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2 Days in Tuscany Itinerary: Enchanting Vineyards and Romantic Tuscan Towns

Tuscany Italy

No amount of time in Tuscany is truly enough, but in 2 days you can get a good taste of Tuscany, its incredible vineyards, romantic villages, and delicious wine. Spend time walking around the Tuscan villages of San Grimignano, Montepulciano, Pienza, and Montalcino. Taste wine at beautiful vineyards such as Albola Castle and Ricasoli. Drive through the windy roads between the Tuscan hills of Chianti and Val D’Orcia wine regions. Keep reading this two day Tuscany itinerary for the best things to do in 2 days in the Tuscany countryside.

What You Can Find in This 2-Day Tuscany Itinerary

Which Tuscany wine region should you visit?

This is the first question people ask when starting to plan their Tuscany trip. Both wine regions are beautiful and have those Tuscan towns we have all dreamt of visiting. The wine regions are right next to each other, so I recommend visiting both to see the difference in landscapes, villages, and wine.

Chianti Tuscany

Chianti: This wine region is closer to Florence. We had an easier time finding vineyards in Chianti online that we could reserve tastings at ahead of time. In early September it is often grape picking season which is a great time to visit to see everything in action. Chianti was also very green in September with beautiful vineyards along the hills.

Tuscany Italy Itinerary

Val D’Orcia: Known as the famous rolling hills of Tuscany, Val D’Orcia is undoubtedly beautiful. The Tuscan villages in this region are more unique, less crowded, and have breathtaking views. We had a harder time finding information regarding wine tasting in vineyards in this area, but enjoyed driving through it for the incredible landscape.

Where should you stay in Tuscany?

Tuscany Airbnb
Where to Stay in Tuscany

There are many unique accommodations in Tuscany where you can stay on a vineyard or in a Tuscan town. We experienced both staying on a vineyard and in the center of a Tuscan town called Montepulciano. You can find a variety of beautiful properties on vineyards by searching on or Airbnb. Staying in a Tuscan town is a special experience to be able to explore the town as it starts to wake up and be able to walk to stores and restaurants. 

You could stay in one place the whole time in Tuscany and explore from there, or try a couple different spots to experience staying both in a Tuscan town and a picturesque vineyard setting. Start searching for a place to stay during your 2 days in Tuscany here:


What is the best way to explore the Tuscany countryside?

Val D'Orcia Tuscany

With an organized tour

If you have limited time to explore Tuscany then booking an organized tour is a convenient way to see a lot in a short amount of time. The other benefit of an organized tour is that you don’t have to worry about driving in Tuscany or booking wine tastings and tours. You can enjoy a relaxing day in Tuscany that is already planned for you. Spend a day exploring Tuscany with this tour of Tuscany from Florence which takes you to Siena, San Grimignano and Pisa as well as a family-run wine estate for lunch and wine tasting.

If you want to enjoy a wine tasting experience in the Tuscan Countryside but skip the Tuscan cities then this small group wine-tasting experience from Florence is perfect for you! This 4-hour wine tasting tour takes you to two different wineries in Chianti. The first winery you will visit is Fattoria di Montecchio, a hill-top winery in Chianti, where you will taste wine and olive oil. Next you visit Casa Emma, where you will get to see an incredible view of Tuscany from the terrace and taste wine and olive oil paired with cheese, salami, prosciutto and bruschetta.

Driving around on your own

Tuscan Town Italy

Exploring Tuscany on your own gives you more flexibility and the ability to choose exactly where to go and how long to spend there. You will also be able to explore Val D’Orcia which is the wine region further from Florence as not many tours from Florence make it there.

In order to explore Tuscany on your own you would need to rent a car. I recommend booking your rental car on Discover Cars where you can compare rates across rental car companies to find the best fit for your 2 days in Tuscany. If you are looking for an automatic car make sure that the listing specifically says automatic or you can assume the car is manual. If you can drive a manual car you should reserve manual since it is significantly cheaper.

Make sure you have a data plan so you can use Google Maps or Waze to drive around Tuscany. The easiest way to stay connected is to purchase an eSIM through Airalo which offers short-term affordable data plans for Italy that you can download and install directly on your phone.

