Top Florence Holidays in 2026

This afternoon excursion takes you beyond the tourist hot spots of Florence to the heart of Chianti, famous for its scenic beauty, rolling hills, vineyards, and olive groves. Venture into the Tuscan countryside on this private day trip, which includes a personal driver-guide who saves you from having to worry about driving after imbibing. Tour the notable wine region of Chianti—and choose to visit a local winery, where you can enjoy a tasting (own expense)—before enjoying free time to explore the town of Greve.

Experience Tuscany's wine culture on this private wineries tour. Ideal for travelers based in Florence, explore beyond the city without having to hire a car. Travel with a knowledgeable sommelier guide through rolling hills and vineyards, visiting three estates to sample regional wines and olive oil. Enjoy a traditional Tuscan lunch at a family-owned winery paired with wine. Perfect for food lovers looking to immerse themselves in local flavors.

Discover Florence like never before in a collection car: ORIGINAL vintage Fiat 500 Spiaggina — an icon of Italian style and la dolce vita. The tour includes a bottle of wine with ice bucket. This is not just a tour, but a private journey through time. Over 1.5–2 hours, the route is fully customizable to your interests. Drive past along the Lungarni, through Porta Romana, and up to Piazzale Michelangelo for breathtaking views. You can also escape to San Miniato al Monte or the hilltop town of Fiesole for unforgettable panoramas. Why choose this experience? – Rare & Original vintage Fiat 500 (not modified) – Iconic landmarks + hidden gems – Perfect for couples, or special occasions (3-4 people max) Feel Florence in the most authentic way — intimate, slow-paced, and unforgettable.

One of the best ways to see the Tuscan countryside is up close by bike. This half-day small-group bike tour conveniently departs from Florence and takes care of the itinerary and equipment rentals for you. Focus on sightseeing while your guide handles the navigation. Enjoy a tasting of local foods such as olive oil, fresh bread, and Tuscan cold cuts paired with a glass of Chianti wine.

Explore Florence without getting sore feet, and after the afternoon heat has cooled, on this scenic group bike tour. Ride past historic sites as you follow your local guide, stopping at landmarks like the Duomo, Medici Palace, and Santo Spirito Square. Enjoy a picnic with snacks and wine by the Arno River as you watch the sunset over Florence’s skyline.

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.

Spend a day in the Tuscan countryside without having to puzzle through tricky transportation on this Chianti and San Gimignano day trip that includes a driver from Florence. Stop in Montefioralle for photos, then visit a Tuscan winery in Greve in Chianti, where you’ll tour the vineyards, learn about the wine-making process, and enjoy tastings of Chianti Classico and other regional specialties. Next, explore the medieval town of San Gimignano before heading to a nearby farm for a light lunch with Tuscan appetizers, wines, and oils.

Experience the allure of Tuscany without the hassle of tricky logistics with this all-inclusive day trip from Rome. Save time with a high-speed train to Florence, where you’ll hop on a minibus with your tour leader and small group to visit Monteriggioni, Siena, and San Gimignano. End your Tuscan adventure with a wine and olive oil tasting in Chianti before heading back to Florence for the return train to Rome.

Riding a Vespa is a quintessential Italian experience and, with this small-group tour, you don’t need a motorbike license to enjoy it. Simply join an intimate gathering of like-minded folk, meet your personal driver, don your helmet, and hop aboard. See Florence’s UNESCO World Heritage–listed center up close and enjoy stunning city views from Piazzale Michelangelo, the village of Fiesole, and a hilltop church.

Most Tuscany tours from Florence include hours cooped up in a tour bus on the main highways. On this unique experience, you'll take the wheel to drive along idyllic country roads in a vintage Fiat 500, plus get a taste of local cuisine. Travel in convoy behind an expert guide so you can focus on the Tuscan views rather than a map, and wind your way through the hills to the villa. Then, enjoy time to stroll among the gardens and enjoy a gourmet picnic lunch with a wine tasting.

Italy's culinary traditions run deep, but it can be hard to decipher as a first-time visitor. Eliminate the guesswork and embark on a culinary journey through Florence's San Lorenzo Market to sample Tuscan delicacies like cheeses, meats, truffle olive oil, and balsamic vinegar. Enjoy a private wine tasting at a historic wine shop and end the tour with an authentic gelato (ice cream) with commentary from your guide.

