Let’s Go to Tuscany!
One of the questions I’ve been asked most often over the years is, "When can I travel with you?"
I'm delighted to finally say that the time has come. I've created a special Tuscany tour for those who share my love of authentic travel, meaningful connections, wonderful food and wine, and discovering the heart of a destination. We would love for you to join us!
Join Me!
I'm so excited to explore Tuscany with you and introduce you to the people, places, and flavors that make this region so special. I have been traveling here for decades and its time to take you with me!
Together with Jan and Tim Rawlinson of iCastagni, we have created a carefully curated experience featuring charming hill towns, exceptional food and wine, breathtaking scenery, and authentic Tuscan culture.
Your home for the week will be iCastagni, a beautifully restored historic property in the picturesque village of Montefollonico. Perfectly located between Pienza and Montepulciano, and within easy reach of Siena and Florence, it's the ideal base for exploring Tuscany's most beloved destinations.
With just 10–14 guests, this intimate tour offers meaningful connections, personalized experiences, and plenty of opportunities to savor the slower pace of life in Tuscany. Whether you're traveling solo, with a partner, or gathering a group of friends, you'll quickly feel part of our Tuscany family. Private group departures are also available.
From unforgettable winery visits and incredible meals to stunning landscapes and some of my favorite lesser-known corners of Tuscany, every day is designed to help you experience the very best of this remarkable region.
Even if you have been to Tuscany before, you have never experienced it with us!
I can't wait to explore it with you.
“It was the greatest trip of my life!”
— Linda Hubert, Spring 2026
What is it like to travel with us in Tuscany?
Expect days filled with incredible food and wine, beautiful landscapes, fascinating history, and wonderful company.
We'll wander through medieval villages, linger over long lunches, meet passionate local artisans and winemakers, and embrace the slower rhythms of Tuscan life.
Our itinerary includes regular walking, often on cobblestone streets and uneven surfaces, so a good level of mobility and comfortable walking shoes are essential.
We want every guest to have the best possible experience, so please let us know about any dietary restrictions or mobility needs before the tour begins.
"I learned so much about wine! I came home and impressed my family!”
— Erin Talafus, Spring 2026
Spring 2026
- April 19 - April 25, 2026
It was a grand success!
2027 Tours!
- September 12 - 18, 2027
- September 19 - 25, 2027
- We are also happy to create custom dates for private groups of 10-14 guests.
Escape the ordinary at i Castagni — a historic, fully renovated and gorgeous boutique luxury hotel with swoon-worthy views.
Upon arrival in the charming medieval village of Montefollonico, everything is included: all meals, wine, accommodations, and local transportation.
Unpack once and enjoy superb service and calm surroundings. Dreams do come true here!
- Winery visits with local experts
- Pasta-making class
- Get to know village life
- Day trip to Siena and tour with an expert guide
- Visit Pienza and Montepulciano
- Discover Montalcino and learn more about Brunello
- Exquisite local dining and personal chef-hosted dinners
- ...Plus so much MORE!
Price and Details
2027 Rates: $6600 USD Per Person ~ 7 days 6 nights
A deposit of $1,000 USD is required to secure your spot.
To reserve a spot for any of the weeks or ask a question, please use the contact form below and we will send you booking instructions or answer any questions you may have.