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This trip is being organized by Carl Landau, (and his wife Diana), host of the popular I Used to be Somebody podcast and newsletter. This tour was created with our friends at Taste Vacations. 

Just like our show, this adventure is targeting people that are planning to or are recently retiring from their career job. But they don’t want to retire, they want to do something NEW, something more FUN and something more MEANINGFUL. We call this (Un)Retirement!

This is your opportunity to network with creative people just like you, as you begin this new phase of your life. Plus, you get to do this while experiencing the beauty, history, and culture of Italy. Did we mention the amazing food and wine tasting too? (Max size group is 20.)

Three one-hour, lively, educational “I Used to be Somebody” sessions are included in the tour to make your trip complete. (Check with your tax advisor regarding the possibility of a tax deduction for this educational experience.)

Topics include:

  1. Who are you? When you were “someone”, what did you do and where are you in planning or implementing of your new “(Un)Retirement” stage of life?
  2. The 8 secrets to a Successful (Un)Retirement Life.
  3. Plan your (Un)Retirement post-trip, with accountability markers.

(Sipping Italian wine might help to make the discussions even better!)



  • Tour Date: September 15 – 21, 2024
  • Trip Price Per Person: $4,950
  • Single supplement: $900
  • Tour Size: 20 people
  • Guide: Giovanni Ramaccioni or other Tuscany-based guide
  • Meals: All meals included except two lunches and one dinner
  • General Tour FAQs

Tour the very best of Tuscany one of the most beautiful places in the world!


We'll be visiting all the wonderful walled cities and hill towns:

  • Florence
  • San Gimignano
  • Arezzo/Anghiari
  • Città di Castello 
  • Sansepolcro
  • Pieve Santa Stefano
  • Umbria/Assisi
  • Cortona 
  • Pienza
  • Montepulciano


About Your Hosts

Carl and Diana are hosts of the popular I Used to be Somebody podcast and newsletter, inspiring 50+ professionals on how to build their (Un)Retirement good life. They are also co-authors of the Amazon best-seller Pickleball for Dummies. Carl and Diana Landau produce the I Used to be Somebody podcast in their tiki bar. Next stop Tuscany!



  • Engage in truffle hunting and a cooking class
  • Tour a local pecorino (sheep’s cheese) farm in Pienza followed by a picnic
  • Taste the region’s wines: Brunello di Montalcino, Chianti, Nobile de Montepulciano, Super Tuscans
  • Learn about the art of coffee roasting and chocolate making at a cafe in Arezzo
  • Sample artisanal gelatos and small-batch family-made olive oil

Select Tour: 2024 I Used to be Somebody World Tour - First Stop: Tuscany! (September 15 – 21, 2024)