Getaway Compass

Two Days in Tuscany Itinerary

Tuscany View

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 try a variety of delicious wine. Spend time walking around the Tuscan villages of Ridda, San Grimignano, Volterra, Montepulciano, Pienza, and Montalcino. Taste wine at unique wineries like Albola Castle and Ricasoli. Drive through the windy roads between the Tuscan hills of Chianti and Val D’Orcia wine regions. Follow this two days in Tuscany itinerary for the best things to do in Tuscany in a couple of days.

Is it better to explore Tuscany on your own or with a tour?

There are benefits to both exploring Tuscany on your own versus booking an organized tour. Exploring Tuscany on your own gives you more flexibility and the ability to choose exactly where to go and how long to spend there. 

The 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 including transportation. 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 have 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.

Which Tuscany wine region should you visit?

I will try to help you answer the first question I searched for when I was trying to plan my Tuscany trip. Both wine regions are beautiful and have the Tuscan towns we have all dreamt of visiting. I recommend visiting both to see the difference in landscapes, villages, and wine.


We had an easier time finding vineyards here online that we can reserve before. 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.

Val D'Orcia

Known as the famous rolling hills of Tuscany, Val D’Orcia is undoubtedly beautiful. The Tuscan villages in this region were more unique, less crowded, and had 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?

There are many unique Airbnbs in Tuscany where you can stay directly on a vineyard or in a Tuscan town. I recommend staying one night in Chianti and one night in a Tuscan town so you can experience both perspectives. The first night we stayed in an incredible house on a vineyard near a town called Ridda in Chianti. The next night we staying and in an Airbnb apartment in Montepulciano with breathtaking views of surrounding vineyards. 

I recommend choosing Monepulciano as the Tuscan town to spend a night in, this was my favorite town! If you prefer a hotel, you can find many options on

Tuscany Airbnb
Airbnb that we stayed in near Ridda

How do you get to Tuscany?

The two closest airports to Tuscany are Florence (FLR) and Pisa (PSA). You could also fly into Rome (FCO) or Milan (MXP) if it is cheaper but then you will need drive or take a train for 3.5 hours. It is possible to find an affordable flight to Italy! We flew from PHX to Milan (MXP) for $582 and we found this incredible deal through Going. Sign up for Going to get flight deals to Italy sent directly to your email. You can also search for flights on Skyscanner to compare prices across dates and airlines.

How do you get around Tuscany?

I recommend renting a car for your time in Tuscany if you want to experience Tuscany on your own.  This gives you the flexibility to enjoy different Tuscan towns and a variety of wineries. You can rent your car from Florence through Discover Cars where you can compare rates across rental car companies to find the best fit for your 2 days in Tuscany. You can save money by booking a manual car instead of an automatic car, just make sure you know how to drive it!

If you don’t plan on renting a car I recommend booking a tour that includes transportation. Make sure to book a tour in advance so that you don’t miss out! One of the best tours of Tuscany is 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.

eSIM to Navigate Tuscany

If you are navigating Tuscany on your own, you want to make sure you have data to be able to use Google Maps or Waze to get around. 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. Use the code GETAWAY10 for a 10% discount.

Tips for Visiting Tuscany

  • In the Tuscan towns most restaurants close between 3 pm and 6 pm. Plan ahead and make sure that you eat lunch before 3 pm, or you will end up eating gelato for lunch (which isn’t necessarily a bad thing).
  • Buy water and snacks at the grocery store which is a lot cheaper than the small markets. The grocery store chain in Tuscany is called Coop. Don’t forget to check the type of water (naturale = still water, frizzante = soda water).
  • Buy your souvenirs (wine, pasta) at the grocery store or small market instead of the small tourist shops to save money.
  • You don’t need to plan for more than an hour in each Tuscan town as most of them are very small.

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Day 1: Wine Taste in Chianti and Visit Tuscan Towns

Albola Castle (Winery)

Albola Castle
Albola Castle Vineyard
Albola Castle Tuscany

Start the day by drinking a glass (or two) of 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 are looking for a tour they offer tours twice a day which include a wine and olive oil tasting. You can also do a wine tasting separately from the tour. Make sure to email the winery to get updated tour times.


Ridda Street

A quiet Tuscan town not far from Albola Castle and worth a quick stop. There is a pizza restaurant where you can get the largest pizza you might ever see and several small shops. Note that the shops and restaurants close very early.

San Grimignano

San Grimignano

A very popular medieval hill town known for its fourteen watch towers, San Gimignano is a great place to walk around and experience a busy Tuscan town. Recognized as a UNESCO World Heritage Site, it gets very crowded in the main areas but if you walk away from the main squares you can find quiet streets and views of the surrounding countryside.



Walk around this quiet and romantic Tuscan town with beautiful 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: Tour a Winery and Explore Tuscan Towns in Val D'Orcia

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

Ricasoli, Castello Di Brolio

Ricasoli Vineyard
Albola Castle New Part

Ricasoli is a winery in Chianti known for creating the Chianti Classico wine recipe (by Baron Bettino Ricasoli). There are several tour options which you should book ahead of time because they do sell out. The classic tour is a great option if you are interested in the history of the castle from the 11th century and 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 a tasting of three great wines in a private room.
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.


Montepulciano View

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, lots of local restaurants, small 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. A visit to Montepulciano is not complete without climbing 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.

If you want to spend a night in a Tuscan town this is the one that I would recommend. There are many Airbnbs right in the town.



Pienza is a Tuscan town in the middle of Val D’Orcia. Pienza 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.



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 lunch (just remember to eat lunch early because almost everything closes at 3!)

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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