Want to Travel Italy More Meaningfully? Try Slow Travel

If 2020 has taught us anything, remote work is going mainstream, and this high-speed train doesn’t have reverse.¹

As it turns out, productivity does care where you work from and how long it takes to get there. Remote work is 13% more productive, and I say hallelujah because I do all my work (if you call it that) from a sturdy, German-built couch desk.² Any boss (I thankfully don’t have) would be appalled.

When push comes to shove, we’ve seen that humans are capable of creating new habits in a hurry. What if we imagine a world where working remotely does become the new norm? Would that mean we can work from anywhere?

If so, why pay £1400/month for a dingy one-bedroom apartment in London when you can live it up in a Tuscan villa with a pool? Wouldn’t you rather be riding your bike in Italy instead of spending hours on the train or bumper to bumper in traffic?

With millions of people forced to stay put, I’ve experienced Italy first hand without mass tourism. Getting a photo of Florence’s Ponte Vecchio is child’s play. Italians outnumber tourists in Venice. Getting around is as civilized as having a cup of tea with the Queen (well, almost).

Who can argue with the rate we’re populating cities, ticking off destinations like scorecards and working morning to night without seeing the light of day is sustainable?

While the entire travel industry is essentially on pause and no clear answer about when things will return to normal, it’s hard to imagine business as usual post Coronavirus.

Now, I know it’s unlikely stocks on couch desks will skyrocket, but, is there more? Can we commingle our careers with our interests and hobbies?

Slow Travel: A deeper, more balanced approach to life (and travel)

Humans are built for connection. We’re social beings. We expand through relationships, interactions, and diverse experiences. Yet, how much time do we devote to broadening our horizons and pursuing meaningful experiences? We work the majority of the year to afford the luxuries of a few weeks of vacation.

Rather than compartmentalizing work and vacation, the philosophy of slow travel marries the two. It relies on the idea that travel is meant to educate, make an emotional impact, and build relationships with local people.

Slow travel is more of a mindset than a cadence. Rather than frantically jumping from city to sight, the slow traveler takes on the challenge to know and understand one particular region at a time.

It takes weeks to scratch the surface in almost any given area in Italy. The most cycling-friendly towns offer at least 10-20 unique rides (with exception of the high mountains). Wouldn’t it be exciting to spend weeks or months in your dream destination combining remote work and discovering new things to do?

The perks of slowing down in Italy

In a world of instant gratification, it’s easy to forget that quality comes with time and focus. We’re not wired to multitask and we’re certainly becoming less and less aware of how much of it we spend glued to devices.

Science tells us Americans now spend nearly five hours a day on their phones. This addiction to technology isn’t by accident, it’s by design. Tech companies pour billions of dollars into engineering new ways to get us more and more hooked.

Whether we’re aware of it or not, our time, attention, and data have become their product. The essence of slowing down is becoming more present and intentional about creating and sharing our own lasting value. Here are a few benefits:

Serendipitous experiences

Rather than feeling overwhelmed by a never-ending list of roads to ride, restaurants to try and sites to see, slow travel favors becoming present and appreciating the distinct moments along the way.

You may never check every single item off your bucket list, but you’ll instead focus on the meaningful experiences that pop up during those in-between spaces. Who knows who you’ll meet, what you’ll find, or what types of light-bulb moments you may stumble upon.

New connections

Often the most difficult yet stepping outside of our comfort zone is where the magic happens. Short trips show us what a place looks like, but more extended stays show us how people live, the culture, and the social dynamics. Spending time in a reality dissimilar from our own is where our perspectives shift.

The Italian people are known to be naturally curious and inquisitive. They love to talk to anybody about almost anything (but especially about food). As a cyclist, you are already recognized and accepted by many.

Personal Growth

The common denominator in the human experience is we all want to live the truest, highest expression of ourselves. No matter where we are in life, there’s always the next level until we take our last breath.

Bronnie Ware tells us in her book The Top 5 Regrets of the Dying that most people she encountered as a palliative care nurse had not honored even half their dreams. Here are the five most common themes that surfaced:

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
2. I wish I hadn’t worked so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish that I had let myself be happier.

Slow travel isn’t about quitting your job, selling your house and becoming an Instagram influencer. It welcomes you to consider the idea of working remotely abroad for a week to a few months a year. Does it really have to wait until retirement?

How to embrace slow travel and learn Italian at any age

Lucca Cycling Club happens to have an honorary member living and breathing the slow travel philosophy. His name is Michael Victor, 60-year-old California resident who now calls Siena his second home.

