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Under the Tuscan Sun – Planning the Perfect Trip to the Region

The Tuscany region is filled with countless picturesque mountain towns, each with its own personal charm, though they share in common magnificent views of hills and valleys, vineyards and neat rows of cypress trees, dreamy villas, and medieval castles surrounded by ancient stone walls, and villas that are simply a dream. And the wine, oh, you can not talk about Tuscany without mentioning the region’s excellent wine that comes from there, and flows there like water.

Sienna || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips

Pisa || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


Tuscany is the perfect place to visit when traveling in Italy for the first time, but it is also a wonderful place to return to over and over again. The first time I went to Tuscany was on a family trip, more than a decade ago. This year,  Daniel and I decided to include this romantic area once again in our long trip to Italy. Tuscany was our second stop, and after some hectic days in Rome, the transition to the calm countryside was simply a blessing 🙂 We dedicated a week of our time to the region, and divided our stay between an Airbnb apartment in Florence, and the Castel Monastero Resort & Spa Hotel, which is 15 minutes form Siena. {Click here to read the full post I wrote about my stay!}.  


A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


Planning a trip to Tuscany is no simple task. There are so many tiny towns, famous places, amazing wineries and churches, which made choosing what to include in our trip and what to pass up on a hard choice. To me, what was most important in planning the trip, was to find a balance between the cities and the small towns. Of course I wanted to see the famous Florence and Siena, but I also wanted to get to smaller, quieter towns, the kind that tourists haven’t got their hands on yet.


Pisa || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


I believe I successfully accomplished the task, and so I wanted to share here on my blog all the places we visited during our trip to Tuscany.

Click here to download my map of Tuscany

{Click here to watch my IG stories highlight from Tuscany!}




For more information on my full itinerary to Italy – when is best to fly, how to get around {including car rental tips!}, internet services, and more basic information that is important to know when traveling to Italy, Click here 

{P.S. Have you signed up for my free traveling e-course that will help you plan all of your next vacations like a pro?}




In Italy, there are many companies to rent a car from, but it is always best to compare prices before going on your trip, and to book a car and insurance in advance. We decided to rent a car through AVIS, which we picked up from the train station in Rome and returned in Milan.

Besides this car, we thought it would be nice to rent a vintage Italian car for two days in Tuscany, to really get into the Italian ‘dolce vita’ atmosphere. After serious searching online, we found ClassyCar.Rentals, a company that offers ten different kinds of beautiful vintage car for daily renting {or for longer, with the right budget 🙂 }. Our car of choice was an Alfa Romeo Spider, a classic Italian convertible from 1966, which made us feel as if we were in an old Italian film. Driving the stunning Tuscan roads, crossing small medieval villages and breathtaking views, is a wonderful experience in any car, but no doubt that thanks to the car, our drive felt even more special. Luckily, the weather was on our side, and we could keep the top down, so we really enjoyed every minute with this babe! 🙂


A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips

Booking is done through an online form on the company’s website, followed by an email correspondence with a company representative, and finalized by a credit card payment. The company provides an especially convenient service of bringing the car right up to the front of the hotel, so everything works smoothly and at a maximum convenience.

Update: I received a lot of questions about vintage car rental, so I decided to contact the company owners and they agreed to give 10% discount to my readers !!! ? If you want to rent a vintage vehicle through ClassyCar.Rentals, add the ‘HEDONISTIT' coupon code to your form to get the discount.




There is something really special about Siena, a charm that is difficult to put into words. Although all the  towns in Tuscany look alike, lined with cobblestone alleys and old houses, and each and every one is of course amazing, but Siena stole my heart from the first moment we entered through the old walls surrounding the city.

Because our hotel in Tuscany was a short drive from Siena, we got to visit it 3 times during our trip, and each time was more charming than the next. I heard, and read, a lot about Sienna even before we planned to visit it on this trip. During the Middle Ages, Siena was one of the largest, wealthiest and most well-known cities in Europe, and still today it is considered as one of Italy’s most toured cities. But only when I made it there myself, did I manage to feel the magic that rests on every city corner.


