Tuscany Wine Paradise

Seven Nights for Eight People

Experience the enchanting world of Tuscany’s wine country, where rolling vineyards and ancient olive groves paint a breathtaking landscape. With a lineage tracing back centuries, this is a rare opportunity to experience the beauty that Tuscany has to offer. You and seven additional people will enjoy superb cuisine, stunning vistas, and the splendors of Italian art all while tasting incredible wines from esteemed Italian regions. 

Your Tuscan adventure includes a seven-night stay in a four-bedroom villa overlooking the expansive Tuscan countryside near the charming town of Cortona. The villa is surrounded by iconic olive and cypress trees and rolling green hills — the perfect backdrop for your Italian excursion. The villa also boasts a private pool, a gazebo overlooking breathtaking views of Cortona, and spacious green gardens. Your own private chef is onsite to prepare daily breakfasts and dinner one of the nights. 

Your first day will take you on a wine tour in the Montalcino area, a beautiful village immersed in the breathtaking Val d’Orcia Natural Park, renowned for its production of Brunello. The visit will include tastings at two esteemed wineries as well as lunch. 

The next day you will be whisked off to the Chianti region, revered as one of the most beautiful areas in Tuscany. This charming region stretches from Florence to Siena and is famous for its unique landscape characterized by olive groves, winding country roads, and undulating green hills covered with vineyards. You will taste at two of the area’s esteemed wineries alongside lunch. 

Your trip is capped off with a trip to Montepulciano, a walled hill town full of elegant Renaissance palaces, ancient churches, and vast panoramas embedded in a picture-postcard landscape. Montepulciano is considered to be one of the finest winemaking regions in the world, best known for its Vino Nobile, one of Tuscany’s most globally valued wines made from grapes grown in vineyards that surround the town. 

If you desire and time allows, appointments can be made at neighboring wine estates to further discover wines of the region, or visits to the villages and ancient abbeys of Tuscany can be arranged. 

In advance of your Italian excursion, you will be treated to dinner at COMO waterfront restaurant in Kirkland with the winemaker of Va Piano Vineyards, Justin Wylie. Justin will share his insights on Italy, the wine region and the delectable cuisine to get you prepared for your trip. He may even provide a lesson in Italiano!

This lot includes:

Seven nights in a stunning four-bedroom villa including

a private pool in the Tuscan countryside near the charming town of Cortona 

Daily breakfast prepared by a private chef 

Full day wine tour in the Montalcino area, including tastings 

at two wineries and lunch

Full day wine tour in the Chianti region, including tastings

at two wineries and lunch 

Full day wine tour in the Montepulciano region, including tastings at two wineries and lunch 

Excursions with your private driver with the option

to add extra activities 

One dinner in the villa prepared by a private chef with

wine pairings led by a professional sommelier 

Transportation included all week for eight hours per day

(max 200 km per day) 

Travel assistance and concierge service 

Pre-dinner with Justin Wylie, winemaker for Va PIano, at COMO

Terms & Conditions: 

Excludes airfare 

Transportation not included on arrival/departure day Upchurch’s home in Kirkland

Thank you: HHT, Va Piano Vineyards

Value: Tutto Italiano


2200 6th Ave Suite 411
Seattle, WA 98121
(206) 741-0212



The Northwest Wine Benefit Foundation, DBA Auction of Washington Wines, is committed to supporting the growth and awareness of the Washington state wine industry through a series of celebrated events benefiting our community. We have raised over $63 million since our inception in 1988. 

The Auction of Washington Wines is an equal opportunity employer and prohibits discrimination based on race, color, national origin, sex, religion, age, disability, political beliefs, sexual orientation, marital or familial status.

OUR newsletter

Website by

Photos courtesy of Curbow Photo, Duval Images, and Suzi Pratt © 2008-2023 Auction of Washington Wines
Read our Privacy Policy