Expat Essentials

Trading Chicago for Madeira: ‘Sometimes, the universe thanks you for your service and vistas are reopened’




(Editor’s note: See Beth’s accompanying Madeira travel post here.)

A little over a month ago, I packed up the few belongings I still owned in my carry-on, bought a rolling pet carrier for my dog, and left for a long-term stay in Madeira, an autonomous region of Portugal off the coast of Africa.

I am not, by nature, a minimalist. Having grown up in a military family that moved from state to state and country to country more times that I care to count (13 — we moved 13 times before I graduated from high school), minimalism should be ingrained in every fiber of my being.

Alas, it is not a way of life that comes naturally to me. I like to collect mementos from places I have been. I am a sucker for family photographs, books, craft supplies, and home decor.

To make this move – one that I hope will be the first of many in my renewed travels – I had to pare everything down to the bare essentials. So I sold pretty much everything I owned, stashed a few boxes of mementos at my parents’ house, and scanned any important documents I thought I might need on the road.

Why Madeira? I’ll confess. I saw it on The Bachelorette. One look at the beautiful scenery and sub-tropical weather and I was hooked.



Having lived in the suburbs of Chicago for the past twenty-five years where the summers are scorching hot and the winters are unbearably cold, I longed for mild temperatures.

Funchal, Madeira’s capital city, has high temperatures in the mid-70s year round. This climate produces stunning flowers, deep blue waters, and the ability to spend all day outdoors in the sunshine.

Let me back up and share how I got to this point.

After growing up in the military, I went to college, married, had two children, and lived the suburban lifestyle for the next 25 years. Some days, it was fine. Some days, it was soul-crushing.

For someone who moved as much as I did in my younger years, staying in one place for so long was one of the most difficult things I have ever done, but to quote Frankie Heck from “The Middle,” “You do for family.”



Sometimes, the universe thanks you for your service and vistas are reopened.

A year and a half ago, my eldest daughter left to finish her education at Syracuse University in upstate New York, and my youngest left for her freshman year at the University of St Andrews in Scotland.

I promised them I would stay in their hometown through their first summer at home, but warned them after that I would not commit to staying in one place any longer.

We spent that summer planning a wedding for my older daughter and her new husband, who will be reporting for duty in Germany in a couple of weeks … placing both daughters on the European continent for at least the next two and a half years and giving me the perfect excuse to make my move.

I’m far from alone.

There are a growing number of expats in Madeira, particularly retirees who moved to the island for its temperate climate and its wide variety of leisure activities.

Expats who still wish to work will find success in the tourism industry, but jobs outside this industry are few and far between, and the island has a 14.7-percent unemployment rate.

The laws of supply and demand have influenced housing prices, and Madeira now has some of the highest property prices in Portugal, a country which has seen a 14.3-percent increase in the last year, according to a current RE/MAX housing report.

Airbnb properties offer a good solution for those who wish to eventually relocate to the island, but who aren’t ready to commit to a particular locale or haven’t been issued a residence permit.

Through Portugal’s Golden Visa Programme, non-EU citizens who make a property investment of 350,000 euros (for properties more than 30 years old or located in areas of urban renovation) to 500,000 euros qualify for a residence permit.

The Golden Visa Programme also allows for residency through capital investments and job creation – great news for those who are citizens of countries outside the EU who want to move to this sub-tropical paradise!

My visa-free status as an U.S. citizen staying in the Schengen Area will expire at the end of January.

I hope to find a job here in Madeira or another path to residency in the EU by then that will allow me to stay here for an extended period of time. In the meantime, I will continue to enjoy the beautiful weather, stunning scenery, and hospitality of the local residents, while I escape from the harsh winter weather in Illinois.


Beth is rejoining the expat life after spending her childhood in Europe and the United States, then settling in Chicagoland to raise two daughters. Now an empty nester, she is roaming Europe, armed with a TEFL certificate and an online position teaching English for EF.

Website | + posts

Most Popular

To Top

Subscribe to our newsletter

Receive the latest news and updates from Dispatches Europe. Get lifestyle & culture, startup & tech, jobs and travel news dispatched to your inbox each week.

You have Successfully Subscribed!