Top Florence Holidays in 2026

Learn to appreciate some of the most prestigious reds from the Chianti region without the logistical hassle of getting around the countryside on your own on this full-day wine tasting tour from Florence. Join a small group and take a deep dive into the ‘Supertuscan’ world, plus get tips on developing your palate from a wine expert. Taste regional varietals at three different wineries, learn about wine-food pairings, and top it off with a Tuscan lunch at a boutique winery paired with more wine.

Discover the beauty of Tuscany on this evening tour from Florence, featuring a visit to the Chianti countryside and a 4-course dinner. Head to a charming farmhouse winery to sample up to three glasses of Tuscan wine. Then head to a second estate to enjoy a relaxing evening of wine, dinner, and stunning views before returning to Florence.

Tuscany is home to some of Italy’s premier wine country, but taking on the rural roads to reach the top wineries on your own can be a challenge. Skip the hassle of navigating the Montalcino countryside and set off directly from Florence with a private driver. Stop for tours and tastings at three award-winning wineries (tastings are an additional expense) plus visit the top wine shop in Montalcino’s medieval old town.

Escape far from the crowds and traffic—and enjoy an immersive way to explore the iconic Chianti countryside that few other visitors get to experience—on this small-group, full-day hiking tour from Florence. Ramble for 4 miles (7 kilometers) on trails through vineyards and olive groves to really soak up the scenery. Along the way, visit three wineries to sample up to 10 wines, and enjoy Tuscan specialties for lunch.

With spotty public transportation and winding rural roads, the Brunello di Montalcino wine country can be tricky to explore on your own. Discover the history and flavor of one of Italy’s premier wines with ease on this full-day tour from Florence. Travel through the Tuscan countryside to the Brunello hills and the village of Montalcino. Visit a small, family-run winery to learn about traditional production methods and taste renowned varietals like Brunello DOCG and Rosso di Montalcino DOC. Savor a farm-fresh lunch of Tuscan specialties at the estate, and finish the day with more tastings at another local winery.

Florence looks magical when illuminated during Christmas time, and this tour is a great way to discover the city’s most beautiful sites, get top photography tips, and see secret parts of Florence that you wouldn’t discover alone. You won’t have to worry about navigating, as a photographer accompanies and gives you top tips on how to take great photos during the evening. Beginners and advanced photographers with any type of camera are welcome.

The rural hills of Chianti are almost impossible to explore with public transport and navigating the country roads on your own can be frustrating. With this private tour, set off for an afternoon with a professional driver to take in the iconic landscape, hilltowns, and wine country stress-free. Visit the historic villages of Castellina, with a stops at exclusive wine estates.

Join a one-of-a-kind experience that goes beyond a traditional wine tasting: become a winemaker for a day. In this exclusive masterclass, you'll sample six premium single-varietal wines, exploring their aromas, nuances, and unique characteristics under the guidance of an expert sommelier. Then comes the most exciting part, blend your own perfect wine, balancing body, intensity, and fragrance to craft a truly personalized creation. As you uncover the secrets of Tuscan winemaking, you'll also indulge in a selection of local gourmet specialties. To top it all off, you'll bottle your custom blend with a personalized label, bringing home a unique and authentic taste of Tuscany. A sensory and creative adventure, ideal for wine lovers who want to experience the artisanal and authentic side of Tuscan enology.

Embark on an intimate adventure from Florence through the stunning Chianti hills in an open-air tuk tuk, perfect for two. Feel the fresh breeze in your hair as you pass by charming vineyards and olive groves, with your guide sharing enchanting local tales. End the day at a picturesque winery, where you'll enjoy a guided tour, wine tasting, and a delicious homemade Tuscan lunch.

Learn to distinguish authentic Tuscan cuisine from tourist traps on this great-value sightseeing and tasting tour. Florence’s Central Market can be daunting to approach on your own, but a guide shows you how to find the best olive oil, fresh pasta, truffles, wine, and more as you shop alongside residents. Walk it off while exploring top sights like Duomo Square and Santa Croce, stopping for a savory lunch with wine at a hand-picked restaurant.

Small family-run winery, certified organic, which produces exclusively from its own grapes with a strong focus on sustainability. We will offer you a private tasting of 3 - 5 wines with appetizers, accompanied by a visit to the barrel cellar and the wine cellar. Tasting: 100% Sangiovese rosé, Chianti Classico Vintage and Gran Selezione, with platter of cold cuts, cheeses and bread. With a minimum purchase of €90 per person, the cost of the tasting will be fully refunded. - - - A small family-run winery, organically certified, producing exclusively from its own grapes with a strong commitment to sustainability. We offer a private tasting of 3–5 wines with appetisers, including a visit to the barrel cellar and winemaking facility. Featured wines : Rosato 100% Sangiovese, Chianti Classico Vintage and Gran Selezione, served with a charcuterie, cheese board and bread basket. If you spend at least €90 per person, the tasting fee will be fully refunded.

Relaxation, suggestive landscapes, perfumes and above all uncontaminated nature are the setting for this experience rich in typical and unique flavors.

