Tuscany, Italy·May 21 - 28 2023
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.
May 21 - 28 2023
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.
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.
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. You can lunch in town or 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 is our last day together, but we never say goodbye, just see you on the road later! In fact, one of the most common things to happen on the last day is for you to travel with some of your new Unsettled community members onwards from Tuscany!
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 and at departure (from Pisa)
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.
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.
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.
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
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:
Please review our latest travel policies here.
It is best to arrive at Pisa International Galileo Galilei Airport (the main airport in Pisa) anytime on your designated arrival day. We will be running 2-3 airport pickups that day to our villa in Palaia. If you arrive before the start date of your retreat, you will need to take care of your own accommodations and transport until we open the doors to our villa.
We cannot arrange airport transfers before or after the first day of your retreat.
For departures, it’s best to depart on the last day of your retreat. We will have 2-3 shuttles departing in the morning to get people back to the Pisa Airport 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 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.
Drop us your email and we'll keep you posted with news, fresh stories, exclusive trip updates, and special offers. Don't worry. We hate spam as much as the next person, and respect your privacy.
Unsettled’s Updated Travel Policies & Precautions