We keep moving forward, opening new doors, and doing new things, because we’re curious and curiosity keeps leading us down new paths.
– Walt Disney
When we hit two years as roving retirees, Robie thought it would be fun to take a look back at where we’ve been. Instead of replaying the greatest hits, we thought we’d share some of the weird, wild and sometimes difficult lessons we’ve learned from 24 months on the road.
Most of the experiences came with our new lifestyle. Others pertained to a specific destination. All were things we didn’t know before setting out.
Here’s how it all started
After selling our house of 13 years, in July 2024 Robie and I became homeless. We took a tour of the Southeastern United States to see friends and family then flew to the UK and learned our first difficult lesson.
Landing at Heathrow, we rode the Underground to Euston Station to catch a train to Liverpool. After all, the Tube was cheaper than a cab. What we didn’t know was that when we needed to change trains at Leicester Square, the station – opened in 1905 – didn’t have lifts.
While Reid stood at the bottom of a flight of steps wondering how to get her 50-pound, oversized suitcase up the stairs, an elderly man came by and carried it for her. It was a humbling experience for a former travel professional who thought she knew everything about minimalist packing.
Lesson No.1 – We packed too much.
How did we let that happen?
While overpacking seemed like an easy mistake to make, it was also mostly inevitable.
When we first started talking about retirement plans, we envisioned a move to Spain, Mexico or possibly Costa Rica. Then despite shifting from a permanent move to a roving retirement, the original idea never got dislodged from our minds.
When it came time to buy luggage, we ordered the largest suitcases allowed by the airlines. While our new bags were spacious and good for a move, they were also heavy, unwieldy and a poor choice for changing residences every few months.
After catching the train to Liverpool, we dragged the bulky suitcases up a steep flight of stairs to our first apartment. Before we ever even unpacked, we knew we had to pare down our things. In preparation for a move to Greece, Reid got rid of sandals and summer clothes while Robie donated his heavy coat before experiencing his first winter in Europe.
That process became part of a new routine. Now before every relocation, we sift through our belongings for things we no longer use or wear. Then we take any well-loved clothes to thrift shops and pass along books to our hosts.
Lesson No. 2 – Donate what you don’t need.
A new outlook
Our overpacking misstep wasn’t helped by the fact we were newly retired and on a fixed income. After all, it seemed wasteful to get rid of clothes we could wear when we had so many in our closets at home. This idea was compounded by the fact that we didn’t know what we needed for a five-year, six-continent journey across varying climates and cultures. So, we took a little of everything.
That approach was a mistake.
Being mobile was more important than having extra pants or worrying about spending €15 on a new shirt. Once we shed the clothes we might “someday” need, everything changed.
By just carrying items we actually wore, we only bought to replace. When Reid needed new khakis, she found them at a Madrid department store. When Robie’s belt broke, he picked up a new one from a street vendor in Naples. Over two years, we replaced a pashmina in Istanbul, socks in Morocco, shoes in Greece and a sweater in Scotland. They were worth every penny and better than lugging around backups.
Lesson No. 3 – Buy as you go.
Don’t throw it away
While at home it was easy to toss broken items and order new, elsewhere in the world people still fix things.
In Sicily we picked up a new battery for Robie’s watch. When his shoes started coming apart in Sarandё, we asked around and found an Albanian who hand stitched them together for less than $5.
Robie has refused to part with those shoes.
Lesson No. 4 – Repair shops are our friends.
Are we doing it wrong?
When we got to Albania, we started meeting other nomads. Thanks to the tiny country’s program that allows Americans to stay for a year without visas, many retirees and digital nomads transit through Albania at one time or another.
In Sarandё we met seasonal nomads who traveled part of the year before heading home for the holidays. Others got short-term residency visas in Romania or Greece to stay in Schengen. Some planned to travel a year before returning Stateside. They knew what they wanted to see and didn’t worry about the rest.
When we met Sandy and Dave at Taverna Laberia in January, Sandy rattled off a dozen places they were planning to visit throughout the year. They were headed to Germany in February then the Czech Republic and Slovenia in March and April. Come May they’d be back in Albania before going to Montenegro in June, Kosovo in July, Italy in August, Austria in September and France in October. That’s when Robie and I discovered we were doing things differently than everyone else.
Rather than move every month, we were staying put for an entire season. Despite eliminating excess clothes, I wondered if our preference for staying in one place came from wanting to linger and get to know a region or did it stem from the hassle of lugging four suitcases around every time we changed residences.
In other words, was even our pared-down stuff still holding us back?
After spending seven months in Albania, we downsized our luggage and made a decision to be more mobile. Instead of choosing between Syracuse and Palermo, we split our stay in Sicily and enjoyed both. Along the way we discovered our sweet spot for staying in one place—somewhere between eight and nine weeks. While that’s double other people’s month, it’s a third shorter than our first stops.
We also realized that what makes sense in one place may not work in another. It’s about being flexible, testing new ideas and challenging old ones. Because there is no wrong way to make a roving retirement work, and it’s Lesson No. 5.
What would happen if we moved more often?
A roving retirement isn’t about being on vacation every day. We don’t rush around before collapsing at the end of two weeks. For us, the lifestyle is about blending sightseeing activities with relaxation, choosing the comforts of indoors over getting out when it’s cold or wet. Still, I wondered if we were missing out by not moving more.
I imagined repositioning twelve times a year instead of four or five. What I saw was having to start over a lot more frequently. Every move involves pounding the pavement to get the lay of the land and lingering in cafés or pubs to feel the rhythm of a city. We also spend hours scouting local markets and buying foods in the smallest possible quantities. Even then, ingredients can last months.