Make it a bigger Italy adventure: One Week Italy Road Trip Itinerary

Tips for visiting Tuscany

Best Tuscan Towns Italy
  • Most restaurants in the Tuscan villages are closed between 3-6 pm. You can always find gelato if you are hungry during those hours!
  • Save money by purchasing food and drinks at the grocery store chain called Coop. Don’t forget to check the type of water before buying it (naturale = still water, frizzante = soda water).
  • You can find better deals on gifts such as wine and pasta to bring back to friends and family at the grocery store than small souvenir shops.
  • Most of the Tuscan towns are very small so you don’t need much time to explore the town.

Don’t forget to get a travel insurance policy for your trip! SafetyWing offers affordable, flexible, and reliable travel medical insurance that can be purchased ahead of your travels or while you are already traveling.

2 Days in Tuscany Itinerary

Day 1: Visit vineyards and towns in Chianti

Enjoy a glass of wine at Albola Castle

Albola Castle
Albola Castle Winery Tuscany Italy
Albola Castle Tuscany

Start your first day in Tuscany with a glass if wine at Albola Castle. They have a restaurant located in a courtyard in the castle which offers a relaxing place to try good food and Chianti Classico wine. You can then walk around and enjoy the vineyard surrounding the castle.

If you want to learn more about their wine making process they offer tours twice a day which include a wine and olive oil tasting. Contact the winery by email for the latest tour times.

Learn about Chianti wine at Ricasoli, Castello Di Brolio

Ricasoli Vineyard
Albola Castle New Part

One winery you cannot miss during your 2 days in Tuscany is called Ricasoli. The first Chianti Classico wine recipe was created in this winery by Baron Bettino Ricasoli. You can find several different tour options to choose from which are best to book in advance.

The classic tour is a great option if you are interested in the history of the castle from the 11th century and learning about Chianti Classico Wine. The classic tour is about 2 hours and allows you to tour Brolio castle as well as the wine facilities. This tour finishes with an organized tasting of three delicious wines.

Tip: There is parking right next to the castle but it is very limited. Get to the castle at least 15 minutes before the tour starts to make sure that you get parking and don’t have to hike up the hill.

Add Cinque Terre to your Italy trip: How to Visit Cinque Terre in One Day

Explore the medieval town of San Gimignano

San Grimignano
San Grimignano Tuscany Italy

San Gimignano is a popular medieval hill town known for its fourteen watch towers. The busy town is recognized as a UNESCO World Heritage Site. Meander through the narrow streets while enjoying the architecture of San Gimignano. Make sure to venture away from the center of the town to find quiet streets with beautiful views of the surrounding countryside. 

Get Dinner in the Romantic Town of Volterra


Finish your first day in Tuscany with dinner in the romantic Tuscan town of Volterra while enjoy the mesmerizing views. 

Tip: Near parking number 1 pedestrian entrance there is an incredible view of the town and the surrounding vineyards (as seen in the above picture).

Day 2: Explore Tuscan towns in Val D'Orcia

Val D’Orcia is where you will find the famous rolling hills of Tuscany. Here there are vineyards where you can wine taste and romantic Tuscan towns to explore.

Enjoy the views in Montepulciano

Montepulciano View
Montepulciano Tuscany Italy

A dreamy Tuscan town perched on a hill, Montepulciano will steal your heart. This town is known for the delicious Vino Nobile di Montepulciano and Rosso Di Montepulciano which you can enjoy at any restaurant or winery. With narrow streets, countless local restaurants, shops, and incredible views, Montepulciano is a must-visit. 

Walk to Piazza Grande, Montepulciano’s center, where you will find the Cathedral and the clock bell tower. Climb the clock tower to get a view of the town and the Tuscan Countryside, with Val D’Orcia and Val Di Chiana on either side. This will most likely be your favorite town during your 2 days in Tuscany.

Wine and cheese with a view in Pienza

The Best of Tuscany Pienza

Pienza is a Tuscan town in the middle of Val D’Orcia. This cute town is worth a quick stop for a glass of wine and cheese with views of the rolling hills. You don’t need more than 30 minutes to see the entire old town, but you can always spend more time relaxing and enjoying the views.

Have a nice dinner in Montalcino


Montalcino is a quiet Tuscan town in Val D’Orcia known for its Brunello wine. This is the perfect town to relax, drink wine, and have dinner.

Disclosure: Please note that some of the links above are affiliate links for products and services I recommend. At no additional cost to you, I earn a commission if you make a purchase. As an Amazon Associate I earn from qualifying purchases.

Reut and Zack Elopement-5

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