13 Mistakes to Avoid When Visiting Tuscany, Italy

So, you’ve set your heart out on traveling to Italy’s dreamy Tuscany. And who can blame you?

The picturesque hilltowns, unmistakable rolling hills peppered with vineyards and olive trees, endless historical sights, and the Renaissance of it all. 

Rich in history and culture, topped with some of the most sumptuous food and wines you’ll taste — Tuscany’s got it all.

But let’s not get ahead of ourselves. Like any other destination, there are a few do’s and don’ts to consider before you go. 

It’s all about creating the best memories and not allowing anything to ruin your trip.

While life may be unpredictable, here are a few mistakes to avoid when visiting Tuscany to get the most out of your stay!  

Also Read: How to make money while traveling full time. 

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1. Not Booking Everything in Advance

If you think you can simply get away with just going with the flow — think again.

While it may be perfectly fine to visit Tuscany with a “la bella vita” mindset, preparing well in advance is always best.

This way, you can avoid missing out on accommodation options and attractions as well as waiting in long lines. 

Also, many popular attractions and sights like the Duomo sell out extremely fast, especially during peak season.

So, if you’ve got an Tuscany itinerary and a list of must-visit places, you’ll want to buy tickets in advance. 

Booking flights and accommodation also has many advantages besides securing your spot.

For starters, you have peace of mind. Then, it allows you to budget when planning your trip, and booking well in advance can help ensure lower rates due to lower demand. 

Finally, keep in mind that restaurant reservations are pretty necessary for popular restaurants. This helps you avoid waiting for a table, being put on a waiting list, or even being turned away. 

2. Planning Activities on Sundays

Sundays all over Italy are for relaxing and spending the day with your friends and family.

Thanks to the country’s traditionally Christian roots, Sunday is seen as a day of rest, with many attractions, stores, and restaurants closed or operating with reduced hours.

Not only that, but the Italian Constitution guarantees workers one rest day per week, usually on Sunday. So, expect things to be on the sleepier side.

That doesn’t mean you can’t enjoy the quiet, though, as it’s the perfect time to go on a relaxing stroll and leisurely lunch. 

3. Not Validating Train Tickets or Following Strikes

If you plan on exploring Tuscany by train, be sure to validate your ticket at a train station in order to ride.

So, check your seating class, timetable, and expiration date before you hop on board in case of any mishaps. 

Then, one other thing you should definitely know is that Italian cities are prone to occasional rail strikes.

That said, these strikes are always scheduled in advance, and Italy’s national railway, Trenitalia, guarantees some service on strike days. 

The best you can do is to check the next rail strike on the Trenitalia site before your trip and plan around it.

The good thing is that they generally don’t last too long — perhaps an hour or so and shouldn’t be too disruptive.

4. Not Wearing the Right Clothing

You’ll no doubt feel tempted to dress to impress all over Tuscany’s luxurious cities like Florence and Arezzo.

While it’s perfectly reasonable to chase down those Instagram-worthy moments, you have to be mindful of what you’re wearing at certain places. 

Let me explain. Like other regions of Italy, Tuscany is not overly religious or modest per se.

However, many of its sights are sacred places of worship, such as the Cathedral of Santa Maria del Fiore or the Basilica of Santa Croce in Florence. And these places require respectful attire for entry.

If you plan on visiting cathedrals and other religious sights, wear closed-toe shoes, scarves, or shawls, and cover your shoulders and knees.

Also, avoid bringing bulky bags and backpacks.

Finally, you have to remove hats and head coverings when entering cathedrals. 

5. Not Clueing Up on Proper Italian Food

Forget everything you think you know about Italian food. Want to order pepperoni on pizza?

Well, you can expect sliced bell peppers instead, as that’s what they’re called in Italy.

Then, if you ask a waiter for Fettuccine Alfredo, you’ll get a confused look in return as it’s an Italian-American invention. 

You get the idea. The main thing you need to be aware of is how regional Italian food is.

Do your research on traditional Tuscan dishes so you’ll know what to expect and order without feeling utterly clueless.

Tuscany is known for simple, high-quality dishes made from fresh ingredients like pecorino cheese, olive oil, Chianti wine, and truffles.

6. Trying to Tip Waiters

One thing tourists always get wrong is when they try to tip waiters in Europe.

