Space. Calm. Community.
A week in Tuscany for the executives and entrepreneurs who keep meaning to write — and don’t find the room. 17 seats. Four are taken.
A WRITING RETREAT. NOT A CRUSH-IT SUMMIT.
Somehow, when a bunch of executives convene, it becomes a crush-it summit. Everyone’s exiting, vesting, getting promoted, and buying themselves new toys.
This retreat is for people who do epic sh*t but aren’t consumed by it. Who need time to metabolize their lives. Who need space to define their own joy. Who prefer community over networking.
It’s a tight-knit room — alive, safe enough to tell the truth in, with the crush-it vibes stripped out before they start.
YES, YOU’RE A WRITER. OWn IT.
We turn down the voice in your head that yearns to write - but tells yourself not to.
We come with 33 tested prompts that turn anyone who’s seen some sh*t into
a masterful storyteller.
Every day, you get to travel back through your own life. Together.
COFFEE. three hours of writing. Every day.
You’ll wake each morning on a beautiful estate in Tuscany. Coffee, then three hours to write — fifteen others doing exactly the same a few feet away. Then we eat, explore, share if you want to, and eat some more.
The villa has reinvented itself more times than you have: a monastery, then a train station, now a boutique hotel — vineyards in every direction, the shore twenty minutes off,
Rome two hours south.
We’re not promising a book deal or a spot on a bestseller list.
We’re promising calm, clarity, and community —
the feeling of finally saying the thing out loud to a room that gets it.
THIS MIGHT BE THE MOST IMPORTANT WORK
YOU DO ALL YEAR.
THERE ARE 17 Seats. FOur are Taken.
Life requires a Punk pause, and this is the one we’re offering: putting it off is like waiting until you’re old to start living.
Greg Larkin
Your host is Greg, founder of Punks & Pinstripes, best-selling author of This Might Get Me Fired, and GP of Okina Ventures.
His writing has appeared in the Financial Times, Harvard Business Review, The New York Times, and BusinessWeek.
He runs a weekly writers’ group in New York and once wrote this story about an insane job interview to meet Libyan dictator Muammar Qaddafi.
Daily Schedule
All participants must commit to getting to the retreat and being present from 5:00pm on June 27th to 11:00am on July 3rd.
Morning Meditation (Optional)
7:30 - 8:00am
Breakfast
8:00 - 9:00am
Heads-Down Creativity Time
9:00 - 12:00pm
Lunch
12:00 - 1:00pm
Local Activity & Excursion (Optional)
1:00 - 4:00pm
Help A Punk*
4:00 - 5:00pm
*A semi-structured small group conversation for a “Punk” to raise
a challenge and receive guidance and perspective from peers
who’ve also experienced that same struggle.
Dinner & Cocktails
6:30 - 9:00pm
Registation
If this is the week you’ve been quietly needing, apply below. We read every application ourselves.
Pricing is inclusive of dinners, lodging, and programming. Space is limited to ensure quality and an intimate, collaborative, and mindful experience.
This professional development retreat is one that employers often sponsor. Here’s a templated letter that can help you effectively make the case.
*Punks & Pinstripes is a vetted community for executives unlocking greatness through reinvention. Members are vetted through a series of in-person events in NYC.
Punks & Pinstripes Members*
Early Bird Registration until Sept. 30th, 2026
Shared room per person: $3,000.00
Single room per person $3,500.00
General Registration
Shared room per person: $3,500.00
Single room per person $4,000.00
Non-Members*
Early Bird Registration until Sept. 30th, 2026
Shared room per person: $3,500.00
Single room per person $4,500.00
General Registration
Shared room per person: $4,500.00
Single room per person $5,000.00
Still have questions?
Check out our FAQ below or email us.
FAQs
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The retreat is located at:
Tenuta di Monterufoli
Località Villetta di Monterufoli, Canneto, PI, Italia -
Accepted participants are expected to coordinate transportation to the retreat themselves.
We recommend flying into Rome, Leonardo da Vinci International Airport (FCO). From the airport, we expect members to coordinate their own land transportation. If you might require logistic support or carpooling to get to the retreat, please contact Punks & Pinstripes.
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Include any dietary restrictions in your application. For those who have a concern around the menu, we’ll confirm alternatives with you in advance.
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Email Punks & Pinstripes at hey@punksandpinstripes.com.