Italian Itinerary for Tuscany & beyond

To plan or not to plan.

Being a Travel Planner, I feel a need to plan my trip to Italy in November. I was only going to concentrate on Tuscany, but the draft itinerary is already taking me into other areas.

The traveller in me, the one who is finally travelling solo, wants to keep things free.

I’m torn. But I think the travel planner is going to win out. At least partly. I have decided the specific locations I want to visit, and then I have a couple of additional places that I can visit either as day trips or if time allows, to stay a night or two.

So, what I think I will do is organise accommodation for the first week of my trip and leave the rest of the trip free. That way I can see what comes up and book accordingly.

Of course, being the control freak that I am, I will have a list of accommodation ready, so I don’t have to worry about wasting time researching.

This itinerary is officially not all Tuscany, but that’s OK. It’s good to experience diversity, and if you are looking to plan a trip solely to Tuscany, then this post will have more than enough for you to choose from.


It's hard to choose what to include on your Italian Itinerary and Tuscany is the perfect choice #itinerary #tuscany #italy #italian


Itinerary for Tuscany and more

Florence – 5 nights

I plan on staying initially for five nights.

Florence is a city I have wanted to visit for a long time. I am beyond excited to finally be going.

There will be no shortage of things to fill my time. Florence, the capital of Tuscany, is renowned for its architecture, Renaissance art and food.

Located approximately 1.5 – 2 hours from Rome by train, it will be a relaxing way to unwind after 27 hours of travel.

I plan on finding accommodation within walking distance of most sites. I am not a fan of public transport and prefer to walk. I am looking forward to spending days walking and see where it takes me. Having said that there are a few things on my list, I would like to see, but that’s it.


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italian


On the agenda will be:

The Piazza del Duomo to see the Duomo

Uffizi Gallery

Accademia Gallery

Ponte Vecchio

Piazza della Signoria

A walk up to Piazzale Michelangelo, possibly in the evening.

And the rest, I will just wait and see.


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italianThe Uffizi Gallery


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italianPonte Vecchio




Walking Food Tour

Florence Food Tour with Eating Europe (formerly Eating Italy)

This company has been highly recommended to me by a member of my Ladies who want to Travel Group, although she joined one in Rome. They have been on my radar for a long time I was sorry to have missed one of the tours when I was last in Rome.

Being a solo traveller, this will be the perfect way to meet other travellers and include a meal. I will be choosing either the Florence Sunset Food Tour or The Other Side of Florence Food Tour.

You can find out more about Eating Europe Italy Food Tours here.


YOU MIGHT ALSO LIKE: How to Experience Florence, Your Way


Free Walking Tour

Florence Free Walking Tour – La Bussola

Another tour recommended by a member of my group (thanks ladies!)

I love doing walking tours as soon as I can after I arrive in a new destination, so I get to know my way around. And the bonus for this trip is I can meet other travellers and ask the guide for recommendations.

This company offers both a morning and afternoon (early evening) tour each including different areas of the city.

You can find out more about this Free Walking Tour in Florence here.


Day Trips

San Miniato

My friend, Sandy, tells me there is a Truffle Festival in San Miniato on the weekends that I plan to be there. It’s not far from Florence, and fingers crossed, I can add it to the list.

San Miniato hosts a Truffle Festival on November 11 &12, 18 & 19, 25 & 26 each year. I had no clue that there were six types of Truffles each with its own distinct flavour, but I believe this festival is all about the White Truffle.


Pisa has never been on my list to see. I have always thought it too touristy. But if I am this close, then I guess I will take a look. Pisa might be a good stop on my way to another location and spend half a day exploring, at the very least seeing the Tower and the Square of Miracles (Campo dei Miracoli) as well as the Cathedral of Santa Maria Assunta.

For more information on booking tickets read more here.


It's hard to choose what to include on your Italian Itinerary and Tuscany is the perfect choice #itinerary #tuscany #italy #italian


San Gimignano and Siena

Although these towns are not accessible by train, I can take a bus. However, I would like to do some wine tasting too, preferably on a full day trip, even though I am not usually one for bus tours.

There are quite a few options for wine tasting including Vespa tours and more and would like to see what my options are when I arrive. Possibly get some recommendations.

That is the advantage of not travelling in peak season; I don’t have to worry too much about booking in advance.

I found this tour which includes a lot of what I want to do. I’m trying not to cringe, I don’t usually go in for bus tours, so I will have to think on this one.



I had already spent a day in Arezzo on my last trip to Italy when I was staying with my group in Cortona.

Since I have long been a lover of anything antique, old, rustic and worn visiting Arezzo’s antique markets would be a dream. My purse might hate me, and the carry-on only luggage may find itself underneath in storage instead of with me, but it’s a dream nonetheless.

