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CASTIGLION FIORENTINO: 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. Our private villa will be filled with old world charm (wood beam ceilings), modern comforts (hello air-conditioning!), and have the best spot to watch the sunset with a glass of prosecco in hand!
During the week, we will visit the famed town of Cortona (featured in Under the Tuscan Sun, Succession and Rachel Ray's Show) and spend another day driving through the countryside to visit Pienza! We’ll also have cooking classes, relaxed art instruction and sample wines and olive oils made fresh by some of our favorite locals. It's a magical week and we can't wait to share this charming hill town with you! And since we’ll be enjoying Tuscany in late summer / early fall, we’ll get to enjoy some benefits of the upcoming harvests, including an incredible Vendemmia Dinner at Buccelletti Winery right in the middle of their vineyard! ITINERARY*
Day 1: Transfer from Train Station | Check in throughout the day at Villa la Guardata | Evening group aperitivo feast and welcome drinks by the pool Day 2: Breakfast at Villa before transfer to Castiglion Fiorentino | Walking tour of town | Lunch and afternoon sketching | Group dinner in town Day 3: Breakfast at Villa before transfer to Cortona | Day trip Cortona for visit to Santa Margarita, DelBrenna Jewelry and Laura Laureto | Dinner in Cortona or Castiglion Fiorentino Day 4: Breakfast at Villa or in town | Free Day: transportation to train provided or pre-arranged as group via car Day 5: Breakfast at Villa or in town | Day trip to Pienza by car Day 6: Breakfast at Villa or in town | Visit into Castiglion for local market | Afternoon wine tasting at local vineyard with time for sketching | Evening Vendemmia Dinner at Buccelletti Winery Day 7: Quiet morning at the villa or in town for painting | Early afternoon wine tasting with light lunch | Evening cooking class at the villa Day 8: Check out of Villa by 10 | Transfer provided to Train Station *Itinerary is subject to change -- this is Italy after all ;) |
AUG. 31 - SEPT. 7, 2025
AVAILABILITY: 1 double room / 1 queen Retreat Cost: $3350 - Double Occupancy (cost per guest in a shared room) $3650 - Single Occupancy Spaces Available: 3 - 4 total Early Bird Specials
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LUCCA: There’s so much hiding inside these city walls. Lucca has a rich history that dates back to 180 BC. It may be old, but the shopping is chic and the food is fantastic!
The main feature of Lucca is the intact surrounding walls, a popular spot for bike riding, picnics or an evening passeggiata with a gelato in hand. Inside the walls you’ll find 8 prominent churches, museums, the Anfiteatro, the birthplace of Puccini and even a tower with trees on top. During the summer, Piazza Napoleone gets converted into a concert center for the Lucca Summer Music Festival. There is SO much happening inside these city walls just waiting to be discovered...and we'll spend a whole week doing just that. We'll explore this amazing town and have some fabulous day trip destinations, all while being able to call Lucca home for a week! A lovely perk of being in Lucca in the fall will be attending the Luminaria, a special historic candle-lit procession of an ancient sculpture through the streets of Lucca! It will be such a memorable week! ITINERARY*
Day 1: Afternoon transfer from Train Station | Check in at apartments | Evening aperitivo feast and group stroll around the city...gelato, anyone? Day 2: Orientation and breakfast at apartments | Walking tour of town | Lunch and afternoon sketching around town or along walls | Group dinner in town Day 3: Day trip north of Lucca to Ponte della Maddalena and Barga for lunch | Afternoon wine tasting in the hills above Lucca | Dinner in Lucca Day 4: Morning climb up the Guinigi Tower | Afternoon Botanic Garden visit for sketching | Evening viewing of the Luminaria Procession in Lucca Day 5: Free Day | Transportation via train or bicycle Day 6: Pisa day trip via train | Climb Leaning Tower before lunch in Pisa | Return to Lucca for dinner Day 7: Quiet morning for sketching or exploring | Early evening cooking class outside of Lucca Day 8: Check out of apartment | Transfer provided to train station if needed *Itinerary is subject to change -- this is Italy after all ;) |
SEPT. 10 - 17, 2025
AVAILABILITY: *FULLY BOOKED* Please message us to get on the waitlist Retreat Cost: $2950 - Double Occupancy (cost per guest in a shared room) $3250 - Single Occupancy Spaces Available: 4 - 6 Early Bird Specials
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"Blessed are the curious for they shall have adventures."
