Tuscany is the gorgeous region of Italy that should definitely be visited at some stage of your travelling life! Home to a multitude of hilltop towns, some of the best wine in the world, gorgeous bustling little cities, excellent cuisine, amazing villa’s to stay at.. and even an underrated coastline. This isn’t a complete guide of where to visit in Tuscany, it’s more of a gallery highlighting the recent road trip through the region. However, at the end of this guide we will link to a plethora of Tuscany guides that will help you plan your itinerary in the region!
A gallery from Ky’s recent Tuscany road trip
Note: this road trip doesn’t include iconic locations like San Gimignano, Monteriggioni, Chiati, Siena, Volterra, and others.. we have visited many of these before. The purpose of this trip was explore a little of the beaten track, and heading up to a friends wedding near Lucca. See below for some highlights, and links to our best Tuscany guides!
Stop 1: Montepulciano
This is the iconic city well known in the south of Tuscany. Offering hilltop views, winding alleyways and all the things a good Tuscan town offers, Montepulciano is definitely worth adding to your list.
Stop 2: Certaldo
A relatively unheralded little town in the north of Tuscany. Certaldo is a tiny hilltop town with one main street and lots of amazing views. Perfect for a day trip, a coffee in the square, or a lunch at one of the busy restaurants. Don’t stay due to the small nature of the town, but definitely consider adding it to your visit.
Stop 3: Villa Ravano
This was the base for our friend’s Tuscany wedding! We have shared a few snaps from the gorgeous location below!
Stop 5: Lucca
Those followers of 2 Cups of Travel will know that we love Lucca! Home to one of the more unique main squares.. an oval centrepiece, Lucca is definitely a must visit. Enjoy the winding streets, have a drink in the main square, and walk the impressive walls the encircle the historic town.
Stop 6: Castiglione della Pescaia
This coastal town is seriously underrated, and likely unknown beyond those who are Italians or know the regions well. It’s not the Amalfi Coast or Cinque Terre, but it is budget friendly, has a local feel, and offers excellent food! Definitely one to consider!
Want to plan your Tuscany itinerary? Check out a few of our guide below!
- Castiglione della Pescaia – gem on the Tuscany coast
- Lucca day trip guide
- Where to stay in Tuscany?
- Road trip guide for Tuscany
- Road trip guide for Umbria
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