NEVER Do THIS in TUSCANY – I Wish I Knew
Planning a trip to Tuscany? Before you step off the plane or pick up that rental car, make sure you avoid these costly mistakes that too many travellers regret. After years of exploring every corner of this stunning Italian region, I’ve compiled the definitive list of what NOT to do in Tuscany.
These aren’t just minor inconveniences – they’re the kind of mistakes that can seriously impact your experience, waste your precious vacation time, or cost you unnecessary money. Let’s make sure your Tuscan adventure is memorable for all the right reasons.
Don’t Stay Only in Florence and Siena
One of the biggest mistakes first-time visitors make is basing themselves exclusively in Florence and Siena for their entire Tuscan adventure. While they are both undeniably magnificent with their Renaissance masterpieces and historic charm, they represent just one facet of what Tuscany has to offer.
By limiting yourself to Florence or Siena, you miss the true essence of Tuscany – the rolling countryside, the medieval hilltop towns, the vineyards that stretch to the horizon, and the authentic rural experiences that define this region.
Instead, split your stay with at least one countryside location. The Chianti region, Val d’Orcia, or the area around San Gimignano, all make excellent bases for exploring rural Tuscany. This approach gives you the best of both worlds – the artistic and cultural wealth of Florence plus the breathtaking landscapes and slower pace of life in the countryside.
If you’re worried about logistics, don’t be. Many agriturismi (farm stays) and countryside hotels can arrange transportation or provide detailed directions for day trips. The extra effort of splitting your accommodation is more than worth it for the complete Tuscan experience.
Don’t Drive into ZTL Zones
This is perhaps the most common and costly mistake tourists make in Tuscany. ZTL zones (Zona Traffico Limitato) are restricted traffic areas in the historic centres of most Tuscan towns and cities, including Florence, Siena, Lucca, and San Gimignano.
These zones are monitored by cameras that automatically photograph license plates and issue hefty fines to unauthorised vehicles. What makes this particularly tricky is that the signs indicating ZTL zones can be easy to miss if you’re not specifically looking for them, especially when you’re distracted by navigating unfamiliar streets (check out the video below for a complete overview).
Even more confusing, some ZTL zones operate only during certain hours, while others are permanent. And here’s the kicker – you might not even know you’ve made this mistake until weeks or months later when a fine arrives at your home address via your rental car company.
Always research the ZTL zones of any town you plan to visit by car. Most towns have parking lots just outside the historic centres, from which you can easily walk into the restricted areas. If you’re staying at a hotel within a ZTL zone, contact them in advance – they can often register your vehicle for temporary access.
Don’t Book Accommodations Without Checking the Location
I’ve lost count of how many travellers I’ve met who booked what looked like a charming countryside villa, only to discover it was isolated on a difficult-to-navigate dirt road, 30 minutes from the nearest restaurant or shop.
While the idea of a secluded Tuscan retreat sounds romantic, the reality can be challenging if you haven’t considered the practical aspects. Before booking, ask yourself:
- How far is it from towns, restaurants, and shops?
- Is the road access good, or will you be navigating steep, unpaved roads?
- If you’re not renting a car, is there public transportation nearby? Most probably not
- Does the property provide essentials, or will you need to bring everything with you?
On the flip side, some accommodations advertised as being “in” popular towns like Montepulciano or Pienza might actually be several kilometres away in the countryside. This isn’t necessarily bad, but you should know what you’re getting.
Always check the exact location on a map, read reviews carefully for mentions of location issues, and don’t hesitate to contact the host or hotel with specific questions about the surroundings and access.
Don’t Skip the Smaller Towns
Many first-time visitors to Tuscany create itineraries that include only the famous highlights: Florence, Siena, Pisa, San Gimignano, and perhaps Lucca. While these places are undoubtedly worth visiting, limiting yourself to only the “big names” means missing out on the authentic charm of smaller, less touristy towns.
Places like Volterra, with its Etruscan ruins and alabaster workshops; Monteriggioni, with its perfectly preserved medieval walls; Pitigliano, dramatically built into tufa rock; or Certaldo Alto, accessible by funicular and virtually untouched by mass tourism – these offer equally rewarding experiences without the crowds.
In these smaller towns, you’re more likely to stumble upon local festivals (sagre), find restaurants where tourists are a rarity rather than the norm, and experience a more authentic slice of Tuscan life. You’ll also find that prices for everything from accommodation to meals are often significantly lower than in the major tourist centres.
Try to include at least two or three lesser-known towns in your itinerary. You might discover that these become the highlights of your trip, the places where you make the most meaningful connections and memories.
Don’t Eat at Restaurants with Tourist Menus
You’ve been walking all day, you’re hungry, and you spot a restaurant with a “Tourist Menu” sign outside, promising a three-course meal for a suspiciously low price. It’s tempting, but resist!
These tourist menus are almost always a sign of mediocre, mass-produced food designed to turn tables quickly rather than provide an authentic culinary experience. They typically feature generic, watered-down versions of Italian classics that bear little resemblance to the real thing.
Tuscany has one of Italy’s most celebrated culinary traditions, with dishes that vary significantly from one area to another. Each town and village has its own specialties and traditional recipes that have been perfected over generations.
Instead of settling for tourist traps, look for restaurants where:
- Menus are in Italian (with translations available if needed)
- There are locals dining there
- The menu changes seasonally (only seasonal dishes)
- There are regional specialties featured
- The restaurant is located away from the main tourist squares
Don’t be afraid to ask locals for recommendations. Your hotel staff, shop owners, or even people you meet in cafes can often point you to hidden gems where you’ll experience the true flavours of Tuscan cuisine.
