Best Way to Visit Wineries in Tuscany — 10 Tips to Plan Your Wine Tour
10 practical tips for planning a wine tour in Tuscany — from choosing which sub-region to focus on, to why Antinori and Biondi Santi need advance booking.

Embark on a journey through the heart of Tuscany's legendary wine-producing landscapes with our exclusive private wine tours, carefully crafted by expert and passionate guides and sommeliers. Immerse yourself in the beauty of the Tuscan countryside, renowned worldwide for its rolling hills, charming medieval towns like Montepulciano, Montalcino, and San Gimignano, and scenic panoramas as in Bolgheri. Stroll along the iconic cypress-lined roads seen in films and paintings, or walk through the vineyards where some of the finest wines in the world are crafted.
Your experience begins with a pick-up directly from your accommodation in Florence. A private, air-conditioned vehicle with an expert driver/guide will ensure that your day is both comfortable and stress-free. Each tour includes private access to prestigious wineries and cellars, guided by the owners and winemakers themselves, with a delicious, regionally inspired meal awaiting you at a local restaurant at midday.
Every private Tuscany wine tour includes a customized itinerary built around the best of the region's wine areas, private transportation with a dedicated English-speaking driver, exclusive winery and cellar visits — with options for truffle hunting or truffle-and-wine experiences — and authentic, wine-paired local meals.
Carefully designed to showcase the best of Tuscany's wine regions, ensuring you experience the highlights of each area.
Travel in comfort with a dedicated English-speaking driver and private vehicle. Pick-up and drop-off is directly at your accommodation in Florence.
Winery visits, cellar tours, and scenic vineyard strolls, with options for exciting truffle hunting or relaxing truffle-and-wine experiences.
Enjoy traditional, wine-paired meals that celebrate Tuscany's rich culinary heritage.
With our dedicated private vehicles and English-speaking drivers, you are picked up directly at your accommodation. Here is how long it takes to reach the cellar doors across Tuscany:
Gallo Nero estates, rolling cypress hills & closest cellars to Florence
Vernaccia DOCG white wines & iconic medieval skyline
Legendary Brunello di Montalcino & UNESCO World Heritage scenery
Vino Nobile di Montepulciano, Etruscan cellars & Renaissance piazza
World-famous Super Tuscan estates along the Mediterranean breeze
Private woodland truffle hunts & boutique hilltop winemakers
11 private itineraries with dedicated transport and the freedom to enjoy each stop at your own pace.
Private · Full dayA full day from Florence to Bolgheri, birthplace of the Super Tuscan movement, with guided cellar visits and tastings.
Departs 8:30 AM
Private · Full dayA private tour through Chianti Classico's hills, tasting Chianti Classico, Riserva, and Super Tuscan wines at top estates.
Departs 9:30 AM
Private · Full dayJust 30 minutes from Florence, explore Chianti Rufina's ancient cellars with a tasting, cheese pairing, and vineyard lunch.
Departs 9:30 AM
Private · Full dayA full day with an English-speaking wine expert across three Chianti Classico wineries, from DOCG to Super Tuscan.
Departs 9:30 AM
Private · Full dayTwo Montalcino wineries, guided tastings of Brunello and Rosso di Montalcino, and a Tuscan lunch among the vines.
Departs 9:00 AM
Private · Full dayFrom Chianti Classico to San Gimignano, tasting Vernaccia — Tuscany's celebrated white wine — in one guided day.
Departs 9:30 AM
Private · Full dayTwo wineries in Montespertoli, pairing sparkling wine production with a boutique Chianti tasting and Tuscan lunch.
Departs 9:30 AM
Private · Full dayHunt white truffles in San Miniato with an expert and her trained dog, then feast on a multi-course truffle menu.
Departs 9:00 AM
Private · Full dayTruffle hunting in the Tuscan woods followed by a Chianti Classico winery tasting and truffle-based lunch.
Departs 9:00 AM
Private · Full dayExplore medieval Montepulciano's 700 years of winemaking with private tastings of Nobile and Rosso di Montepulciano.
Departs 9:00 AM
Private · Full dayAn off-the-beaten-path day pairing artisanal goat cheese with a prestigious Chianti winery and olive oil tasting.
Departs 9:30 AMExclusive private moments: rolling vineyards, subterranean cellars, and relaxed winery lunches designed around you.
Essential DOCG appellation guides, scenic travel routes, and local winery etiquette written by our Florentine wine team to help you prepare your private tasting experience.
10 practical tips for planning a wine tour in Tuscany — from choosing which sub-region to focus on, to why Antinori and Biondi Santi need advance booking.
The territory of Chianti Classico stretches between Siena and Florence — and why the word 'Classico' matters more than most travelers realize.
Inside the Montalcino production area, its unique microclimate, and the Sangiovese Grosso grape that defines Brunello.
Bolgheri is where the Super Tuscan wine movement began in 1968 — a guide to the region's top estates, from Tenuta San Guido to Ornellaia.
For a classic private Tuscany wine experience from Florence, we recommend a day in Chianti Classico and the Super Tuscan countryside. It offers beautiful landscapes, renowned red wines, welcoming family-run estates, and the flexibility to enjoy the day at your own pace.
