Tuscany, Italy·September 30 - October 8 2023

Unsettled: Tuscany

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A community-driven food & wine experience

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. This retreat packs a lot into one week! Expect to dive more into food, wine, and community experiences more than you will go “heads down" and be productive. You’ll have daily experiences from our custom rustic wine tour (bring your boots, not your fancy shoes for this one), pizza-making night, a journey through the Tuscany wine, and much, much more. Very limited space. Maximum of 10 participants.

Retreat Overview


Tuscany, Italy


8 nights



Upcoming Trips:

September 30 - October 8 2023SOLD OUT

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.



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



This retreat is packed with local experiences, but when you find downtime, you’ll have wifi and space to work in each villa. Don’t expect rocket-fast speeds, but everything you need to work. Enjoy a slower pace for a change.



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




The Unsettled Itinerary

Sample Itinerary 

Day one: We meet you at Pisa International Airport – the starting point of our adventures – and travel together to Palaia, where we will have a relaxing evening and get to know each other.


On day two we will get to know each other through Unsettled’s signature orientation, to both Tuscany and to your Unsettled community. We lunch and relax by the pool before our evening Welcome Dinner + Intro to Tuscan Wine. 


On day three, we visit an award-winning cheesemaker at his diary farm that’s centuries old to learn the artisan craft right on the farm. Expect to get your hands dirty and your bellies full. 


Day four is open and yours to explore - we have plenty of suggestions to help curate your own day, whether you want to hang back at the pool, get a little work done, or travel to Florence. 

On day 5, we will spend a full day at our favorite, family-owned vineyards, getting up close to the production process. This is a rustic wine tour, so bring your boots and overalls! 

On Day six, we’ll host an Unsettled workshop in the morning, that helps put all of these life experiences into perspective. You can take an afternoon to rest or work before we invite some locals over to make homemade pasta this evening!


Day seven through nine is full of great food, happy hours, making pizza and pasta from scratch, a truffle hunting experience with a local, and much, much more! 

What's Included

Unsettled provides...

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

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.

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

Airport transfer upon arrival and at departure (from Pisa)

Daily breakfast and aperitivos with a view served each afternoon we are not on a wine, farm or food visit offsite of our villa.

Welcome orientation, dinner, and community design activities.

A half-day tour of a local winery with all you can eat and drink in an afternoon

A half-day farm visit to one of the most award-winning cheese farmers and chefs in Tuscany

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

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

Our Villa

We’ve chosen the villa of our dreams to live Unsettled from, perfectly tucked away in the Tuscan countryside. It’s remote, but not too remote –equidistant between Pisa and Florence.

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


It is best to arrive at Pisa International Galileo Galilei Airport (the main airport in Pisa) on your arrival day, Saturday, September 30th. You can also fly into another airport (e.g. Florence), but you will be responsible for arriving at Pisa International Airport at the set shuttle time. 

We will offer two airport picks ups on Saturday, September 30th: 2 pm and 6 pm. You are welcome to arrive earlier and can explore Pisa until the next airport pickup. 

We do not arrange airport transfers before or after these times, but we can provide you with a shuttle service that does. 

For departures on Sunday, October 8, we will provide two shuttles departing in the morning to get people back to the Pisa Airport for their fights and onward travel, one early in the morning for early departures (~6/7 am) and the other shuttle time will be at 10 am checkout. 

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. 

Unsettled Tuscany is a rural, slow-paced food and wine experience for creatives from around the world to sit back and enjoy the natural beauties of life in Tuscany. Our villa is in the heart of Tuscany, meaning it's rural and not in the center of any village (though a 20-minute walk to a quaint village). It's set among Tuscan views, farms, and wineries. 

There's wifi on site since most of us need to stay in touch back home these days, and we do leave 3-4 hours of unstructured time most days for you to check in with work, get creative on a side project, or catch up on sleep or a good book. 

There's also a food or wine experience daily to explore what Tuscany offers and plenty of community events, workshops, dinner parties, and more. 

You can learn more on Our Experience page.

This retreat is centered around community, fun, and, yes, food and wine. You can expect lots of food and wine. Breakfast is included daily and so is one big meal or an aperitivo. There are several food or wine experiences included, and on the evenings when we do not have something planned, participants often cook family-style dinners or go try a local restaurant. 

You should set aside some pocket money for food to cover your personal meals that aren't included. Everyone's food budget looks different, as you might grab groceries from the local market or order food directly from the restaurant on-site for meals that are not included. 

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.

Most days we have a food or wine experience that'll take 3-4 hours along with a family-style meal, a workshop to gain perspective on our personal lives, and some other fun activities mixed in there. 

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.

Please review our latest travel policies here.

Unsettled: Tuscany

Italy· September 30 - October 8 2023· 8 nights


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Unsettled’s Updated Travel Policies & Precautions