Planning a trip to Tuscany

Planning a trip to Tuscany

For anyone else who has read Under the Tuscan Sun by Frances Mayes (or seen the movie), I think we can all agree that it’s a surefire way to inspire your own trip to Tuscany.  Hopefully this post can get you started with the basics of trip planning like how to get there, what to do, and where to stay. For the 3-day detailed itinerary from our recent trip to Tuscany, be sure to check out my next post: Travel Diaries: Tuscany.

Getting to Tuscany

There are two international airports in the Tuscany region: Pisa and Florence; But in my experience there are more direct flights from the US into the larger nearby airports: Rome and Milan. (Bonus: These flights are also generally more affordable). From either of those airports, several cities in Tuscany are accessible via major rail line (e.g. Florence), smaller rail line (e.g. Siena) and even train followed by bus for some of the smaller towns. But I personally recommend renting a car instead to give you the most flexibility to explore the region. Depending on where you are staying in Tuscany, the drive from Rome airport averages 2 to 3 hours. (Tip: Most cars are manual so be sure to plan ahead if you need to reserve an automatic car). I would also recommend an international data plan that includes GPS navigation for getting around.

Top 5 Things to do in Tuscany

1. Explore as many charming towns and small villages as you can
Beyond Florence you have the smaller cities of Pisa, Siena and even Lucca, but in my opinion the essence of Tuscany is better experienced in the smaller (and less touristy) towns dotting the countryside. Many of the walled hilltop cities have watchtowers, churches and other interesting architecture and offer picture-perfect views of the surrounding countryside. There are SO many towns in Tuscany worth exploring, but here are just a few of my favorites from our last trip:

Pienza:  Home of Pecorino cheese and known for its romantic atmosphere; Does a better combination exist?

Montepulciano: The medieval architecture here is stunning and I loved exploring the quiet streets. Don’t forget to taste their local Nobile wine.

Montalcino:  More bustling than Pienza & Montepulciano, this town is famous for its world-renowned Brunello wine, which brings us to number two…

2. Visit a vineyard (or a few) and taste the famous Brunello wine of Montalcino
Do not leave Tuscany without doing this. There are over 100 wine producers in Montalcino, each with its own character and style, so you have plenty of options to choose from. On our recent trip, we picked two vineyards on opposite sides of the spectrum: Castiglion del Bosco (a massive and immaculate estate owned by the Ferragamo family) and La Fornace (a small and charming family-run vineyard). Maybe pick up a few bottles to bring back with you or even have wine shipped directly back to the US as many vineyards do this for a shipping fee.

3. Get lost driving through the hills of the famous Val D’Orcia
The Val D’Orcia refers to the region in Tuscany south of Siena comprised of gentle rolling hills broken up by charming hilltop villages; I am not exaggerating when I say driving through Val D’Orica is like being in a screensaver… except better since it’s real life. I can see why this landscape has been depicted in works of art across centuries (and even in the movie Gladiator). The good news is that Pienza and Montalcino are in the heart of Val D’Orcia so you can take it all in between exploring these towns. Don’t forget to stop for photo ops.

4. Have a countryside picnic at sunset
Along your travels be sure to collect some wine, olive oil, and fresh produce from the region (don’t forget cheese from Pienza) and indulge in it all over a countryside picnic, ideally at sunset. If you have access to a kitchen during your stay, even better: Try cooking your own authentic Tuscan meal using fresh local ingredients (tagliatelle al tartufo, anyone?).

5. For culture, spend a few days in Florence
Florence is considered a mecca for Renaissance art and architecture. Don’t miss the Uffizi Gallery (a world-famous art museum) or Michelangelo’s David, which is housed at the Accademia Gallery.  Other attractions include the Duomo (a massive gothic cathedral where you can climb 463 steps for an amazing view of the city – I promise it’s worth it), the Ponte Vecchio (an iconic bridge), and Giotto’s Bell Tower. You could easily spend several days in Florence (and you should if you can, it is an amazing city) but it would be impossible to squeeze a road-trip through Tuscany and the best of Florence into a few days so make sure to give yourself enough time if you want to do both. Also note: Florence is not a car-friendly city. If you are spending a few days there you should plan on returning your rental car and leaving via train (which is very convenient).

Where to Stay

If you only have a few days in Tuscany, you may want to narrow down which region to focus on exploring. In the northern part of Tuscany (essentially Florence to Siena) you have the Chianti region and smaller towns like San Gimignano, Panzano and Gaiole. In southern Tuscany (below Siena toward Rome) you have the beautiful region of the Val d’Orcia and towns like Montalcino and Pienza. If you stay in the middle of these areas (outside of Siena), many of these towns are theoretically within an hour or so driving in various directions. For hotel options, Castello di Casole is located outside Siena and looks amazing but also very expensive.

In southern Tuscany (where we decided to stay on our recent trip to Tuscany) we discovered there are a ton of lodging options ranging from casual countryside farmhouses to five-star hotels. For those looking for luxury, Rosewood Castiglion del Bosco and Banfi il Borgo have come highly recommended by friends. Both are located on the outskirts of Montalcino. Monteverdi, a ‘rustic-chic’ boutique hotel with only 12 rooms and an incredible spa and art gallery, has also received great reviews. For a great location and more reasonable prices, try Locanda dell’Amoroso. Beyond that, there are a lot of casual lodging options like boutique hotels, bed & breakfasts, and even house rentals (although many are rented by the week in the summer). I’ll float the idea that some of these less “luxurious” options may offer a more authentic Tuscan experience (plus your wallet will thank you). For our trip we ultimately decided to stay in a restored-farmhouse turned boutique hotel: Poggio Piglia (See more details in my other post here).

And let’s not forget Cortona: the charming town in the eastern region of Tuscany (bordering Umbria) that Under the Tuscan Sun is based on. For those fellow fans of ‘Relais & Chateaux’ branded properties, there are two outside Cortona: Relais Borgo San Pietro and Relais Il Falconiere. Both offer 4-plus-star accommodations and Michelin-starred restaurants. Time to start planning our next trip to Tuscany! That’s it for now but make sure to check out my next post with our detailed itinerary: Travel Diaries: Tuscany.



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