• Skip to main content
  • Skip to header right navigation
  • Skip to site footer
The Travels of BBQboy and Spanky

The Travels of BBQboy and Spanky

  • About Us
  • Blog
  • Destinations
    • EUROPE (A to M)
      • ALBANIA
      • AUSTRIA
      • BOSNIA AND HERZEGOVINA
      • BULGARIA
      • CROATIA
      • CZECH REPUBLIC
      • FRANCE
      • GERMANY
      • GREECE
      • HUNGARY
      • ITALY
      • MOLDOVA
      • MONTENEGRO
    • EUROPE (N to Z)
      • NORTH MACEDONIA
      • POLAND
      • PORTUGAL
      • ROMANIA
      • SERBIA
      • SLOVAKIA
      • SLOVENIA
      • SPAIN
      • SWITZERLAND
      • TURKEY
      • UKRAINE
    • CAUCASUS
      • ARMENIA
      • GEORGIA
    • ASIA
      • BHUTAN
      • CAMBODIA
      • HONG KONG
      • INDONESIA
      • JAPAN
      • LAOS
      • MALAYSIA
      • PHILIPPINES
      • TAIWAN
      • THAILAND
      • SINGAPORE
    • NORTH AMERICA
      • MONTREAL, QUEBEC
      • REGIONS OF QUEBEC, CANADA
      • MEXICO
        • Pueblos Magicos of Mexico
      • U.S.A
    • CENTRAL AMERICA & CARIBBEAN
      • COSTA RICA
      • CUBA
      • DOMINICAN REPUBLIC
      • GUATEMALA
      • NICARAGUA
    • SOUTH AMERICA
      • ARGENTINA
      • BRAZIL
      • CHILE
      • COLOMBIA
    • AFRICA
      • SOUTH AFRICA
      • MOROCCO
      • TUNISIA
      • ZAMBIA
      • ZIMBABWE
    • OCEANIA
      • Australia
      • New Zealand
  • Topics
    • Hikes & Adventures
    • The Best and Worst
    • This or That
    • Blogging
    • Travel Accessories
    • Deep Thoughts
    • Expat
    • rants & things that suck
    • Looking Back…
    • religion, morality, patriotism
    • Coronavirus
    • Airbnb
    • plane travel
  • Guides
  • Newsletters
  • Resources
  • Work with Us
  • En español

A trip through the hilltowns of Tuscany: Siena to San Gimignano to Cortona

A trip through the hilltowns of Tuscany
A trip through the hilltowns of Tuscany

The hilltowns of Tuscany – some of the most beautiful towns (and geography) you’ll see in all of Italy. We started this day in wonderful Siena and ended the day in Cortona, seeing lots of little Tuscan hilltowns in between.

 


Related: Why Siena is Incredible


 

San Gimignano

Leaving Siena, our first stop was the beautiful town of San Gimignano. The town is famous for the towers built by its wealthiest citizens as symbols of their power. There used to be 72 towers in the town, only 14 are still standing which is nevertheless amazing considering the small size of the place. In the Middle ages San Gimignano was a stop for pilgrims on the Via Francigena, the ancient road that linked France to Rome and the Vatican.

 

the hilltowns of Tuscany. San Gimignano views
San Gimignano’s skyline

One of the many things I love about Italy are all the towers, every town seems to have one. The most famous one in San Gimignano is the Torre Grossa. The tower is actually kind of deceiving from the bottom. Looking up from the piazza, it doesn’t look like much. But climb up and you’ll find the views extraordinary. It is a highlight of San Gimignano and climbing it is a must.

 

the town of san gimignano, tuscany, Italy
far right: The tower from the piazza. Doesn’t look very high, right?

 

San Gimignano views. The hilltowns of Tuscany
incredible Tuscan views from the top

 

San Gimignano views in Tuscany

 

 

The Towns of Chianti

After San Gimignano, we drove into the Chianti hills, the heart of the Chianti region. We stopped in a few of the small towns; Castellina in Chianti and Radda in Chianti, medieval little towns with more towers and old buildings. Only wines from this area can have the Chianti Classico label (the black rooster). It is a beautiful area that is popular with cyclists, wine enthusiasts, as well as those wishing to visit the region’s castles.

A trip through the hilltowns of Tuscany: Siena to San Gimignano to Cortona

A trip through the hilltowns of Tuscany
our guide showing off the black rooster label

 

Driving up higher into the hills, we toured the Casamonte farm for some wine tasting. It is a beautiful estate where they not only produce their own Chianti Classico wines, but also Olive Oil and pork (from Sinta Senese pigs, rare pigs that they breed). I fully recommend coming here for a tour – my only caution is that you don’t have wine shipped unless you have experience/knowledge of the import laws at home. I fell in love with Casamonte’s Super Tuscan wines (Sangiovese grapes mixed with Cabernet Sauvignon and Merlot in varying degrees) and made the mistake of have a case shipped home. I would end up having to pay double to price at home in import taxes. Never again.

