3 days in Keswick
Virginia Wine Country by Carolyn
Explore our favorite vineyards and experience Virginia’s vibrant culinary scene during Virginia Wine Month.
From $2,950
Oct 9 – Oct 11, 2026 · 3 days, 2 nights
+$750 single occupancy
No card needed. Apply today.
The Trip
Sip exceptional local wines, take in sweeping views of the Blue Ridge Mountains, and enjoy unforgettable meals prepared by some of the region’s most talented chefs. This thoughtfully curated Virginia Wine Month getaway celebrates the very best of Virginia wine, food, and hospitality.
Your Host
Meet Carolyn Covington
Carolyn is a WSET Diploma-certified wine educator and Charlottesville local with a deep love for Virginia wine country. Traveling with her means discovering the region’s standout wines, beautiful vineyards, and hidden gems through the eyes of someone who knows it best.
Highlights
Signature Moments
Where You'll Stay
Your Packages
Wine Night Package
From $95
For locals who want to join the first night's wine tasting only.
- Wine tasting at Ethos on October 8th
Commuter Package
From $1,445
For locals who want to join activities and sleep at home.
- Everything except for a hotel.
Luxury Package
From $2,950
Keswick Hall
For out-of-towners who want a high-end hotel included with their trip.
- Everything including Lodging
The Itinerary
Carolyn's Virginia Wine Country Escape
Experience the charm of Virginia with Carolyn, where each day unfolds with wine tastings, scenic walks, and culinary delights in breathtaking landscapes.
Itinerary subject to change without notice.
- 5 PMWine Night at Ethos Wine & TeaIncludedHostedEthos Wine & Tea
Investment
Your Experience Awaits
$2,950
per traveler · all hosted experiences included
+$750 single occupancy
Oct 9 – Oct 11, 2026 · 3 days, 2 nights
No card needed. Apply today.
Reserve your place- 1Reserve Your Spot — Secure your place with Carolyn for a memorable experience in Virginia's beautiful wine country.
- 2Plan Your Trip — Check the itinerary and choose optional activities that excite you during your stay.
- 3Join the Group — Meet Carolyn and fellow travelers at Keswick Hall for a warm welcome and wine tastings.
- 4Enjoy the Experience — Relax, explore, and savor the flavors and sights of Virginia's vineyards and culinary scene.
Reserve
One Click In. Everything Else Handled.
Reply to reserve your place. We will walk you through the details and hold your spot while you decide.
Reserve your placeNo card needed. Apply today.
What's Included
- Everything including Lodging
- Wine Night at Ethos Wine & Tea
- Optional Morning Walk on the Monticello Trail
- Monticello Guided Tour
- Lunch at Southwest Mountains Vineyards
- Wine Tasting at Jefferson Vineyards
- Welcome Dinner, Prepared by Chefs Ian & Allie Redshaw
- Estate Tour & Tasting at Pippin Hill
- Lunch at Pippin Hill
- Wine Tasting at Veritas + Optional Horseback Ride
- Private Vineyard Dinner at Merrie Mill
- Optional Morning Walk on the Keswick Grounds
- Farewell Brunch at 1799, The Clifton
- Optional Polo Match at King Family Vineyards
What's Not Included
- Alcohol past tasting
- Optional Spa Treatment
Itinerary subject to change without notice.
Transportation
GettingAround
Transportation is included for all hosted trip activities and from the airport to your accommodations.
Sit back and enjoy — we handle the logistics so you can focus on the experience.