Tuscany, Cinque Terre, and Milan (for foodies)

November 2, 2015

Best of Tuscany (for foodies) |

Every time I travel, I get caught up in the magical moments and tell myself I’ll have to share those experiences with you the moment I get back. However, once I am back home, reality hits with its many daily tasks and details of the trip quickly start to fade away.

This trip, however, was so incredibly good (and as always, mainly revolved around food) that I had to share my itinerary with you in case you’re also planning your trip. So here we go!

Best of Tuscany (for foodies) |


Day 1: Civita di Bagnoregio

After landing in an airport in Rome early that morning, we took our rented car and drove to Civita. Our initial plan was to also visit Orvieto that day—which should have been doable since Civita is tiny and Orvieto isn’t a long drive from it—but unfortunately it didn’t work out with our schedule. Civita is a stunning little gem accessible only by foot. To get into town you’ll need to cross a bridge which has its own beauty and is an integral part of Civita’s landscape. There’s free parking just below the bridge, or paid parking all around the area. Make sure to get as close to the bridge as possible if you bring a car. Those who are unfamiliar with the area tend to park far away and walk for nearly one hour until they get to the bridge. As you probably know, I’m not one of those people; I do my homework ahead of time. I will mention, though, that just before the bridge there’s a three-minute drive on a steep inclined road.

At night we drove to the Chianti area, our base for the next three nights, where we stayed at the gorgeous Villa Di Geggiano. The photos speak for themselves.


Alma is the best restaurant in Civita, but if it’s packed, my next favorite would be Osteria Al Forno.

Best of Tuscany (for foodies) |

Civita di Bagnoregio

Best of Tuscany (for foodies) | Best of Tuscany (for foodies) | Best of Tuscany (for foodies) |

Day 2: Montepulciano, Pienza, Montalcino

This day was dedicated to visiting several little towns while driving along the gorgeous views of Val d’Orcia. Going from one town to another took 20-30 minutes. Since they’re all rather small, visiting all three towns in one day is doable unless you’re the strolling type who likes to see everything (in which case, I can’t blame you). Montepulciano seems to be a favorite among many, although personally we loved Pienza.

While driving, you can pass through a town called Monticchiello where there’s the famous winding road lined with trees that you’re sure to have seen before in pictures.

Another beautiful place on the way that’s worth a short stop is Bagno Vignoni.


  • For lunch or dinner in Montepulciano, be sure to try Le Logge del Vignola. Both locals and tourists claim it’s the best restaurant in town. Their fresh porcini meals were out of this world.
  • Pienza is known for its delicious Pecorino cheeses. There are many kinds to choose from, and some shops offer free tastings. Also try Buon Gusto Gelateria, one of our favorite ice cream shops on the trip.
  • Montalcino is famous for its Brunello wine. Just at the entrance of town is a large store that offers wine tastings, but you can find this offering in many other shops in the area, too. Wine tours are another popular activity you can try while you’re there.
Best of Tuscany (for foodies) |


Day 3: San Gimignano and Siena

Siena is a must-see in Tuscany, and considered to be its jewel. The Cathedral and Piazza del Campo are nothing short of spectacular. But before getting there, we visited San Gimignano, a truly unique stony village with plenty of old-world charm.


  • San Gimignano: Dondoli is a famous ice cream shop in the main square. If you’re looking for fast food, then the pizza in RiccaPizza is delicious.
  • Siena: While they don’t serve the best food I’ve ever eaten, La Taverna Di San Giuseppe is a fun, authentic restaurant that’s always packed and has a fantastic ambiance. Reservations are a must. GROM is another well-known ice cream shop, but you can also find it in other places such as Florence and Milan.
Best of Tuscany (for foodies) |

San Gimignano

Best of Tuscany (for foodies) |


Best of Tuscany (for foodies) |


Day 4: Chianti Area

Whenever there’s wine involved, you can count me in! Chianti is known for their wine, and traveling between the small towns in the Chianti area and visiting wineries is a relaxing experience that feels like it’s taken straight out of a movie. Each town has its own magic (we loved Panzano, but it’s just a matter of taste) and you can easily visit several in one day. Some of the more known ones are Greve, Panzano, Castellina, Radda and Gaiole.

