Wine in


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

Chapter Details


Siena, Italy


Starting at $4,099




4 weeks

Chapter Dates

May 1-28, 2022
Limited availability

May 29 - June 25, 2022

Oct 16 - Nov 12, 2022

What to expect

Immersion into the Italian culture

Learn the basics of how to grow, pair, taste and order wine

Meet and make new friends from around the world

Gain a new perspective on life

Continue to work remotely with ease

Photo Jun 13, 9 01 20 PM.jpg

Find yourself in the enchanting charm of Tuscany.

Picture yourself indulging in long Sunday lunches filled with savory dishes and aromatic wine pairings. Your morning ‘commute’ means walking down historical cobblestone streets. 


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


This is the chapter of your life in which you get to enjoy the best of Tuscany for a whole month as you learn about wine and soak up its rich history, hospitality and beautiful landscapes.

Image by Gabriella Clare Marino

Work al fresco.

For those who are bringing work with them, we don’t want you to skip a career beat. While we're partial to taking calls from the piazza while sipping on a delicious glass of Chianti, we understand you may need a place to get some serious work done - no distractions. 

So, we've partnered with a local space to turn their unused areas into a productive co-working space that can cater to a range of needs.Here you will find super fast wifi, plenty of outlets, and even private rooms in case you need to get some privacy or just spread out. 

If a little more action is your work vibe, we've also got you covered. Within Siena, we have created partnerships with local cafes and restaurants to turn them into Sojrn Spaces - places you're always welcome to pop into to socialize, get some work done, or grab a bite to eat. 

Wine time.

Every week you’ll have dedicated time to learn about the world of wine along with other Chapter members. 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.

Note: for anyone wanting to join us in Tuscany who doesn't drink alcohol, we're happy to arrange substitute activities focused more on food than wine. That said, the educational aspect of this chapter is wine-specific.

Choose your stay.

The Wine in Tuscany Sojrn has three different tiers of accommodation options available. All are centrally located and within walking distance of the workspace.

  • Budget - $4,099  | A small private room in shared apartment (twin or double-sized bed)

  • Standard - $4,499  | A large private room in shared apartment (queen or king-sized bed)

  • Private - $5,499   |   A private 1 bedroom apartment that comes furnished with a double bed, Wi-Fi, a fully equipped kitchen and space to work or relax


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




Let's start from the beginning - making wine. This week, you have the opportunity to learn about the history of wine, it's significance in Italy, and how it's made.

Included Activities:

  • Welcome Dinner

  • Half Day Winery Visit

  • Aperitivo - Chianti



Week two is about the taste of wine and your relationship with it. Where do the various flavors come from? What do you like and not like? What exactly is a tannin? 

Included Activities: 

  • Wine tasting and personal taste profile analysis with a sommelier 

  • Aperitivo - Brunello

3 Photo Credit Anna Richey.jpg



When wine and food are appropriately paired, it enhances the experience of both. This week, you'll learn what goes with what and how to appreciate a perfectly paired duo.

Included Activities

  • Pairing workshop

  • Game night

  • Aperitivo - Vernaccia di San Gimignano



Ever sat down to a nice dinner and asked for wine list and quickly became confused and overwhelmed about what to order? Never again.


This week, you'll learn exactly how to approach wine menus and labels so you can deftly select the perfect grape and vintage.

Included Activities:

  • Workshop on deciphering a wine bottle label and ordering like a pro

  • Aperitivo - Super Tuscan

  • Farewell Dinner


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 (workspace and partner cafes)

  • Guaranteed wifi connection

  • Four included activities (one per week)

  • Two group meals

  • An existing community to join up with of other Chapter participants

  • 24/7 access to a local host 

  • Airport transportation

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

What's Not:

Our Sojrn Chapters are created to cater to your needs and allow you the most amount of 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

  • Meals (unless otherwise noted)

  • Optional activities/experiences

  • Insurance

  • Visas and related fees 

Additional Information


All accommodation tiers consist of a private bedroom within walking distance of local facilities. For Wine in Italy, we use a combination of shared apartments and local hotels to house all participants. If you have a preference for an apartment or a hotel, please make a note in your book. However, we cannot guarantee any specific housing. For shared apartments, you will be matched with other Sojrn participants (usually 2-3 bedroom apartments) but you will always have a private room to yourself. Bathrooms are usually shared. If you would like to guarantee having your own apartment, please select Level 3 when booking. Your Tuscan home away from home will always come furnished, inclusive of:

  • Wireless internet
  • All utilities
  • Bi-weekly cleaning service
  • Basic kitchenware
  • Sheets and bath towels
If you book private accommodations with someone (shared bed), the second person gets 50% off of their Sojrn. Note: Tier 1 cannot be booked as a shared room as it is often a twin bed size that will not fit two people. For couples or friends wanting to share a room, please book Tier 2 or 3.

