Tuscany, Italy·September 25 - October 2 2022

Unsettled: Tuscany

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An immersive food & wine experience for remote workers

Slow down. Take a step back. Let your senses lead as you eat, drink, and laugh your way through the heart of Tuscany. This intimately crafted retreat is for those seeking a sensory experience while staying productive amidst a stunning landscape that boasts nearly 100 acres of olives, wild oleander, and cypress. In the daytime, you can open your laptop and be productive around our property: there’s wifi and ample indoor, outdoor, and poolside places to be productive. In the evenings, there’s a bucket list of food, wine, and adventures waiting for you in Unsettled Tuscany.

Retreat Overview


Tuscany, Italy


1 week


From $2000

Upcoming Trips:

September 25 - October 2 2022

Join Unsettled: Tuscany

The Community & Experience

Unsettled is a community for those who refuse to settle in their pursuit of growth, meaning, and adventure. We bring together creatives, entrepreneurs, artists, freelancers, and the intellectually curious who seek to replace routine with adventure. You will share this retreat with like-minded peers who hold a wealth of experience far deeper than just their careers and join our growing community of Unsettled alumni spread out over 80 countries around the world.

Read what Unsettled alumni are saying about their experience.

This experience is about you. It’s about taking an intentional break from your routine, finding new perspective, building new relationships, growing new ideas, and exploring with intention among an incredible backdrop of people and place. We provide housing, workspace, and an unforgettable experience filled with regular dinner parties, peer-to-peer workshops, happy hours, and excursions.

Unsettled: Tuscany Highlights



Our location in Tuscany is surrounded by working vineyards. You’ll take classes with a local sommelier, spend the day on our rustic vineyard experience, and have plenty of red, white, and bubbly at the villa.



Lunch & learns. Peer-to-peer workshops. Family-style dinners. Themed discussions. Fire-side poetry nights.



You’ll have wifi and space to work in each villa. Don’t expect rocket-fast speeds, but everything you need to work productively. Enjoy a slower pace for a change.



From road trips through the heart of Tuscany to day trips to Florence, adventures are calling.



From our first welcome dinner party to exploring local restaurants or baking homemade bread, pasta, and pizza in our wood-fired oven, you’ll eat with the passion and stomachs that Italians are known for.

A Day In The Life




By day ...

There’s always an adventure to be had. Here’s what one of your days could look like:

7:30am: Wake up and grab a coffee. It’s still quiet around the villa. There’s a farm-to-table breakfast happening at 8:30am, so you enjoy an early morning walk or workout around the villa grounds.

8:30am: A local honeybee keeper has organized a breakfast, and has brought one of his hives, some traditional honey extracting equipment, and a very sweet breakfast. 

9:30am – 1:00pm: You set up your work station under a cedar tree for the next few hours. 

1:00pm: Unsettled is running a workshop on career design over a spread of cheeses, meats, and fresh veggies from local farms. 

3:00pm - 6:00 pm: For the afternoon, you’re stimulated, so you work from the coworking space at the villa with a dozen other participants….and you’re in that perfect state between mingling and focused.  


By night ...

6:00pm: Aperitivo and sunset. A dozen or so participants meet at the villa’s sunset view for an aperitivo and Prosecco. You’re planning your weekend road trips together. 

7:00pm - 9:30pm: Pizza night. We’ve been building a fire in the outdoor pizza oven all day, and everyone is meeting there with a bottle of wine and some toppings to contribute. Unsettled’s wine sommelier has made some recommendations for the evening, and he joins us to eat and drink at sunset. 

9:30pm… A few participants are going to continue to have some wine and playtime games by the pool. Others are calling it a night to get a good rest. What will you choose? 

What's Included

Unsettled provides...

A fully dedicated team of experience leaders and local experts who challenge your perspective and support your exploration, growth, and adventures.

A curated calendar of events with community sessions, dinner parties, happy hours, local experiences and classes, peer-to-peer and facilitated workshops, excursions, and more.

Private country cottages nestled among nearly 100 acres of olive trees, oleander and the herbs and rolling hills that make up Tuscany.

Airport transfer upon arrival (from Pisa) and a local SIM card for your phone.

Welcome orientation, dinner, and community design activities.

A full-day rustic wine experience to get hands-on with the winemakers

Family-style dinners, pasta making, farm-tours, and much more thought the experience.

Wifi in each cottage, and spaces to work around the property

Post-trip access to great alumni perks and benefits, including special discounts, alumni trips, and a global community of over 2500 alumni from 80+ countries.

Tuscany, Italy

What Our Community Says...


Unsettled introduced me into a community I know are my kind of people, a family really… with no judgment and just with a raw purpose to uplift each other, whether its to help you with your business venture or just talk about your purpose in life…

Mangalee Goonetilleke | VP of Research


The Unsettled trip ranks on the best trips I’ve ever taken (and I’ve been to 75 countries). Great organization and curation with the ability to take a bit of a leadership role in the activities. All in all it is hard to find a better group and trip.

Andrew Hyde | Founder, Startup Weekend


I was able to run my business smoothly from a different hemisphere, make life-long connections with people from around the globe, and return home with an incredible sense of purpose and focus.

Seth Haber | Founder of Trek Light Gear

Read More on Unsettled: Tuscany


The boundaries between work, life, and travel are becoming blurred, fundamentally changing how we live today. Unsettled brings together groups of travelers and professionals from around the world for uniquely co-created experiences. Each one-week, two-week, or one month retreat is designed to break your routine and inspire a renewed sense of growth, meaning and adventure through transformational travel and peer-to-peer learning.

Whether you're working full time, or going through an intentional career transition, our retreats are designed to help you break out of your routine and explore a new destination with an incredible group of peers.

