Maybe I’m just a simple gal who enjoys the simpler things in life but in all of our travels, my favorite vacations have been the ones in which I can let go of all of my stress.
I’m a casual jeans and T-shirt, comfort over style, laid back type of person and my most favorite vacations are the simple ones.
Don’t get me wrong. I’ve been incredibly fortunate and privileged to have seen the gilded ceilings of the Vatican museum, ridden in a private boat on the sparkling blue waters of Lake Como pretending I was Amal Clooney, and relaxed beachside at an all-inclusive resort in Puerto Vallarta. Those were all amazing experiences and I am so grateful to have experienced them.
However, my favorite, most special moments occurred after everything went “wrong” and all of our planning didn’t match reality.
I think back on our trip to Tuscany and my heart aches to be “stranded” again in the middle of a tiny Italian village in the Tuscan hills.
Simply known as “The Watchtower” we rented a historic castle nestled in the hills of the Chianti region in Tuscany, Italy for a very affordable $102/night.
In my typical, travel-light-and-buy-items-when-we-arrive fashion, I packed only a few diapers for our 14-month-old daughter to last the airplane ride plus a few extra.
“There are plenty of grocery stores in Florence. We’ll grab some extra diapers and supplies once we land,” I assumed.
Except we didn’t know that in August, in Italy, nothing is open. Nothing.
Stores are closed (or have extremely limited hours) on weekends, and our rental car wouldn’t be available for pick-up until Monday. We arrived on a Saturday afternoon.
No diapers, no food, and no rental car for two days. Disaster, right?
We hopped on a bus and hoped that we’d recognize our stop when it was announced in Italian over the loudspeaker like they do on Swedish buses. Except that never happened because there was no loudspeaker, and even if there was, I highly doubt we would’ve recognized the proper Italian pronunciation of the bus stop name.
“Was that San Domingo or San Donato? I don’t know!?!”
The directions from our Airbnb host were surprisingly accurate while remaining incredibly vague. Written by someone who knows the geography and landmarks, the instructions were nearly impossible for a foreigner to sort out with specifics like, “You’ll pass the red farmhouse on the left and the large yellow villa on the right.”
If you’ve ever been to Tuscany, you’ll know that there are yellow villas everywhere. Was it that that yellow villa or that one?!
During the entire bus ride, my eyes never stopped scanning villas and farmhouses wondering which stop was ours.
Before our trip, I had the ridiculous foresight to explore the area a bit using Google Maps where you can virtually “drive” through the neighborhood and see what it looks like. I thought I recognized the tiny village of San Donato–the tiniest town (a street, really) that housed our humble watchtower.
“I think this is it!” I told my husband.
“Are you sure?”
“No, but push the button just in case.”
If incorrect in my reading of our host’s directions, there would be no easy recourse. We had no cell phone reception and we’d be walking on narrow and winding roads with no sidewalk for miles completely lost in the Tuscan hills. Only hopes and prayers could save us from getting hit by the Italian drivers whizzing expertly around the blind turns.
I’m all for fun adventures, but I’m not so thrilled about the possibility of getting hit by a car on my vacation.
Magically, my Google Maps stalking and bizarre attention to detail paid off, and we scrambled to grab our bags and jumped off the bus at the correct stop. The watchtower, looming on the hill, beckoned to us at the top of a steep pebble stone driveway.
Come here and relax, it seemed to say.
Sigh. We made it.
The watchtower was everything you might expect in a 13th century stone building. It had all of the typical castle-like qualities—stone spiral stairways, heavy wooden doors with iron knockers, and exposed wooden beams in the roof.
Like many other Airbnb apartments, former renters had left behind bits of uneaten dry goods. Desperate for anything to eat, we scrounged up a bit of dry pasta and discovered a small glass container of tomato sauce for dinner.
Funnily enough, our “picky eaters” ate everything we put in front of them. They were too hungry to be picky. With full bellies, we relaxed on the roof while they played with all of the new toys in the bedroom downstairs.
“I’ll take the bus back into Florence on Monday to pick up the rental car and get some food,” my husband proposed.
It sounded like as good a plan as any. Despite being surrounded by cute little shops and stores, everything was closed for the summer holiday. All of the Italians were also away on vacation.
Technologically, we were isolated. The WiFi, unable to penetrate its signal through 13th century stone walls, was limited to the kitchen area.
Blissfully, we were spared the constant interruptions of emails, texts, and messages, and we stayed at the top of the watchtower to soak in the beautiful 360-degree views of the Tuscan hills. Groves of olive trees surrounded us, and in the distance, the skyline of Florence.
That night, after successfully getting the kids to sleep, we headed back up to the rooftop to stargaze. The night sky was black and full of stars. Never before had they appeared so close or so bright.
With a bottle of wine in hand, we sat in our deck chairs in silence, only speaking when pointing out another shooting star falling from the sky.
The summer night air was warm and calm. Our bodies relaxed and our brains quieted. There was nothing to do except unwind and drink in the sight of the galaxies.
The Best Moments
For the next two days, we stayed on that rooftop, not doing anything special. It didn’t matter that we had only two diapers left—our daughter played naked, and we saved the diapers for bedtime.
It didn’t matter that we didn’t have much food. The kids ate the pasta and tomato sauce happily and didn’t seem to mind the lack of variety.
It didn’t matter that there wasn’t much to do around the watchtower except go for walks among the olive groves. We were too busy splashing in the garden hose on the rooftop and playing with the clothespins on our noses and fingers.
After a few days of “doing nothing,” we decided to leave the isolation of the watchtower roof and head out to a nearby winery. We slowly walked along the dirt roads at the pace of our three-year-old. Happy to stop and look at the beetles and birds.
For five days, we got slower and slower yet we were never bored. The scenery was never tiresome, and the kids were content playing throughout the watchtower. It seemed there was always something new to discover.
Our favorite holidays aren’t the ones where we zing around the city, stopping in all of the museums, cafes, and restaurants.
They aren’t the ones with the fancy dinners that require high heels or dressy clothes. Those are great, but they aren’t the ones that make my heart sing.
Instead, my favorite holiday entailed being “stranded” on a 10 square meter rooftop overlooking the Tuscan hills, with no WiFi, little food, no luxuries, and the happiest kids I have ever seen. (The happiest the adults had been in a long time, too.)
I want to go back to those moments and relive those moments all over again, but I know that it won’t be the same.
We can always return to the watchtower, but our kids are older now, and the apartment has been renovated.
The best part about loving simplicity and slow travel is that it is easily replicable wherever you are and wherever you go. For us, the best times are when we can unplug, relax, and let go of our worries.
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We may not see all of the museums or eat at the fancy restaurants but our life isn’t in that stage right now. With young kids, it is much more enjoyable to sit back, do nothing, and watch them play and run around.
Our days of fancy vacations will happen soon enough. Right now, we enjoy doing nothing the most.
Find your own watchtower, your own special place, and then recreate it in as many different ways and in as many different places as possible.
Turn off your phones and go for a slow walk. Let the kids stay up late, giggling long into the night. Drink good wine and simple food and relax.
What was your favorite travel moment or holiday?
Let me know in the discussion on Facebook.
*This trip was not sponsored by anyone except us. It simply was my favorite vacation to date and I wanted to share our experience.*