A shortened schedule would mean less time to cook. After all, eating out is quick and painless. Building a pantry from scratch, planning meals with strange ingredients and learning to use unfamiliar appliances and cookware isn’t easy.
And it doesn’t happen overnight.
For us, feeling acclimated in a new environment usually happens somewhere between weeks two and three. If we planned to leave after a month, half our time would be spent getting settled. Plus, we’d never get around to finishing that small bottle of olive oil we bought before picking up and moving again.
That realization led to Lesson No. 6 – How we travel is inherently intertwined with how we eat.
What we don’t know can hurt
From the beginning, Robie and I were determined to cook rather than eat out every day. Not only was it bad for our health, it wouldn’t do our finances any favors either.
Before leaving home, we figured good knives would be hard to come by in rental apartments. It’s why Robie insisted on buying a knife roll and packing it with our favorite cutting tools along with a steel rod to keep them honed.
Unfortunately, after a year our knives were liberated by security at Atocha Station in Madrid. The result wasn’t just expensive. It was heartbreaking. We lost our beloved Wüsthof blades.
Lesson No. 7 – It’s illegal to carry knives on Spanish trains.
Cooking naked if we had to
Fortunately, we found affordable, sturdy replacement knives in Palermo. They haven’t been the only additions to our mobile kitchen.
Over the two years we bought a small roasting pan, nested Tupperware and not one but two cheese graters. We purchased a universal measuring cup, a small strainer and bamboo cutting board. Not everything we buy leaves with us. When we added a kitchen towel to the apartment in Greece, we left it for future guests. When we got smaller suitcases, we left the Tupperware in Granada, and when Robie splurged on a charcoal grill in Sarandё, he gifted to our host.
While we continue to get rid of clothes, our stockpile of kitchenware keeps expanding. But we’ll happily part with clothing to make room for cooking utensils. Because if you’re going to cook, having reliable tools to work with is important.
That was Lesson No. 8.
The surprise
Not everything we learned in two years was about the lifestyle change or our choice in luggage. A few came from unexpected places. Like Lesson No. 9 that explained how just because people spoke English in the UK didn’t mean we understood what they were saying.
In Liverpool it’s called Scouse. In Scotland, it’s known as Gaelic. Neither are anywhere close to English.
From left field
We also learned about going places in the off-season. After traveling for decades when others didn’t – like seeing Poland in November or the Great Barrier Reef in February – we thought we knew all there was. Then we arrived in Greece toward the end of tourist season and discovered a new twist.
While we were looking forward to quiet beaches and uncrowded restaurants, on Ikaria the businesses catering to tourists were preparing to close. After finding a lovely café near our apartment, it shuttered the following day. When we stopped by Therma’s only market, we interrupted the owners taking inventory before shutting down until spring. Soon hotels closed, thermal baths shut and the church doors gained a padlock. With everyone gone, we were two of only a dozen people wintering in tiny Therma.
Then for a little action, we decided to visit Mykonos. Except the world-class destination that annually welcomes 1.5 million tourists was uninhabited in December. Nightclubs were closed, shops boarded up and hotels sat empty. We strolled down narrow streets that had been packed a few months earlier yet were suddenly devoid of any life but our own.
That taught us Lesson No. 10 – Sometimes off-season means “closed for business.”
Food, glorious food
A lot of my favorite lessons have come from trying new foods.
There was discovering how bland British fare came with cute names like Bubble and Squeak or Spotted Dick. How else were parents supposed to get kids to eat griddle cakes made from leftover vegetables or steamed pudding that had suet and dried currants?
There was the discovery that Moroccan tagines didn’t come served over couscous. Instead, the semolina with steamed vegetables is considered a side dish. I also never knew how delicious a kebap could be until we ate lamb raised on wildflowers and mountain thyme in Istanbul.
Some of our tastiest lessons happened in Italy where we learned to eat made-to-order cannoli in Syracuse and tried Neapolitan pizza at a restaurant that’s been making pies for more than 150 years. But who could have guessed that the best food in Palermo was in the markets?
At Mercato del Capo, spleen sandwiches were confited to perfection. Lamb intestines were grilled until charred and seasoned with salt and a squeeze of fresh lemon. Then there was the smoky, sweet combination of spring onions wrapped in bacon that tasted like heaven.
Lesson No. 11 – The best food is often found on the street.
Nice legs!
Before we spent the summer in Aberdeen, I hadn’t been to Scotland in more than 40 years. Then I quickly discovered what the Scots have long known.
Lesson No. 12 – Men look better in kilts.
Will it ever be enough?
Another lesson brought back memories of something I’d long forgotten.
When Robie and I left Florida years ago, I thought life on a sailboat meant we could go anywhere the ocean touched. Before setting out on our roving retirement, I believed being full-time nomads meant the world was our oyster. We could go anywhere, do anything, see everything.
Unfortunately, every life is limited by time and money. That means even though we have fewer commitments and resources to fund our adventures, we still have to make choices, and there will always be something left unseen.
It just gives us a reason to return because Lesson No. 13 is there’s no such thing as doing it all.
Last but not least
It probably seems obvious that a roving retirement involves a lot of travel. Like right there in the name, even.
After two years Robie and I have clocked more miles on trains, buses and ferries than we can count. We’ve also been stranded on the rails, displaced from one bus and told to wait for another because routes get canceled, ferries change schedules and trains break down. Is it frustrating? You bet. But it’s all part of life on the road, so you gotta roll with it.
For us it was Lesson No. 14.
What does any of it mean?
In two years, we made classic mistakes. But if this trip down memory lane explains anything about life as roving retirees, we hope it shows that mistakes are opportunities in disguise.
And in the end, isn’t that the most important lesson of all?