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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. 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 Portugal. 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.)

(Sipping Portuguese port might help to make the discussions even better!)

This comprehensive Portugal vacation will have you visiting remarkable wineries (and port wine lodges), gathering ingredients in the market for our private cooking class focused on traditional Portuguese cuisine, delighting in wine-paired meals and hillside picnics, relaxing on a rabelo boat ride down the Douro River, exploring several historic cities and towns, and basking in luxurious hotels each night.



  • Tour Date: April 27 - May 3, 2025
  • Trip Price Per Person: $4,950
  • Single Supplement: $900
  • Tour Size: 20 people
  • Guide: Francisco Franco Afonso
  • Meals: All meals except one dinner and one lunch
  • General Tour FAQs

Tour Portugal and savor its renowned cuisine and world-class wines!


Expect a selection of extraordinary experiences, including:

  • Phenomenal wines and ports
  • Traditional Portuguese dishes
  • Private cooking class
  • Douro River boat excursion
  • Historical sites and towns
  • Luxurious hotels
  • And, of course, expertly wine-paired meals

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.



  • We’ll visit the best of Portugal including walled cities and tiny villages — Porto, Pinhão, Folgosa, Vila Nova de Gaia, Evora, Monsaraz And Azeitao
  • Tour and taste a wide variety of Portuguese wineries (including boutique, family-owed) and enjoy wine-paired lunches and picnics
  • Take a private cooking class to learn all about traditional Portuguese cuisine
  • Visit several UNESCO sites and historic places

Select Tour: 2025 I Used to be Somebody World Tour - Next Stop: Portugal! (April 27 - May 3, 2025)