July 18, 2022

Five Weeks in Tuscany

We finally made it to Italy!

Naturally, I had grandiose plans to write a weekly blog about our Italian adventures. Or, at the very least, write a brief story about each stunning hilltop town, vineyard or amazing (insert a kajillion options) we visited that particular day.

I envisioned myself poolside or sitting at a bistro table sipping my americano and taking in the breathtaking views from our villa. Inspired by these surroundings, I would feel compelled to write. My thoughts and words flow with pages and pages of incredible stories to share.

Ummm…so clearly, that didn’t happen!

It’s hard to motivate oneself while on vacation. I mean, it’s a tough gig, and yes, I’m making excuses for laziness and too many distractions.

“Is my wine glass empty again?!

So instead, I’ll give you the full details of ALL the incredible sites and stops we touched upon in one blog.

Lucky you;)

Grab yourself a glass of something yummy, and I hope you enjoy the read as much as it was fun putting this together!

Three days in Florence

We landed! And I can’t decide what excited me more: the first glimpse of terracotta roofs of the warm ochre-coloured buildings or the magnificent Duomo in the distance?


Our stubborn (or determined, depending on how you look) taxi driver Priscilla, refused to budge to an oncoming SUV driving in the wrong direction on a one-way street. Neither the SUV nor Priscilla was letting up. We sat awkwardly for a bit, not knowing whether we should leave or wait. We waited.

Finally, the SUV driver, now furious, got out of his car, smacking his hands and gesturing as if to say, I’m right because I have a bigger penis car. Oh yeah, this is road rage at its finest.

Priscilla stood her ground, “I don’t like these people with their big fancy cars; they think they have no rules.” Thankfully, the standoff ended without any further conflict. The SUV screeched away, and Priscilla claimed victory.

Oh, and by the way, welcome to Italy!

We’ve arrived, and after spending four days in Paris, Florence or Firenze seems ancient in contrast. However, the people are vibrant, and their energy is contagious. The food and wine aren’t bad either;)

Even though we’ve both visited Florence in the past, we couldn’t pass up the opportunity to soak up Tuscany’s capital city one more time before heading to the countryside.

The lovely Hotel Hermitage was our home away from home for three nights, smack between the Ponte Vecchio and the Uffizi Gallery. The location was brilliant.

So, with only two full days, we kept our “must-see” list short, which meant forgoing a few favourites. Instead, we decided on a guided tour of the Uffizi Gallery, knowing it would take a more significant chunk of our day. Which still left us enough time in our day to wander the streets, stop for a coffee, or do whatever came our way.

After nearly three hours of art history overload and rumblings from our stomachs, it was time to eat!

Italy serves up the best Italian food, obviously! I dare you to find a Thai restaurant or a sushi bar; it may exist, but why would you go? When in Florence, it’s Italian food all the way, and it heaves a vast selection of Trattorias, Osterias, Restorantes and Pizzerias, so hard to choose!

Not to be missed are the Enotecas which serve small bites and delicious local wines.

Mercato Centrale is a bustling public market filled with fresh-produced foods made by the region’s local artisans, beautifully arranged produce and lots of wine! In addition, there’s a large food court alla Italian style upstairs. It’s worth checking out, if just for the samples alone. Prices are reasonable and a great way to experience like a local.

Roaming the streets of Florence wouldn’t be complete without a visit to Piazza Della Signoria, Piazza Del Duomo, and Piazza Santo Spirito.

Via de’ Tornabuoni, Via del Parione, and Via Roma are well known for their luxury fashion houses and jewellery labels. However, while you may find fashion heaven from the likes of Prada, Armani and Bulgari, your credit card might tell you a different story. The good news is, it’s free to look!

The Ponte-Vecchio (old bridge) will have your eyes wide open for all that sparkles. Holy wow! Busting with jewellery shops filled with beautiful objects. Diamonds, Emeralds and Rubies, Oh my!

So, if high-end shopping has you gasping for air, then a visit to one of the several markets is perfect. There’s excellent value but be prepared to work for your purchase.

