5-Days Private Wine Holiday in Tuscany
Experience Chianti and Brunello – 5 Nights
About This Holiday
An unforgettable 5-day, 4-night journey through Tuscany's finest wine regions — from the cultural heart of Florence to the rolling hills of Chianti and the medieval town of Montalcino, with two full days of tastings and cellar visits spanning Chianti Classico to Brunello di Montalcino.
Day by Day
Arrival in Florence
Private transfer to your 4/5-star hotel in Florence. Evening meal in the hotel restaurant — or, if you prefer, we can book a table for you in a special restaurant.
Truffle Hunting Experience
Join an expert truffle hunter and their trained dog for an exciting hunt through the Tuscan woods, followed by a delicious truffle-based lunch at a traditional restaurant. Free afternoon to explore Florence at your leisure, with the evening also at your leisure.
Quintessential Tuscany: the Chianti Classico Wine Region
Hotel breakfast and pickup for a private visit to the Chianti Classico area. Visits and wine tastings at two wineries, sampling world-famous Chianti Classico DOCG and Super Tuscan IGT wines. Lunch stop in a small winery for tasty local dishes and Chianti Classico wines. Dinner at the hotel.
Medieval Montalcino in Brunello Country
Breakfast at the hotel and pickup for a private visit to the Brunello-producing area around the medieval town of Montalcino. Visit two different wine estates to sample the renowned Brunello DOCG and younger Rosso DOC wines. Lunch in a small winery with another typical Tuscan menu paired with Brunello di Montalcino wine. Wine collectors can purchase — and have shipped home — rare bottles of Brunello directly from Montalcino's leading wine store. Drive back to the hotel for dinner.
Leisurely Wind Up Your Vacation
Breakfast at the hotel and check out. Enjoy the swimming pool and the charming countryside surroundings before your private transfer to Pisa or Florence airport later in the morning.
What's Included
- Private transfer to/from Florence Airport or Railway Station
- 4 nights stay in a 4-star hotel
- Three full-day tours with tastings and a food experience
- Two wine-paired lunches during the wine tours
- Professional wine expert guide
- Private minivan transportation with English-speaking driver
- International flights
- Dinners on free evenings
- Gratuities
Price by Group Size
| Group size | Price per person | Total |
|---|---|---|
| 2 travelers | €4,100 | €8,200 |
| 3 travelers | €3,700 | €11,100 |
| 4 travelers | €3,200 | €12,800 |
| 5 travelers | €3,100 | €15,500 |
| 6 travelers | €2,650 | €15,900 |
| 7 travelers | €2,500 | €17,500 |
| 8 travelers | €2,400 | €19,200 |
Your Trip Designer
Vittorio Del Bono Venezze
Every private day is planned by hand, not booked from a menu. Once you enquire, the team puts together a proposal tailored to your dates, pace and taste — usually within 24 hours, with no obligation to book.
Your Accommodation
Handpicked stays for your trip — the exact property is confirmed with your trip designer.
Plaza Hotel Lucchesi
A historic 4-star hotel that first opened in 1860, fully renovated while preserving its original character, on the banks of the Arno with views toward Santa Croce. 82 rooms and 10 suites, with the rooftop Empireo pool bar as its signature feature.
Villa I Barronci
A 4-star boutique resort and spa in a restored 13th-century villa in the heart of Chianti, just 15 minutes from Florence and 7 km from the Antinori winery. Features a year-round heated outdoor pool (30°C), the Namaste wellness spa, and an on-site gastronomic experience with tastings and sunset aperitivi.
Villa Il Poggiale
A Renaissance-era manor house dating to the early 1400s, once owned by the noble Corsini family, now a boutique 'Historical Residence' hotel in the Chianti Classico countryside near San Casciano in Val di Pesa. 24 rooms and suites with frescoed ceilings and antique furnishings, a spa center using Tuscan olive oil, wine, and honey, an outdoor pool, and the La Tinaia restaurant — about 15 km from Florence.
The Wineries
Pickup
Private transfer included from Florence airport or train station on arrival day, and back again at the end of the trip.
Cancellation Policy
| Notice before departure | Charge |
|---|---|
| Up to 90 days | Deposit only |
| 80–71 days | 35% of tour cost |
| 70–51 days | 55% of tour cost |
| 50–31 days | 75% of tour cost |
| 30 days or less | 100% of tour cost |
Frequently Asked Questions
How many wineries will we actually visit over the 5 days?
Across the two full tasting days you'll visit four wine estates — two in Chianti Classico and two in Montalcino for Brunello — with the other days set aside for a truffle hunting experience, free time in Florence, and a relaxed final morning before your flight.
Is airport transfer included?
Yes — private transfers to and from Pisa or Florence airport are included at the start and end of the trip.
Can the itinerary be adjusted once we arrive?
Yes — your guide can adjust the pacing and stops day to day based on how the trip is going and what you're most interested in.
Reviews
Mark Pfitzner
This multi-day Chianti and Brunello package is something every wine lover visiting Tuscany should do. Matteo guided us through it all and gave us a real taste of the old-world pace of life here. One lunch in particular stood out — served in a farmhouse that's stood for a thousand years — where we picked up more about winemaking than we expected: how much work goes into getting the grapes from vine to bottle, and what the DOCG rules actually mean in practice. It was one of the real highlights of our trip to Italy. We shipped wine and olive oil home afterward, and every bottle we open still brings us right back to Tuscany.
5-Days Private Wine Holiday in Tuscany
