Be inspired by stunning views of Val d’Orcia, enjoy wine and olive oil tasting with locals, hunt for truffles in Chianti, and devour award-winning gelato in San Gimignano.
All itineraries are sample itineraries and can be customized to suit your preferences.
- Florence
- Pienza
- Montepulciano
- Cortona
- Montalcino
- Siena
- Panzano in Chianti
- Certaldo
- Val d'Orcia
- Chianti countryside
Please inquire for a custom trip quote based on your travel preferences and travel dates!
Your custom trip package will include accommodations, transportation within the country, guided tours and activities, unique experiences, trip planning, a downloadable, printable, and online itinerary, and personal support during your trip.
DAY 1: DEPARTURE TO FLORENCE, ITALY
Board your overnight flight to Florence, Italy. Transfer available upon arrival.
DAY 2: WELCOME TO FLORENCE
Welcome to Florence, the capital city of Tuscany and the birthplace of the Renaissance. Transfer to your hotel, rest, and freshen up. Join a local guide for an orientation walk around the historic center.
DAY 3: FLORENCE - THE CITY OF ART
After breakfast, join a local expert for a guided tour of the Accademia to see Michelangelo's statue of David. Continue to Giotto's bell tower next to the cathedral and see the "Gates of Paradise" before visiting the Piazza della Signoria, to this day the political heart of Florence. Continue to Piazza Santa Croce, famous for its Basilica and luxury shops. Then visit Palazzo Pitti, a current day museum housing over 250,000 works of art and splendid gardens. Have lunch at leisure before heading to the Uffizi Gallery, a prominent art museum located in the heart of Florence. Enjoy an evening of shopping, cafes, and dinner at leisure in the historic center of the city!
DAY 4: LOCAL FLORENCE
This morning, join your expert local guide to visit the Giardino dell’Iris, a stunning botanical garden (note: open only in May) that specializes in cultivating Iris flowers, the historical emblem of Florence. Stop and admire hilltop views of the city of Florence before a morning visit to a leather work school where you will learn the history of the school and the tradition of working leather in Florence, the gilding process, and explanation of different techniques and skins. Enjoy lunch at leisure and free time to wander Florence or with your expert guide to see the city from a local's perspective! Don't forget to visit Il Porcellino! Put a coin in the boar's jaws, let it fall through into the grate, and rub its snout to make sure you return to Florence! This evening, you bid farewell to Florence in style: dine in a vineyard with a family of local chefs at Machiavelli's former residence!
DAY 5: VAL D'ORCIA & TUSCAN COUNTRYSIDE
After breakfast, you will make your way with a local expert to one of the most spectacular regions of Tuscany: Val d'Orcia. First stop: Pienza, where you will visit an award-winning pecorino cheese farm. Enjoy a guided tour of this fascinating farm and learn everything that you want to know about the famous, 100% Tuscan pecorino cheese, followed by a cheese-themed gourmet lunch with a stunning view of the Val d'Orcia valley from the farm's restaurant. After lunch, check in to your hotel, a former Franciscan convent dating back to the 13th century located in the center of the magnificent hamlet of Pienza - the heart of Val d’Orcia. Enjoy a peaceful dinner in the countryside!
DAY 6: MONTEPULCIANO & CORTONA
After a relaxing breakfast, visit the beautiful, medieval hilltop village of Montepulciano with a local expert. As this area is known for its Vino Nobile red wine, have lunch and tastings at a Vino Nobile di Montepulciano winery, discovering exquisite local flavors and learning about its production. You will then make your way under the Tuscan sun to Cortona with an early afternoon visit to a local producer of Syrah including tastings. After an incredible day in Val d'Orcia, dine at leisure in a local village. Return to your hotel after a fun-packed day in the Tuscan countryside!
DAY 7: MONTALCINO
Today, discover Montalcino and its wines! After a morning visit to Montalcino, a hill town immersed in the beauty of the Val d'Orcia Natural Park, continue with a local expert to enjoy lunch and tastings at an organic, family-owned Brunello di Montalcino wine producer, the most prestigious and well known wine of Tuscany. After a guided tour of the vineyards and the cellar, gaining insight and tasting the world famous wine, we enjoy a delicious homemade lunch at the winery, with recipes traditional of the area. After lunch, visit a second Brunello winery with a guided tour and tastings. Enjoy a dinner of local flavors in Pienza.
DAY 8: SIENA & PANZANO
This morning after breakfast, head to the medieval Tuscan city of Siena, where a local expert will take you through the historic center, a UNESCO World Heritage site, with a visit to its famed Duomo. Wander the streets, shop, enjoy free time, and have lunch at leisure near its central square, the Piazza del Campo, also famous as the site of the Palio horse race. After lunch, make your way to the charming Tuscan hilltop town of Panzano in Chianti, located in the heart of Chianti Classico country. After checking into your bed & breakfast, owned by the family of famed butcher, Dario Cecchini, make your way to a beautiful agriturismo in the Chianti countryside for an afternoon fun, delicious, and strictly Tuscan cooking class with a lovely family where you will learn how to make fresh pasta and many other Tuscan specialties, followed by dinner.
DAY 9: CHIANTI COUNTRYSIDE
Today, after a homemade breakfast, your journey will begin with a visit to a unique olive oil farm run by a wonderful family who has always been committed to producing and sharing the culture of excellent extra virgin olive oil. Here, you receive an explanation of olive oil production, learning many curiosities about this fundamental element of Tuscan and Italian cuisine. Sample the different oils in combination with the best uses and food pairings that showcase each ingredient. After an olive oil themed lunch, you visit an organic & biodynamic wine producer and "vignaiolo" enjoying a guided tour through the vineyards and the cellar with tastings. Your hosts welcome you into their classroom of vineyards, where you will see an organic and passionate approach to wine and farming in the Chianti countryside. Enjoy a free evening in Panzano in Chianti and dinner at leisure in town.
DAY 10: CERTALDO & SAN GIMIGNANO
This morning after breakfast, begin the day with a fun truffle hunt in Chianti with a lovely Tuscan family. Among the woods and vines of the Chianti hills there are hidden, priceless treasures and, today, you will be following Luigi and his dogs in search of the prestigious truffle. The experience will begin in the woods and will end in Giuseppina's kitchen in the lovely village of Certaldo, where she will cook a truffle-based, delicious lunch. In the afternoon, a local guide will walk you through the Italian hill town, San Gimignano, a UNESCO World Heritage site. Surrounded by 13th century walls and boasting a skyline of medieval towers, San Gimignano is also a delightful place to visit an international award-winning gelateria that makes unique flavors fresh from the Tuscan countryside.
DAY 11: CHIANTI WINE & CUISINE
This morning, rest up before visiting a family-owned Chianti Classico winery, enjoying a guided tour through the vineyards and the cellar. The finale? A tasting of exquisite products and a homemade lunch where you will sample the real "cucina chiantigiana," or Chianti cuisine! After lunch and an afternoon of relaxation in Panzano, you will have an incredible Farewell Dinner and evening with the famous butcher, Dario Cecchini, featured on the Netflix culinary series, "Chef's Table," to try the Bistecca alla Fiorentina, Florentine steak.
DAY 12: DEPARTURE
Say farewell to la bella Italia (until next time!). Transfers to Florence-Peretola Airport are available.
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