5-Day Private Tuscany Wine Holiday Tour from Florence
5 Days / 4 Nights Private Tuscany Wine & Truffle Vacation — Chianti Classico, Brunello di Montalcino & San Miniato
- Duration
- 5 Days · 4 Nights
- Group
- Small group · 2–8 travelers
- Stay
- Chianti Classico
- Languages
- English
About This Holiday
Italy and Wine offers an all-inclusive 5-day, 4-night private Tuscany wine holiday starting and ending in Florence (from €4,100 per person based on party size), combining 4-star hotel accommodation with three privately chauffeured full-day wine and food excursions. Accompanied by a dedicated English-speaking wine expert and private Mercedes driver, you experience a woodland truffle hunt in San Miniato, a full day across two boutique wineries in Chianti Classico, and a full day tasting Brunello di Montalcino DOCG at two estates in Montalcino.
After private arrival transfer from Florence Airport or Santa Maria Novella train station to your hotel, Day 2 takes you into the forests of San Miniato with a master tartufaio and Lagotto dog followed by a gourmet truffle lunch and a free afternoon in Florence. Day 3 explores the heart of Chianti Classico for guided cellar tours, Chianti Classico DOCG and Super Tuscan IGT tastings, and a winery lunch, while Day 4 journeys south to Montalcino to taste aged Brunello di Montalcino DOCG and Rosso di Montalcino at two contrasting estates.
Every detail — from airport/station transfers and 4 nights of accommodation with daily breakfast to winery appointments, two wine-paired vineyard lunches, and hotel dinners — is coordinated by Italy and Wine’s concierge team. Collectors can also arrange insured door-to-door international shipping of rare Brunello and Super Tuscan bottles directly from the estates before a private departure transfer to Florence or Pisa airport on Day 5.
Day by Day
Arrival and transfer to your hotel
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 & Not Included
Included in the Tour
- 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
Not Included
- 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.
Villa le Calvane
A 5-star wine estate among the vineyards of Montespertoli, in the Chianti hills near Florence. Spacious suites with marble bathrooms and rain showers, panoramic views over the vineyards and rolling hills, an outdoor pool, and the estate's own vineyards and wine production.
Boutique Family Wineries across Chianti Classico, Montalcino
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
★ 5.0 · 1 verified reviewMark 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.
