As lovers of immersive exploration and a deep passion for our heritage, we love returning to our Italian roots to experience the beauty of Italy’s many charming regions, such as Tuscany! The Tuscan countryside is a region whose rolling hills never fail to beckon with timeless allure.

Get inspired by this luxurious journey, where every moment is an indulgence in art, cuisine, and culture. Let your mind wander as you explore the hidden gems of Florence, master the art of Tuscan cooking, and savor the renowned wines of Chianti as we guide you on an adventure through one of Italy’s most enchanting destinations. Are you ready to dive in?

Let’s go!

©sborisov, Getty Images Pro via Canva

Day 1: Arrival in Florence

As you touch down at Florence Airport, prepare to be whisked away into the lap of luxury. Your representative awaits you at a sumptuous hotel in the heart of Florence’s historic Piazza della Republica.

Picture of Statue of Leopold II, Piazza della Republica square, ©Dave Porter via Canva

Day 2: Exploring Florence

After a rejuvenating night’s sleep, dive into the cultural tapestry of Florence with a captivating walking tour. Discover hidden treasures like the Uffizi Gallery and the Church of Santa Croce, where the legacies of Michelangelo and Galileo come to life. Indulge in a tantalizing tasting of local cheeses and wines at a charming enoteca.

The Tribuna Room was the first nucleus of the Uffizi Gallery. Uffizi Palace in Florence, ©paologallophoto via Canva

Piazza Santa Croce with Santa Croce Basilica at the center, ©Nektarstock, Getty Images via Canva

Day 3: Tuscan Culinary Delights

Get ready to tantalize your taste buds as you venture into the art of Tuscan cuisine! Join a private cookery lesson at a prestigious culinary institute, starting with a visit to the bustling Mercato Centrale, where your chef will explain how to select the best produce. Then, return to the kitchen for a hands-on lesson and enjoy the fruits of your labor for lunch. The rest of the day is yours to enjoy at your leisure.

The historical Mercato Central (the Central Market) in Florence, Tuscany, ©gionnixx, Getty Images via Canva

Day 4: Journey to Chianti

Today, you will venture into the renowned Chianti region with your driver-guide, immersing yourself in the splendor of its vine-clad hills! Explore charming hilltop towns like Greve and Castellina and delight in two wine tastings at local vineyards. Experience the seamless blend of art, history, and natural beauty that defines the essence of Tuscany. Stop for a ‘refuel’ of local Tuscan wine before heading to your beautiful hotel in the Tuscan countryside.

A glass of red Chianti wine rests on the ledge of an outdoor patio with the beautiful Tuscan countryside in the background, ©Good Focused via Canva

Day 5: Siena and San Gimignano

It’s time to embark on a captivating walking tour of Siena, where Gothic cathedrals and medieval marvels await. Visit the Piazza del Campo, one of the finest main squares in Italy, and see the Palazzo Pubblico, which has served as Siena’s Town Hall since the 1300s.

Downtown Siena Skyline, ©f11photo, Getty Images Pro via Canva

As the afternoon sun hits, you’ll set off on a scenic excursion to San Gimignano, accompanied by your knowledgeable driver-guide. Wander through cobbled streets with your driver-guide, who will know the best local spots to savor the flavors of wild boar salami and Vernaccia wine amidst timeless surroundings.

An Old street in San Gimignano, Tuscany, a medieval town in Italy, ©Ekaterina Belova, from Getty Images Pro via Canva

San Gimignano, ©denisav, Getty Images via Canva

Day 6: Leisurely Exploration

Relish a day of leisure amidst the serenity of the Tuscan countryside, basking in the beauty of your surroundings and indulging in moments of pure relaxation.

Tuscan Vineyard with Grapes, ©Antonio Gravate via Canva

Day 7: Montepulciano and Montalcino

Prepare for a day filled with beautiful hillsides as you venture to the iconic towns of Montepulciano and Montalcino. Montepulciano is an archetypal Tuscan hilltop town set 605 meters above sea level, offering superb views over the surrounding countryside. You will find winding streets and a wealth of Renaissance-style palazzi and churches inside the ancient city walls and fortifications.

La Canonica, Montepulciano, ©scrisman via Canva

Similarly, Montalcino, famous for the Brunello wine, is everything you hope for in a Tuscan hilltop town: winding, narrow streets and charming flower-covered houses. Your immersion into the charm of these hilltop havens culminates with a visit to Castello Banfi Wine Estate, where you’ll taste some of the region’s most celebrated wines while reveling in the legacy of this esteemed winemaking dynasty.

La Fortezza di Montalcino, Italy, ©Otavio Clemente via Canva

Day 8: Departure

As this journey draws to a close, bid farewell to the splendors of Tuscany. Your private driver awaits you at Florence Airport as you leave with cherished memories of an unforgettable adventure through one of Italy’s most captivating regions.

Cityscape of Florence with famous bridge Ponte Vecchio from above, Florence Italy, ©Anastasia Collection via Canva

Interested in bringing an experience like this to life for yourself?

Let Villagro Travel Design help you create an indulgent and immersive journey tailored just to you. Our streamlined four-step design process helps our clients save time while giving them confidence that their trip investment is right. Contact us today to learn more and schedule your complimentary discovery call with our team.

About Villagro Travel Design

Villagro Travel Design is a boutique luxury travel advisory that crafts immersive journeys tailored to your unique passions and interests. With Villagro, you can expect unforgettable moments and meaningful encounters through a holistic planning approach designed to delight, inspire, and revitalize you.

As an independent affiliate of Gifted Travel Network, a Virtuoso member agency, we boast profound industry connections worldwide. We continuously nurture these relationships through direct engagements with hotel proprietors and general managers and strategic collaborations with tour partners to ensure privileged access for our clients.

Culinary Travel

A Taste of Tuscany: a Meticulously Curated 8-day Itinerary

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