Go beyond the Renaissance history you'll find in most guidebooks and learn about Florence's dark past on this unique walking tour. Listen to tales of betrayal, murder, and mystery as you explore the city in the evening, taking in some of the most famous landmarks with your guide along the way. Break up your walk with two tasting stops to sample Tuscan charcuterie and wine, plus traditional cantucci cookies and sweet vin santo (sweet wine), and come away with a better understanding of Florentine lore.

Shun the beaten track and discover the Tuscany most travelers rarely see on this private 4WD wine safari direct from your Florence hotel. Taste nine different wines as well as cheese, cured meats, and olive oil as you explore three separate Chianti wineries, two set in historic villas. Along the way, get off-road amid cypresses, farms, and churches, explore ancient cellars and an olive mill, and savor a Tuscan lunch.

Immerse yourself in Italian wine culture on this half-day tour around the revered Chianti Classico wine region. There’s no crowding into cellar doors on this small-group tour of the region. Instead, spend your afternoon exploring the cellars and sampling the products of some of the region’s vineyards. All transport is provided, so you can fully enjoy your tastings.

Explore the Tuscan countryside near San Gimignano on a classic Ape Calessino—a 3-wheeled Italian tuk-tuk. Depart from San Gimignano or nearby and travel the panoramic roads of Tuscany and the Chianti hills, passing vineyards, cypress forests, and rural houses. Stop at a local winery for an authentic Tuscan meal with wine and olive oil tastings.

If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine of the Chianti lands, immersed in the green countryside, this is the tour for you. The small group size of no more than 6 pax will make you appreciate the tranquility and peace of Chianti

Live an authentic experience in the heart of Chianti Classico with a visit to two family-run wineries, where you will be welcomed directly by the producers. In an intimate and relaxed atmosphere you can taste excellent wines, extra virgin olive oil, cheeses and typical cold cuts, discovering the most genuine flavors of Tuscany. The Guide, born and raised in the region, will accompany you by private car, telling the history, traditions and curiosities of the territory. Along the way there is also a stop in a small village in Chianti, to immerse yourself even more in local life. The tour is designed for those looking for a personal and non-tourist experience: familiar and welcoming wineries, direct dialogue with the owners, quiet rhythms and an authentic contact with Tuscan wine culture.

Discover Florence’s rich flavors and iconic landmarks on this lively group food and wine tour. Led by a local Florentine guide, you’ll wander through the charming streets from the city center to El Duomo, stopping at handpicked spots to savor authentic regional dishes and local wines. Comfortable shoes are a must—you’ll be exploring plenty!

Join a fun mozzarella-making class in Florence with wine tasting, local dishes and expert guidance in a small-group atmosphere. Let’s be honest: you didn’t come to Florence just for the museums. You came for the food, and now, it’s your turn to make some. Come hungry. Leave happy. Smell slightly like mozzarella. No regrets. - Learn hands-on from a master cheese maker how to shape bocconcini, nodini, treccine and create rich, creamy burrata and stracciatella - Sip and swirl your way through a curated selection of Tuscan wines, paired perfectly with your fresh cheese creations - Enjoy your handmade cheeses alongside creative seasonal dishes in a cozy, music-filled atmosphere with max 12 guests for a personal experience

While standard Chianti tours take you through the region in a coach or minivan, this full-day excursion puts you behind the wheel. After a transfer from Florence, hop into your own electric Fiat Topolino and follow your guide in a lead car through vineyards and olive groves, stopping in Impruneta for a winery visit and a three-course Tuscan lunch.

Discover the essence of Tuscany on this immersive tour that combines history, stunning landscapes, and exquisite flavors. Departing from Villa Costanza, journey to Monteriggioni, a medieval fortress town where cobbled streets and artisan shops await. After exploring its historical charm, indulge in a guided wine tasting at a picturesque Chianti winery, savoring local varietals and regional delicacies. Continue to a renowned family-run winery in San Gimignano for another rich tasting experience that reflects the region's winemaking passion. This tour promises a blend of cultural immersion and culinary delight, perfect for history buffs and wine enthusiasts alike. - Depart from Villa Costanza at 14:45 for a half-day adventure - Explore the medieval fortress-town of Monteriggioni with free time - Enjoy guided wine tastings and cellar tours at two charming wineries - Experience the richness of Tuscan terroir with local cuisine pairings

Devote a day to discovering Siena and the Chianti Classico wine region on a private tour. Following a carefully crafted itinerary around Tuscany, you’ll check off highlights like Siena Cathedral and Piazza del Campo, along with picturesque villages like Castellina in Chianti. Enjoy a meal at a Tuscan farm, prepared by the farm owners themselves, to complete your authentic experience.

Go “under the Tuscan sun” like absolute royalty on this exclusive private tour of the local vineyards and countryside. Escorted by your driver, you’ll travel between the Chianti hills and San Gimignano, sampling exquisite wines and local goodies—think olive oil, sweets, cheeses, and truffles—and exploring vineyards, villages, and more. You’ll also sit down to a delicious 3-course lunch (included), getting a taste of rural Tuscan life.