Savor Tuscany’s beauty with Chianti countryside stays, medieval towns, private wine tastings and a hands-on cooking class—culminating in unforgettable flavors, landscapes and culture. Starting from $1,594 per person.
The Chianti Experience package with Private Driver
4 Days/3 Nights
Starting from
$
per person*
Unforgettable Italian Journeys, Designed for You
Curated by passionate Italy experts, this sample itinerary is just the beginning of your Italian adventure. Every journey we design is unique, crafted around your interests, pace, and dreams so you can experience Italy’s beauty and culture like a true insider. Let us transform your vision into a one-of-a-kind travel experience, filled with authentic moments and lasting memories
Day 1
FLORENCE, TAVERNELLE VAL DI PESA
Renaissance Streets To Vineyard Peace
- Afternoon private transfer from Florence to countryside hotel in Chianti
- Free time to relax by the pool or gardens
- Welcome dinner with local wines
- Overnight in Chianti countryside
Day 2
TAVERNELLE VAL DI PESA, SAN GIMIGNANO, MONTERIGGIONI, SIENA
A Medieval Triple Feature From Hills To City
- Breakfast at hotel
- Full-day private tour with English-speaking driver
- Visit medieval San Gimignano
- Explore Monteriggioni’s walled village and fortress history
- Afternoon in Siena
- Return to hotel in Chianti, dinner on your own
Day 3
TAVERNELLE VAL DI PESA, GREVE IN CHIANTI, TUSCAN COOKING CLASS
Where Every Step Leads To Supper
- Breakfast at farmhouse
- Morning tour with private driver through Chianti wine region
- Visit Montefioralle
- Explore Greve in Chianti, market square, Franciscan Monastery
- Tasting at a historic butcher shop
- Winery tour and wine tasting
- Afternoon Tuscan cooking class at your hotel
- Prepare and enjoy your own Tuscan dinner with local wines
- Overnight at Chianti accommodation
Day 4
TAVERNELLE VAL DI PESA, FLORENCE
A Florence Finish After Days In The Hills
- Breakfast at accommodation
- Check-out and private transfer to Florence
- Tour concludes upon arrival in Florence
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
FLORENCE, TAVERNELLE VAL DI PESA
Renaissance Streets To Vineyard Peace
In the afternoon, enjoy a private transfer from Florence to your charming hotel nestled in the heart of the Chianti region. Upon arrival, take the opportunity to unwind—whether by lounging beside the pool, strolling through serene gardens, or simply soaking in the peaceful Tuscan landscape. As evening falls, delight in a welcome dinner featuring local specialties and expertly paired Chianti wines—your first taste of the region’s culinary excellence. Settle in for a restful night surrounded by the rolling hills of Tuscany.
Day 2
TAVERNELLE VAL DI PESA, SAN GIMIGNANO, MONTERIGGIONI, SIENA
A Medieval Triple Feature From Hills To City
Begin your day with a classic Italian breakfast, then set off with your private driver to explore the jewels of the Tuscan countryside. Your first destination is San Gimignano, a medieval town renowned for its iconic towers and rich artistic heritage. Wander its cobbled streets, visit the Sant’Agostino Church adorned with Renaissance masterpieces, and admire the Town Gallery’s collection. Continue to Monteriggioni, a perfectly preserved medieval village with a storied past—learn about its strategic role in regional power struggles and the dramatic “great betrayal” that transferred its control to Florence. Enjoy lunch (optional) inside the village’s formidable walls. In the afternoon, arrive in Siena and immerse yourself in its medieval splendor. Marvel at the black-and-white marble Cathedral, gaze at frescoes by Ghirlandaio, and stand in the legendary Piazza del Campo, home of the Palio horse race. Later, return to your Chianti hotel for a relaxing evening and dinner at your leisure.
Day 3
TAVERNELLE VAL DI PESA, GREVE IN CHIANTI, TUSCAN COOKING CLASS
Where Every Step Leads To Supper
After a hearty farmhouse breakfast, embark on a scenic drive through the rolling vineyards of Chianti with your private driver. Your first stop is Montefioralle, a picturesque fortified village that feels frozen in time. Continue to Greve in Chianti, the vibrant heart of the region—explore its charming market square, perhaps visit the Franciscan Monastery, and sample local delicacies at a renowned butcher shop. Next, tour a celebrated local winery, delving into the art of winemaking and savoring a tasting of their best vintages. After lunch (at your leisure), return to your countryside retreat for a hands-on Tuscan cooking class. Under expert guidance, craft your own authentic Tuscan dinner, paired perfectly with local wines. Relish the fruits of your labor and enjoy another peaceful night in Chianti.
Day 4
TAVERNELLE VAL DI PESA, FLORENCE
A Florence Finish After Days In The Hills
Enjoy a final breakfast amidst the Chianti hills before checking out of your hotel. A private car and driver will return you to Florence, where your Tuscan countryside adventure comes to a close, leaving you with unforgettable memories of medieval towns, rolling vineyards, and the flavors of Tuscany.
