Medieval hilltop villages and green rolling hills covered with vineyards and olive groves, here is the Tuscany loved all over the world! On a visit to Chianti, both your eyes and taste buds are in for a treat, as the region is the epitome of captivating scenery and acclaimed wines. This private tour of Tuscany will engage seasoned connoisseurs and first-time tasters with historic wineries and iconic landscapes.

The Chianti area is one of Italy best destinations especially for countryside lovers and wine enthusiasts. Indeed, here it is hard to drive even a few minutes without encountering verdant vineyards tucked between hillsides not overflowing with grape vines. There is no doubt the mighty grape is the beating heart of Chianti but be sure to go exploring beyond the vineyards.

Discover the True Essence of the Chianti Region

For Italy wine aficionados, the Chianti Classico is the introduction to Tuscany wine country and with so many wineries to choose from, it can be overwhelming to plan a visit. At Nancy Aiello Tours, we pride ourselves on the personal relationships that we have with winery owners and winemakers. These relationships allow us to take you to selected famous and off-the-beaten-path wineries and vineyards in beautiful locations around the region.

On this private Chianti tour from Florence, a full day excursion, it is all taken care of. You will experience a carefully tailored itinerary built around your tastes and needs combined with our firsthand personalized recommendations. We will help you to discover the true essence of this popular Italian region for wine tasting and picturesque hilltop towns assisted by our experienced local driver/guides team. You will travel through the hills of Tuscany with an expert who in addition to navigating for you will bring your destination to life with care and passion.

Private Wine Country Tour Curated to Your Preferences

With our firsthand experience, clients appreciate the way we hone tours to meet their needs, with expert driver-guides, and itineraries matched to them. Our travel advisors can expertly personalize itineraries that adapt to favor families with kids and even teetotalers interested in the wine country. Make the most of your time with this day trip from Florence crafted to fit you and your party, including pick up location, length of tour, types of wineries and tasting experiences.

Indulge in epic landscapes dotted with medieval castles and ancient churches. Get a taste of both wineries, vineyards and historical cellars. Discover the secrets to the production of wonderful award winning wines in a private and personalized way. From family-run wineries where the owners themselves may show you around to large estates, there is a taste of Tuscany here just waiting to be discovered! Whether you are a wine novice or aficionado, we will create an outing with wineries matched to you.

The Chianti Classico is of one of Italy’s most famous wine making regions. But wine is not the only reason for the region’s fame and visitors will quickly realize it is only the beginning. The landscape has a unique type of beauty. Tuscany is a land of softly rolling hills where a perfect balance between nature and human activity has been reached. The views belong in a Renaissance painting and we have many interesting stories to share about it.

You will visit wineries, learn about the art of wine making, or perhaps simply explore the scenic countryside and its scattered charming villages. With a wide choice of wineries and extensive things to see, we can customize your itinerary based on length of day, the types of wine that you are interested in, and the experience you would like to have.

Family Friendly Private Tour of Tuscany

Sure, the Chianti wine region is known for its excellent wines and as a top travel destination for romantic getaways and vinous vacations, but it is a welcoming spot for families too. The Chianti Classico Road is actually one of our most popular family trip requests when planning a wine tour in Italy with kids. Treat your family to a lighthearted experience you will all remember fondly.

The Tuscan countryside is a family friendly vacation destination in Italy. Delight your kids (young children or interested teens) with a wine country tour that accommodates the young, the old and everyone in between. With us, you can bring the kids along for the ride, the education, and the sights. In addition, among the large historic estates and smaller boutique family-owned wineries available, we can arrange personalized visits to wine producers where kids are welcome and parents can indulge in tastings. Not to mention that with teenagers, we can include stops for tasting extra virgin olive oils or artisanal cheeses. No itinerary can include all these attractions. But we can certainly put together a child-friendly tour of Tuscany from Florence that focus on the ones that would work best for you and your family.

Truly our private Chianti Tuscany tour offers plenty opportunities to enthrall and delight adults and children. Luscious landscapes of rolling hills, cozy towns combined with gastronomic experiences, family-friendly wineries, and castles that conquer the little ones result in itineraries that appeal to all. Then, if you are seeking a playful and fun approach to tasting and learning about wine while you see the region’s most beautiful spots, this is the right kid friendly wine country tour in Tuscany that entertains every member of the family!


Head into the heart of the Tuscan countryside for a day of wine education, tasting and relaxation. Enjoy private, round-trip transportation in a plush Mercedes car. Get personalized attention from your own dedicated driver/guide who will handle the driving, provide personalized commentary to your specific interests and introduces at the wineries ensuring that your day is smooth and enjoyable.

