waters, take in the beautiful views, and enjoy some quality time together in nature. Pack a picnic lunch to enjoy on the riverbank for a romantic touch.

Alternative options: Adventure Kayak Tours, Chesapean Outdoors

Live Music at Berret’s Seafood Restaurant and Taphouse Grill

Catch a live music performance at Berret’s Seafood Restaurant and Taphouse Grill while enjoying fresh seafood and drinks. Sit back, relax, and listen to talented local musicians as you unwind after a long week.

Alternative options: Hound’s Tale, DoG Street Pub

Date Night Ideas in Williamsburg, VA

Painting Class at All Hands Workshops

Get creative with your partner at All Hands Workshops by taking a painting class together. Explore your artistic side as you paint, sip wine, and enjoy each other’s company in a laid-back and fun atmosphere.

Alternative options: Paint on Pottery, Wine and Design

Movie Night at Kimball Theatre

Enjoy a classic movie date night at Kimball Theatre, where you can catch a screening of a popular film while snuggling up with your loved one. Get some popcorn and candy, and transport yourselves to a different world for a few hours.

Alternative options: Regal New Town Cinema, Movie Tavern Williamsburg

Couples Massage at Spa of Colonial Williamsburg

Relax and unwind with a couples massage at the Spa of Colonial Williamsburg. Treat yourselves to a luxurious spa experience, complete with soothing massages and pampering treatments. Leave feeling rejuvenated and refreshed.

Alternative options: The Flowering Almond Spa, The Williamsburg Salt Spa

Stargazing at York River State Park

Head to York River State Park for a romantic evening of stargazing with your partner. Pack a blanket and a thermos of hot chocolate, and spend the night marveling at the twinkling stars above. Share stories and enjoy the peaceful ambiance of the great outdoors.

Alternative options: Jamestown Island, Freedom Park

Dance Class at 7 Cities Ballroom

Put on your dancing shoes and take a ballroom dance class at 7 Cities Ballroom. Learn new moves, laugh together, and experience the joy of dancing with your partner. Whether you’re a beginner or a seasoned dancer, this activity is sure to bring you closer.

Alternative options: Dance Artistry Unlimited, Mambo Room

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Frequently Asked Questions

Use Wyndy, a trusted babysitting platform that connects parents with local, experienced sitters. Simply create an account, browse available sitters, and book your preferred sitter for the evening.

Consider hiring a sitter through Wyndy and enjoying an adults-only evening out. However, if you're looking for family-friendly activities, Colonial Williamsburg, Busch Gardens Williamsburg, and the Virginia Living Museum are great options for a fun day out with the kids.

With Wyndy, you can browse available sitters in real-time and book a sitter for the same day if needed. Simply check the app for sitters in your area and choose one that fits your schedule.

Babysitting rates vary depending on the sitter's experience, location, and the number of children to be cared for. You can view each sitter's rate on their profile when booking through the Wyndy app.

Wyndy occasionally offers promotions and discounts for booking sitters through the app. Check the Wyndy website or app for any current deals or offers when booking your date night sitter.