What to see and do in Tuscany

Here at Italy Beyond the Obvious, we get a lot of Tuscany requests. This central Italian region is heaven for photographers and we’re lucky to be able to feature spectacular images by photographer Jim DeLutes below, in our recommendations for what to see and do in Tuscany. Thanks so much Jim!

Tuscany is a big region, with many small villages, castles, vineyards and olive groves, and endless jaw-dropping panoramas. We aim to create balanced Italy itineraries for our travelers to focus on a few incredible experiences and places to savor. Let’s start with the recommendations below.


In Tuscany, Explore the Famous Countryside

What to see and do in Tuscany

Madonna della Vitaleta Chapel by Jim DeLutes

If you want to see what all the fuss is about, rent a car and head into the Tuscan countryside to explore. Allow a day or two, or a few half-days, for just driving and wandering. If you’re there in the spring, look for fields of sunflowers or poppies. If you enjoy hiking or cycling, Tuscany has a lot to offer (although cyclists, note: it’s hilly!)

If you’re not sure where, exactly, to drive, head to the Val D’Orcia area (and UNESCO World Heritage site) in southern Tuscany. To find it on a map, look for the towns of Pienza and Montepulciano and Montalcino. The photo above, the famous Madonna della Vitaleta chapel, is considered by some to be the quintessential Tuscan countryside photograph and is taken from the road between the towns of Pienza and San Quirico D’Orcia.

If the Val D’Orcia area is too far south, drive around the Chianti region, visiting towns such as Castellina, Radda, or Gaiole. Stop at castles such as Meleto or Brolio.

Or, visit the lesser-known corners of Tuscany: the southwest corner (the Maremma) or the northwest corner which borders the Italian region of Liguria, called the Garfagnana.


In Tuscany, Go Wine Tasting

What to see and do in Tuscany

Vineyards in Chianti by Jim DeLutes

Tuscany is covered in grape vines so options for wine lovers abound, but some of Tuscany’s most well-known wines outside of Italy include the reds made in the Chianti region and the Brunello from Montalcino.

Two more worth experiencing are the Vino Nobile of Montepulciano and San Gimignano’s white Vernaccia wine. Wine tasting in Tuscany is a very user-friendly experience compared to other places in Italy, but not as user-friendly as, for example, Napa Valley in California. Many of the Tuscan wineries have official opening hours and extra staff on hand to help with tastings and tours (not necessarily a given in other wine areas of Italy such as in Piedmont or the Valpolicella or Sicily). That said, even in Tuscany, you’ll have a better experience if you call ahead and don’t just show up unannounced.

A few tips for wine tasting in Tuscany:

  • Always check days of operation and opening hours on the vineyard’s website. The smaller the establishment, the less likely they will be open to visitors on weekends.
  • Book at least one behind-the-scenes wine tour, and pop in to a few places for additional tastings. In Chianti, this is a great tour. In the Val D’Orcia, this one is wonderful. You can walk to this winery from the center of the town of San Gimignano.
  • Allow extra time. Don’t arrive late for your visit, but take into consideration that Italians love visitors who are truly interested in their passions so if you hit it off with the owners, don’t be surprised if you stay a few hours beyond the scheduled end of the tour.
  • Visiting during the harvest is a double-edged sword. While there are more activities and even wine festivals happening, there are more visitors and wine makers can be tired. During the harvest, visit places that have more staff and infrastructure for a better experience.
  • Think about food. Many wineries have a combo lunch/wine tasting package such as this one near Montalcino. Most wine tastings will be accompanied by food, although ask for details because it can range from a bowl of crackers to a spread of local delicacies paired with the wines.
  • Have a plan for a designated driver, or have someone else drive you. In order to visit wineries, you need a car. It cannot be done by train, so plan accordingly.


In Tuscany, Visit an Abbey

What to see and do in Tuscany

Sant’Antimo Abbey by Jim DeLutes

It’s quite an amazing experience to enter a 13th century abbey and listen to the resident monks perform Gregorian Chants. A few of our favorite abbeys are in the southern Val D’Orcia area: the Abbey of Sant’Antimo near Montalcino, where chants, also known as vespers, can be heard daily at 6.30 or 7 pm.

The Abbey of Monte Oliveto Maggiore, a little further north than Sant’Antimo, has weekday chants at 5.30 pm and Sunday chants at 11 am, and sells a liqueur and other products made by the monks.

The roofless Abbey of San Galgano is also quite spectacular but for obvious reasons there are no resident monks. Still, an amazing place to stop for a visit, especially if you are traveling to Italy with kids.