 

A trip through the hilltowns of Tuscany
Casamonte farmhouse

 

 

Castello di Meleto

After Casamonte, we visited Castello di Meleto (click on that link if you want to stay there) a large castle close to the town of Gaiole in Chianti. Besides having it’s own winery, the castle provides accommodation. I’d love to come back and stay here. We were given a tour, seeing underground tunnels and a small theatre dating from the 18th century (photos below). The castle is another great stop in the region.

Castello di Meleto. A trip through the hilltowns of Tuscany

Castello di Meleto. A trip through the hilltowns of Tuscany

Castello di Meleto. A trip through the hilltowns of Tuscany

 

To Cortona

We were dropped off in Cortona (Cortona is our favorite Tuscan town). 

Cortona, Italy. Hilltowns of Tuscany

 



Organized Tours of the region

From Florence, you can take  this Full-Day tour . You’ll see  San Gimignano, Siena (which I wrote about here), and go to a wine estate in Chianti for wine and lunch. Recommended.

From Siena, you can take this Full-Day tour. It will take you to San Gimignano as well as to the beautiful walled town of Volterra.

This is a stunning region.

 


Related: 3 Days in Florence


 


Have you been to this area? Do you have a favorite town?


Ps. If you find our blog helpful, please consider using our links to book your flights, hotels, tours, and car rentals. Have a look at our Travel Resources page.

 

If you haven’t subscribed yet and want to get our posts and newsletters sent to your email, just insert your email address below

Great! Thank you for subscribing. If you don't receive a confirmation email, please check your Spam box.

Filed Under: EUROPE, ITALY

Reader Interactions

Comments

  1. Ryan

    November 21, 2016 at 5:44 pm

    Tanks so much for sharing. This town looks like such a cool place. I’m definitely gonna try to visit Tuscany before too long.

    Reply
    • Frank (bbqboy)

      November 21, 2016 at 10:08 pm

      Tuscany is fantastic, especially if you love wine! 🙂

      Reply
  2. Carlos

    June 11, 2015 at 2:12 pm

    I have been twice to the Chianti region, both times we took a tour in Florence to Siena and San Gimignano, you can take it with guide or without which is cheaper, it all depends on your budget. both towns are beautiful and full of history, I remember the first time when approaching San Gimignano, the towers from the distance looked like skyscrapers. We haven’t done the wine tasting but we are planning to come back next year with a couple of friends and maybe we will do it. Excellent pictures and very useful tips. Thank you

    Reply
    • Frank (bbqboy)

      June 11, 2015 at 2:33 pm

      Thanks for the comment Carlos! You’re right they look like skyscrapers, must have been amazing in the days when all the towers existed.
      Italy is great, we look forward to coming back to this region as well.

      Reply
  3. Jennifer

    July 9, 2014 at 11:10 pm

    The biggest tip for San Gimignano is to go in the morning before the hoards of tourists arrive on the tour buses. That’s the cue to get the heck out of dodge!

    Reply
    • admin

      July 10, 2014 at 11:29 am

      Very true! Thanks Jennifer.

      Reply
  4. Dale

    June 20, 2014 at 9:34 am

    It’s all about the smaller towns in Italy, just as you found yourselves!

    Though we’re in Alberobello right now and it’s really quite lovely, it’s the smaller towns around here that are full of the most character and make for great people watching.

    Reply
  5. Bob R

    June 9, 2014 at 1:37 pm

    In my world San Gimignano is famous for vernaccia. And that’s what will lead me there one day. That, and reminders like yours. Some really nice shots here of what I’m sure is a fabulous corner of the planet.

    Reply
    • admin

      June 9, 2014 at 2:35 pm

      Vernaccia: http://en.wikipedia.org/wiki/Vernaccia. I had never heard of it (I’m more a drinker of red). But will keep in mind for the next time we’re in Tuscany. Thanks for the tip Bob!

      Reply
  6. Laura

    May 31, 2014 at 4:24 pm

    I love the first pic that you put from the Castello di Meleto. Really great post and nice pics.

    Reply
    • admin

      June 1, 2014 at 12:50 am

      Thanks for the comment Laura, happy you liked the photo!

      Reply

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *


This site uses Akismet to reduce spam. Learn how your comment data is processed.

Sidebar


Hi! We are Frank & Lissette from Canada. We sold our home in 2014 and have been travelling the world ever since.

About Us

Interested in Spain? See Mapping Spain, our new website that focuses exclusively on Spain

Follow us on Social Media

Copyright © 2022 · The Travels of BBQboy and Spanky · All Rights Reserved · Privacy Policy

We use cookies to ensure that we give you the best experience on our website. If you continue to use this site we will assume that you are happy with it.Ok