If you are especially interested in Brunello di Montalcino or Vino Nobile di Montepulciano, we can also arrange a private itinerary further south in Tuscany. These areas are ideal for wine enthusiasts, although the journey from Florence is longer. Your private tour can be tailored around your preferred wine region, the number of wineries you would like to visit and whether you would like to include a traditional Tuscan lunch.
Yes — the vehicle, driver and guide are reserved exclusively for your party for the entire day. You won't be grouped with other travelers at any winery.
Hotel pickup is available on our private tours. However, some streets in Florence’s historic center, including pedestrian-only streets within the ZTL, are inaccessible to our minivans. If your hotel is in one of these areas, we will arrange a convenient meeting point near the hotel, where one of our guides will meet you and arrange your pickup in a minivan.
Shared tours do not include individual hotel pickup — all guests meet together at a designated meeting point in Florence and depart at the scheduled time.
Our Chianti Classico and San Gimignano tours are the most popular starting points — they combine well-known wines, classic Tuscan scenery and a manageable drive from Florence, making them an easy, representative introduction to the region.
Yes — as a private tour, your sommelier guide can customize the estates visited around your personal wine preferences, whether you favor historic Chianti Classico DOCG producers or cutting-edge Super Tuscan cellars. If you have specific wineries you would love to visit, we are delighted to arrange private cellar tours and tastings at your requested estates, subject to their hospitality availability and provided they are located within the wine sub-region selected for your day's journey.
Tuscany is a vast and varied region with winding countryside roads. When planning a wine route, geographic pacing is essential: what appears deceptively close on a map can easily translate into a 1.5 to 2-hour drive over undulating hills, cutting into your relaxed tasting time. For this reason, we gladly accommodate specific winery requests as long as each estate is comfortably reachable within approximately 30 to 40 minutes of driving from the other stops on the itinerary.
Simply let us know your preferred producers or wine styles when inquiring: our local wine team will review their locations and craft a seamless, beautifully paced itinerary so you spend your day enjoying world-class wines rather than sitting in transit.
Lunch is included on most of our tours — check the specific tour page, since this is shown per itinerary (a wine-paired lunch at a winery or a local restaurant).
Yes — on our private tours, pickup and drop-off are included in the published price if your accommodation (hotel, villa, or country estate) is located within approximately 20 minutes of central Florence (such as the Santa Croce district, Piazzale Michelangelo, or the immediate surrounding hillside).
If your pickup location is further than 20 minutes away, we will evaluate whether it lies naturally along the route toward the wine region visited that day, or if it requires a significant detour or is situated in another Tuscan province (such as Siena, Arezzo, Lucca, or Pistoia). In these cases, please let us know your exact address and accommodations when inquiring: we will provide a transparent supplemental fee to add to the base tour price based on additional travel time and mileage.
If you are staying in another Italian region (such as Rome/Lazio, Umbria, or Emilia-Romagna), we recommend using public transit — comfortable high-speed trains arrive directly into Florence at Firenze Santa Maria Novella (SMN) or Firenze Campo di Marte station. Meeting your guide directly at the Florence station allows you to keep travel costs well under control while maximizing your time in the vineyards.
“A beautiful tour through some of the most enchanting wineries we have ever visited. Andrea made the entire day truly special with his warmth, knowledge, and thoughtful attention to every detail. From the stunning scenery to the memorable tastings, it was an experience we will always treasure.”
Tour: Chianti & Super Tuscan Wine Tour from Florence
“We absolutely loved this experience—it exceeded even our highest expectations. Every detail of the day was perfectly planned, from the beautiful locations and wonderful tastings to the relaxed, personal atmosphere throughout. Andrea truly is an exceptional guide: knowledgeable, welcoming, attentive, and genuinely passionate about sharing the best of the region. His enthusiasm made the whole experience feel special, memorable, and far more than just a tour.”
Tour: Chianti & Super Tuscan Wine Tour from Florence
“What a tour — genuinely informative and personal, and everyone was made to feel so welcome. Funny too, with real depth of knowledge about the wine region. Such a great small group, we really got to know each other along the way — an unforgettable day, so grateful for it.”
Tour: Chianti & Super Tuscan Wine Tour from Florence
“Our guide, Andrea, had an excellent knowledge of both the areas we explored and the wines we tasted. He was engaging to listen to and, thanks to his great relationships with the wineries we visited, he was able to point out several interesting details and local highlights along the way. If you are staying in Florence and love Brunello, this is a tour well worth booking.”
Tour: Brunello the Big Red Wine Tour
Brittany ZimmermanUS · Sep 2026 · via tripadvisor★★★★★“A really well-run experience — Andrea's knowledge of wine came through clearly, and every wine we tried was excellent. Never once did it feel like a sales pitch. The whole day felt private and personal, and the food was delicious too.”
Tour: Montalcino Wine Tour
Marc TranUS · Sep 2026 · via google★★★★★“A wonderful day touring Chianti Classico — we stopped at three small, artisanal wineries, with a delicious lunch at one of them. I have visited wineries elsewhere in Italy and beyond, but this stood out: meeting the winemakers felt like catching up with old friends, and the conversations gave me a real appreciation for natural Italian wine I did not have before. Nico, our guide and sommelier, made the day — his enthusiasm for wine, food pairing, and Italian culture was infectious, and we got around in a comfortably air-conditioned car despite the summer heat. Highly recommend Italy and Wine, and I would book again. ”
Tour: Chianti and Super Tuscan Wine Tour
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