Tuscany Day Trips & Wine Tasting

Tuscany Day Trips & Wine Tasting

A complete guide on Insanely Romantic Medieval Towns in the Tuscany Region. After living for a year in Siena, I got the chance to enjoy many times day trips to these little towns: Montalcino, Montepulciano and San Gimignano. Now that I know them best, I would like to share with you guys my top recommendations on: how to get to these towns, what to see and more.

How to get to these towns from Florence, Siena or Pisa: Rent A Car or Book a Wine Tour?


If you are planning to visit Tuscany Towns, you will need a car because in Italy using public transport is not as easy as we think and you will surely lose time trying to find trains heading to your destinations. So my recommendation for you is: if you are not interested in booking the wine day trips, then please book a car, is going to make your day trips more manageable.

What You Need To Know

  • You can reserve your rental car online before you head to Tuscany.
  • A credit card is required for the reservation
  • Non-European Union citizens will need, an International Driver’s License along with your license to be able to drive in Italy.
  • The majority of car rental agencies offer rentals with extra fees including satellite GPS navigators and baby car seats.
  • In Italian, “carburante” and “benzina” are both words for gasoline/petrol. But diesel is diesel in Italian as well. SO BE AWARE and know by heart the kind of car you are renting to avoid extreme problems later.
  • Bring your GPS or any other navigational device.

Estimated price for 2 days in a 4-seat car: 52€ (+ gasoline & other costs involved)

Click to find info on: Car Rental In Italy


Visit the heart of Tuscany, be invited to a vineyard to taste 5 or more glasses of wine from the region while listening to real stories of the vineyard families.

It goes without saying that these are valuable experiences.

I share with you the option to book a wine tour because honestly, I think it’s the best, the fact of being able to visit these cities with a native guide and to attend vineyards of local citizens would for sure make your experience more memorable.

To give you an idea of how the Wine Tour is:

You start the day from very early, so be ready to taste wines at early hours. In a private minivan, you will leave from a meeting point, or maybe they can pick you up at the place where you are. Already on the way, you will listen carefully to everything the guide will tell you and you will notice all the beauty that it’s surrounding you.

Before arriving at the cities you chose as your destination, you will stop at a vineyard where you will taste different wines of the region, eat appetizers and meet people from all over the world. When you are a bit toned, you will continue your journey visiting the cities and maybe attending more vineyards. They will give you free time for walking the towns freely and having lunch.

Depending on the tour you choose, you will visit specific vineyards and towns. So be sure to inform yourself about the trips you will select.

The prices vary from 45 to 80 € & Can last from 8 to 12 hours.

I’ll provide some ideas of tours you can book but remember that you can also find several options in tourist offices!

Click to find out more:

Brief Guide To Montalcino

Locality In The Province Of Siena Known For The Production Of Brunello Wine.

Credits: Quattrocalici
Places of interest:
  • Fortezza, the highest point in the city
  • Musei Riuniti, a Civic and Diocesan Museum
  • The Duomo (cathedral), Neoclassical appearance.
  • The Piazza del Popolo, with the Town Hall (Palazzo Comunale) as the main building.
  • Chiesa di Sant’Agostino, with Romanesque façade.
Visit To The Vineyard
City View In Montalcino

Brief Guide To Montepulciano

City in the province of Siena, known for the charm of its great vineyards, from which the Montepulciano Wine is obtained.

Places of interest:

There are many great places & views in this charming little town, so I recommend you to get lost and if you still have time, try to go to some of these following mentioned places:

  • Palace Avignonesi
  • Palace Bucelli
  • Medicea fortress of Antonio da Sangallo
  • The Elder Big square
  • Poliziano Theater Clock Tower (with the popular Pulcinella)
Free Wine Tasting in Fattoria Pulcino
Via di Gracciano nel Corso, 94-96
Discovering Underground Places in Wine Shops
“You give me a coin, I’ll bring you luck”

Brief Guide To San Gimignano

Once again in the Province of Siena, you found one of the Most Beautiful Towns In The World, commonly known by Vernaccia Di San Gimignano.

The “Historical Center of San Gimignano” has been declared a World Heritage Site by UNESCO in 1990.

Places of interest:
  • Main churches: the Colegiata and San Agustín, representation of works of art by some of the leading artists of the Italian Renaissance.
  • The Communal Palace
  • Piazza della Cisterna
  • Piazza Duomo
  • Piazza Pecori
  • Piazza delle Erbe
Sunflowers In The Middle Of The Tuscan Heart
Enjoying Views in St. Gimignano
Find The Best Ice Cream Shop In The World – Gelateria Dondoli

Piazza Della Cisterna, 4, 53037 San Gimignano SI, Italia

Located in the central Piazza della Cisterna in San Gimignano, Gelateria Dondoli is known all over the world. Of the best ice cream I’ve tried, come back more than two times to try different flavors. My favorite without a doubt, nocciola (Hazelnut)

Find Out More About This Insanely Gelateria: Gelateria Dondoli

Mom Enjoying An Ice Cream From Another Planet!
Photo Credits: Jennica B

Check Below My One Year Abroad In Siena, Tuscany:

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