Que Sera Wine Tours

Your Tuscan adventure begins today. Fly into Florence (recommended), Pisa, or Rome and make your way to our villa near San Giovanni Valdarno. Private airport transfers can be arranged for an additional fee. The afternoon is yours to explore—unpack, enjoy a leisurely walk through the gardens and vineyard, slip into the pool, and start to unwind. As the sun sets, we'll come together for our first dinner at the villa, prepared by our private chef. This evening, we'll also introduce you to Que Sera Wine Tours, which perfectly complement your exploration of local flavors, reminiscent of a Willamette Valley wine trip. Welcome to Tuscany! *This evening: Welcome dinner at the villa.*

This is a day for serious wine lovers. Your private driver picks you up at the villa at 9:30 a.m. for a full day exploring some of the finest boutique wineries in the legendary Chianti Classico region, similar to those offered by Que Sera Wine Tours. Your first stop is an exclusive, family-owned estate where the owner or winemaker personally hosts you through a private tour of the historic aging cellars, followed by a seated tasting of their limited-production, niche-label wines that you won't find at the grocery store. After the tasting, you travel scenic Chianti back roads to a second boutique winery, where you're welcomed by staff for a private estate tour — followed by a relaxed vineyard lunch featuring homemade dishes, organic garden ingredients, and a combined wine and extra virgin olive oil tasting served right at the table. This experience rivals any Willamette Valley wine trip or wine club tastings you may have attended. Your driver returns you to the villa by 3:30 p.m., leaving the evening open for relaxation or a quiet dip in the pool before dinner on your own in a nearby village.

Your driver picks you up at 9:30 a.m. for a full day discovering two of Tuscany's most beloved medieval towns. First stop: **Siena**, a UNESCO World Heritage Site. Here you'll meet your private local historical guide for a two-hour walking tour of the city — including the magnificent Piazza del Campo (home of the famous Palio horse race), the stunning Romanesque-Gothic Cathedral, Palazzo Pubblico, and the soaring Torre del Mangia. Siena's perfectly preserved medieval center is among the most beautiful in all of Europe, and seeing it with a private guide changes everything. After a leisurely lunch on your own at a traditional Sienese restaurant, you might even consider pairing your meal with a local selection from Que Sera Wine Tours, showcasing the region's exquisite wines. You'll continue on to **San Gimignano** — the 'Manhattan of the Middle Ages,' famous for its 13 surviving medieval towers that rise dramatically above the surrounding valley. You'll have free time to explore this extraordinary hilltop village, browse local shops, and taste the region's famous Vernaccia white wine before your driver brings you back to the villa, arriving around 5:30 p.m. *This evening: Chef-prepared dinner at the villa, a perfect end to your Willamette Valley wine trip, complete with selections from our wine club tastings.*

If Chianti made you swoon, Brunello will leave you speechless. Today, we venture south to the Val d'Orcia, one of the most breathtakingly beautiful landscapes in all of Italy and home to the renowned Brunello di Montalcino, Italy's most celebrated and age-worthy red wine. Join us on a Que Sera Wine Tours journey as your private driver picks you up at 10:00 a.m. The scenic drive takes approximately 90 minutes each way, passing through rolling UNESCO-protected landscapes filled with golden fields, charming hilltop villages, and cypress-lined roads. Upon arrival at your first exclusive estate, you’ll be greeted by the owner or winemaker, followed by a private tour of the vineyards and production facilities. Enjoy a delightful multi-course vineyard lunch paired with specially curated Brunello wines. After lunch, your driver will guide you through more stunning scenery to a second exclusive Brunello winery for a private tasting, led by a wine expert. You'll return to the villa around 5:00 p.m.* This evening: Leisurely dinner at your own arrangement.* (Van shuttle available) If you’re looking for a weekend escape, this is the perfect complement to any Willamette Valley wine trip or wine club tastings experience.

Today belongs entirely to you. Sleep in. Linger over breakfast. Spend the morning by the pool with a good book and a glass of something cold. Take a walk through the olive groves. Explore the nearby village. Take a nap. We may arrange an optional informal wine tasting featuring selections from our Que Sera Wine Tours collection — a chance to compare notes on everything we've experienced so far during your Willamette Valley wine trip. Or not. That's the beauty of today. *This evening: Dinner on your own in a nearby village. (Van shuttle available) Don’t forget to check out our wine club tastings while you're here!

A return to Chianti — but with a different lens. Your driver picks you up at 9:30 a.m. for a half-day visit to two more carefully selected niche wineries in the region, part of your Que Sera Wine Tours experience. At the first estate, you'll enjoy a private visit of the historic aging cellars followed by an exclusive tasting of their limited-production wines. At the second, you'll be warmly welcomed for a private tour of the property before a relaxed vineyard lunch featuring homemade dishes, organic garden ingredients, and a curated pairing of wines and extra virgin olive oil served at your table. You'll return back at the villa by 3:30 p.m. with the afternoon free, perfect for those planning a Willamette Valley wine trip or wine club tastings. Tonight is our final evening together — and we'll make it memorable. *This evening: Farewell dinner at the villa. Transfers available (at extra cost) on Sunday to departure airport.