A Tuscany Food Lover's Dream Itinerary: The Best of Italian Cuisine

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Advisor - Lizz Callaway
Curated By

Lizz Callaway

  • Babymoons

  • Bachelorette Party Destinations

  • Bachelor Party Destinations

  • Couples Travel

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  • Food & Wine

  • Honeymoons

  • Italy

  • Tuscany

  • Foodie

  • Gourmet

  • Small Town

Aerial views of a village surrounded by green fields in Tuscany.
Curator’s statement

As a food lover, Tuscany has a special place in my heart. With its rolling hills, beautiful vineyards and farm-to-table cuisine, Tuscany offers a culinary experience like no other. From the famous wines to the delicious cheeses, cured meats and pasta dishes, Tuscany has something for everyone. This itinerary is perfect for those looking to indulge in the best of Italian cuisine while exploring the beauty and charm of Tuscany.

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Day 1: Arrival in Florence

Aerial views of sunset over the city of Florence.

Arrive in Florence and check into your hotel. In the evening, take a short drive to Chianti and enjoy a delicious dinner at a local restaurant, where you can try some of the famous Chianti Classico wines. Get some rest, but wait until it is bedtime in Florence to help avoid jetlag!

Day 2: San Gimignano

Views of rooftops in the village of San Gimignano.

Take a scenic drive to San Gimignano and visit a local vineyard for a wine tasting. In the afternoon, take a cooking class with a local chef and learn how to make some of the region's most famous dishes, like homemade pasta and tiramisu.

End your day with a visit to the charming town of San Gimignano and explore its medieval architecture.

Day 3: Pienza

The rolling hills of Tuscany.

Take a drive to the beautiful town of Pienza and visit a local cheese farm for a cheese tasting of the famous Pecorino cheese. Afterward, visit a local olive grove for an olive oil tasting and learn about the production process. End your day with a delicious dinner at a local restaurant, where you can enjoy some of the region's specialties.

Day 4: Italian Cooking Class

Making pasta by hand.

Take a tour of the local market and pick up some fresh produce and ingredients for a cooking class. In the afternoon, go truffle hunting with a local guide and learn about the history and importance of truffles in Italian cuisine. End your day with a cooking class and enjoy the delicious meal you prepared together.

Day 5: Montalcino

Views of rolling hills of Tuscany.

Take a tour of the famous Brunello di Montalcino vineyards and learn about the production process. Enjoy a delicious lunch and wine tasting in a local winery. In the afternoon, explore the charming town of Montalcino and its medieval architecture.

Advisor - Lizz Callaway

Travel Advisor

Lizz Callaway

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Looking for more travel inspo? Check out my guide, Ultimate Oahu Travel Guide. This guide is part of our ongoing series on travel to Tuscany.