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Visit Tuscany for the first time- 10 Amazing things to do in Tuscany for first timers

Visit Tuscany for the first time- 10 Amazing things to do in Tuscany for  first timers

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Tuscany is definitely worth mentioning when we talk about Italy as it is completely flooded with the treasures of beauty and aspiring places to visit it all around. There are tons of Tuscan holiday rentals to choose from for your holiday here – budget to luxury, localized to isolated. Widely known as the most popular wine region of Italy, Tuscany is filled with vineyards as far as your eyes can see and according to many people, these vineyards are the main tourist attraction of Tuscany.

However, Tuscany has a lot more to offer than its famous vineyards. If you are planning to visit Tuscany for the first time, then keep reading. You will end up with a lot of useful suggestions for your trip. Here are the 10 most interesting activities in Tuscany for first-timers!

Before we get to the actual list, I just want to share this special offer by Qatar Airways that will help you get the cheapest flights to mutliple different cities in Tuscany. Also, if you need help planning your first trip to Tuscany or Italy, check out our guide to spending 10 days in Italy.

1. Wine tasting

visit Tuscany for the first time

A trip to the Tuscan region wouldn’t be complete without visiting a vineyard and tasting Italian wine straight from the producer’s wine cellar. There are organized tours that can take you to vineyard hopping, where you’ll taste some excellent wines while getting to know some wine basics and history.

2. Val d’Orcia

visit Tuscany for the first time

When I think about Tuscany, a couple of things that come to my mind after the amazing wine are the lush green fields and rolling hills. What if I told you that this idealized image of Tuscany actually exists? You’ll find it in the Val’d Orcia, extending from the hills south of Siena to Monte Amiata. This picturesque valley hides some charming small towns that you probably heard of but never really thought about visiting. Some of them include Pienza, Monticchiello, San Quirico d’Orcia, Bagno Vignioni, and Montalcino. Wherever you go, you will find World Heritage sites, as the whole area is protected by UNESCO.

Enjoying this article? Then, you’ll surely like my guide to Sicily off the beaten track or this list of hidden gems in Northern Italy.

3. The island life on Giglio

giglio things to do in tuscany

Hiding from the tourist development in the Tuscan archipelago, you will find Giglio. Giglio is one of the last relatively unspoiled (by tourists) places dotted with citadels, charming villages, and panoramic views. The island has a strict policy when it comes to motorbikes/cars, which just adds to its unspoiled, authentic beauty.

Related: best places to visit for your honeymoon

4. Take a pilgrimage to La Verna


St Francis’s mountaintop hides a thriving Franciscan monastery that offers some of the most amazing views of the Apennines. The La Verna sanctuary is Tuscany’s major pilgrimage site. Some people visit out of curiosity, others to pay homage, and you can even stay in the guesthouse adjoining the monks. If you’re looking for a place to experience peace away from Tuscany’s tourist hubs, LaVerna is definitely a great choice.

5. San Gimignano

visit Tuscany for the first time

Worthy of the nickname ‘Medieval Manhattan’, San Gimignano is arguably the most beautiful hill town in Tuscany. Hidden deep in the countryside, the narrow streets and typical stone towers of San Gimignano host some of the best Italian vineyards specialized for producing the famous Vernaccia. The town is also home to some of the most beautiful medieval palaces in Tuscany, like Palazzo del Popolo and Palazzo del Podestà. The whole town looks like it came out of a postcard but you will experience the most iconic view if you climb the Torre Grossa. You will get a 360 panoramic view of the surrounding countryside and hills looming over San Gimignano.

6. Get lost in Monti dell’Uccellina

tuscany for first timers

The protected area of Monti dell’Uccellina is one of the last pristine stretches of coastline in Tuscany. Lying in the corner of Maremma, Tuscany’s long forgotten region, Monti dell’Uccellina managed to preserve its beautiful nature. The forest-covered hills and coastal plains have been a place of exile throughout history but is today a regional park that hides some of Tuscany’s most amazing natural treasures.