Each destination and experience is different, however most one-month and two-week experiences include comfortable and centrally located accommodations, a coworking space, full-time staff dedicated to lead your experience, a productivity-driven environment, regular dinner parties and themed conversations, peer-to-peer workshops, curated events, epic adventures, spontaneous activities and hopefully one of the best experiences of your life. Our one-week experiences are more adventure driven, whether urban or nature focused -- and you can explore what each trip holds by visiting that particular retreat page.

You can learn more on Our Experience page.

Yes! In fact, most of the time while away is up to you. The Unsettled experience is your experience, don't forget! We create just enough structure so that you can plug into the different activities, workshops, and connect with people as you wish.

Nothing is required, and everything is voluntary; however, we do look for people who contribute, and highly recommend that you do. Typically, the more you put into your experience, the more you get out. Our role is to provide a platform so you are informed and can participate as you like.

Most days are unstructured work days, exploration days or adventure days (whatever your current activity!) You can work from our central coworking space, a coffee shop, the beach or a park, depending on the destination if you need to. Or, you can go explore with other participants to places we recommend or discover your own new secret spots. We tend to have a fixed family-style group dinner once a week where everyone can check in and catch up with each other, as well as numerous other dinners, events, activities and surprises throughout each week that everyone is welcome to join. You never know the kind of inspiration that can come through connecting with a community, so be sure to try and take advantage of it while you're able.

For our two-week retreats, these are focused a bit less on work, and much more around living in the moment for the time you are there. Our two-week retreats are specifically built to give you a personalized community experience -- one where you can sync up daily with a group of fellow participants, opt in or opt out of a shared calendar of cool happenings, and live alongside us as we visit the world's most vibrant cultural capitals or natural wonders.

Most people on an Unsettled retreat are professionals with multidimensional personalities and vast interests. This isn't a post-college party trip. Our average age of participants is mid 30's to mid 40's, but we've hosted folks of all ages. Living Unsettled is truly ageless.

We've hosted CEOs and entrepreneurs, artists and experience designers, and people who are active, even experts, in everything from transcendental meditation to CrossFit, from Bikram yoga to kiteboarding, and from diving to flying. On any given day however, most of us are content hanging out with each other, exploring new places and trying new things.

Since thinking big about our work and careers is one of the organizing principles of Unsettled, many participants are high achievers who organize major conferences, run businesses, or are recognized experts in their field. We have a lot of designers, developers, entrepreneurs, and startup enthusiasts on our trips.

All of this being said, it's not required to be working on something or have a "professional CV" in order live Unsettled with us. Many joining us are retired, taking a sabbatical, or deciding what comes next in life and looking for some inspiration.

At Unsettled, we truly focus on building retreats full of dynamic people who have much more to offer to the group than just work experience. These experiences are social by definition, and so one of our main qualifications is to look for people who share some simple principles:

  • Open to spending time with people from different cultures with different value sets
  • Curious about the people and the world around them
  • Considerate of others
  • Basically, as long as you're not an asshole, you'll fit right in.

Deposits are fully refundable up to 60 days before the start date of your trip. Your spot is held as soon as you make your payment. Final payments are due no later than 60 days before your retreat's start date. You can transfer your credit to another trip (within 6 months) one time, up until 45 days before your trip start date. 45 days before your trip's start date there are no refunds or transfers. However, if Unsettled postpones the trip, your full payment amount will be credited and available for you to use up to 1 year from your trip start date.

 As we ease back into travel, we will review trips on a constant basis. We will do a final review at 60, 45, and 30 days before (or closer as necessary) any trip's start date to determine that it is still feasible and safe to run the trip. If we postpone your trip, we will place 100% of your trip payments into trip credit used for future travel. For any trips that we postpone in 2021, you will have 1 year from the trip start date (so sometime in 2022) to use your credit on a new trip.

Each of the villas is equipped to work from with communal tables and couches in the shared living spaces, in addition to a small chapel that was recently renovated into a coworking space that is available to take calls or simply knock out some work from your laptop!

Each apartment has its own wifi router for people to stay connected, but the focus of this retreat is not coworking, but rather about connecting with each other and your surroundings. 

This retreat is more about "disconnecting to recconnect", and a great opportunity to work offline, on side projects, creative projects, or strategy/brainstorming work. Most people will probably work ~4 hours per day, but you are free to work as much or as little as you want!

It is best to arrive at Pisa International Galileo Galilei Airport (the main airport in Pisa) anytime on May 22nd, our designated arrival day. 

We will be running airport pickups throughout the day and will have a few shuttles going to and from the airport to our villa in Palaia.

If you arrive before May 22nd, you will need to take care of your own accommodations and transport until we open the doors to our villa. If you can get back to the Pisa airport on May 22nd, you can still join one of our shuttles. If you arrive after the morning of May 22nd you will miss some of our initial orientation but we can still arrange an airport pick up for you. 

For departures, it’s best to depart on our check out day, June 5th We will have several shuttles departing in the morning to get people back to Pisa for their fights and onward travel. Most people will leave Italy that day but some might stay around on their own to travel a bit more after the program ends.

Because this retreat is centered around food + wine, you can expect an activity around food and wine every few days or so. This can include anything from a curated breakfast by a local beekeeper to a pizza-making workshop on-site or a pasta-making workshop with an Italian nonna. Our team also includes a welcome breakfast, welcome dinner, and farewell dinner. 

You should expect to set aside a small budget for food to cover your personal meals on the days that we don't provide meals. Everyone's food budget looks different, as you might grab groceries from the local market or order food directly from the restaurant on site. 

Unsettled: Tuscany

Italy· September 25 - October 2 2022· 1 week


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