Sienna || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips

I will never forget my very first time in Siena. Daniel and I decided to spend our first evening in Tuscany by having dinner in the city’s main square Piazza del Campo, which is by far one of the most amazing squares I have seen in my life. I swear, the minute we walked into the square from one of the side streets leading to it, my heart skipped a beat. The square is paved with red-brown bricks and shaped like a huge fan, surrounded by bustling cafés and restaurants, and is considered the heart and symbol of the city. Situated in this remarkable square is the famous Palazzo Comunale and the bell tower Torre del Mangia {this is the highest bell tower in Italy and is said to have the most amazing view, but we gave up the pleasure of climbing 500 stairs this time, after our experience in Rome 🙂 }.  It’s fun to hang out in the square during the day, but I especially enjoyed it in the evening, when it’s colored in an orange hue from the street lights, and is particularly romantic. By the way, the Campo square is also where the Palio di Siena festival, a traditional horse race, takes place every July and August since the Renaissance. I can only imagine what a special experience that is, as the entire race takes place around this magnificent square.


Sienna || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


Besides the main square, we also enjoyed walking around the city’s main commercial street, Banchi di Sopra, where you can find well-known fashion brands alongside boutiques, cafes, pubs and restaurants. Siena also has a Duomo of course, like every Italian city, and Siena’s is designed in a Gothic style.




♦ Il Bandierino This restaurant, located in the Campo square, was where we chose to have our first Tuscan dinner. We showed up totally by chance, with no reservation, and were lucky to have had one of the best dinners of our entire trip. Although we were a bit worried about dining at a restaurant that is right in the square, because usually they are the most  touristy, especially when the place has set menus that include an appetizer, a main course, and a dessert for a fixed price, but already from an the outside something about the restaurant seemed right to us, and put us in the right mood, and we decided to sit down for dinner without overthinking it. After a short review of the menus, a choice was made to order one meal from the fixed meat menu, and a pizza {because how could you not, right? ? }. To our surprise, we ended up enjoying not only the ambiance in the place but also and especially the food which was simply delicious! The meat menu came with a small toast and a wonderful paste as an appetizer, for the first course a sausage platter with cheeses was served with bruschetta, and for the main course we had filets and Pici pasta {Tuscany’s local pasta}, which turned out to be no less than a dream. For dessert we had a mouthwatering cheese cake with figs. The pizza we ordered {mushroom and artichoke} is absolutely the best pizza we tasted during our entire time in Italy. We enjoyed it so much that we decided to have our last dinner in Tuscany at the same restaurant. Very, very, recommended!



♦ La Trofea –  Right next to Il Bandierino is this excellent, little pizzeria. It is so much fun to grab a slice, have a seat in the square and enjoy the atmosphere.

♦ Nannini –  This city’s famous old cafe, has 4 branches around town. We ate cookies and pastries in the shop located on Banchi di Sopra, the the city’s shopping street, and it was finger lickin’ good. Perfect for a quick snack on the go.




The enchanting green landscape, the authentic look that has been preserved since the Middle Ages, and, primarily, the 14 towers from that period that still stand, are what make San Gimignano one of the most famous and iconic towns in Tuscany. No wonder this little picturesque town, which I visited with my family more than a decade ago, left such a vivid impression on my memory.


San Gimignano || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips

San Gimignano || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


In this small town you can spend at least half a day, visiting the cathedral, the museums and even climb up one of the ancient towers, but since Daniel and I had already been here in the past, we decided to take it easy and just soak up the beauty of the place and the atmosphere.

We enjoyed walking through the narrow, charming alleys, exploring the quiet side streets, eating huge savory slices of pizza, watching the passersby in Palazzo Del Popolo, and eating not one, but two, gelato cones, in the town's famous square, Piazza Della Cisterna. One of the things I enjoyed most while wandering around San Gimignano was the little authentic shops selling local goods – from cheeses to special sausages, to fine wines, sweets and pastries. If you’re looking for a nice gift,  or a souvenir for yourself, this is, without a doubt, the perfect place to find the most special things.



In my opinion, the only downside of San Gimignano is the amount of tourists that flood it. Not much you can do about it, that’s what it’s like when your beautiful and famous 🙂 We arrived around noon, and the town was really packed. I guess the ideal time to show up is in the morning, before the tourist buses arrive, or in the afternoon when the town empties out a bit.




♦ RiccaPizzaIt is impossible to ignore the aroma coming from the little pizzeria found in the street leading to the main square… Service is good and fast, slices are big, and the pizza? Simply perfect.

♦ Gelateria DondoliThis ice-cream parlor, considered to be the best in the world, is easily identified by the long line of people at its store front. I personally didn’t crown it as the best on our trip, but it is no doubt that this is some pretty excellent gelato.

