Have a bouquet of fresh local flowers waiting in your room (Sunflower or wildflower arrangements from a local florist like Cape Charles Flowers).
Sunset Beach Walk
Take a bundled-up stroll along Cape Charles Town Beach (just off Bay Ave). Even if the air is cool, bring blankets, thermoses of hot cider or wine, and enjoy the calm.
Dinner at The Oyster Farm
Romantic waterfront dining with fresh seafood and oysters. Indoor seating has bay views if it’s too cold outside.
Day 2 – Saturday
Morning Coffee & Cozy Start
Start at Cape Charles Coffee House—old bank building charm with lattes and pastries.
Nature & Wine Excursion
Visit Chatham Vineyards (20 minutes from downtown). Tour the vineyard, sample wines, and buy a bottle for later.
If weather allows, stop at Eastern Shore National Wildlife Refuge for birdwatching and short nature walks.
Afternoon Spa or Cozy Downtime
Couples massage at a local spa or quiet downtime bundled up inside your rental/home with wine and cheese.
Dinner at Hook @ Harvey
Upscale yet relaxed spot in town with excellent seafood and cocktails.
Bonfire on the Beach
Bundle up with blankets, your wine from Chatham, and s’mores. Many rentals allow small portable fire pits, or you can set up a safe beach bonfire (check town fire permit rules first).
Day 3 – Sunday
Morning Beach Walk & Photos
A gentle walk along the Cape Charles pier. If it’s chilly, hot cocoa in hand makes it charming.
Brunch at The Shanty
Bayside brunch with Bloody Marys, crab cakes, or a classic breakfast overlooking the water.
Send-Off Gesture
Leave with a keepsake: grab a bottle of wine, artisan chocolates, or a seashell found during your walk to remember the weekend.