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 🧭


Click to find info on: Car Rental In Italy

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 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.
⏺Bring your GPS or any other navigational device.

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


Visit the heart of Tuscany and be invited to a vineyard to taste 5 or more glasses of wine. -All of this- while listening to captivating stories from the families of these vineyard and their histories throught the ages.

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.

How´s the Wine Tour 🤓🍷?

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 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.

Tours you can book 👇

🎫 Guided Tour From Florence
🎫 Guided Tour From Siena
🎫 Siena, San Gimignano, Monteriggioni and Chianti

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)
📍 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 💛

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

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.

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

Find Out More About This Insanely Gelateria: Gelateria Dondoli

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)

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

Check Below My One Year Abroad In Siena, Tuscany

Leave a Reply