9-Day Tuscany Wine Tour

Wine & Cheese Tasting in the Tuscan Countryside

Countless pages of glossy magazines and breathless travelogues have been devoted to Tuscany, and with good reason: This section of central Italy remains one of the loveliest places on the planet. Especially for those interested in wine, this itinerary encompasses the best this region has to offer: the Renaissance glories of Florence, the storied hill towns of Tuscany and the unspoiled countryside of Maremma. Just as important, it affords insider access to top wineries. Lovers of La Dolce Vita will be hard-pressed to find a better way to spend nine days of their lives.

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • Tour the romantic landscape of vineyards, olive groves and fortified medieval towns of Chianti
  • Taste various types of pecorino at a cheesemaker's workshop
  • Delve deep into the wines of Montalcino

Trip Overview

Day 1 - 3 : Florence
Spend some time in Tuscany’s capital
Day 4 : Chianti
Visit notable Chianti wineries and taste local olive oil
Day 5 : Winemaking in the Heart of Chianti
Prepare and seal bottles, finished with a personalized label of your own design
Day 6 : Pecorino Tasting
Tour a cheese producer's workshop and learn about various types of Pecorino
Day 7 : Siena
Take a walking tour of this atmospheric city
Day 8 : Bolgheri
Make a day trip to this charming, undiscovered town
Day 9 : Return to Florence
Return to Florence and the airport, or continue your journey in Rome

Day 1 - 3 : Florence

After checking in at J.K. Place, spend some time in Tuscany’s capital, Florence. We can help with anything from reserved entries to blockbuster sights such as the Uffizi to finding exquisite hand-crafted goods with a personal shopper to a private cooking class with a noted Florentine chef.

Where to Dine

IO Osteria Personale Enoteca Pinchiorri
J.K. Place Firenze

This centrally located 20-room boutique hotel will appeal to those seeking stylish contemporary luxury as well as a high level of personal service.

Florence, Italy
Florence, Italy

Day 4 : Chianti

Transfer with your driver into the Tuscan countryside, an extravagantly romantic landscape of vineyards, olive groves, fortified medieval towns, hilltop castles and rolling pastures dotted with cypresses. 

Chianti, one of Italy’s most famous wine regions, lies just south of Florence, with silver-green olive groves, well-kept vineyards and small stone cottages. 

Stroll through the towns of Greve, Montefioralle and Radda in Chianti on your own, wandering among their charming piazzas and churches. 

Visit notable Chianti wineries such as Castello Monterinaldi and taste their famous Chianti Classico and Chianti Riserva wines, along with local extra virgin olive oil. Check in at the enchanting, historic Castello del Nero Hotel & Spa nearby, and have dinner paired with local vintages.

COMO Castello Del Nero

This historic hotel, housed within an imposing 12th-century castle, is set on a hilltop in a nature reserve equidistant from Florence and Siena.

Olive orchard in Chianti
Olive orchard in Chianti

Day 5 : Winemaking in the Heart of Chianti

Spend a full day at a top winery in the heart of the Chianti countryside. Blend your own Tuscan wine alongside an oenologist, surrounded by barrels of Sangiovese, Merlot, Cabernet Sauvignon, Gamay and Syrah. Once you are satisfied with the final result, prepare and seal 60 bottles, finished with a personalized label of your own design. 

At midday, take a break from your efforts and enjoy a full Tuscan wine-tasting lunch. Your bottles arriving in the U.S. will serve as a lovely reminder for months to come of your Tuscan adventure.

Return to your hotel for a relaxing evening.

Vineyard in Chianti
Vineyard in Chianti

Day 6 : Pecorino Tasting

Take a pleasant journey through the Val d’Orcia with your local guide and enjoy a walking tour of the quaint town of Pienza, an architectural masterpiece of Renaissance design where you will see the Palazzo Piccolomini and Duomo, along with shops selling every type of pecorino cheese imaginable.

Head into the countryside to a cheese producer, Fattoria PianPorcino, and tour his workshop to learn about the various types of pecorino he produces. End the tour with a tasting of the various cheeses, accompanied by cold cuts and bruschetta. 

In the afternoon, delve deep into the wines of Montalcino, including Brunello di Montalcino, one of the finest wines in Italy. Take a guided visit of the cellars of a boutique Brunello producer, followed by a wine-tasting of the various blends. 

Explore the town of Montalcino and stop at the Abbey of Sant’Antimo, known for its ethereal Gregorian chants at Mass. Be sure to grab a bite and a glass of Brunello at Enoteca la Fortezza di Montalcino.

Before checking in at Castiglion del Bosco, stop at another top Brunello winery for a tasting at their wine bar.

Rosewood Castiglion del Bosco

This captivating stone hamlet straddling a hilltop was restored and transformed into a sophisticated resort with 34 suites and multibedroom farmhouse villas.

Pecorino cheese wheels
Tuscan vineyard

Day 7 : Siena

Spend the morning in the atmospheric city of Siena, taking a walking tour with an expert guide, before transferring to the Maremma. Once the heartland of the enigmatic Etruscans, this Tuscan coastal area is now one of Italy’s most exciting wine regions. 

Check in at Hotel Le Fontanelle, and take the afternoon to relax and enjoy the property. Alternatively, spend the afternoon visiting one or two wineries in the nearby Morellino di Scansano region, which produces wines with Brunello-like character from richly ripe Sangiovese.

Hotel Le Fontanelle

About eight miles east of Siena, this welcoming and understated family-run hotel in a handsome 13th-century brick-and-stone farmstead is set on a hilltop overlooking acres of rolling countryside.

Old brick archway in Siena
Old brick archway in Siena

Day 8 : Bolgheri

Make a day trip north to the charming town of Bolgheri, popular with Italians yet relatively undiscovered by international tourists. 

After a walking tour of the town, visit the prestigious Tenuta dell’Ornellaia, surrounded by natural splendor. 

Stroll through the vineyards, tour the cellars and of course do a tasting of the winery’s full range. It’s possible to visit other wineries in the region on request as well.

Day 9 : Return to Florence

Return to Florence and the airport, or continue your journey south and head to Rome. 

The Colosseum in Rome
The Colosseum in Rome

Discover more Tuscan wines, read expert reviews and share your personal recommendations on Delectable.


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