That night, we stayed in a magical place called Castello La Leccia, located in Castellina. It wasn’t cheap, but it was worth every penny and one of the best experiences of the trip. Everything was absolutely perfect. The modest and likeable owner gives all guests a tour of the winery right in front of the hotel, complete with a tasting of his delicious organic wine.


  • Try the Chianti Classico, the well-known wine in this region.
  • If you really want to try out the large selection of the wines Chianti has to offer, then (1) can we be friends?, and (2) you must go to Enoteca Falorni in Greve where you can grab a prepaid card and serve yourself as many types of wine as you like.
  • I also enjoyed the wine tasting in Accademia del Buon Gusto in Panzano as it was a different and very enjoyable experience. If you go there, you’ll understand.
  • In Panzano we had lunch at Il Vinaio Enoteca Pub, which had some fantastic authentic food. For dinner, we ate at Rosticceria Il Re Galo in Castellina—a restaurant recommended to us by the hotel. It was packed, but their tiramisu was amazing and made the wait worthwhile.

Best of Tuscany (for foodies) | prettysimplesweet.comBest of Tuscany (for foodies) | prettysimplesweet.comBest of Tuscany (for foodies) |

Best of Tuscany (for foodies) |

wine tasting – yes, please!

Best of Tuscany (for foodies) |


Day 5-6: Florence

Florence is a large city with many shops, gorgeous streets, and outstanding museums (if you need to pick just one, go to Uffizi) and deserves more than a 1-day visit—that is, of course, unless you don’t like spending your time relaxing, shopping, or sightseeing.

If museums are what you’re after, I highly suggest booking tickets in advance online; otherwise, you may be stuck waiting 3 hours in line at the ticket office. A last minute strategy (and what we ended up doing) is to go to the My Accademia Libreria bookstore, which is located right near the Accademia’s exit Via Ricasoli 105 red. It’s open from 8:00-17:30, closed on Monday, and you can purchase museum tickets there. It will cost you a €4 reservation fee per ticket, but there’s usually no line because few people are aware you can do this.


  • Panini Toscani is a neat place for a high-end panini, and is conveniently located near the Duomo. You can even taste the variety of cheeses and salami before they put them in your meal.
  • For lunch we ate at Ora d’Aria, one of the best restaurants I’ve ever been to. This is a Michelin star restaurant, and one that isn’t too expensive compared to the others. We paid €35 per person for a 5-course tasting menu, and every single dish was beyond amazing. I loved everything about this place—modern décor, friendly service, and a lovely ambience.
  • For dinner we went to Il Vezzo (yes, we still went to dinner after that huge lunch). This was another restaurant that I highly recommend with excellent stylish food.
  • For pizza, try this cute place called Mangia Firenze.

Best of Tuscany (for foodies) |

Day 7-8: Lucca and Cinque Terre

On our way to Cinque Terre, we stopped in Lucca and fell in love with it. It’s quite big, but not huge, and the charming streets are full of clothing shops, pastry shops, and coffee shops. We had a short stop there, but if you have the time, you can easily spend a night there.

From there we headed to Cinque Terre in the Italian Riviera, which consists of five villages all with breathtaking views. There aren’t many hotels there, mostly B&Bs and apartments, but if you prefer staying at a hotel, then head toward Monterosso for the Margherita hotel, or the La Mala in Vernazza.

Monterosso is the biggest of the five villages, more resort-like, and the only one with an extensive full-service beach. Vernazza seems to be the most favored village among tourists, and although it is indeed charming, it’s super tiny.

There’s a convenient train that passes through all the towns, although it can be less convenient when crowded with people. I thought the train would pass more frequently, but we sometimes waited for 20 minutes, so you may want to check the times beforehand. You can also hike between towns and enjoy the breathtaking views, but it’s neither easy nor short.

Cinque Terre is touristy and crowded, although that’s what makes the ambience so lively. Make sure to book a place to stay at least a few weeks in advance if you plan to spend your nights here.

