10 Tips for Visiting Tuscany in Italy: How to Plan the Best Holiday

Tuscany in Italy

Visiting Tuscany is a dream for many travelers heading to Italy… And once you see the rolling green hillsides full of vineyards, beautiful villas, and medieval towns, it will be easy to see why! So what do you need to know before planning the ultimate road trip to this amazing region of Italy? Here are some of our best travel tips to guide you on your visit to Tuscany!

10 Helpful Tips to Visit Tuscany in Italy

1. Take a Tuscany Road Trip

The best way to see as much of Tuscany as possible is to rent a car! While trains and buses are available, they do run with limited service.

This is especially true when it comes to the smaller towns and villages of Tuscany Italy. Since most people only have a few days for their Tuscany vacation, it is so much easier to see these places with a car.

One of our best Tuscany tips is to set up an itinerary to stay in select places and do your driving earlier in the day. That way you can enjoy some of the best wine in the world after you get to your final stop!

We always use Discover Cars when renting vehicles abroad and have gotten some amazing deals. Make sure to check the weekly rate as well for discounts.

Tuscany Italy

2. Look into All Airports in the Area

Florence is well known as the “gateway to Tuscany” and is set up perfectly to start your Tuscany road trip from. However, there are many other places to fly into that could make more sense. Depending on your itinerary, it could be cheaper and more sensible to fly into Pisa or even Rome. 

You could even fly into Bologna and take the fast train to be in Florence in less than 45 minutes! It all really comes down to what you want to see and do.

Also, be sure to look into one-way rentals if there is a better flight in a different city. For example, it might be more cost-effective to fly into Florence and out of Rome even with a drop fee.

Tuscany in Italy Tips

3. Pick a Few Places to Stay Two Nights 

Most travelers heading to Tuscany have one thing on their minds… Wine! For this reason, you may want to stay multiple nights in different towns. Now this isn’t only to be able to hang out and drink copious amounts of your favorite beverage.

It’s also about taking in the entire town or city you’re in and absorbing the unique culture of Tuscany in Italy. Each village has its own special character, traditions, and food to embrace!

We know not everyone will have the time to do this on their Tuscany road trip. Still, we highly recommend spending more than one night where you can to make your trip more relaxing.

Tuscany Italy Hotel

4. Time of Year to Go to Tuscany in Italy

Like many popular tourist destinations in Europe, the best time to visit Tuscany in Italy is outside of the peak summer months. In April and May, you’ll find cooler temperatures and fewer crowds. June is a great month to go as it’s a time for many festivals and celebrations. 

Also, after the most popular months of July and August is when the vineyards are fully in bloom! Tuscany will still be busy in September and October, but you’ll find that the fall weather and surrounding nature will make up for it. Whatever time of year you choose, you’re sure to have a great trip to Tuscany Italy! 


5. Plan Around Local Tuscany Festivals 

We mentioned the festivals during June in Tuscany, and they are not to be missed! In fact, if you do visit this region of Italy in the summer months there are many throughout July and August as well. 

We recommend looking into the calendar and planning to visit while a festival is going on. There is no better way to experience Italian culture than to attend one of these fun events!

Typically they are centered around food, music, sports, and even dancing. Below are a few of the most popular festivals to attend in Tuscany Italy.

Tuscany Italy Tips

6. Spend at Least One Night on a Vineyard 

Back to the wine! You’d honestly be doing yourself a disservice without spending a night on a vineyard in Tuscany. Yes, that’s right!

There are actually amazing hotels in Tuscany that are set among the vineyards. Some are directly on site while others have magical views of the Tuscan countryside. 

Spending the night on one is a unique experience that everyone visiting Tuscany in Italy should have. One of the hotels we enjoyed even had a swimming pool overlooking the vineyards! We have listed some of the most popular winery hotels in this region below. 

Tuscany in Italy Vineyard

7. Visit the Smaller Tuscany Villages

For us, one of the main draws of exploring Tuscany was enjoying the many charming hillside towns. Florence and Pisa are great don’t get us wrong. There is just something about being in a medieval countryside village that takes your breath away!

We spent one month in the small mountain town of Montepulciano and instantly fell in love. Using it as our home base, we were able to take the bus and even hike to many other nearby Tuscany villages. This is such a relaxing way to see this area of Italy without the crowds of the city. 

โ†’ 14 Fun Things to Do in Montepulciano Italy On Your First Visit

Tuscany Villages

8. Shop for Traditional Products 

Some of our favorite days in Tuscany were when we bought meats, cheeses, and wine and went for a picnic. What an amazing experience it is to taste the local products while overlooking the rolling hills of central Italy!

In addition to the classic Tuscany deli items, you’ll find other specialties at the local shops and farmers markets. Some of which you may even want to take home or send to someone as a gift! Things like wine, olive oil, and honey can make for a great Tuscany Italy souvenir. 

Tuscany in Italy Cheese

9. Get Out into Nature in Tuscany Italy

Tuscany is one of the most beautiful and scenic parts of Italy. Specifically, when the vineyards are in full bloom, it looks like something out of a fairy tale. There are plenty of ways to get out into the gorgeous nature of Tuscany! 

We preferred hiking in between the towns and wineries. Another way to enjoy the outdoors is to take a bicycle tour or rent one yourself. There are even tours that combine vineyards and biking for the ultimate Tuscany day!

โ†’ Fun Tuscany Hike From Montepulciano to Montefollonico Italy 

Tuscany Italy Guide

10. Don’t Miss Out on Umbria!

Just next to Tuscany is the region known as Umbria. While many consider them one and the same, you won’t want to miss out on the unique destinations of Tuscany’s neighbor. One of our favorite parts of our Tuscany road trip was stopping in historic towns like Castiglione del Lago.

There are actually no massive cities in Umbria which gives it more of the small town vibe you’ll love. Plus, it has plenty more amazing outdoor activities and culinary delights! Here are a few must-visit places to check out in Umbria.

  • Perugia
  • Orvieto
  • Assisi
  • Gubbio
  • Spoleto

Italy Tuscany

Have any questions about visiting Tuscany in Italy or want to share your own Tuscany tips? Let us know in the comments below! 

Safe Travels,
Brigitte & Jake

 Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar


Tuscany Italy

More Italy Tips


Italy Travel Planning 

 Flights: We always check Skyscanner and Kayak to search for cheap flights. That’s how we got from Rome to Venice for under $30 USD!

 Accommodation: Compare multiple sites to get the best deal such as Booking.com and Agoda! Also,  Hostelworld should be your go-to source if you’re traveling on a budget. 

 Rental Car: We use Discover Cars to explore when traveling. Consider renting a car in one city and dropping it off in another for an epic Italian road trip! 

 Tours: Check out Get Your Guide for thousands of activities around the world. Book a Florence winery tourCapri Boat trip, or street food tour with a local guide in Rome! 

 Travel Insurance: Never travel abroad without protection! We’ve been using SafetyWing for the last few years on the road and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

Italy Travel

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  1. Melanie
    April 7, 2024 / 2:22 pm

    This is such a great guide. I am a little apprehensive about driving in Europe, but you may have convinced me that renting a car is the way to go. I agree that smaller towns can really be hidden gems, so perhaps a car is the best way to get there. This is going to be a dream trip! Your pictures have really pumped me up.

  2. July 25, 2023 / 9:59 am

    Amazing destinations and the great tips …
    I invite you to visit our website if you consider to explore the Chianti area ๐Ÿ™‚
    All the best

    • Brigitte & Jake
      July 25, 2023 / 10:14 am

      Thank you! Chianti looks incredible (-:

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