The Antique Markets held on the first Sunday of every month (and the Saturday before) in the Piazza Grande, dates back to 1968. It would be an ideal place to find that quirky souvenir if antiques are your thing of course.


It's hard to choose what to include on your Italian Itinerary and Tuscany is the perfect choice #itinerary #tuscany #italy #italianArezzo



I fell in love with Cortona, and I will keep this as an option if I have the time. But I admit I am a bit of an all or nothing person, and if I can’t stay for a decent amount of time and spoil myself by staying at the Villa Marsili, then I don’t really want to go back. Not just for a day.

Now, a month, on the other hand, would be amazing.


Another trip to Italy and this time including towns in Tuscany and beyond #itinerary #tuscany #italy #italian

Verona – 5 nights

Ah, Verona! The home of Shakespeare’s Romeo and Juliet.

But apart from being famous for its romantic lovers, Verona is a beautiful medieval town located in the north of Veneto and is one of the most visited cities in Italy. I plan on staying here for approximately five nights giving me plenty of time to explore and relax.


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italian



On the agenda will be:


Free Walking Tour

Free Tour Verona runs free walking tours from Monday to Saturday at 10.30 am.

I am looking forward to joining this tour and being shown around Verona by a local.

I love the fact that the guides are locals, passionate about their home and showing off Verona through their eyes.

You can find more information on Free Tour Verona here.


YOU MIGHT ALSO LIKE: The Best of Verona, Italy


Juliet’s Balcony

Drawing over half a million visitors every year this is a place I would usually avoid, but I can’t help it I have to go. I loved the movie Letters to Juliet (don’t crucify me for it) and I will sneak in early and take a look, although I will probably skip the museum. You can find details here if you are interested in the museum.


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italianJuliet’s Balcony


After that, I am going to let Verona surprise me.

With Piazza dei Signori with the Arche Scaligere monument, Piazza delle Erbe, the square of herbs, the Castelvecchio, a castle built in the middle ages and now a museum and a visit to Piazza Bra with the Roman Arena, I think I will be easily occupied.

But in my true Slow Travel fashion, I just want to take my time, explore on foot and see where my days take me.


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italian



Day Trips

Lake Garda

I am contemplating a day trip to Lake Garda, however, from my research, I think I would rather stay in the area and explore the towns around the lake at leisure.

Travelling by train, you arrive in Desenzano del Garda a lovely little town on the edge of the lake boasting a marina. It’s a great place to start exploring and there is also the excavation of Villa Romana near the old town centre.

From here I can catch a bus to Sirmione where I can see the Castello Scaligeri in Sirmione.

I’ll see. The purpose of travelling on my own with few plans is to see where things take me.



Not a day trip as such but thinking about spending a night or two on my way to or from Verona to Florence.

What’s the reason for visiting Bologna? Food. Simple. I want to join a food tour or two.

And the fact that it is a beautiful city with two leaning towers and a gelato museum. Need I say more? Well yes, they even have the Carpigiani Gelato University. And amazing food markets like Mercato delle Erbe and … ok, I will stop now, but you see my point. Food.

The food tour I am considering is the Classic Bologna Food Tour with Taste Bologna.


YOU MIGHT ALSO LIKE: How to Plan Your Ultimate Trip to Bologna


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italianBologna


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italian



Lucca – 4 nights

I will admit that I don’t know anything about Lucca except that it is a city within well-preserved walls with paths to walk and a tower growing a garden.

But I like that I don’t know anything about it. I have no expectations and nothing I “have” to see.

What I am planning on doing is a self-guided tour, starting with the City Orientation Walk and start from there. There is a lot I can do, so I won’t be bored.

Or if I want some company, I can always join the walking tour that leaves from the Tourist Information Office in Piazzale Verdi. I would have to time this one right as it only runs on weekends from November 1 to March 30. This one is not free but is only €10.

If I decide to stay longer in Florence or Verona or choose another destination like Cinque Terre to explore then Lucca is a great day trip from Florence. Who knows by this time I might like to see a different outlook, and the ocean is a perfect choice.



I am contemplating Casa Laura. You can read this article by my friend Sandy about Casa Laura and Lucca.

Casa Laura is listed on HomeAway and I have often looked on this site for accommodation. I think it is a great alternative to Airbnb. Years ago, when staying in Rome and Paris, I booked apartments for my family through different rental sites and had great experiences. I was an apartment convert from then on, liking the option of a kitchen to cook in.


Other places to visit

Montepulciano, Pienza and Montalcino

On my last trip, my group joined a wine tour to all of these. I absolutely loved the area and would like to go back and explore in more depth. However, what I would really like to do is stay in Montepulciano, but without a car getting around could be more difficult. It is one of my favourite must-see towns in Tuscany.

Montepulciano and Montalcino are famous wine areas with my favourite red Brunello coming from Montalcino.


