We knew it would be a challenge to top last year’s blogiversary prize, but this time we’re thrilled to offer an unforgettable adventure and luxury-filled Virginia vacation valued at about $3,000. The team behind Virginia tourism invited us to take part in a new series showcasing real Virginians, and they kindly featured our day trip to Virginia’s Eastern Shore. That visit was full of sun, sand, antiquing, fresh seafood, and even a paddling trip to a vineyard—so we worked with them to recreate that experience for one lucky winner and a guest from anywhere in the world.

This curated prize package covers round-trip airfare as well as a rental car, making travel to and around the Eastern Shore easy and relaxed. Accommodations include one night each at two historic and charming bed & breakfasts: The Inn at Onancock and Cape Charles House. Both inns capture the region’s coastal charm and offer a quiet, restorative place to return to after a day of exploring.

Food is a highlight on the Eastern Shore, so the prize includes meals at three waterfront restaurants known for serving fresh, locally sourced seafood. Spend evenings savoring the catch of the day while watching the sunset over the water, or enjoy a leisurely lunch after a morning exploring nearby towns and beaches.

The Eastern Shore is perfect for slow, low-key days, but this trip blends relaxation with a few memorable activities. One included experience is a Wine Kayak Tour led by experienced guides who will take you through gentle waterways to a tasting at Chatham Vineyards. Paddle at an unhurried pace, take in marshland views, and finish with a vineyard tasting that highlights local wines.

For a bigger adrenaline rush, the package also includes hang gliding for two with a professional operation in the area. If you want to get your heart racing and see the coastline from a unique perspective, this guided flight offers an unforgettable viewpoint and expert instruction.

We’re genuinely excited that one of our readers will get to enjoy this rich mix of history, food, relaxation, and adventure in our home state. The prize is open to anyone worldwide who is 18 years of age or older, and the trip can be redeemed within the next year. Because many of the activities are seasonal, you may prefer to schedule travel during warmer months when kayaking and vineyards are at their best.

To enter, please use the official giveaway entry form provided on this page. The form may take a moment to appear; please be patient while it loads. We’ve also started a conversation in our community forums for anyone who wants to share thoughts about the trip ideas or swap travel tips with other readers.

We aimed to assemble a prize that captures what we love about the Eastern Shore: uncrowded beaches, historic towns, excellent seafood, and a mix of calm and excitement. Whether you want to relax with a good meal overlooking the water, stroll through coastal towns hunting for antiques, paddle through serene waterways to a vineyard tasting, or soar above the shoreline, this package is designed to deliver a full and memorable Virginia experience.

If you have questions about the prize, eligibility, or scheduling, please check the rules and details provided in the entry form or contact the giveaway organizers directly. We can’t wait to hear from the winner and to see how you make the most of a quintessential Eastern Shore escape.