In Tuscany, A Traveler’s Dream Day (Part 1)

FOR TRAVELERS AND VACATIONERS there’s a wide range of different ways available to describe a truly, great travel day.

Some dream of doing nothing and others dream of doing everything.

Yes, some dream of a day of utter nothingness, a day in which there is absolutely no stress, no movement, no effort, no…nothing. Imagine if you can, a no-fuss tropical resort, set on a perfect sandy beach with palm trees gently swaying in the breeze. This is the setting for a truly great vacation day. If we continue with the image, you can imagine yourself sprawled face down on a lounge chair, on this very beach, while three gorgeous women of varying ethnic backgrounds, gently (but not too gently) rub, tickle, and massage away at your tired flesh. Intermittently, a fourth beauty approaches to place a freshly made tropical drink by your side and see if you will be needing anything else. Then a simple smile on your part and the most effortless wave of the hand signals: “No, not right now. Everything is just fine…”

OK, that’s one type of vacation for sure – one where you do nothing and it feels oh-so-good. On most days, ask me what type of vacation I would you like and my answer will be…THAT!

Now, of course, there are other days and other ways.

I do love a real travel day and that’s what I’m going to ramble on about. Real days made of travel are complex: filled with all sorts of ups and downs and packed with action, stress, and accomplishment. Yes, I’m talking about early wake ups, running for trains and buses, map folding and unfolding, photo snapping, conversations with strangers, (one of my favorites), getting lost, getting in and out of trouble, finding a tucked away cafe or secret tavern, and much, much more. That’s a real traveler’s dream day.

I had one such day while hopping towns in Tuscany and it went something like this.

5:53 AM – Waking up early is dreadful and should never happen, unless you’re traveling. That’s what I told myself at least, springing out of bed and packing with my eyes still closed – savoring darkness for a few more moments. Bag packed. Hostel bed made (sort of). I jumped into the shower and stepped out 5 minutes later a new man. Then it was a coffee and quick planning with my travel companion for the day, Lucas. Sitting huddled over our free little hostel breakfast, at an hour when no one else was awake, we made hurried plans in whispered voices.

I had met Lucas two days before in Florence at our hostel. Really it was more of a bed and breakfast. The point being, for the past two days we had strolled through the birthplace of the Renaissance, admired art, haplessly flirted with any and all girls crossing our path, and indulged in the region’s superb food and wine. Hailing from Argentina, he spoke Spanish with the italian-lilt I find relatively easy to understand (having studied in Buenos Aires for a debaucherous semester).

6:30 AM – Too early to function properly, our blank faces stared at the train schedule flashing and updating on the giant screens around the Santa Maria Novella train station. Finally, we found our train. Good ole train #1.

We boarded, sat down, and sighed ooooof…what a relief. Then, then we heard murmurs of concern, scrambled italian conversations, and then Lucas picked up the jist of it – this train was not going where we needed to be going. WRONG TRAIN!

We spun out of the train and sprinted back to the main platform, scanning back and forth, another train marked #1A was getting ready to depart. Frantic, sweaty, hungover and puffy faced, we made a mad dash for it and entered the cabin with such force that all fellow passengers looked at us as if we had just barged into a movie theatre, flicked on all of the bright lights, and frenched their sister. Awkward. But nothing a traveler is not accustomed to.

After the train pulled away, we relaxed and enjoyed the ride to a town named, Poggibonsi. We got off, had a coffee and waited 20 minutes for the next local bus to carry us up into the hilltops to see the spires and sweeping views offered by the famous little town of, San Gimignano.

8:42 AM – Amazing town. One of Italy’s finest little day trips. San Gimignano is an exquisite little town straight out of a fairy tale – so whimsical and so cute, one can easily imagine Pinterest users happily adding photo after photo to their little happy page.

Set in the beautiful, rolling hills of Tuscany, this town clearly has served as a fortress in another life. The narrow cobblestone streets weave through the walled city with tall, towering spires and vantage points – one can imagine these lookouts and towers were just perfect for spotting an oncoming attack, crapping oneself, and then silently diving off like an Olympic champion.

During the summer months, when all of Tuscany is under siege by tourists, this town can be jam-packed and sweltering in the sun. However, on this day the town was ours and so we made our way around effortlessly, strolling the entire, cobblestone town, in less than an hour.

At one point we stopped at a tiny deli and opted for a pre-noon picnic lunch of salami and cheese sandwiches, olives, and a cold birra (because it’s good for you), then exited the town through it’s enormous front door and found ourselves at the bus stop moments before the one we needed to take lumbered our way.

Bored and with little to do for the 20 minutes or so, we, for unknown reasons, began to hum the song, Volare. Perhaps it was a joke from the evening before? But bottle after bottle of the regions earthy, chianti clasico made remembering too difficult. Regardless, the song would stick with us for the rest of the day and we whenever the moment seemed right, we’d launch into humming and singing, Volare! Woah oh oh, Volare! Woah oh oh, VOLARE!

With one great day-trip under our belt, we boarded the bus, kicked back and plugged in our music (Volare was cued up on repeat).

Sights of San Gimignano 




12:07 PM – Next up, the famous city of Siena. Measuring the route on a crumpled map of Tuscany, it was clear to see, from Florence, we had traveled the majority of the way and the trip to San Gimignano had taken us almost to Siena, and now we roughly a 30 minute bus ride to Siena.

Perhaps it was all the tower climbing, perhaps it was the breakfast beer, but I passed out on the bus and awoke with sticky contacts in my eyes and a bit of drool forming in the corner of my mouth. With a forceful courtesy wipe and smack to the face I was starting to wake up, then the view from the bus window of Siena got my full attention. There’s nothing quite like the rush you get as you arrive to a new destination – a place you’ve heard is great and full of things of interest – but it’s all unknown and brand new. When the bus lurched to a final stop, I smacked Lucas with the map and we grabbed our bags and stepped out into a slight drizzle with a new city to explore.

Let’s go!



Siena is a beauty. You will like Siena and it may be better than Florence. Bold words, but after exploring Siena, you’ll at least understand the rivalry with Florence and see why people make this claim.

Yes, for hundreds of years Florence and Siena have been rivals – fighting to be the true center of Tuscany. Even if you do not agree, everyone enjoys walking the center of Siena and snapping a photo in the shell-shaped town center known as the Piazza del Campo, home of the unique horse race, Il Palio.

1:30pm ??? 

Want to hear what we did next? Post a comment below or let us know on Twitter @TakeYaThere



3 thoughts on “In Tuscany, A Traveler’s Dream Day (Part 1)

  1. Pingback: In Tuscany, A Traveler’s Dream Day (Part 2) | Take Ya There

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