Unlike in the USA, waiters do not have to rely on tips to supplement their wages. Therefore, tipping is not expected nor customary in Italian restaurants and bars. 

Most establishments already include a service charge in their bills.

However, if you feel like you’ve had exceptional service, you’re more than welcome to leave an extra tip. 

7. Only Visiting Florence and Pisa

I get it. Florence and Pisa are two of Tuscany’s biggest draws. These cities are filled with must-see attractions, rich in culture and history.

Florence will show you invaluable remnants of the Renaissance period with attractions like the Uffizi Gallery or Michelangelo’s David.

Then, who’d want to miss the opportunity to snap a pic with the iconic leaning tower of Pisa? 

The point is these places are not to be missed, but if you can, try to explore beyond their borders.

After all, Tuscany is also Italy’s world-renowned wine country and is home to many hidden medieval villages you won’t experience anywhere else. 

For example, this Chianti wine tour from Florence gives you an unfiltered experience of the Tuscan countryside.

Read more: Amazing things to do in Tuscany, Italy.

8. Not Exploring Off-The-Beaten-Path

Expanding on the previous point, not exploring the unknown side of Tuscany would be an injustice.

So, where do you begin to follow the paths least traveled?

Start by visiting Monteriggioni, a walled town with 13th-century fortifications and watchtowers. It’s one of the best-preserved medieval towns that genuinely looks like you’ve traveled back in time. 

Then, Val D’Orcia showcases the tranquil countryside like no other with its charming villages and rolling manicured hills dotted with vineyards and Cyprus trees.

Finally, visit Montefioralle, a beautiful and ancient hill town in the heart of the Chianti wine region. 

These are just some of the hidden gems in Tuscany and trust me, there are plenty more. 

9. Not Carrying Cash

One of the biggest mistakes you can make is exploring Tuscany without any cash.

You’ll feel tempted to grab a few bites, crafts, or keepsakes when passing street vendors, markets, pizzerias, gelato shops, and more.

There’s one issue, though: most of these local shops do not accept cards. Making sure you always carry a few Euros on you will be wise. 

10. Forgetting About the Weather

No matter how excited you are to travel to Tuscany, don’t forget about this one crucial thing: the weather.

It can either make or break your trip, and the key is to be well-prepared.

Italian summers are intense, and Tuscany averages highs of 86°F and lows of 64°F. It’s hot and dry, plus most buildings are not equipped with air-conditioning. 

On the other hand, winters are cool and damp with cold nights, averaging between highs of 60°F and overnight lows of 44°F.

Keep that in mind when packing for your trip and planning activities. 

11. Not Watching Out for Pickpockets

While safety is not really an issue in Tuscany, its larger cities are no strangers to petty crimes like pickpocketing.

These attacks usually happen in large, crowded places and on public transport.

Regardless of where you are, it’s always better to be aware of your surroundings, as losing valuables like wallets and keys can seriously dampen your trip.

The countryside is a different story though, since here you’ll feel perfectly safe.

Florence is where you’d want to be more mindful. Try not to go out alone at night and cling tight to your belongings at train stations.  

12. Not Renting a Car When Visiting the Countryside

Consider renting a car if you plan on traveling to Tuscany’s countryside.

Yes, there are buses and trains that operate in the countryside, but you’re going to spend a lot of time waiting.

So, unless you want to waste your time on public transport or spend a lot of money on a driver, you’d want to rent a car in Tuscany. 

13. Renting a Car Last Minute 

Now that you know it’s best to rent a car for Tuscany’s countryside, you should also avoid renting one at the last minute.

Otherwise, you might end up paying for a vehicle that does not meet your needs. 

Rental car rates tend to fluctuate based on supply and demand. That said, you can get much better prices by booking in advance.  

Traveling to Tuscany, Italy | FAQs

We’ve come to the end of this Tuscany travel guide, but have a look at these popular questions in case you need more insight. 

Is Tuscany, Italy Safe?

Yes. Tuscany has low crime numbers and is very safe to visit, especially around the countryside.

However, prepare for common crimes that could happen in all popular tourist destinations around the world. These normally range from pickpocketing to scams but very rarely dangerous. 

When Not to Visit Tuscany?

Tuscany is amazing throughout the year, but if there’s a least favorable time to visit, it would be between November and March. The days are shorter, it’s chilly with wet weather, and nights are cold. 

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