Unsettled: Tuscany

Creative exploration | Family style | Sensory experience

Welcome to Tuscany. Your Journey Begins Now.

Slow down. Take a step back. Let your senses lead the way through eating, conversing, creating, laughing and learning in the heart of Tuscany. This intimately crafted retreat is for those seeking a more connected and communal setting, while staying productive amidst a stunning landscape that boasts nearly 100 acres of olives, wild oleander and cypress.

We’ve chosen the villa of our dreams to live in and work from, perfectly tucked away in the Tuscan countryside. It’s remote, but not too remote – equidistant between Pisa and Florence. Dating back to the 1300s, the estate was once a local monastery, where the three story main house was originally occupied by monks and designed for social gatherings. The pool is set amongst the trees with a great lawn for picnics and yoga, and a stunning view of the rolling hills and vineyards in the distance.

The Basics

Tuscany, Italy

2 Weeks

$2,250 – $2900 USD

Experience Dates:
Upcoming dates TBA

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.

Unsettled: Tuscany Highlights

Unsettled: Tuscany is a uniquely co-created experience dedicated to connecting us to each other and the rituals and traditions that define the fundamentals in life -great conversation, food, farming, nature, and wine. We believe in engaging with the creative process that goes into the things we consume. Learn how to make pastas and hand-pressed olive oils before we sit down to a family-style feast. Explore viticulture and regional wines before we make heartfelt toasts. We will dig deep, and get our hands dirty.


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


Winding country trails for strolling, biking, or going on a private Vespa adventure. We’re just an hour from the Tyrrhenian Sea and Florence.


Peer-to-peer workshops. Family-style dinners. Curated local experiences in the Tuscan countryside. Lots to explore and learn.


Idyllic, rustic country-living. Great food, wine, art, conversations, and the time to create – in whatever sense that means for you.


Explore Tuscan traditions, or head an hour north to immerse yourself in the Renaissance art, architecture, and bustling cafes and gastronomy of Florence.

Unsettled introduced me into a community I know are my kind of people, a family really… with no judgement 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

What’s Provided

  • Private country cottages nestled among nearly 100 acres of olive trees, oleander and fruit trees in the heart of Tuscany.
  • Airport transfer upon arrival (from Pisa) & a local SIM card for your phone.
  • Welcome orientation, dinner, and community design activities.
  • Peer-to-peer workshops, goal-setting sessions, and family-style dinner parties.
  • Immersive local experiences ranging from Italian cooking classes, vineyard explorations and tastings, and more surprises.
  • A full-time Unsettled Experience Leader & local staff member who are there to facilitate workshops, organize activities and connect you to each other and your surroundings.
  • 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.

Upcoming Dates

Upcoming dates TBA


$2,250 – $2900 USD


Take a look at our FAQ’s to find answers to commonly asked questions. If you don’t find an answer, then reach out to us and say hello!

Ready to join us in Lebanon for the adventure of a lifetime?

Embrace the unknown. Apply today...

Unsettled is a global community for those who embrace the unknown and value meaningful human connection. Our mission is to inspire a lifelong pursuit of growth, meaning, and adventure through travel and shared experiences.