“My bike has taken me to far-flung places, introduced me to some amazing people, and surprisingly, opened doors. The door it has opened the widest is Italian,” he says.

Mike and I met on one of his many bike tours. He’s a naturally gifted cyclist and can hold his own no matter who he’s with.

I suggested he learn Italian. The pursuit would give him roots in Italy and I know from experience it’s a humbling yet rewarding journey. He surprised me some months later showing a hint of studiousness:

“Purely for the entertainment value, I decided to secretly begin the Rosetta Stone Italian course so I could surprise Alison by ordering my mid-ride lunch in Italian. That was the extent of my ambition. I tried. I was terrible at it, but it was so fun.

The Italian people are warm, tolerant, enthusiastic, and welcoming. Whenever I would try to speak in Italian, they would smile and encourage me despite the punishment I was inflicting on their ears. I decided to stick with it because, as my wife reminded me, we don’t really need a reason to learn something.”

I encouraged him to take his studies to a language school in Italy. He’d seemingly mastered so many areas of his life that it was only appropriate to give Mike another mountain to climb. I sent him a few potential candidates and he established a connection immediately with Mauro Faleri of Saena Iulia in Siena.

“I went to the school for two weeks that winter, and for most of the last five winters, have been calling Siena home. It’s a captivating city filled with culture and tradition, a thoroughly Italian vibe, and the Piazza del Campo. And, of course, I bring my bike.

Siena is located in picture-postcard Tuscany. Each day after class, I look forward to riding beautiful Tuscan roads with hardly any cars. You can access fantastic rides in any direction from town, and many of my regular routes include segments of the famed strade bianche.”

He says that despite the lack of natural ability, he’s now fully functional in Italian, if not fluent. The decision to go for it changed his life—a whole new world of opportunity has opened up. After several tries, he found the perfect apartment and, of course, his Italian family.

“I recall telling Mauro a couple of years ago that even though I was only learning the language for fun—I wanted to become fluent for a tourist.

He looked at me a little perplexed and then replied, ‘But you’re not a tourist, you’re a visitor. And there’s a big difference between the two.’”

Three ways we can help you travel slow in Italy

1. Find you a place to stay

Finding a great place to stay isn’t always as simple as scrolling through Airbnb or booking.com. What if it’s not as lovely as the photos make it out to be? Or you get there to find out your bedroom window is a few floors above a bar? If it smells like antique furniture—then what? Many weekly rentals aren’t even listed because they fill up via word of mouth.

Either send us your dream place, and we’ll scout it out personally to make sure it ticks off all your boxes. Otherwise, check out our list of apartments, villas, and agriturismos (with photos) vetted for cyclists. No villas with steep gravel driveways or trip-over-your-bike-apartments. Want views? You can have sensational views, and we’ll let you know how many uphill kilometers to the front door.

2. Show you fantastic riding

Beyond our traditional guided rides and self-guided Lucca Region & Ride Guide, we’re always up for a custom adventure. Imagine you’re based in Lucca and want to ride to Bologna, Florence or Siena—you name it and we’ll support it. It could be a weekend trip, a day trip, or a self-guided trip. Try me, and I’ll honestly let you know what it takes.

3. Everything else: We have your back

Slow travel can have a steep learning curve, especially if you don’t speak Italian. Going to the gym or local pool isn’t as simple as paying an entrance fee. You’ll need a medical certificate… from a sports doctor… with an appointment.

Plan your trip with us, and we’ll lay it all out step-by-step.

Italian Language school, post office, English speaking nannies, wine tasting, art classes, bike rentals (or repair & cleaning), doctor’s appointment, dry cleaner? Just say the word—we’ve got you covered. We’ll happily show you how to master the art of La Dolce Vita. It’s taken me ten short years to no longer be phased by Italian bureaucracy.

Available in Lucca, Siena, and other areas of Tuscany. See our Bespoke Trips for more information.

1. In case you’ve been living under a rock, Twitter, Facebook and Shopify have all announced they will continue to allow employees to work from home indefinitely. Other corporate giants such as Morgan Stanley, JP Morgan, and Nationwide Insurance are strongly considering doing the same. REI’s brand new, unused corporate headquarters is listed for sale as they attempt to retain its remaining workforce. ↩︎
2. Lynch, Shana. “Why Working from Home Is a ‘Future-Looking Technology.’” Stanford Graduate School of Business, June 22, 2017. https://www.gsb.stanford.edu/insights/why-working-home-future-looking-technology. ↩︎