Florence is the perfect jumping-off point to explore Tuscany. Could we have stayed longer? Absolutely! But, this time, we wanted to spend our days exploring Tuscany’s smaller hill towns and vineyards.

We picked up our Opel, Mokka, from the car rental, calling her “our little Mokka.” Laughing that our luggage barely fit in the hatchback. Okay, so we may have overpacked slightly?

Right out of the gate and missing our exit, we drove in circles, as you do, eventually making our way onto the highway. Both of us sighed with relief for having made it this far. We were so excited to be heading (in the right direction) south for sunshine and all things Tuscan. Oblivious to the 1800 kilometres, we would soon be adding to our little Mokka and the many fantastic memories we would make.

Two Weeks in Chianti

Villa Crognole is situated in the vineyards of Castello di Albola in Radda in Chianti, located 56 kilometres southeast of Florence. Accessible off the main highway by a 1 km gravel road and far from neighbours, we were remote. Crognole was our beautiful home for two weeks while we explored the Chianti region.

The stunning views, endless vineyards, manicured gardens, and a welcoming freeze-your-ass-off pool made getting an early start difficult most days. But, indeed, a pleasure to enjoy returning from a busy and hot day of sightseeing.

We used Radda as our base camp to spend less time driving and focus more on the areas closest to us.

The main objective of our holiday was to enjoy our surroundings and experience Tuscany like a local. Cramming too much into our days was not an option. I know, shocking! We enjoyed several lazy days of doing nothing. Opting to lounge poolside, read OR take a well-deserved siesta;)

Towns and Villages

We read several travel books on Tuscany prior to our trip, laying the groundwork for the areas we wanted to explore. Then, we compiled our wish list and let our days play out; it was merely a function of deciding when to go. Honestly, we didn’t overthink this.

Surveying our Italy map was so much fun in helping us to strategize (using the term loosely) our days. But our indispensable GPS saved us from getting lost; it’s a game changer!

Our day trips included Radda, Monteriggioni, Castelina in Chianti, Greve, Siena, San Gimignano, Volpaia, Panzano, Castello di Montefioralli, Badia a Passignano, Certaldo, Fonterutoli, Castello di Brolio.

Below are a few highlights from our two weeks in the Chianti region.


Castellina in Chianti

Castello di Albola – wine tasting




Poggio Al Sole – wine tasting


Castello di Brolio – wine tasting

Three Weeks in Cortona (Camucia)

Villa La Capannina was our second villa for exploring southern Tuscany. Located 90 kilometres south of Radda, Camucia sits at the base of the hill on which Cortona lies.

Our villa in Cortona was quite different from the one in Chianti. For one, our location was in town and within walking distance of all the amenities, including the train station, which was very convenient. The surrounding gardens were beautiful and lovingly maintained by the owners who lived next door. You can’t escape the sweet smell of star jasmine, my absolute favourite! We loved having a pool. It was cold on impact but much appreciated during temperatures of 30-plus degrees. Otherwise, I don’t think we would have survived the heat.

To avoid the busy main road, Google Maps (also indispensable) provided us with the safest and fastest hiking route up the hill to Cortona. Oddly it felt as though we were trespassing and cutting through people’s backyards, and “Oh, hello, nice doggy.”

We covered a lot of territory in three weeks, driving through some of the most scenic countryside. Imagine picture-perfect golden hills laden with large round bales of hay, rows upon rows of lush green vineyards, with castles and century-old farmhouses in the distance. Truly magical and so hard to capture in a photo.

Our day trips included Montepulciano, Pienza, Castiglione del Lago, Passignano sul Trasimeno, Gubbio, Torreone, Arezzo, and even a quick 24 hours in Rome (stay tuned for a separate blog).




Castiglione del Lago


Borgo Trerose – wine tasting


Bramasole – Under the Tuscan Sun

Torreone – lunch

Cantine DEI – wine tasting

Villa rentals – Emma Villa’s

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