Tuscany Uncorked: Wine, Landscapes & La Dolce Vita
May 2nd - May 11th (10 Day Trip)
Overview
Few places in the world capture the imagination quite like Tuscany. This ten-day, nine-night journey takes guests through some of the region’s most celebrated landscapes and wine territories – from the coastal elegance of Bolgheri to the rolling hills of Chianti and the timeless beauty of Val d’Orcia. Along the way, you’ll experience boutique wineries, Brunello tastings, medieval villages, sunrise hot air ballooning, Michelin-starred dining, and deeply rooted culinary traditions that define the Tuscan way of life.
Trip Summary
Italy is unmistakably one of the most beautiful and culturally rich countries in the world, but Tuscany holds a special place within it, a region where wine, food, landscape, and history come together with effortless beauty.
This journey begins along the Tuscan coast in Bolgheri, one of Italy’s most celebrated wine regions and home to some of the country’s most prestigious Super Tuscan wines. Surrounded by vineyards, cypress roads, and the relaxed elegance of the coast, we begin experiencing Tuscany through exceptional wine and hospitality.

From there, we travel into the heart of Chianti, where medieval villages, historic estates, and rolling hills create the Tuscany most people dream about.
The journey continues south into Val d’Orcia, a UNESCO World Heritage landscape known for its cypress-lined roads, hilltop towns, and timeless beauty. In Montalcino, we explore the world of Brunello wine, while Pienza and Montepulciano reveal Tuscany’s slower rhythm through artisan traditions, pecorino cheese, and village life.
This is Tuscany Uncorked at its most beautiful and indulgent. Exceptional wines, unforgettable meals, breathtaking landscapes, and the simple joy of slowing down and savoring it all together.
Salute!
Jason Capps
Photo Gallery
Highlights
- Super Tuscans, Chianti, and Brunello wines.
- Hill towns, vineyards, and Val d’Orcia landscapes.
- Hot air ballooning, Michelin dining, and Tuscan cooking.
Daily Itinerary

Day 1: Arrival Along the Tuscan Coast
Sunday, May 2nd
Your Tuscan journey begins in Bolgheri, where vineyards stretch toward the sea and cypress-lined roads lead into one of Italy’s most celebrated wine regions. After settling into your elegant coastal resort, we enjoy a welcome lunch at Tenuta Argentiera, including a 4×4 ride through the estate’s tree-lined paths and vineyards. Later, we gather for sunset cocktails and light bites on the beach.

Day 2: Super Tuscans & Bolgheri Elegance
Monday, May 3rd
Today we experience the refined side of Tuscany through Bolgheri, home to some of Italy’s most prestigious Super Tuscan wines. We begin at Petra Winery before traveling along the iconic Viale dei Cipressi into Bolgheri for lunch and time to explore the town center. After a relaxed afternoon at the hotel, we gather again for a sunset aperitivo at the iconic Guado al Tasso state, followed by dinner.

Day 3: Into the Heart of Chianti
Tuesday, May 4th
Leaving the coast behind, we travel inland toward Chianti, stopping in the medieval town of Volterra along the way. After lunch, a local guide leads us through the Etruscan Museum and shares the history of Volterra’s ancient fortress and prison. We continue into Chianti, arriving at our countryside retreat in the late afternoon before an exceptional dinner at the hotel.

Day 4: Vineyards, Villages & Chianti Traditions
Wednesday, May 5th
Chianti reveals itself through wine, villages, and tradition. We visit Castello di Brolio for a tasting and lunch, surrounded by the landscapes that have shaped Tuscan wine for centuries. Later, we continue to Radda in Chianti for free time before returning to the hotel, where the evening includes dinner and an intimate blind tasting experience.

Day 5: Tuscany from the Sky
Thursday, May 6th
Before sunrise, we head into the countryside for a private hot air balloon flight above the Tuscan hills. The rest of the day is yours to relax at the hotel, enjoy the swimming pool, or choose optional countryside activities. Later, we will make our way to Il Palagio for a visit through the vineyards and honey production, followed by an early dinner at this beautiful estate owned by a world-renowned musician.

Day 6: Toward the Timeless Beauty of Val d’Orcia
Friday, May 7th
Today we travel south into Val d’Orcia, one of Italy’s most iconic landscapes, and settle into our countryside retreat in the Montalcino area for the next four nights. The afternoon becomes more playful with a vintage Fiat 500 drive through the roads around Montalcino. The day ends with a relaxed picnic-style dinner in the countryside.

Day 7: Brunello & the Soul of Montalcino
Saturday, May 8th
Montalcino is one of Tuscany’s great wine destinations, and today we experience it through the flavors of the region. The day begins at our villa with a private cooking class led by a local chef, where we’ll prepare a beautiful Tuscan lunch together. In the evening, get ready to savor the magic of Brunello at a special estate surrounded by vineyards.

Day 8: Southern Tuscany Revealed
Sunday, May 9th
Today we explore two of southern Tuscany’s most beautiful hill towns. We begin in Cortona, with free time to wander its stone streets, browse local shops, and enjoy lunch on your own. In the afternoon, we continue to Montepulciano for a guided visit through its historic streets, Renaissance palaces, and deep wine culture. The day concludes with a tasting at The Ricci winery, one of Montepulciano’s historic and most respected wine families, followed by dinner in the unforgettable atmosphere of this beautiful hill town.

Day 9: Through the Tuscan Table
Monday, May 10th
Food has always been at the heart of Tuscany, and today we experience it at Podere Il Casale, a beautiful working farm near Pienza. Together with the owner, we learn about local cheese-making traditions before enjoying a relaxed farm lunch surrounded by the landscapes of Val d’Orcia. After time back at the hotel, we gather for a celebratory farewell dinner – the perfect close to a journey shaped by wine, countryside, food, and Tuscan hospitality.

Day 10: Arrivederci Toscana
Tuesday, May 11th
A final slow morning in Tuscany before departing for Florence, Pisa, Rome or your next destination. As the countryside fades behind us, we leave with memories of vineyards, villages, extraordinary meals, and the unmistakable beauty that makes Tuscany one of the world’s most beloved destinations.
Trip Details
What’s Included
- Nine nights, Ten days around Tuscany
- Arrival transfer (day-of) from Pisa airport to hotel
- All hotel accommodations, meals, wine / beverages, guided tours & experiences
- All transportation throughout trip
$10,895 per person
(based on double occupancy)
What’s Not Included
- Airfare
- Departure transport
See it on the Map

Spaces are Limited
May 2 - 11, 2027
$10,895 Per Person
Based on double occupancy
Reserve Your Spot with $2000 Deposit
- Credit Cards Accepted
- Pay in Installments
- 24-Hour Risk-Free Booking
Small Group — Very Limited Spots
Published Dates Fill Quickly