Private Wine Country Tour from Florence

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.

Beautiful wines always spring from beautiful lands. Follow the path of taste through unique itineraries blending wine, food, landscapes and people. This private tour inside the region of Chianti will engage seasoned connoisseurs and first-time tasters with historic wineries and natural wonders.

Chianti Classico: For the Sangiovese Enthusiast

The Chianti Classico territory has more than 7200 hectares of vineyards, so 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 Sangiovese grapes. There is no doubt the mighty grape is the beating heart of Chianti but be sure to go exploring beyond the vineyards.

Beyond the Tasting Rooms

Sprawling vineyards, historic towns, and old stone farmhouses on hills with lines of cypress trees all add up to the Chianti Classico being one of the most scenic wine making region in Italy. However, wine tasting is not the only reason for the region’s fame and visitors will quickly realize it is only the beginning. Further along the wine trail you will explore the beautiful countryside and its scattered charming villages.

Curated to Your Tastes

Chianti is topping the chart of the most sought after Tuscan locations. We have been arranging tailored trips for more than a decade and we certainly know how to put together itineraries that adapt to favor families with kids, first-time winery visitors or collectors, and even teetotalers.

Personally Selected Wineries

Planning a trip in Chianti conjures many inviting images, not the least of which is your smiling self in the rolling, grapevine-covered hills of its wine country, soaking up the atmosphere with a glass of wine in hand. But with so many vineyards to choose from, it can be overwhelming to plan a visit. Not to mention that most wineries in Chianti require a reservation.

At Nancy Aiello Tours, we pride ourselves on the personal relationships that we have with winery owners and winemakers. These intimate connections allow us to take you to famous and off-the-beaten-path wineries and vineyards in beautiful locations around the region. Most of the wineries also produce Extra-Virgin olive oil DOP.

A True Tuscan Experience 

Indulge in epic landscapes while getting a taste of both vineyards and 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 historic estates, we will create an outing with wineries that match your palate.

We will help you to experience the true essence of this popular region for wine tasting and picturesque hill towns in an intimate and lighthearted way. On this beautiful planned itinerary, we will take you to two wineries in Chianti for a day of education, tasting and relaxation. Best of all, you will travel with one of our local driver-guides who in addition to navigating for you will introduce at the wineries, ensuring that your day is smooth and enjoyable.

Kid Friendly Approach

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

The Tuscan countryside offers fun distractions for adult and kid visitors. It makes for a spectacular road trip with unspoilt views and fairytale villages to stop by. But families can also learn how grapes are turned into wine, how wine gets its color and how long it takes to produce. Delight your young children or interested teens with a wine country tour that appeals to all. With us, you can bring the kids along for the ride, the education, and sightseeing.

Family Friendly Winery Experiences

While this may seem like a parents-only destination, there are tons of family-friendly vineyards in the Chianti region to visit…if you know where to go. Among the large historic properties and smaller boutique vineries in the region, we can arrange personalized visits to vineyards and farms where kids are welcome and parents can indulge in tastings. Not to mention that we can include stops for tasting extra virgin olive oils or artisan cheeses at family-owned properties that are happy to have children tagging along. No itinerary can include all these terrific spots in a day. But we can certainly put together a tour that focus on the ones that would work best for you and your family.

Then, if you are seeking a playful and fun approach to wine tasting 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!

Itinerary Overview

Stretching from Florence to Siena, Chianti is best known for being one of the most prominent wine-producing regions in the world. The extraordinary climate and soils do wonders for the grapes, but it also provides an amazing setting for visiting unique wineries where you can enjoy exceptional tasting experiences.

Most likely, the day will start with 50/60 minutes’ drive from your accommodation in Florence to the first winery in the morning; typical Tuscan lunch based on food and wine pairing and sightseeing in the afternoon! For the optimal day, you will visit two of the best wineries in the area. That is a reasonable number of wineries that will allow you to study and savor the delectable differences between the wines. Plus, it will allow you time to combine the educational wine tasting tours along with sightseeing, history and medieval highlights.

What to Expect

This morning, your private driver-guide will meet you at your accommodation. Travel through the landscape of rolling hills, vineyards and poppy fields of Tuscany, stopping at two different properties to taste some exquisite regional varietals and olive oil. Prepare to spend 60-90 minutes at each stop for the full experience, as you will see firsthand where wine is produced, learn about traditional winemaking techniques and enjoy a guided tour of the cellars. A full vineyard destination experience with educational tasting of local wines paired with fresh products followed by a casual lunch at one of the two vineyards. Then stop for sightseeing at one of the many medieval hilltop villages like Panzano, Radda, or Castellina before returning to your lodging in Florence.

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.

What is Included
✔️ Full-day tour with private air-conditioned Mercedes Benz car and driver-guide speaking in your language some languages are subject to availability
✔️ Round trip door-to-door pickup and drop off at your accommodation
✔️ Arranged appointments at wineries matched to you 
✔️ Visit to the winery cellars 
✔️ Selected tastings of great wines and precious typical products 
✔️ Our care for the smallest details of your personal travel experience

How it Works

Flexible pickup and drop off. Tour starts and concludes at your accommodation in Florence, alternatively we offer custom pickup options from any place in the surrounding area, for an additional fee. Quotes will vary depending on pick-up location.

Firsthand travel advice. Whether you are novice wine lovers or steeped in wine knowledge, we design private wine country tours for first-time winery visitors or collectors. Based on availability and your specific interests our Italian-based team will help you to choose the best option for you.

Highly personalized service. On this private Tuscany wine tour experience from Florence, you will enjoy a carefully tailored itinerary built around your needs including pick up location, length of tour, types of wineries and tasting experiences, all backed by our firsthand-personalized recommendations.

How to Book

The tours we offer are on a private basis only and advance booking is required.
All of our tours are available upon request, for you and your private party of 2 person minimum. When you are ready to book, tell our Italian-based team when, what you would like to tour, and from where. You will also have the opportunity to tell us if you have a particular winery, you would like to visit. With that in mind, we will curate the perfect Tuscan escape for you and yours.



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 either 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 with so many wonderful wineries in this area, there is no reason to put on a “one size fits all” wine tour. Therefore, we will customize this wine tasting itinerary through Chianti 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. The cost of the meal is NOT included in the tour price. Nevertheless, your private driver-guide would 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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