Don’t Underestimate Driving Times
Looking at a map of Tuscany, distances between towns often seem deceptively short. You might think, “It’s only 40 kilometres from Siena to San Gimignano – that’s a quick 30-minute drive!” In reality, that journey could easily take an hour or more.
Tuscan roads, particularly in the countryside, tend to be narrow and winding. What looks like a straight line on a map is actually a series of curves following the contours of hills and valleys. Add to this the occasional tractor, local drivers who know every turn, and the temptation to stop for photos of the breathtaking views, and travel times can be much longer than expected.
When planning your itinerary, a good rule of thumb is to add at least 30% to the driving time suggested by navigation apps. Also, limit yourself to visiting no more than two towns in a single day if you want to actually experience them rather than just tick them off a list.
Remember that part of the joy of Tuscany is the journey itself – the cypress-lined roads, the panoramic vistas, the unexpected discoveries along the way. Build in time to stop and appreciate these moments rather than rushing from one destination to the next.
Don’t Visit During August Without Planning Ahead
August is when many Italians take their annual vacation, and coastal Tuscany becomes incredibly crowded with domestic tourists. Meanwhile, many family-run restaurants, shops, and even some smaller accommodations in inland towns close for part or all of the month as their owners take their own holidays.
If you must visit in August (and there can be good reasons to do so, such as attending the Palio in Siena or experiencing summer festivals), be aware that:
- Accommodation prices will be at their peak
- Advance reservations are essential for restaurants and attractions
- Coastal areas will be extremely busy
- The heat can be intense, often exceeding 35°C (95°F)
- Air conditioning is not universal in older buildings and budget accommodations
Consider visiting in the shoulder seasons instead – May, June, September, and October offer pleasant weather, lower prices, fewer crowds, and a more authentic experience as locals go about their normal lives.
If August is your only option, book everything well in advance and consider focusing on the less touristy areas of Tuscany, such as the Maremma region or the Garfagnana in the north.
Don’t Ignore the Heat When Planning Activities
Tuscany in summer can be blisteringly hot, especially in July and August when temperatures regularly climb above 35°C (95°F). Yet I often see tourists attempting to tour Florence’s unair-conditioned museums or climb the steep streets of hilltop towns during the hottest hours of the day.
This is not only uncomfortable but can be dangerous, particularly for older travellers, children, or anyone with health concerns. Heat exhaustion is a real risk and can ruin your vacation.
Instead, adopt the local rhythm during hot months:
- Start your day early, visiting outdoor sites and towns in the morning
- Take a long lunch break and rest during the hottest hours (roughly 1-4 PM)
- Resume activities in the late afternoon when temperatures begin to drop
- Enjoy the pleasant evening temperatures with dinner outdoors
Always carry water, wear a hat and sunscreen, and don’t hesitate to duck into churches (which are often naturally cool) or cafes for a break from the heat.
Don’t Forget to Validate Your Train Tickets
This mistake can be costly and frustrating. If you’re using regional trains in Tuscany (the most common type for travel between towns), you must validate your ticket before boarding. This means inserting it into the small green or yellow machines located on train platforms or in station hallways.
Failure to validate your ticket can result in a fine, even if you’ve purchased the correct fare. Ticket inspectors have heard the “I didn’t know” excuse countless times and are rarely sympathetic, especially on routes frequently used by tourists.
The validation requirement applies to paper tickets purchased at stations or from tobacco shops. If you buy your ticket online or through an app, it’s usually already validated electronically.
Make this a habit: as soon as you arrive at a train station, locate the validation machines and stamp your ticket before heading to the platform. It takes just seconds and can save you from an unwelcome fine.
Don’t Expect Everyone to Speak English
While tourism professionals in major destinations like Florence and Siena generally speak good English, this isn’t always the case in smaller towns and rural areas. Don’t assume that everyone you encounter – from shop owners to bus drivers to elderly locals giving directions – will understand English.
This isn’t a criticism; it’s simply the reality in a region where the local language is, unsurprisingly, Italian. Approaching situations with the expectation that everyone should accommodate your language needs can lead to frustration on both sides.
Instead, learn a few basic Italian phrases before your trip. Even simple greetings like “buongiorno” (good day) and “grazie” (thank you) are appreciated. Always greet shopkeepers when entering and leaving stores.
Always carry a translation app on your phone for more complex communications. Google Translate’s camera feature, which can instantly translate signs and menus, can be particularly helpful.
Final Thoughts: Embrace the Unexpected
Perhaps the biggest mistake of all when visiting Tuscany is adhering too rigidly to a pre-planned itinerary. Some of the most magical Tuscan experiences come from unexpected discoveries – the tiny village you stumble upon while lost on a country road, the family-run trattoria recommended by a local shopkeeper, or the impromptu wine tasting with a passionate producer you meet by chance.
Leave room in your schedule for spontaneity. If you’re enjoying a particular town, stay longer. If something doesn’t meet your expectations, move on. Be willing to adjust your plans based on local recommendations, weather conditions, or simply your changing moods and energy levels.
Tuscany has been enchanting visitors for centuries, and its true charm lies not just in its famous sites but in the overall experience – the quality of light at sunset over the hills, the taste of perfectly ripened local produce, and the warmth of conversations with locals despite language barriers.
