Spend a week in one of the charming hillside towns of Southern Tuscany, Castiglion Fiorentino! Known for it's olive oil and close proximity to Chianti, Castiglion Fiorentino is one of the undiscovered towns of Italy, often overlooked for it's busier neighbors Cortona and Arezzo. But we assure you, while it may not be full of tourists, it's full of charm, delicious food, friendly locals and lots of inspiration! 

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Are you ready to discover the hidden gem of Tuscany? Lucca is often a day trip destination of folks staying in Florence but we get to call this charming town home for a whole week! Right along the train route between the coast and Florence, Lucca is easy to get to even though it may seem off the beaten path. These bustling cobblestone streets are filled with bikes, food and shopping and more!

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​2 Rooms left!

Itinerary:

• Day 1: Transfer from Train Station | Check in at Villa la Guardata | Evening group aperitivo and welcome cocktails by the pool.
• Day 2: Orientation and breakfast at Villa before transfer to Castiglion Fiorentino | Walking tour of town | Lunch and afternoon sketching | Group dinner in town
• Day 3: Guided Painting at the Villa in the morning | Afternoon trip to Cortona for walking tour and visit to Del Brenna Jewelry before dinner
• Day 4: Day trip to Assisi in our private shuttle | Dinner provided at Villa upon our return
• Day 5: Free Day (activity suggestions & transportation to Train Station provided if needed) or optional day trip to Pienza
• Day 6: Quiet morning at the villa or in town for painting | Afternoon wine tasting at Buccelletti winery with time to sketch in the garden or vineyard
• Day 7: Transfer into town to see the Local Market and lunch | Afternoon cooking class at the Villa with a private local chef
• Day 8: Check out of Villa | Transfer provided to train station

Relax poolside under the Tuscan sun while surrounded by olive trees and vineyards. Villa la Guardata will be our home for the week, tucked up on the hillside overlooking the Val di Chio with the charming town, Castiglion Fiorentino, just over a mile away. 

The city hosts many cultural events and festivals throughout the year, including the Palio dei Rioni, an ancient horse race and smaller version of the famous Palio of Siena, as well as an eclectic weekly market.  It’s a quiet town with lots of charm that’s easy to fall in love with!

Retreat cost:

$2650* - Double occupancy (per person in one shared room)
​$2950* - Single occupancy
*Payment plans are available ​​

Click here for more information about our Castiglion villa retreat

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​Only 1 Room Left!

Itinerary:

• Day 1: Transfer from Train Station | Check in at apartments | Evening group aperitivo and group stroll around the city...gelato, anyone?
• Day 2: Orientation and breakfast at apartments | Walking tour of town | Lunch and afternoon sketching | Group dinner in town
• Day 3: Day trip north of Lucca to Ponte della Maddalena and Garfagnana hill towns | Dinner in Lucca
• Day 4: Free day (activity suggestions can be provided) or optional day trip to Pisa
• Day 5: Quiet morning in apartments before transfer | Private cooking class in the hills above Lucca | Evening dinner in Lucca
• Day 6: Florence day trip via trains with guided tour around the city
• Day 7: Morning sketching and painting around town | Afternoon transfer to private wine tasting at Colle di Bordecheo | Group dinner in town
• Day 8: Check out of apartment | Transfer provided to train station if needed

Our two private apartments are located right in the historic center of Lucca in a historic building that dates back 7 centuries. Locals commute across town on bikes as most of the streets are closed to outside car traffic. 

While it has the old world charms you’ll expect of Tuscany, it has plenty of bright natural light and modern conveniences (an elevator, for one). You’ll have the convenience of a larger city to explore with a quiet apartment to escape to at the end of the day for a glass of wine with your new friends.

Retreat cost:

$2650 - Double occupancy  (per person in one shared room)
​$2950 - Single occupancy ​
*Payment plans are available ​

Click here for more information about our week in Lucca!

"Blessed are the curious for they shall have adventures."

- Lovelle Drachman