Experiences, Podcast episodes

Episode #269: Extended stay in Italy? Tips for a Working Vacation

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Ever dreamed of combining work and travel in one of the world’s most enchanting destinations? We meet an adventurous empty nester couple who share their innovative approach to working vacations in Italy, offering tips on making the most of extended stays, navigating time zones, and finding that perfect balance between exploration and productivity amidst the beauty of Italian towns.

Summary

In this episode, we welcome Kristen and Jason, a couple of adventurous empty-nesters from the US, who have discovered a unique way to balance their work commitments with their love of travel. They saw an opportunity during the remote work boom triggered by Covid to explore Italy in a way many of us dream about. They’ve mastered the art of the working vacation, intertwining their professional lives with breathtaking Italian vistas, historical wanderings, and, of course, delightful culinary experiences. From the ancient streets of Rome to the charming walled city of Lucca and the picturesque Spello in Umbria, they share how they organize their trips, the logistical magic of time zones, and the joys of life on the road – or on Italian cobblestones, to be exact. Be inspired by Kristen and Jason’s creative approach to travel.

What you’ll learn in this episode

  • Kristen and Jason share the concept of working vacations – how to travel while working remotely, leveraging time zone differences for productivity and leisure
  • Longer term travel can work out as cost-Effective. Tips on making extended trips affordable – like spending three weeks in Italy for less than a typical U.S. beach week
  • Strategies for choosing locations, testing remote work viability, and scheduling work around sightseeing
  • Accommodation wise, Airbnbs generally work better than hotels for working vacations – think kitchens, laundry, and designated workspaces
  • Italy travel highlights – memorable experiences in cities like Rome, Lucca, and Bologna, plus unique day trips and local adventures
  • There will always be challenges to overcome, which is part of the experience. Solutions for connectivity issues and adapting to the realities of working in new environments
  • Exploring Rome Differently – offbeat experiences like biking the Appian Way and visiting the Vittorio Emanuele Monument
  • You can get real cultural immersion through this type of travel. There is value in experiencing daily life in a foreign country – not just as a tourist, but while living and working like a local
  • Driving in Italy – Insights into navigating Italian roads, dealing with ZTL zones, and adapting to different driving norms
  • Looking ahead, this style of travel has shifted their perspective – retirement no longer feels like the ultimate goal. Ideally, Kristen and Jason hope to take working trips to Italy twice a year, but the beauty of this flexible lifestyle is that it allows them to prioritize important family moments along the way

Timeline Overview

  • 03:36 Being able to work remotely in Italy not only means you can spend longer periods there but also, with the right planning, makes for a really cost-effective trip
  • 09:50 It’s best to work out how to schedule and optimize your time for stress-free travel
  • 13:06 Using Italian cities as a base makes for easy transit adventures to nearby locations. Lucca proved to be a fantastic base for Kristen and Jason
  • 14:39 You need to do plenty of research on where you are staying if you need guaranteed good Wifi – be flexible and have backup plans
  • 19:41 Despite knowing Rome well from previous trips, being able to stay longer and outside the tourist center, they have been exploring Rome anew
  • 21:44 Discovering Spello – a hidden gem and another great base
  • 26:05 Driving is generally straightforward – though they have come a cropper to accidental ZTL entry, inappropriate electric car booking, and heading up a mountain by mistake
  • 30:33 Kristen and Jason plan to go away twice a year but are flexible, which is the magic of this kind of travel

About our guests – Kristen and Jason from Work and Wander Italia


Jason and Kristen are empty nesters who have been married for 30 years and have three grown children. After spending more than 20 years in the hustle of suburban Washington, D.C., they now call Charlottesville, VA, home. Since Covid, both have jobs that can be or are fully virtual, allowing them to embrace a new way of traveling. Instead of rushing through hot, crowded trips planned around school vacations, they now take extended “working vacations,” immersing themselves in a place while staying connected to their careers. They especially love exploring Italy in the slower off seasons, when they can truly experience local life. They are excited to share what they’ve learned about this rewarding way to travel and spend time in their favorite place.

Follow Kristen and Jason here

Italian places, foods and concepts mentioned

Places

  • Lucca – charming hilltop town in Tuscany 
  • Le Mura – the walls surrounding the medieval city of Lucca
  • Bologna – fantastic foodie city, a perfect base to visit nearby cities like Parma, Padua and Verona
  • Victor Emmanuel II Monument – the huge white monument in Piazza Venezi in Rome, known as the wedding cake
  • The Aqueduct Park on the Appian Way – in Rome, the ancient Appian Way road, with the park which is the second largest urban park in Europe
  • Garbatella – neighborhood in Rome
  • Spello – small Umbrian town famous for its flowers and flower festival
  • Monte Subasio – mountain near Spello
  • Ostuni – city in Puglia, known as the white city for its streets full of whitewashed walls

Words / Concepts

  • colazione – a typical Italian breakfast – usually a light, sweet meal with coffee and pastries or cake

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