Que Sera Black Mountain 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 entirely yours — unpack, take a slow walk through the gardens and vineyard, slip into the pool, and begin to exhale. Tonight we'll gather for our first dinner together at the villa, prepared by our private chef. 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.

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. These are not wines you'll 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.

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'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.

If Chianti made you swoon, Brunello will make 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 Brunello di Montalcino, Italy's most celebrated and age-worthy red wine.

Your private driver picks you up at 10:00 a.m. The drive itself — approximately 90 minutes each way — passes through rolling UNESCO-protected landscapes of golden fields, hilltop villages, and cypress-lined roads. When you arrive at your first exclusive estate, you'll be welcomed by the owner or winemaker and treated to a private tour of the vineyards and production facilities, followed by a multi-course vineyard lunch with a curated Brunello wine pairing.

After lunch, your driver takes you through more spectacular scenery to a second exclusive Brunello winery for an intimate private tasting, always guided by a wine expert. You'll arrive back at the villa around 5:00 p.m.

*This evening: Leisure / dinner at your own arrangement.* (Van shuttle available)

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 from our own curated selection — a chance to compare notes on everything we've experienced so far. Or not. That's the beauty of today.

*This evening: Dinner on your own in a nearby village.  (Van shuttle available)

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.

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 — homemade dishes, organic garden ingredients, and a curated pairing of wines and extra virgin olive oil served at your table.

You'll be back at the villa by 3:30 p.m. with the afternoon free. 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