Sojrn Spaces

We know that having a reliable Wi-Fi is crucial to the success of working remotely. Our co-working space is always located near to you and set up for you to open your laptop and get work done. Your workspace comes with:

  • High-speed internet
  • air-conditioning
  • private rooms on request
  • printer and scanner


Besides the two group meals at the beginning and end of your stay, there is no set meal plan so you are free to eat what you want, when you want. Your Chapter guide will include a list of recommendations for grocery shopping and restaurants.


Flights are not included. For this chapter, the closest airport is Florence Peretola Airport. If you fly in on Day 1 of the Chapter, we include an airport transfer to your accommodations in Siena. Note: it may be cheaper to fly into Rome and take a train to Siena. In this case, we can arrange for a transfer for you from the Siena train station to your accommodations.


Visa requirements will vary depending upon nationality. Should you have questions, please don't hesitate to reach out to us for assistance. HERE is a great resource to figure out what the visa requirements are for you.

Please note: While we will help point you in the right direction, Sojrn is not responsible for any participant’s inability to obtain the correct visa for any given chapter and cancellation fees will apply if a participant is denied the proper visa.


In-destination budgets vary depending upon your personal spending habits when it comes to food, travel, local adventures and other personal expenses. As a ballpark figure, we would suggest a minimum additional budget of 1,000 euros for the full 4 weeks. However, if you plan on doing multiple optional activities and eating at restaurants for most of your stay, budget at least 2,000 euros.

Example pricing for Italy:
  • Typical Italian Breakfast: 5 euros
  • Average take-away lunch in Tuscany: 7 euros
  • Average restaurant lunch in Tuscany: 12 euros
  • Average dinner in Tuscany (w/o alcohol): 25 euros


The health and safety of our customers is always our top priority. Each Chapter will have clear Covid-19 guidelines in place based on local requirements. As local ordinances are being updated regularly, we will share Sojrn policies closer to the program start date. We reserve the right to update these on an ongoing basis per the available data and recommendations of local authorities. Vaccination Requirement: You’re required to be fully vaccinated against Covid-19 to come on this trip. Proof of Negative Covid Test: In addition, we also require a negative covid test within 48 hours of the first day of the trip (at home tele-med tests are ok!) The local host will ask for you to show proof of a negative test prior to the start of the trip. This can be in the form of an email, letter or a picture showing the result. If you are flying from the US and are required to have a PCR test taken within 72 hours, we will also accept this to join the trip. **Please keep in mind that if you’re starting your travels early, we suggest getting tested before you leave your home country and then either bring a proctored, tele-med self-test kit to take before the trip starts or schedule to get tested locally at a covid testing facility (both antigen or PCR test are accepted). For more information on our COVID protocols, please visit our FAQ page.

Online Portal

A month before your Sojrn, you will be invited to an online hub where you can connect with chaptermates, meet your local host, and get access to the Chapter Guide, which has all the information you need to have a successful Sojrn in Italy.

Through this online hub, you can also book optionals and access resources that will supplement your learning about wine.

In-Country Support

Part of the benefit of traveling with Sojrn is the support we provide throughout your experience. From an on the ground local host, to our team at HQ, there is always someone available to help solve any issues you may encounter.

Local Host & Chapter Host

Every chapter has a local host on hand throughout the 4 weeks of the Chapter with the aim of making sure you have everything you need to have a relaxing, productive and inspiring time in your temporary new home. Whilst your local host is focused on making sure you can enjoy your new city. The Chapter host is on hand to make your evenings and spare time more fun. We think happiness is shared experiences, from finding the best secret bar to weekend adventures out of the city. Your experience host will help make this happen so you can focus on doing the fun things (and work of course).

Have questions for us? Let us know and we'll be in touch as soon as possible.

Thanks! We'll be in touch asap!


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