Travel Recommendations for Toscana

A friend recently let me know that she would be traveling to Tuscany and was seeking recommendations both for tourist travel and wine travel. Having lived in Florence and spent much more time since then traveling around bella Toscana, I compiled the following recommendations for her:


  • Stay away from Florence during the summer! It’s overrun by tourists and you will hear more English spoken than Italian. It can also get decently hot/humid so near the Arno and many buildings aren’t equipped to handle that. Autumn is my favorite time to visit Toscana; there are harvest festivals for wine grapes and olives and the lush green hills begin turning into patchworks of autumnal colors.
  • Pro tip: if you reserve a rental car for pickup in Florence, make sure that you specify Florence, ITALY, not Florence, Alabama. Not that that happened to me once . . .
  • Florence is very walkable so use the opportunity to walk off all the amazing food you will have there!
  • Visit the Duomo and, unless you are prohibitively claustrophobic or acrophobic, climb to the top for breathtaking views of the city. 
  • Allocate an entire day for the Uffizi. Pro tip: reserve tickets for the opening time then head immediately to the top floor (which will be much less crowded) and work your way down.
  • Spend time among the statues in the Piazza della Signoria; my favorite statue, Ercole e Caco, is there. 
  • Visit the Accademia and prepare to be stunned when you turn the corner to see David for the first time.
  • Make a pilgrimage to Vivoli for Florence’s most famous gelato – but also eat gelato everywhere else too. 🙂
  • Generally avoid eating in restaurants near the main tourist spots. Wander a few blocks off the main path and find some unassuming trattoria. Order a carafe of the house wine and enjoy damn fine food at a fraction of the cost of tourist traps. If you’re a carnivore, go for the Bistecca alla Fiorentina, which you order by the kilogram. Generally avoid any place that has laminated English menus with pictures of each dish.
  • Spend time oltr’Arno (south of the river) as well to get away from tourists. While you’re here, visit the Palazzo Pitti and the Giardino di Boboli.
  • There are a million more things to do in Florence but these are my recommendations for a short stay.

San Gimignano

  • San Gimignano is a nice day trip from pretty much anywhere in Tuscany. Climb the tours. Look out over the Tuscan countryside. Swoon. 
  • Visit the Collegiata for some real fire and brimstone, wrath of God, dogs and cats living together frescos.
  • The award-winning Gelateria Dondoli alone is worth the trip!
  • Siena is another day trip-able city that is very walkable.
  • The main religious attraction is the Duomo but make time also to visit San Domenico, where you can visit the most grotesque relic I’ve ever seen: the head of Santa Caterina!
  • Spend time in the Piazza del Campo and, if you ignored my previous advice and traveled during the summer, see if you can witness Il Palio, the famous in-town horse race. 
  • My strongest restaurant recommendation is Antica Osteria da Divo, where you should make sure to order the risotto that is served up from the inside of parmigiano cheese wheels!
Tuscan Countryside
  • I strongly suggest getting off the beaten path a bit to enjoy the beautiful, blood-pressure-reducing life of Toscana outside of the cities.
  • My greatest recommendation for this is Castello di Montalto, an entire hamlet about 20 minutes south of Siena.
  • I can also recommend Hotel Borgo Casabianca as a countryside home base for Tuscan exploration
  • Montefollonico is also a nice hilltop town for getting away from the hustle and bustle of city life. Others have recommended visiting Lucca and Pisa too but I haven’t spent enough time in either to include them in this post.
Wine Touring
  • Now for the most important part: the vino! Let’s start with my favorite: Brunello di Montalcino!
    • I love the little town of Montalcino itself but most can probably skip it.
    • Visiting Italian wineries is much more laid back than visiting in Napa or Bordeaux. There usually is no fee but call/email ahead to secure a time slot and to ensure that there is someone there who speaks English (if you don’t speak Italian).
    • Valdicava is my favorite Brunello di Montalcino stop. It’s a small, unassuming vineyard that has a very non-interventionist approach to its grape growing. They aren’t really set up for tours and often don’t have English-speakers on hand but, if you can get an appointment, barrel-tasting there is not to be missed.
    • Castello Banfi is the polar opposite: a huge estate owned by Americans with a massive tasting room that is very much meant to host English-speaking tourists. If this is more your style, you can drop in without an appointment.
    • Casanova di Neri has a nice, low-key tour.
    • Fattoria Barbi has a nice, low-key tour.
    • Livio Sassetti Pertimali has a nice, low-key tour (but may not have an English-speaker on hand).
    • I can’t recommend Boccon Di Vino highly enough as a place for lunch when touring around Montalcino – fine dining, a great wine selection, and fantastic views!
    • Do NOT under any circumstances go to Castelgiocondo! My one time there not only did they screw up my appointment but they also lied to my face, claiming that all of their grapes were hand picked despite our having driven by their mechanized harvesters in their vineyards on our way in. Bad people!
  • Also very near and dear to my heart: Chianti Classico
    • Villa Calcinaia is my favorite destination by far. I confess bias as one of the members of the family that owns it was my professor when I was living in Florence. It’s really fantastic, though; nice tastings, 300-year-old balsamic vinegar, beautiful views – Calcinaia has it all!
    • Castello di Brolio is another large estate that is well equipped for tourism if that’s your speed. Even if it isn’t your speed, it’s a worthwhile pilgrimage to the birthplace of Chianti.
    • Dievole is a nice estate with a very charismatic proprietor and good wines.
    • The town of Greve in Chianti is best visited during the fall harvest festival. Buy a glass and walk from booth to booth sampling all the local wines.
  • Montepulciano is also a worthwhile stop, not just for its own charm but for the highly underrated Vino Nobile di Montepulciano. If you’re there over the summer, see if you can time your visit with the Bravio delle Botti!
  • One final note on wine touring in Toscana: GPS is easily confused by the windy, hilly roads, so allow plenty of time to get lost and consider using more traditional means of navigation.
I hope this is helpful for those planning to visit Tuscany! Let me know how if I’ve missed something obvious and/or how my recommendations work out for you! Buon viaggio!

Published by Bryan Guido Hassin

These are the musings of a global cleantech entrepreneur. This blog began as a way to document my experience during the IMD MBA in Switzerland and now is the place where I publish eclectic thoughts on business, politics, fitness, entertainment, travel, wine, sports, and . . . whatever else is top of mind.

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