♦ Gelateria Dell' OlmoAnother great ice-cream place, and not any less good, located just a few steps away from the one mentioned above.





When you think of Tuscany, the first picture that comes to mind is of wide green vineyards and excellent wines. The most famous town which specializes in wine is the Tuscan town of Montepulciano, known all over the world for its unique wine Vino Nobile di Montepulciano. Our first wine tour was already booked at a vineyard near our hotel, but we just had to visit this little town, full of small shops that carry a variety of local wines, and offer tastings. After all, there’s no such thing as too much wine {especially when it comes to one of the most famous wines in the world!} 🙂

Before we even made it to Montepulciano, we realized that our choice to visit this town was one of the best decisions we made in Tuscany. The winding roads that lead to it through vineyards and fields with the region’s famous cypress trees and little village houses scattered among them. There is no other way to describe it besides the word – breathtaking.



The town itself, located high on top of a hill, is calm and picturesque, and it seems like the swarms of tourists haven’t discovered its beauty yet. Our first stop was Piazza Grande, Montepulciano’s main square, where there is also Palazzo dei Nobili-Tarugi with its impressive facade, Palazzo Communale city hall, and Cathedral Saint Mary of the Assumption.


Montepulciano || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips

Montepulciano || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


Montepulciano || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


?? Fun fact: If you’ve seen the movie New Moon from the Twilight Saga, you’ll most probably recognize this square, where the Saga’s most iconic scene, in which Bella saves Edward’s life, was filmed. Although the scene in the book takes place in the town of Volterra,  they decided to film the scene in Montepulciano, and so they had to construct the fountain described in the book {Which of course is nowhere to be found}. If you’re a true fan of ‘Twilight’ and would like to see more of where they shot the film, you should click here.

After a short stroll around the square, we climbed up to the bell at the top of city hall to discover the stunning view of the whole entire square and the green valleys that surround the town. It was a relatively short climb and the views were simply amazing, so this is really an opportunity you shouldn’t miss. Later on, we walked around the car-less streets and little shops selling various wines, cheeses, and meats.

Our plan from Montepulciano was to continue on to another small town called Pienza, a town famous for its Pecorino cheese only 20 minutes away by car, but unfortunately we didn’t end up having enough time.




You can’t visit Tuscany without going on a wine tasting tour at one of the region’s many vineyards. There are so many vineyards, and they each offer differently priced tours {some of them include wine tasting only, and others offer an entire meal}. The truth is, the large selection can be really confusing! We didn’t want to work too hard and so we asked the Concierge at our hotel to help us out by recommending some of the vineyards nearby! That is how we ended up at the Fèlsina Family Vineyard, a beautiful Tuscan vineyard just a short ride from the hotel. This was my very first time at a wine tasting tour, so I had no expectations except for enjoying good wine and learn a little bit about the wine-making process. The tour, formed by a group of 8 people and a very nice, English-speaking Italian guide, began in the vineyard’s wine cellar, where we learned about the ancient building and the different ways to produce different wines. After that, we went on to the wine tasting, which included a very generous amount of four wonderful wines. Let’s just say it’s a good thing I didn’t have to drive, because I could barely stand on my feet at the end of the tour ?

The tour of the vineyard requires a making a reservation in advance, and costs 15 Euro per person. booking can be done online or by phone.



A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips




Besides fine wine, Italy is also a synonym of high fashion and excellent taste. World renowned haute couture brands such as Dolce & Gabbana, Gucci, Versace, and many others, were all established in “the boot”, and have left a global mark on the fashion world.



When traveling in Italy, there is no avoiding the many designer shops with amazing window displays wherever you go, not just in the big cities but in the small towns too. If you feel like getting a little more done than just window shopping, but aren’t willing to spend your monthly salary (or more) on a single fashionable item, you’ll be glad to know that just a half hour’s drive from Florence is an especially good couture outlet mall called The Mall Firenze, where you can find a large variety of designer brands selling their timeless items at discounts, up to 70%. Keep in mind that despite the large discounts, these are still luxury brands, so you'll probably leave the outlet mall with a nice little hole in your pocket 🙂

Although I am not a brand junkie, I have been dreaming of owning a Gucci handbag for a very long time, because I think such a classic item can upgrade any outfit in an amazing way. Luckily, I celebrated my birthday during the trip, and Daniel convinced me that this outlet mall was the perfect opportunity for me to buy myself the little classic bag I have been longing for ? After a tour of all of the stores, that started and ended at Gucci, I chose this bag – it stole my heart {and was on sale for almost 60% off!}.



