“Fall is my favorite time in Tuscany – the hearty food, the wine, cooler temperatures, the olive harvest…”

—Trina

“It was amazing! The best tour I’ve taken!”

—Althea, Tuscan Harvest 2022

Tour meets in Siena at 1pm. Stay 3 nights Siena, 3 nights in Radda in Chianti 

Day 1. Monday. We’ll meet at our tour hotel Il Giardino di Pantaneto in Siena and begin our travels together with an orientation meeting followed by a walking tour of this historic medieval city. Tonight we’ll enjoy dinner together at a typical Sienese trattoria.

Day 2. Tuesday. Today we’ll dive deeper into the history and unique culture in this queen of Tuscan hill towns 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 contradiolo (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 3. Wednesday. The Crete Senesi and monastery of Monte Oliveto are our destinations today. After a guided tour of the monastery and its renaissance frescoes, we’ll stop for lunch and some exploring in historic Pienza, itself renowned for its Renaissance architecture. As we make our way from Pienza back to Siena we’ll drive through the Val d’Orcia - a landscape 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 a top quality producer and learn how this sheep cheese is made. Upon return to Siena, dinner will be on your own.

Day 4. Thursday. Today we’ll visit the Etruscan city of Volterra where our local guide will lead us on a tour of this historic hill town. During our walking tour we’ll get to know the Etruscans by visiting the world-famous Guarnacci museum known for the enigmatic masterpiece the Ombra della Sera - inspiration to many modern sculptors including Alberto Giacometti. Known for its artisan craftsmen and alabaster carvers, you’ll have some free time to explore this Etruscan, then Roman, then medieval jewel. Later in the afternoon, we’ll meet a local guide and sommelier who will teach us to better appreciate the subtleties of great Tuscan wines. After settling into our new home, the beautiful Palazzo and Spa Leopoldo in Radda in Chianti, we’ll have a brief orientation walk and then dinner together.

Day 5. Friday. We’ll continue with our harvest theme by heading out with our specially trained truffle dogs as they track down their targets in the countryside. After the hunt we’ll enjoy the fruits of our labor at a lunch of authentic Tuscan fare where you will experience the many inventive and delicious ways truffles are used as we join local chefs in a cooking class followed by lunch. We’ll then head back to Radda in Chianti. Dinner on your own this evening.

Day 6. Saturday. For our final day in Chianti, we’ll start the morning with a visit to the bottega of a local craftsman. We’ll then visit a unique small winery where we’ll enjoy lunch together. On our way back to our hill-top home, we’ll stop for a visit to an olive mill where we’ll learn more about what makes Tuscan oil so special. This evening we’ll gather for our last dinner together in the Tuscan countryside.

Day 7. Sunday. Transportation to Florence Santa Maria Novella Train Station will be provided.

Itinerary subject to change.

“I couldn’t wait to share photos of the truffle hunt—that was amazing. It was a highlight.”

—Anna, Tuscan Harvest 2022

Included:

• A small group experience of no more than 15 people

• Six nights accommodation, including breakfasts

• Three dinners, wine and water included

• Cooking class and lunch

• Wine tasting lunch

• All sightseeing activity entrance fees and local guides

• All local group travel by private vehicle

• Transfer to Florence

• All tips

• Pre-tour travel consultation with Trina

• Flexible reservation and cancellation policy

Not Included:

• Airfare & airport transportation

Conditions:

• Tour itinerary details subject to change. This is an active tour with walking routes accessible to most people, but may not be the right fit for everyone.

Where will this tour stay?

Siena three nights and small Tuscan hill town 3 nights.

How much walking will there be on this tour?

There will be a moderate amount of walking. This is not a particularly strenuous tour.

What’s the balance between group time and free time?

We’ll have a balance of free and group time. This tour has many group activities and meals included so there will be more time with the group than on other itineraries.

When should I plan to arrive in Siena for this tour?

The tour starts at 1pm, so arrival at least the night before the tour starts is recommended.

What’s the best way to get to Siena?

Taking a bus or train from Florence to Siena is pretty simple. My recommendation would be to take a bus from Santa Maria Novella Train station. The bus stops right near the old town of Siena where our hotel is located.

What will we eat?

I don’t call it the “Tuscan Harvest Tour” for nothing! This is a food lover’s tour. It is being held during the olive harvest and at a time of year when hearty Tuscan food is at its best. We’ll be hunting for and eating truffles, tasting freshly-pressed olive oil, eating pecorino cheese, and tasting the seasonal specialties of the Chianti region – oh, and of course, we’ll be tasting a lot of wine!

I'm a solo traveler, can I join the tour?

Yes! There is a single supplement.