We would prepare two classic dishes of the Italian tradition that every Sunday are present on the tables of every self-respecting Italian family. We will visit the Pasta Museum with an expert Guide. We will do both a historical/theoretical introduction and then move on to the practical part where you can make with your own hands two gourmet dishes that have made Italy famous in the world: Lasagne and Tiramisu!

Experience Tuscany’s iconic Chianti wine country without the hassle of navigating the country roads on your own with this private tour from Florence. Head directly to a historic winery in the Chianti hills for a visit and tasting, then continue on to a boutique winery overlooking San Gimignano. Stop for a tasty lunch overlooking the medieval hill town featuring classic Tuscan specialties.

Siena and San Gimignano are two of the most stunning locations in Tuscany, but a driver is essential for visiting them in a single day. Discover both during this full-day private tour, which includes round-trip transportation offered from either Florence or Livorno Port. Travel through rolling hills, vineyards, and villas. Tours include a Tuscan lunch and wine tasting at a hand-picked estate.

Get a taste of Tuscan landscape, wine, and food on this full-day private tour from Florence. Led by an English-speaking driver, discover the regions of Chianti and Val d’Orcia, soaking up the local flavor with several wine tastings. Explore the charming towns of Castellina and Montepulciano, and savor a traditional Tuscan lunch at a farmhouse in Montalcino.

Discover the countryside and towns of Tuscany on a day trip from Florence, and see more of the region than you could manage alone. You’ll travel with a guide in a small group of no more than 12 people, and enjoy a mix of guided tours, free time, and tastings for an in-depth visit. Highlights include Siena, San Gimignano, the Leaning Tower of Pisa, and lunch at a Tuscan winery.

During this private tour designed with wine lovers in mind, spend the day sampling and shopping for wines in the Tuscan countryside. Travel through the medieval villages of Montefioralle, Greve in Chianti, Panzano, and Castellina, to explore their charming streets, visit local shops, and, of course, sample a variety of wines at cellars.

Soak up the Tuscan sun, and delve into Chianti's cuisine, without the hassle of navigating on this open-top minivan tour. Enjoy a scenic drive through the countryside, stopping for a tour and tasting at a local cellar. Take a stroll through the villages of Montefioralle and Greve in Chianti before sitting down to a Tuscan lunch at a second cellar featuring a multi-course meal with wine pairing.

Ideal for travelers looking for off-the-beaten-path adventures, Italian-style, this tour pairs an all-terrain vehicle (ATV) off-road session with wine tastings and medieval village visits. After a quick lesson, explore the Chianti countryside riding your own ATV or on the back of someone else's. Then, hop on the tour minivan and head to the Tuscan hill towns of Montefioralle and Piazza Matteotti for exploring and shopping. Finish the day with a generous lunch and six wine tastings at a classic Tuscan winery.

Explore the Tuscan countryside on this full-day outing to the Italian countryside from Florence to discover the region's wine-making culture. Visit the medieval hill town of Montalcino for a stroll through its streets. Then, continue to Montepulciano—which is famous for the variety of grapes that bear its name—for a wine tasting and a visit to the underground city. On the return journey, drive through the UNESCO-listed Val d’Orcia and make a couple of panoramic stops.

Squish grapes between your toes and have a laugh before settling down to a delicious wine tasting while learning about how Tuscan wine is produced on this private tour from Florence. Besides wine, try an aperitivo, cold cuts, jam, and fresh garden vegetables before a main course and desert.

Chianti wine country is known for its magical scenery, but exploring the area can be tricky for out-of-town travelers. Leave traffic and navigation to your private driver as you sit back and enjoy the ride on this half-day wine-tasting tour. Savor both red (Chianti Classico) and white (Vernaccia) wines, capped off by the chance to explore the beautiful medieval town of San Gimignano.

No trip to Florence is complete without experiencing the city’s historic wine windows—and this small-group walking tour makes discovering them easier. Led by your local guide, stroll past many of the city’s highlight medieval and Renaissance attractions, from the Duomo to the Piazza della Repubblica. Along the way, enjoy a glass of wine—then, cap off your experience with an extended wine tasting, alongside classic Tuscan appetizers.

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.