If you’re visiting Florence without a car, and you feel like going to the amazing outlet mall, you’ll be happy to hear that there is a special bus service for an excellent price that works all day long.



Florence is without a doubt Tuscany’s treasure, and no trip to Tuscany would be complete without paying the special place a visit. Thanks to the famous Medici family, Florence became the center of Tuscany in terms of art, architecture, and literature, and also was to become the one of the most famous cities in the world known for its enormous contribution to the Italian Renaissance. This was my third time in Florence, Tuscany’s capital, and every time I come I fall a little bit more in love with the city. Although this time the visit was pretty short, only a day and a half, I had the chance of celebrating my birthday in it in the most amazing way.

A detailed post about Florence will be up on the blog very soon ?




The town of Lucca is located about halfway between Florence and Pisa, which is why we decided to pay it a short visit on our last day in Tuscany, on our way to the leaning tower. Lucca, like Montepulciano, is a small town, quiet, and empty of tourists, and yet its vibrant feeling reminded me more of Sienna than the other small towns we visited. Lucca is famous for the thick stone walls that surround it, which were built during the Renaissance period and have remained intact today, even after the city has expanded its borders. You must be wondering how come the walls of Lucca have become such a famous symbol, I mean, throughout all of Tuscany’s length and breadth you can find incredible ancient walls. The thing is – Lucca’s walls are one of a kind! The old city can be surrounded by walking or cycling on the city walls {yes, they are that wide 🙂 }.

Lucca || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


We explored the old city and enjoyed roaming through the old, shop-filled alleyways, with stores that sells local goods as well as large, well-known chains, restaurants, cafes, and food stands. We walked around the beautiful piazzas, were impressed by the extraordinary church exteriors, and also visited Piazza dell'Anfiteatro, the famous Amphitheater square, built around the elliptical structure typical of the Roman amphitheater. There are two beautiful towers in Lucca, Torre Guinigi and the clock tower Torre delle Ore. Both towers can be used to climb up and get a glimpse of the city and its surrounding areas from above.




Our final stop in Tuscany was Pisa, or, more precisely, its Leaning Tower. Although there are other attractions in the city besides the famous tower, we were short on time because that day we were making our way to our next destination – La Spezia. Since Pisa was really in a convenient location on the way, we decided to make a tiny stop to take some silly, but so obviously necessary, pictures with the tower.


Pisa || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips

Pisa || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


You may be asking yourself if the Leaning Tower of Pisa is an overrated tourist attraction or an actual, worthwhile destination… In my opinion, it is always so cool to see such famous landmarks in real life, and the Leaning Tower is no exception. With that being said, considering the crazy amount of tourists around there, which kinda clouds the experience, if you only have a short amount of time in Tuscany, the Leaning Tower is no must-see. True, it is an incredible structure that took almost 200 years to be built, and the tower and next door cathedral were named a UNESCO World Heritage Site, and Pisa as a city in itself is so beautiful form I briefly saw, but still, there are so many small towns and villages in the region of Tuscany that are no less beautiful, and much less touristy, which makes visiting them a lot easier to enjoy.


Pisa || A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips


If you still want to visit the Leaning Tower of Pisa and its nearby attractions, and really enjoy them, I suggest that you sleep in town, or arrive as early as possible to walk around the touristy area. {By the way, this goes for all famous tourist attractions around the world 🙂 }. If you plan to climb the tower and visit the cathedral, and don’t feel like waiting in the long lines at the entrance, I highly recommend that you purchase ‘Skip-The-Line' tickets in advance here. If you don’t want to risk booking tickets in advance, I recommend that you get there before 8:30 am, when visiting hours begin, so that you can be first in line. {Though, to be honest, best would be to skip the headache and just use Skip the Line}.


I hope you enjoyed traveling through the charming Tuscany with me. Don't miss the full post about the amazing hotel we stayed at during our time in the region.



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Have you already been to Tuscany? Is it on your bucket list? Tell me all about it in a comment below  ♡




A Guide For Planning A Trip To Tuscany, Italy - Things to do, including food & restaurants tips, wineries, and road trip tips

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