We knew it would be hard to top last blogiversary’s prize of $2,500 in swag, but this year we managed to secure an adventure- and luxury-filled Virginia vacation worth an estimated $3,000 for one lucky reader. Virginia’s tourism team reached out to profile us as part of a series highlighting real Virginians, and during our own day trip to the Eastern Shore we fell in love with the quiet beaches, antique shops, fresh seafood, and the unexpected thrill of paddling by kayak to a vineyard. Now, the trip we enjoyed is being offered as a prize for one winner and a guest from anywhere in the world—complete with travel, charming accommodations, meals, and a couple of memorable experiences.
The package covers round-trip airfare and a car rental, so you can arrive and explore the Eastern Shore with ease. Accommodations include one night each at two historic, charming bed & breakfasts: The Inn at Onancock and Cape Charles House. Both inns capture the relaxed, small-town character of the region and offer a comfortable base for beach strolls, antique-hunting, and easy access to local attractions.
Dining is a highlight of any coastal getaway, and this prize includes a meal at three waterfront restaurants known for serving fresh, locally harvested seafood. You’ll be able to sample regional specialties while enjoying views of the water and the peaceful rhythms of a seaside town. These meals are a great way to taste the Eastern Shore’s culinary scene, from laid-back lunch spots to relaxed, sunset-ready dinners.
While the Eastern Shore is ideal for slowing down and soaking up the scenery, this package balances relaxation with a couple of activities to make the trip unforgettable. One experience is a Wine Kayak Tour, where local guides lead small groups through calm waterways and land at Chatham Vineyards for a tasting. It’s a serene yet engaging way to connect with the landscape, paddle at a gentle pace, and enjoy local wine in a setting you can only reach by water. For a more adrenaline-fueled option, the package also includes hang gliding for two, an exhilarating way to see the shoreline from above and take home a story you’ll be talking about for years.
We’re thrilled to offer this prize to our readers and fans. To enter, please use the Rafflecopter widget below (it may take a moment to load). This giveaway is open to anyone 18 years or older, worldwide, and the prize can be redeemed within the next year. Because some activities are seasonal, plan to visit during the warmer months if you want to make the most of the outdoor options. If you missed the freebie bonus question on the entry form, we’ve started a related conversation in our Forums so you can share your thoughts and see what others are saying.
a Rafflecopter giveaway
This prize package is meant to showcase the best of the Eastern Shore: unhurried beaches, friendly inns, delicious seafood, and a mix of gentle and thrilling activities that suit a wide range of travelers. Whether you’re dreaming of a peaceful escape to read on a quiet stretch of sand, a food-focused weekend sampling the local catch, or a short adventure that pushes your comfort zone, this trip blends luxury and authenticity. We loved revisiting those small towns and meeting the people who make the area special, and we can’t wait to hear about the memories the winner will bring home.
If you’re considering putting your name in the hat, remember to check seasonal availability for the kayak and hang gliding experiences, and choose travel dates that make the most sense for outdoor activities. The included meals and cozy bed & breakfasts will give you a genuine taste of the region—even if you only have a long weekend to spare, this itinerary is designed to deliver a full, memorable Virginia experience.