How to road trip Tuscany… by train

My first trip to Italy was with my family. Mum, dad, my two sisters and I. We packed into a car and drove allllll around the country for six weeks, made infinitely easier by the fact my parents are Italian, have family scattered all over the country, and speak the language fluently. My second trip was with my husband, a decade later. We didn’t have a car, and stuck mostly to the bigger cities. On my third trip, again with my husband, I wanted get back to some of the smaller Tuscan towns I first saw back in 2002, but using only the rail network.

Siena, Italy

The main reason for this is that all those gorgeous old towns like Lucca and San Gimignano are still encircled by medieval city walls. Even if you can navigate the narrow alleyways and cobbled roads, finding parking inside of them is next to impossible. And when the rail network is as good as it is over there, there’s no need to worry yourself with parking fines and scratched bumpers.

The husband was on board, and our game plan was:
a) Pick out the cities we wanted to visit
b) Book 2 nights accommodation in every 2nd city
c) See the city we were staying in the first day, and day trip on the other day

Because the trains are so regular and reliable, you don’t need to pre-book your tickets months before departing – just roll up to the station on the morning you want to head off, and purchase it on the spot. Just remember to validate your ticket to avoid some serious fines – not speaking the language is not a valid excuse.

Lucca, Italy

Here’s what our 2017 week-long Tuscan itinerary looked like:

Day 1Arrive in SienaSee SienaAirbnb in Siena
Day 2Train to/from San GimignanoDay trip and return to SienaAirbnb in Siena
Day 3Train to LuccaSee LuccaAirbnb in Lucca
Day 4Train to/from VolterraDay trip and return to LuccaAirbnb in Lucca
Day 5Train to FlorenceSee FlorenceHotel in Florence
Day 6More of FlorenceHotel in Florence
Day 7And more of FlorenceHotel in Florence
Day 8Depart Florence

We were able to comfortably cover 5 cities, and in fact had time for at least one more (most people would probably go with Pisa, but we’ve already been and wanted more time in Florence). And that’s all well and good, but how can you do the same thing when you’re in Tuscany? Here are my top 5 tips to organise your own Tuscan road trip (by train):

1. Get a map
And pay attention to the scale. Be realistic about how much distance you can actually cover in the amount of days you have at your disposal. If you have a week, like we did, pick out an area of Tuscany and start circling names of towns that are in relative vicinity of each other.

2. Start looking up the names of the major towns on Google, Instagram, etc
Maybe there are ten bigger towns in the area you’ve marked out – start looking them up online. Check out blogs that mention those town names, online magazine articles, Instagram check ins. Get a bit of an idea of what’s there, maybe some will grab your attention, maybe some you’ll cross off your list.

Siena, Italy

3. Look at accommodation options
If you want to see a few cities, book accommodation in a different location along your path every few nights. See which stops are closer to each other than others. Google maps is nifty here – you can plug in your destinations and drag-and-drop them into an order that flows well. Then, group them together – for example, San Gimignano is just over an hour train ride from Siena, but over 3 hours from Lucca, so it made more sense to take the day trip there from Siena.

4. Start looking at what’s in between the bigger towns
Just because you need to get from Lucca to Florence doesn’t mean you can’t stop off on the way. Maybe you notice on the map the little town of Pistoia on the way, and after a bit of research you decide you’ll stop there for a few hours to check out the sculpture garden or the thermal baths.

5. Leave yourself plenty of time at the train stations
There is nothing worse that being in a rush at a foreign train station. If you’ve looked up timetables before you travel, give yourself plenty of time to get to the station, find the ticket machines, work out how to get your ticket, have it validated, and board the train. It’s a simple process, but when it’s in another language and you’re in a rush, it can get really intimidating, really quickly.

Florence, Italy

** BONUS TIP: Learn a few basic words in Italian
Not so much a planning tip, but in some of these smaller towns, people won’t speak as much English as they will in the bigger cities like Rome and Florence. Even just a few words like hello (ciao), please (per favore), thank you (grazie) and excuse me (mi scusi) will get you a long way! And if you’re feeling a little braver, add these to your vocabulary:
dov’è si trova…?    —-   where can I find…?
quanto costa?         —-    how much does it cost?
non capisco            —-    I don’t understand
parla inglese?         —-     do you speak English?

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