In Tuscany, Visit Small Towns

What to see and do in Tuscany

The mountainous Garfagnana, by Jim DeLutes

Part of the reason people want to visit Tuscany is to find the Italy that belongs to them. This Italy remains with them long after they return home and is the reason we have a lot of repeat travelers here at Italy Beyond the Obvious.

Discovering your own Italy involves independent exploring, making small countryside towns a perfect setting. Virtually any town will do: wander its streets, sit in a cafe, people-watch, and soak up the local atmosphere.

I’ve already mentioned some great small towns in Chianti and the Val D’Orcia, but there are many others. Drive from Siena to Lucca but take the countryside route, avoiding Florence, and zigzagging in a north-ish west-ish direction. The town of Barga, north of Lucca in the mountainous Garfagnana region in Tuscany’s northwest corner, has been voted one of the prettiest towns in Italy.  One of my favorite small towns in Tuscany is Monteriggioni, near Siena.

All of these routes involve renting a car but if you’re traveling by train, wonderful towns to explore include Arezzo, Siena, Pistoia, Grosseto, Pisa, and Lucca.


In Tuscany, Learn about the Renaissance

What to see and do in Tuscany

Florence, by Jim DeLutes

In Rome, learn about the Romans. In northern Italy, learn about Napoleon and the French influence in the west and the German and Austrian influence in the east. In Sicily, learn about the Greeks and the Spanish and the Moors. Keep your ears open for Etruscan history everywhere.

In Tuscany, go to Florence and learn about the birth of the Renaissance. This is where a good local guide is worth their weight in gold. You don’t need to be lectured at in order to learn about the Renaissance: Florence is a living museum and as soon as your guide provides the history and context for you, the pieces will fall into place as you continue touring on your own. You’ll notice evidence of the art, architecture and influence of the Renaissance during the remainder of your trip.


In Tuscany, Visit Gardens

What to see and do in Tuscany

The road to La Foce, by Jim DeLutes

Florence’s Boboli Gardens are probably among the most famous in Tuscany, but there are other wonderful villas with gardens nearby. Here are three of the nicest gardens in and around Florence. If you have time to visit just one garden in Tuscany, make it the gardens at the La Foce estate in southern Tuscany, which are open to visitors just a couple of days a week. In the Chianti area, the botanical rose garden Fineschi is spectacular.

Accommodations and food in Tuscany are also part of an incredible trip. There are fabulous accommodation options in every price range – from castles to farmhouses to luxury hotels – as well as its fantastic food. But I’ll have to leave those for another post!


Photographer Jim DeLutes is inspired by beauty daily at his home in the countryside in the foothills of the Colorado Rockies. After 2 trips to Italy spanning more than 3 months and with over 11,000 miles driven, Jim has thousands of images and just about as many memories. Perhaps the deep connection he feels when in Italy is in his DNA since three of his grandparents came from Italy. You can see more of his images at his website – www.JDLphotos.com or follow his Italy Photography site on FaceBook at www.facebook.com/italyphotography.

Italy Beyond the Obvious will help make your trip truly memorable. Take advantage of our Italy trip planning services for a customized itinerary, or get coaching assistance with our Italy travel consulting services. And if you like what you read, why not subscribe to the Italy Beyond the Obvious blog and get free updates?

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Posted by on Nov 17, 2015 in Tuscany | 4 Comments


  1. Christopher Boles
    November 17, 2015

    We took a “foody” tour where you go to the region of Ruffino. In the morning we went to the Grignano estate, saw how they make olive oils, Chianti and in the afternoon learned the art of making pasta. The day was finished off by having dinner with our tour in a regional home. I highly recommend the Grignano olive oil for the taste as there is nothing like it. I wish I had bought a case. The Chianti from the estate was from 2001 and has been the best wine we ever bought. We stayed in a home in San Donato and took the bus up and back every day. It was a memorable ride to say the least for those of us not used to the curves they take with out any hesitation. The whole experience I would do over in a heartbeat.

    • Madeline
      November 18, 2015

      That sounds amazing Christopher! Thanks for sharing your experience and recommendation — and for giving a specific example of how it can work with a bus so you didn’t have to drive.

  2. Italy Travel Tips - Italy Beyond The Obvious
    December 16, 2015

    […] Florence is a great base for visiting the towns of Lucca, Pisa, Siena, San Gimignano, and the Chianti countryside. All of these can easily be done as day trips, and the first three can be done by […]

  3. Jana Kampfmeier
    July 24, 2017

    I want to visit tuscany with my grandparents and I love the idea of having a wine tasting. Are there vineyards offering accomodation, or where Hotels are near by foot?


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