09/22/2026
Tuscany Group Holiday Announcement
Dates: September 8 – September 15, 2027
We are officially exploring an exclusive, 7-day group holiday through the heart of Tuscany from September 8 through September 15, 2027—and we want to know if you're ready to join us! 🇮🇹✈️
For years, our annual trip has been a private ritual dedicated to discovering the true soul of Italy. Now, we’re opening up our personal itinerary to a small group of friends and fellow travel lovers. Think of it less like a rigid guided tour and more like traveling with friends who already know all the best local secrets, hidden osterias, and top-tier gelato spots!
We’ve reached out to our close friends in Italy, and they are giving us incredible access to our home base in San Gimignano (home to the absolute best artisan gelato on the planet!). We have about 10 private villas and apartments available right there, making it the perfect setup to experience the ultimate highlights of Tuscany together:
* ⚜️ The unmatched art and vibrant history of Firenze (Florence)
* 🐎 The stunning architecture and winding historic streets of Siena
* 🍷 Slow, scenic drives through the sun-drenched vineyards of Chianti
* 🏰 Biking the towering medieval Renaissance walls of Lucca
* 🍇 Tasting world-class Vino Nobile in hilltop Montepulciano
This isn't a packed, scheduled-to-the-minute commercial tour. It is a slow, deeply personal week of pure agriturismo living, sharing our favorite food and wine spots, dedicated villa relaxation, and plenty of casual gelato exploration.
**Want in?** Because we only have access to these 10 villas and apartments, spaces for this intimate getaway will be strictly limited.
If spending a week living the sweet life in Tuscany from September 8–15, 2027 sounds like your dream vacation, send your information directly to **[email protected]** or drop a comment below to get on our early-interest list! 🍦 #🍦 ‼️ ‼️🤔💭⁉️