The Tuscany Experience
Immersive. Intimate. Unforgettable.
Tuscany as few travellers experience it
TRIP SNAPSHOT
September 18–26, 2026 · 8 days / 9 nights · 10 guests
Florence · Chianti · Siena · Montalcino · San Gimignano
Michelin-recognized restaurants
Private luxury transportation
For those who live life passionately — this intimate eight-day journey weaves together Renaissance Florence, the legendary wine estates of Chianti and Montalcino, and the timeless beauty of Siena's hill towns into one unforgettable experience.
With just ten guests, every moment is thoughtfully curated. Private access, unhurried tastings, Michelin-recognized dining, and two WSET-certified hosts who help make Tuscany’s wines more approachable, meaningful, and connected to place.
This is Tuscany as few travelers experience it — personal, beautifully paced, and shaped around wine, food, culture, and connection. Private Mercedes-Benz transportation keeps each transfer comfortable, coordinated, and relaxed.
Rather than rushing from stop to stop, this journey brings together Renaissance Florence, Chianti’s rolling vineyards, Montalcino’s celebrated Brunello, Siena’s historic beauty, and intimate hosted moments chosen for quality, atmosphere, and sense of place.
With only 10 guests, the experience is designed to feel relaxed, personal, and thoughtfully handled from start to finish.
Why This Journey
Journey Highlights
A curated blend of wine, food, culture, and countryside experiences designed for a small group of only 10 guests.
Private Florence Access
Explore Renaissance Florence with curated cultural experiences, including the Duomo complex and Uffizi Gallery.
Memorable Dining
Brunello in Montalcino
Pasta-Making Experience
Truffle Hunting in Chianti
Walk the Chianti countryside with a local expert and trained truffle dog.
San Gimignano & Vernaccia
Visit the famed hilltop town and taste Tuscany’s celebrated white wine.
Take part in a hands-on culinary experience followed by a wine-paired meal.
Taste one of Tuscany’s most celebrated wines in the region where it is made.
Enjoy elevated meals, local flavors, and shared tables designed around wine and connection.
Wine, Food & Culture
This journey is built around Tuscany’s most expressive flavors — from celebrated wines to intimate meals, hands-on culinary moments, and cultural experiences that help guests better understand the wines, traditions, and places behind each pour.
Expect a thoughtful mix of Chianti Classico, Brunello di Montalcino, Vernaccia di San Gimignano, boutique estate visits, regional cuisine, and hosted experiences designed to feel personal rather than rushed.
4 & 5-Star Accommodations
The Tuscany Experience includes thoughtfully selected 4- and 5-star accommodations chosen for comfort, atmosphere, and sense of place.
From Florence to the Chianti countryside, each hotel gives guests a refined home base between days of wine, food, culture, and discovery. Featured stays include Hotel Kraft (Florence), Athena Hotel (Siena) and Hotel Le Fontanelle (Pianella) nestled in the Tuscan countryside.
City comfort • Countryside retreat • Daily breakfast • Refined service
Itinerary Preview
Eight days of wine, food, culture, and countryside — thoughtfully paced from Florence to Chianti, Montalcino, Siena, and San Gimignano.
The journey begins in Florence with Renaissance landmarks, private cultural experiences, and time to settle into the rhythm of Tuscany before moving into wine country for Chianti tastings, truffle hunting, Brunello in Montalcino, Vernaccia in San Gimignano, hands-on culinary moments, countryside relaxation, and memorable hosted meals.
Florence arrival and welcome dinner
Duomo and Uffizi cultural experiences
Pasta-making and hosted dining
Chianti wine country and truffle hunting
Montalcino and Brunello tasting
San Gimignano and Vernaccia
Countryside retreat and relaxed luxury
Meet Your Hosts
Joy and Brian bring warmth, wine knowledge, and decades of shared travel experience to every JB Wine Adventures journey.
As experienced travelers and WSET-certified wine enthusiasts, they design each experience with an eye for beautiful places, memorable meals, thoughtful pacing, and the small details that make a trip feel personal.
Frequently Asked Questions
-
The Tuscany Experience is limited to 10 guests to keep the journey personal, relaxed, and carefully hosted.
-
No. The experience is designed for curious travelers who enjoy wine, food, culture, and beautiful places. Joy and Brian will help make the wine experiences approachable and enjoyable.
-
International flights are not included. The hosted itinerary begins in Italy, and more detailed arrival guidance will be provided after personal follow-up.
-
No. Requesting availability is only the first step. No passport, health, emergency contact, or payment details are required on the public inquiry form.
A few helpful details before requesting availability.
Investment & Availability
The Tuscany Experience investment is $10,500 per person based on double occupancy.
This includes curated accommodations, private transportation within Tuscany, hosted wine experiences, select meals, cultural excursions, and the personal hosting of Joy and Brian throughout the journey.
Flights, travel insurance, personal expenses, and items not specifically listed as included are excluded.