The best way to begin your understanding of Italian wine making culture is to experience it firsthand. You will learn all about the process and grasp the depth of the area. You will see wine and olive oil still produced today according to age-old traditions. You will hear about Italy’s wine production, wine making techniques, and bottle aging. And finally taste some of the world’s most celebrated wines at some of the best wineries in Tuscany.


The area between Florence and Siena, known as Chianti, is one of the most prominent wine-producing regions in the world. This area offers extraordinary climate and soils for producing excellent wines. The natural beauty of our local wine country rich in vineyards, olive orchards, and picturesque farmhouses on hills with lines of cypress trees provides an amazing setting for visiting unique wineries where you can enjoy exceptional tastings.

Our Chianti excursions vary depending on your specific interests. A typical excursion may include a visit to two wineries or tasting rooms, where you can sample our local wines in wonderful scenery and a stop in one of the many stone villages, often built from the ruins of Medieval castles.

We would recommend this private Tuscany wine tour from Florence to anyone wanting to get to know and connect to the world of Italian wine in a meaningful way. You will see the living history of one of the largest wine region in Italy where there is still a genuine and enchanted atmosphere. Moreover, you will learn tidbits of local wine making history and culture. Straightaway you will realize the backstory of Chianti. All of a sudden, the delightful wines you taste will take on new meaning.

Included in the Private Tour

Planning, arranging, transportation, driver-guide, and appointments at wineries matched to you.

✔️Full Day Chianti Region Wine Tasting Day Trip from Florence
✔️Tuscany Wine Country Travel Experience Suitable for Families with Kids
✔️Private Guided Chauffeured Tour
✔️Private Licensed Professional Local Driver-Guide
✔️Private Deluxe Vehicle
✔️Hotel Pickup and Drop-Off
✔️Scenic Drive
✔️Guided Vineyard Tour
✔️Guided Wine Tasting

How it Works

Flexible pickup and drop off. Our private Chianti Tuscany tour from Florence can also depart from any Tuscan town. We will pick you up and drop off at your location of choice. Quotes will vary depending on pick-up location.

Firsthand travel advice. We design private Tuscany wine tours for first-time winery visitors, wine novices, or collectors! Listening to your interests, we can suggest the best options for you. During the booking process, you will have our top, personalized recommendations so that you can make the most of your time here.

Highly personalized service. Because this is a private tour, your itinerary can be customized to your specifications. Tell our Italian-based team when, what you would like to tour, and from where. You will also have the opportunity to tell us how we can personalize the experience to meet your wine preferences and experiential expectations. With that in mind, we will curate the perfect Tuscan escape for you and yours.


Please let us know your needs and details of your trip and we will let you know if we can offer you a private tour of Tuscany especially designed to work around you.


When is the best time of year to visit Chianti?

We usually recommend during spring (April, May, June) and autumn (September, October). These months combine the convenience of peak season with comfortable temperatures.

How many wineries will we visit in a day?
You will visit and taste at two or three wineries handpicked for you. Visiting 2 to 3 wineries per day is a leisurely, relaxed pace that allows you time to talk with the grape growers at each winery and enjoy your surroundings. Sure, winery visits and tastings in Italy have a different time scale and etiquette than in the U.S. where you sip and go. Indeed, visits here are mostly by appointment only and have an average duration of one hour and thirty minutes. For the optimal day, we have found our guests enjoy relaxed visits to two or three wineries. They appreciate the different focus of the winery visits in Italy, and value the more in-depth, personal attention and unhurried pace.

Which wineries will we visit?

We do not have just one set of wineries that we visit, as there are so many great ones! With so many wonderful wineries in this area, there is no reason to put on a “one size fits all” wine tour. We customize the itinerary based on several factors, some of which include, locations of pick-ups, wine preferences, and available wineries for the day (as appointments are usually necessary and they all have different days of operation and special event scheduling).

Do we stop for lunch on tour?

Yes! In a region with so much great food it would be crazy not to. In addition, your driver/guide will be happy to recommend delicious choices matched to you.

Do you combine people to share the tour?
All our tours are private and totally customized to suit your desires, which means that you do not share your tour with anyone else. Our private tours are exclusive to one booking party and we do not combine separate reservations to form groups.

Are tips included?

Tips are optional and is left to individual discretion.

Private Chianti Tuscany Tour Customized For You!


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