5-Days Private Wine Holiday in Tuscany
Experience Chianti and Brunello – 5 Nights

Indulge in 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 charming town of Montalcino, this exclusive wine holiday offers unparalleled access to Tuscany's iconic vineyards and world-class wines. With two full days dedicated to wine tastings and cellar tours, you'll explore the heart of Tuscany's wine production, from Chianti Classico to Brunello di Montalcino.
This wine holiday promises to immerse you in the rich flavors, history, and culture of Tuscany, offering a unique experience for both wine lovers and connoisseurs. Whether you're exploring the vineyards or savoring exceptional meals, every moment of this journey is designed to leave you with lasting memories of Tuscany's extraordinary wine heritage.
Guided Tour in English
Highlights
- Private Transfers: Convenient private transfers to and from Florence or Pisa airport for a seamless travel experience.
- Luxury Accommodations: Stay in a 5-star hotel in Florence’s historic center, with access to the city’s art galleries, museums, and luxury shopping.
- Wine Tastings and Estate Visits: Two full days of guided tours with a wine expert, visiting four premier wine estates and one olive oil producer.
- Exclusive Wine Pairings: Savor traditional Tuscan meals perfectly paired with local wines, including Chianti Classico, Super Tuscan, and Brunello di Montalcino.
- Meet the Producers: Gain insider knowledge as you meet local winemakers, learn about their craft, and sample wines directly from the source.
- Montalcino Excursion: Visit the picturesque hilltop town of Montalcino and explore its renowned wine shops.
JK Place Florence
A 5-star luxury hotel in Florence located in the heart of the historic center, in the magical setting of the stunning Santa Maria Novella Square and…
Plaza Hotel Lucchesi
This elegant 4-star hotel is an 8-minute walk from the Uffizi Galleries, 11 minutes from the shops on Ponte Vecchio and 15 minutes from the Florence Cathedral.
Villa I Barronci
is a charming Tuscan-style residence with private park and pool. It offers stunning views of the Chianti countryside, 20 minutes' drive from Florence, between the beautiful towns of Florence and Siena…
- Transfer to/from Florence Airport or Railway Station (we can provide quotes for transfers to other destinations upon request)
- 4 nights stay in a 4-star hotel
- Two full-day wine tours, each with tastings at renowned wineries
- Two lunches during the wine tours, including wine pairings as outlined in the itinerary
- Wine tastings led by a professional wine expert
- Transportation in a comfortable minivan with an English-speaking driver
not included
- Flights are not included in this package
- Dinners (our staff can assist with reservations)
- Tips
- Please note: Any additional services or activities not mentioned in the inclusions are not included in the package.
• Up to 90 days before departure date: deposit
• 80 – 71 days before departure date: 35% of tour cost
• 70 – 51 days before departure date: 55% of tour cost
• 50 – 31 days before departure date: 75% of tour cost
• 30 days before departure date: 100% of tour cost.
Penalties are also levied on the single supplement. Insurance is recommended.
- Day 1 - Arrival in Florence
- Private transfer to your 4/5-star hotel in Florence. - Evening meal in the hotel restaurant. If you prefer, we may alternatively book a table in a special restaurant for you. - DAY 2 - Truffle Hunting Experience.
- Join an expert truffle hunter and their trained dog for an exciting hunt through the Tuscan woods. Afterward, enjoy a delicious truffle-based lunch at a traditional restaurant. Free afternoon to explore Florence at your leisure. - Evening meal at your leisure. - DAY 3 - Quintessential Tuscany: the Chianti Classico wine region
- Hotel breakfast and pick up for a private visit to the Chianti Classico area. - Visits and wine tastings in two wineries. Sample some world-famous Chianti Classico Docg and Super Tuscan IGT wines. - Lunch stop in a small winery to sample tasty local dishes and Chianti Classico wines. - Dinner at the hotel. - DAY 4 - Medieval Montalcino in Brunello country
- Breakfast at the hotel and pick up for a private visit to the Brunello-producing area around the quaint Medieval town of Montalcino. - Visit two different wine estates to sample the renowned Brunello DOCG and younger Rosso DOC local wines. - Lunch in a small winery. Enjoy another typical Tuscan menu paired with glorious Brunello di Montalcino wine. - Wine collectors will appreciate the opportunity to purchase (and conveniently have shipped home for them!) rare bottles of Brunello, directly from Montalcino's leading wine store. - Drive back to the hotel for dinner. - DAY 5 - Leisurely wind up your vacation
- Breakfast at the hotel and check out. - Enjoy the swimming pool and the charming countryside surroundings, before joining your private transfer to the Pisa or Florence airports later in the morning.
This wine vacation package of Chianti and Brunello is a must-do event if you are in Tuscany. It was a joy to spend the day with Matteo as our guide, and we were introduced to the old world way of life in Tuscany. We had lunch in a 1000-year-old farmhouse, and we learned so much about wine, the effort it takes to bring the grapes from field to market, the doctrines of DOCG certifications. It was one of the highlights of our Italian visit. We ordered wine and olive oil to ship home, and every time we enjoy our Italian 'treasures' we are transported back to Tuscany!









