Feral · The Soirée
Charlottesville Pippin Hill + Monticello Wine Weekend — Charlottesville, VA
Destination: Charlottesville, VANights: 3Group: 4–10Season: April, May, June, September, October, NovemberEstimated: $1,300–$2,400 per person
Boar's Head Resort — 600 acres on the edge of Monticello wine country, the Mill Room for chef-driven dining, 10 tennis courts, the spa. Day-one Pippin Hill Farm + Vineyards for the garden-to-table tasting room (Albariño + Cabernet Franc, the regional varietals). Day-two Monticello tour (Thomas Jefferson's home, 1768, the bridal party walks the kitchen + cellar + gardens). Day three: Keswick Hall for a closing brunch on the Trump Winery side or a winery loop on the Monticello Wine Trail. Charlottesville (CHO) is direct from major hubs.
What she'll do
Wine Tour
Tour
Spa
Horseback Riding
Where she sleeps
- · Boar's Head Resort (600 acres)
- · Keswick Hall (apex sister)
- · Quirk Hotel Charlottesville (boutique)
Where she eats
- · Pippin Hill tasting room + dinner
- · The Mill Room at Boar's Head (chef-driven)
- · The Local (farm-to-table)
Questions
Pippin Hill reservations?
Tasting room walks-in are fine on weekdays. Weekend lunch + dinner books via Resy 2-3 weeks ahead. The garden-to-table dinner ($85-120/person) is the bridal party's evening.
Monticello tour cost?
$32 entry, includes the house tour + grounds + kitchen. Behind-the-scenes tour ($75) is the bridal party upgrade — Hemings family quarters + the cellar.
Wine trail logistics?
Hire a driver service ($150-300/person for the day) — self-driving after wine tastings is illegal in Virginia. The Monticello Wine Trail covers 30+ wineries; a 4-winery day is the bridal party's pace.
Ready to book the story?
Five quick questions, then we build the full itinerary — lodging, daily schedule, dining, bars, the group-chat message — and drop you into a Trip Room you can share with the bridesmaids.