Que Sera Black Mountain Wine Tours
At Que Sera in Black Mountain, NC, https://www.queserarestaurant.com/ our love of wine goes far beyond the glass. Through our monthly wine club tastings, we’ve built a vibrant community of wine lovers who crave connection, conversation, and discovery. Now, we’re taking that passion on the road—curating unforgettable wine-focused journeys for our guests and friends. These small-group trips are designed as a natural extension of our wine club, bringing together adventurous people and great wine in extraordinary places.
Our first adventure was a six-night private barge cruise through Provence, April 2–8, 2026 (click here to view highlights of this trip.) We traveled by Rhone River and canal through southern France’s most iconic wine regions—exploring vineyards, tasting with winemakers, and soaking up the landscape that inspired generations of vintners and artists alike.
Next? A weeklong curated wine retreat in Tuscany June 7-13 2027
Que Sera Wine Retreat in Tuscany
June 7-13 2027
An Exclusive Seven-Day Private Villa Experience in the Heart of Chianti Wine Country
We're thrilled to invite our wine community on an extraordinary journey to one of the world's most revered wine destinations — the rolling hills of Tuscany, Italy. Building on the spirit of our Que Sera wine adventures, this immersive seven-day retreat is designed for those who want to go beyond the bottle and truly experience Tuscany the way it was meant to be savored: slowly, deeply, and surrounded by people who share your passion.
**Trip Dates:** June 7 – 13, 2027
**Group Size:** Limited to 22 guests
**Base:** Private Villa Estate, San Giovanni Valdarno, Tuscany
Price:
-- $8,917 per bedroom (2 people) ensuite
--$12,970 for 4-person two-bedroom suite (one shared bathroom)
--Earlybird discount $900 (Deposit prior to December 30 2026)
--Final Payment in full March 15, 2027
Your Home in the Tuscan Hills
Our home base is a stunning private estate near San Giovanni Valdarno — an elegantly restored Tuscan villa set within its own vineyard, olive groves, and woodland, with sweeping views in every direction.
From there, we venture out each day to some of the most celebrated boutique wineries in the Chianti Classico and Brunello di Montalcino regions.
Immersed in the lush greenery of the Chianti countryside, our private estate is surrounded by woodland, olive groves, and vineyards — offering an atmosphere of peace, privacy, and timeless Tuscan beauty. This is not a hotel; it's an exclusive rental of the entire property, so the villa and all its spaces belong entirely to our group for the duration of our stay.
The estate elegantly combines modern comforts with traditional Tuscan character: refined double guest rooms, generous shared living spaces, a professional kitchen, a beautiful dining room that seats the whole group, and spacious outdoor areas designed for both relaxation and conviviality.
This is not a tour. This is a retreat — thoughtfully paced, privately hosted, and genuinely unforgettable.
The Villa and Grounds include:
*Swimming pool with sun loungers, tables, umbrellas, and a gazebo
*Mediterranean garden
*Vineyard and olive grove walks right from the property
*Fourteen luxurious queen or double-twin rooms (7 ensuite and 7 with adjacent private bathrooms) in four connected or adjacent villas
*Private or shared kitchens or kitchenettes for all bedrooms
What's Included in Your Retreat
*Six nights' exclusive accommodation at a private Tuscan estate villa (entire property — not a hotel)
*Daily chef-prepared breakfast each morning
*Three private multi-course dinners in the villa, prepared by your personal chef and waiter service
*Several on-site wine tastings curated by Taylor Goodale
**Not Included:**
*International airfare
*Airport transfers from Rome or Florence on arrival/departure (available at additional cost)
*Personal expenses, gratuities
Travel insurance (strongly recommended — we're happy to assist)
Four Tuscany Wine Country Excursions
- Full-day Chianti wine experience — private visits to 2 exclusive boutique wineries, with lunch and olive oil tasting included
-Full-day private tour of Siena (UNESCO World Heritage Site with local guide) and San Gimignano,
-VIP Brunello di Montalcino experience — private visits to 2 exclusive wineries in the Val d'Orcia, with lunch included
- Exclusive half-day Chianti wine tasting — private visits to 2 additional boutique wineries, with lunch included
Dining Tuscan Style
Three of our evenings at the villa feature private multi-course dinners prepared by your personal chef, with full waiter service. This is the Italian dinner experience you've always imagined — long, leisurely, abundant, and utterly delicious.
Each morning, a private chef will be at your disposal to prepare a rich, leisuurely breakfast — think fresh croissants, cakes, scrambled eggs, local Tuscan cheeses, fresh fruit, and a full selection of coffees and juices.
For dinners on your own, nearby villages offer a plethora of great restaurants. We can also offer a shopping service if you prefer to utilize your personal or shared kitchen.
Itinerary
Sunday, June 7: Arrive in Tuscany
Monday, June 8: Chianti — Boutique Wineries & Vineyard Lunch
Monday, June 8: Chianti — Boutique Wineries & Vineyard Lunch
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.
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.*
Monday, June 8: Chianti — Boutique Wineries & Vineyard Lunch
Monday, June 8: Chianti — Boutique Wineries & Vineyard Lunch
Monday, June 8: Chianti — Boutique Wineries & Vineyard Lunch
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 histor
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.
Tuesday, June 9: Siena & San Gimignano
Monday, June 8: Chianti — Boutique Wineries & Vineyard Lunch
Tuesday, June 9: Siena & San Gimignano
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),
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.
Wednesday, June 10: VIP Brunello di Montalcino Experience
Friday, June 12: Exclusive Wine Tasting in the Heart of Chianti
Wednesday, June 10: VIP Brunello di Montalcino Experience
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
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)
Thursday, June 11: A Day at Your Own Pace
Friday, June 12: Exclusive Wine Tasting in the Heart of Chianti
Wednesday, June 10: VIP Brunello di Montalcino 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 from our own curated selection — a chance to compare notes on everything
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 nearly village. (Van shuttle available)
Friday, June 12: Exclusive Wine Tasting in the Heart of Chianti
Friday, June 12: Exclusive Wine Tasting in the Heart of Chianti
Friday, June 12: Exclusive Wine Tasting in the Heart of Chianti
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
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 Saturday to departure airport