To get to Cinque Terre, I suggest parking your car at La Spezia Centrale station (which cost about €15-20 per day) instead of driving all the way down. It’s a narrow, winding road, and parking isn’t always easy to find. The train is the best option in my opinion. We left our luggage in the trunk and took anything we needed for 2 days in our bags.


  • In Lucca, you must buy some treats at Caniparoli Cioccolateria. I’ve tasted lots of sweets in my 30 years of living (this blog is evidence), and I thought they were incredible, especially the meringue nut cookies and chocolate Florentine.
  • In general, Cinque Terre is known for its delicious pesto, focaccia, and a local dish called focaccia di recco—a flat bread filled with cheese.
  • A Pie’ de Ma’ in Riomaggiore has beautiful views and is great for an afternoon drink.
  • For dinner or lunch, I’d recommend these restaurants:
    Ristorante Miky in Monterosso
    Belforte in Vernazza
    Cappun Magru in casa di Marin in Manarola
    Trattoria dal Billy in Manarola
Best of Tuscany (for foodies) |


Day 8-9: Milan 

Milan was our last stop on the trip before heading home, so I held myself to keep from crying there. We only had one full day, so we did a similar route to the one suggested here, and it was spot on. The guide walks you through all the main sights and beautiful streets, giving you a great view of the city.


  • Gorgeous coffee shops, pastry shops, and ice cream shops can be found in every corner of Milan.
  • For lunch we ate at a well-known Michelin star restaurant that serves only vegetarian food. If you’re vegetarian, I’d highly recommend going there as this is quite an experience. Although not all of the dishes amazed me, some did, and everything was styled beautifully.

Best of Tuscany (for foodies) |

In general, this is the kind of food you want to try while in Tuscany:

  • Fresh pasta
  • Pizza
  • Paninis
  • Anything with truffle or porcini (yum)
  • Focaccia
  • Having a glass of wine is quite cheap, even in fancy restaurants. Try some of the better known ones for these areas such as the Chianti Classico or Brunello.

A few tips not about the food:

  • Parking: Parking is pretty easy in the small towns, even during pick seasons. Blue lines always indicate paid parking (which is usually about €1-2 per hour), and there will be machines nearby where you can pay. White lines mean free parking. Large cities such as Milan, Rome, and Florence are not recommended for driving; it’s almost always better to stay farther from the center if you have a car with you.
  • Tolls: You can’t a miss a toll road in Italy—they’re very organized. Before entering a toll road you’ll have to pick up a ticket, and when exiting you’ll have to pass through a booth and pay. Follow the signs and always choose the lane with a picture of a hand and coins, and never the Telepass lane. Tolls can be paid in either cash or by credit card.
  • Restaurant reservations: Always make reservations at least a few days ahead, especially on the weekends. It’s the only way to be able to get into the best restaurants during the tourist seasons.

If I was to do this trip all over again, I wouldn’t change a thing. It was just perfect. If you’re travelling there yourself soon, enjoy! And please consider taking me with you!

A huge thanks to Erez, who took these amazing photos!

You Might Also Like


  • Reply
    Jess @ What Jessica Baked Next
    November 2, 2015 at 4:44 pm

    This post is bringing back many great memories of my last trip to Tuscany! Beautiful photos, as always. San Gimignano is one of my favourite places, the gelato from Gelateria Dondoli is incredible – we ate our fair share during visits to the town. This is a brilliant guide for foodies, thanks for sharing Shiran! 🙂

    • Reply
      November 3, 2015 at 3:46 am

      Thanks, Jess! It was amazing, and I can’t wait to go back again!

  • Reply
    November 3, 2015 at 4:19 am

    The photos O_O They are out of this world. Completely and utterly divine. I’m in love. I basically want to travel anywhere and everywhere in the world, but because of this post, Italy has crept up on the list 😛 Glad you had such a wonderful experience.

    • Reply
      November 4, 2015 at 7:45 am

      Thank you so much, Laila 🙂 I’m in love, too! In real life it looks even better than the photos!

    Leave a Reply