7. The Ponte Vecchio


Some say this is just an ordinary bridge with luxury shops in it. However, one cannot ignore the grand stories about the bridge that brought life to Florence. The bridge that has been destroyed and reconstructed many times, is today one of the most popular places to visit in Tuscany.

8. Relive Under the Tuscan Sun in Cortona

cortona tuscany

Cortona is an idyllic hill town in Tuscany that became famous in Francies Mayes book “Under the Tuscan sun”. This picturesque town has another layer of history added by the 3,000-year-old Etruscan walls but the city between those walls is just as impressive. Even though a small town, Cortona is home to some iconic buildings like the Abbazia Farneta, and the Chiesa San Francesco. Additionally, its perfect location offers a grandiose view of the Chiana Valley and Lake Trasimeno.

If you’re enjoying this article, also check out the article I wrote about the best hidden gems in Florence.

9. Vie Cave

When you visit Tuscany for the first time, you should definitely leave some time to visit the Vie Cave, one of Maremma’s best-kept secrets. These mysterious sunken roads carved by the Etruscans during the bronze age. However, the reason for their creation and how they were created remains unknown even today. If you want to visit these magical tight passages, you better hurry up. The Vie Cave has recently been listed as an endangered monument due to their fragility.

10. Pisa

pisa tower italy on a budget

Finally, round up your first visit to Tuscany with a day trip to Pisa and see the famous Leaning Tower of Pisa.  Standing at 60 meters tall, the Pisa tower is one of the most remarkable architectural structures from medieval Europe. This tower was planned to be perfectly vertical but it started leaning during the construction. Ever since it has been one of Italy’s most iconic tourist attractions.

I believe Tuscany, despite being really touristy, is a place that everyone should visit at least once in a lifetime. With its lyrical landscapes, fascinating history, and the superb cuisine, the Tuscan experience is something you really don’t want to miss while visiting Italy.

Helpful resources for visiting Tuscany

Get the cheapest flights to Italy (and Tuscany) by using this special offer by Qatar Airways.

Travel insurance is a must if you want to visit Italy and if you don’t have any, I recommend you buy a package from World Nomads.

If you want to rent a car in Tuscany, you can get up to 30% off by using this AutoEurope offer.

For transportation bookings from and to cities in Tuscany, use this Busbud offer and save up to 10% on all bus and train rides in the region (for more info, check out our Busbud review).

Finally, to save some money on accommodation in Tuscany, use my Booking discount code.

Are you planning to visit Tuscany for the first time? Did you find our guide helpful? Feel free to share your thoughts in the comments below.

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Alexander Popkov

Saturday 9th of February 2019

Cool, I think as a first timer, you can land a lot of good shots with your guide. Would love to go around there with my camera.

Passport Symphony

Sunday 10th of February 2019

Indeed, you can, Alexander :)

The little lai: Beyond limits

Saturday 9th of February 2019

Wow, your blog post about Tuscany is actually loaded with amazing and stunning scenery. I haven't been to any of those places, but hopefully soon I get the chance. Thank you so much for sharing this with us.

Passport Symphony

Saturday 9th of February 2019

Thank you, I'm really glad to hear you liked it. I hope you get the chance to visit Tuscany soon :)

Valentina Djordjevic

Friday 8th of February 2019

This brings me back! I visited last summer and absolutely loved this charming region. I'll make sure to check out Giglio next time!

Passport Symphony

Saturday 9th of February 2019

Thank you, Valentina. You definitely should. Giglio is amazing!


Friday 8th of February 2019

Never been to Tuscany but I have to say that indeed it looks like a very photogenic place. Great post!

blair villanueva

Friday 8th of February 2019

Wow this is one of my dream destination, after I watched Under the Tuscan Sun! Count me in for wine tasting :D

Passport Symphony

Friday 8th of February 2019

Yeah, the movie is amazing, Blair :) and Tuscany looks even better in real life.