This tour begins in Florence and ends in Siena.

Day 1. Wednesday. Benvenuti a Firenze! We’ll start our journey together with a meeting and aperitivo at 3pm. Once we’ve had a chance to get acquainted, we’ll join a local guide as we get to know our neighborhood and the city of Florence. Then we'll have our first taste of Tuscan cuisine as we dine at a small trattoria.

Day 2. Thursday. This morning we’ll meet our local guide for a visit to the world-famous Uffizi Gallery. In our visit to this most important gallery of Italian Renaissance painting we’ll learn about the protagonists of the early Renaissance who provided the foundation for a ‘rebirth’ of humanist art and we’ll see masterpieces by Botticelli, Leonardo da Vinci, Raphael, Michelangelo and more. After some free time for lunch and exploring, we’ll meet again to explore the Oltrarno neighborhood with visits to the workshops of master artisans followed by a wine tasting at a local enoteca. You’ll be free for dinner this evening on your own.

Day 3. Friday. We’ll start our day as many locals do, with a visit to the central market for a thorough introduction to the seasonal produce we’ll be seeing on menus at this time of year. Then we’ll turn our focus to the impact of Michelangelo and the Medici family on the art and architecture of Florence. We’ll join a local art historian for a guided visit of the Medici family’s church, San Lorenzo, as well as the Medici tombs carved by Michelangelo and will end our walk in the footsteps of the Medici with a visit to Michelangelo’s David. After our tour this morning, you’ll be free for lunch, dinner and exploring.

Day 4. Saturday. Today we begin our adventures in the Chianti region of Tuscany with an immersion into the most beloved past-time of Italian fall culture - the olive harvest. We’ll join in on the harvest at a small family farm as we learn all about the complexities of Tuscan olive oil. After working up an appetite, we’ll join them for lunch and will end our day of olive exploration with a visit to the mill to see how high quality cold-pressed olive oil is produced. As the sun sets, we’ll make our way to our accommodations at a beautiful spa hotel in the picturesque hill town of Radda in Chianti followed by dinner together.

Day 5. Sunday. Continuing our focus on the seasonal foods of Tuscany, we start our day with a tour and tasting at a winery famous for the production of, yes, you guessed it - Chianti! For our next stop we’ll join Italians as we dine together at the restaurant of arguably the most famous butcher in the world - Dario Cecchini. Only in Italy is a butcher elevated to the level of the rock star chef. After lunch we’ll return to our hotel. Dinner will be on your own.

Day 6. Monday. Our harvest theme wouldn’t be complete without experiencing the seasonal rite of truffle hunting! This morning we head out with our specially trained truffle dog as he tracks down his targets in the Chianti countryside. After the hunt we’ll enjoy the fruits of our labor at a lunch and cooking class featuring our findings from the morning’s hunt. In the late afternoon, we’ll head back to our home in Radda in Chianti where you’ll be free for dinner on your own.

Day 7. Tuesday. Today we’ll follow the medieval pilgrimage route known as the Via Francigena. Just as with the more widely known Camino di Santiago in Spain, in the middle ages this route was traversed by people who were seeking spiritual renewal. As it’s a Tuesday morning in November - NOW is the time to visit the Tuscan city famous for its medieval towers (and seasonal crowds) - San Gimignano. After a wander through this charming town, and a stop for some world-famous gelato, we’ll follow the pilgrimage route, stopping in picturesque hill towns as we make our way to the queen of them all - Siena. Once we’ve checked into our hotel, we’ll join a local guide for a history-filled walking tour followed by dinner together.

Day 8. Wednesday. This morning we’ll dive deeper into the history and unique culture of Siena with an exclusive visit to the museum, church, and community center of one of Siena’s 17 contrade (or neighborhoods). Our guide will help us understand the history and culture of life as a contradaiolo (contrada member) and how the centuries-old traditions, including the famous bareback horse race known as the Palio, continue on today. This afternoon and evening you’ll have free time to enjoy the city and dinner on your own.

Day 9. Thursday. The spectacular Val d’Orcia and the Renaissance city of Pienza are our destinations today. This landscape is so iconic and unique that its rolling wheat and cypress-covered hills were given UNESCO World Heritage status. While Pienza is in the art history textbooks, in Italy it is arguably better known for its pecorino cheese. Knowing this, we’ll stop for a visit to an artisan producer and learn how this sheep cheese is made. Upon return to Siena we’ll celebrate our adventures together with a final dinner of seasonal Tuscan specialties.

Day 10. Friday. Tour over after breakfast. We’ll help you make post-tour arrangements. Transfers to Florence or Rome are easy from Siena.

Itinerary subject to change.