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Wine in


Spend four weeks living in Italy as you learn about wine from the family-run vineyards that know it best.

Chapter Details


Siena, Italy


Starting at
(with accommodation)




4 weeks

Chapter Dates

April 17 - May 14, 2023

Oct 9 - Nov 5, 2023

What to expect

immerse yourself in the Tuscan culture, countryside, and way of life

Learn the basics of growing, pairing, tasting, and ordering wine

Create connections and friendships with like-minded Sojrners from around the world

Gain perspective and discover a different version of yourself

Indulge in the charm
of Tuscany.

Find yourself enjoying long Sunday lunches filled with savory local specialties and aromatic wine pairings. 


Afternoons are spent exploring different neighborhoods, making friends with local shopkeepers, and savoring the mellow pace of the dolce vita.  


Enjoy the best of Tuscany on this four-week chapter of your life as you learn about wine and soak up the region’s rich history, colorful culture, and breathtaking landscapes

A cafe on the street in Siena.

Work the Way You Want.

If you plan to work while on your Sojrn, you’ll have the opportunity to do so from afar while immersing yourself in the local culture. With a personal WiFi hotspot, your desk can be anywhere you like, from your own apartment to the cute coffee shop around the corner. Sojrn has also partnered with a cafe to create a Sojrn Space, so you’ll always have somewhere nearby to get work done or meet up with Chaptermates whenever you like. Think of it as your friendly neighborhood hangout.

Wine time.

Every week you’ll have dedicated time to learn about the world of wine along with other Chaptermates. We've designed a unique curriculum that includes vineyard visits, workshops on taste profiles, discussions with wine masters, and, of course, lots of opportunities to test out what you’ve learned by drinking wine and spending time with new friends! Get ready to become a wine connoisseur in no time.

Choose your stay.

The Wine in Tuscany Sojrn has two different tiers of centrally-located accommodations available, as well as an option to join the Chapter but arrange your own accommodation.

  • Private Housing - $6,399 | A private 1 bedroom apartment that comes furnished with a double bed, WiFi, kitchen, and space to work or relax.

  • Shared Housing - $5,199 | A private room in a shared apartment.

  • No Housing - $3,199 | If you have specific accommodation needs, you may participate in the Sojrn program but arrange your own housing. While you will need to book and manage your accommodations on your own, you will be fully involved in all other facets of the Chapter and Sojrn community.


PS: If you book the Private Housing option with someone (shared bed), the second person gets 50% off of their Sojrn.

Grapes in a woman's hands.



Welcome to Tuscany, the land of Da Vinci, medieval brick piazzas, and some of the world’s most famous and sought-after wines. During your first week in Siena, you’ll get to know your Chaptermates as you begin immersing yourself in the culture of central Italy.


Your education in wine will start in the rolling hillsides outside the city walls, where you’ll begin to explore the intricacies of vinification and its significance to the region and nation. Throughout the week, activities will range from introductory walks of Siena to tours in vineyards, group happy hours, and your first tasting. There will be several additional optionals to participate in, including local market experiences, live music, and group dinners.



During your second week in Tuscany, you’ll examine the rich, intense, and complex flavors of the region’s wines. From the soil to climate and even variations in altitude, you’ll begin to understand how certain factors influence and affect the aromas and flavors. With that knowledge, you’ll look inward as you begin to recognize exactly which types of wine you enjoy and why.


Your activities (unsurprisingly) will revolve around tastings as you learn about varietals, blends, vintages, and even how to spot a “corked” wine. There will be group happy hours along the way and the opportunity to participate in numerous other events that may include anything from cooking classes to karaoke.

A glass of wine and a notebook.
Wine paired with cheese, bread, and sausages.



While our primary focus this month is wine, in Italy, that’s only half the equation. Now that you’ve begun to understand the subtle complexities of Tuscan wines, you’ll learn how to pair them with different types of food. Bruschetta and vermentino? Salami and Sangiovese? Pecorino and Brunello? Buonissimo. After all, when wine and cuisine are paired appropriately, it enhances the experience of both.


Activities in week three include wine and food tastings aimed at helping you understand the ideal balance between acidity, intensity, or sweetness, while optional experiences will range from local market visits to in-depth wine tours and more.



Now that you’ve familiarized yourself with the region’s flavors and varieties, and started to explore vinification processes and techniques, it’s time to begin looking forward. This week is about fine tuning your palate as you build on what you’ve learned so you can continue confidently ordering, tasting, and enjoying wine.

Activities will include workshops and blind tastings curated to give you confidence when ordering wine no matter how intimidating the wine list. We’ll also share a special farewell dinner to round out an outstanding month in Tuscany in style.

Glasses of red wine.

What's Included:

We've covered the basics so you can arrive at your new home feeling like a local. 

  • Living accommodations 

  • Access to Sojrn Spaces (workspaces and partner cafes)

  • Eight included activities (two per week)

  • Chapter platform with pre-travel prep, important information, menu of curated optionals, and more

  • Two included meals

  • A community of Chaptermates

  • A Chapter Host

  • A Local Host

  • A list of optional curated activities each week

  • Arrival airport transportation

What's Not:

Our Sojrn Chapters are created to cater to your needs and allow you the most flexibility and control over how you spend your time and money. As such, these items are left for you to arrange at your discretion: 

  • Airfare

  • Departure airport transportation

  • Meals (unless otherwise noted)

  • Optional activities/experiences

  • Insurance

  • Visas and related fees

"The SOJRN Wine in Tuscany chapter is such an incredible opportunity to experience the Italian and Sienese culture while meeting new friends, learning about wine and working remotely. SOJRN takes care of the details and provides options for activities, yet gives you the freedom to explore and enjoy daily life for a month in Siena. The local host Georgia was a wealth of knowledge and was there to assist whenever needed. Our leader (and owner of SOJRN), Tara took such amazing care of us all. I had doubts about traveling during the pandemic, but this trip exceeded all of my expectations and I have memories and new friendships I will cherish forever."


Interested in learning more about our Wine in Tuscany chapter?

If you have any questions about our Tuscany Chapter or would like to talk to someone about the Sojrn experience before you book, leave us your info and someone from the team will be in touch as soon as possible!

Thanks! We'll be in touch asap!



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