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italianMontepulciano


Cinque Terre

Or Cinque Terre and beyond. Levanto and Bonassola have been recommended to me. Possibly stay a night or two along the way, explore some of the villages. This is high on my list, first stopping at La Spezia and then a train onto Cinque Terre.

This is what I love about this solo adventure, flexibility. The possibilities are endless, but I don’t think until I am actually there that I will decide what to do. As I like to say, you have to love options.


Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italianBonassola



My accommodation for this trip needs to be simple and safe. I don’t need breakfast included, I am happy to purchase my own. The location is my main priority and because I am travelling solo, I am contemplating a B&B style hotel, to allow for interaction with other guests in a common area.

I’m not interested in hostels.

My two preferred options for finding accommodation when I travel personally is through and Airbnb (sign up using this link and receive a credit off your first stay).

A word of advice, before booking through any booking site, check the prices directly with the hotel. I like to use because I can spend time looking and save my favourites for easy referral later on.  I can also use the filters on the left-hand side to narrow down my requirements including my location. has a broad range of accommodation from hostels to guesthouses, apartments and hotels that I find helpful.

With Airbnb, the price you see on the listing is not always the price you get. You will first need to see if your dates are available and then confirm what they are. Hosts can also include a cleaning and admin fee, which can take what initially looks like budget friendly accommodation to expensive. I love Airbnb, but just be aware of these things when booking

For this trip, I am keeping things open for now. I will be using both of these to narrow down my search. I like to walk everywhere so where ever I chose will be either in a central location or a neighbourhood within walking distance to the main centre.

Because I am travelling in offseason, I am not overly concerned with the cities being overly crowded. Normally I would choose to be in a neighbourhood but being on my own I would like to be a little more centrally located.


Getting Around

The trains in Italy are great. I have never had a problem. And finally, I am going to have to swallow the large lump of anxiety in my throat and catch buses.

Anxiety is something that I must constantly deal with when travelling and most of the time I try and make things easier on myself by arranging private transfers if I feel it’s too much. But this time my budget is tighter, and I am determined to become a more independent traveller, so public transport it is. I will just have to get on with it! And the upside to solo travel is there will be no one I know to see any meltdowns. There’s always a silver lining.



Make sure if you hire a car you are comfortable with it particularly if you will be driving on the opposite side of the road to what you are used to. Things can get a little crazy on the roads so you will need your wits about you.

Also, be aware that roads in cities can be tiny. It really can be a nail-biting experience trying to fit between walls and parked cars. A lot of the towns do not allow cars in and parking is outside the city and you will more than likely need to pay for parking.

On a previous trip to Italy, our lease car sustained damage in a carpark, some large scrapes. We had to file a police report so that we could show a copy to the insurance company. The language barrier was huge and it took a long time.

I am not saying don’t drive, it is a fantastic way to get off the well-worn tourist track, I am just saying be aware.



Tuscany in Autumn

I am looking forward to experiencing Italy in Autumn, with colourful leaves, food festivals, cooler weather and fewer crowds. I can, however, expect more rain, but that’s ok.

Italy in summer is too hot for me, and too crowded. Although I loved our time in Rome, Orvieto and Venice, I wouldn’t travel at that time of year again.

Spring was lovely and together with Autumn would be my seasons of choice. Although, I don’t mind the cold, so Winter is definitely an option as well.

I can expect temperatures ranging from 15°C – 7°C and a little lower going into December, so packing into my carry-on luggage is going to be a challenge. I’m looking forward to using my new Osprey Sirrius 36 backpack, ready for the Camino next year, and providing me with the freedom to not have to carry my bag up flights of stairs or dragging a suitcase (no matter how good the wheels) over cobblestones.


Food of the Season

Travelling in Autumn means I will be able to find freshly pressed Olive Oil, Truffles and Chestnuts. I love Italian food and their way of eating with the season.


Each time I visit Italy, I get to know one or two areas well and then get a taster of other areas to find out where I want to explore more. I anticipate coming back to Italy over and over again, exploring new locations and revisiting favourites.

Going back to Italy is exciting. Solo travel is petrifying. I am sure solo travel has a lot of surprises for me. But I love the surprises that unexpected adventures bring, and I am more than up for the challenge. I long to be back in Italy ordering my un caffè for breakfast and plying it with sugar before gulping it down. It’s the only time I drink espresso, and I enjoy the daily ritual.


Cindy x


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Tuscany and Cinque Terre are the perfect places to include in your Italian Itinerary #itinerary #tuscany #italy #italian

Another trip to Italy and this time including towns in Tuscany and beyond #itinerary #tuscany #italy #italian


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Cindy Reid

Cindy is the founder of Travel Charm and her exclusive Travel Club. She is passionate about travel and planning and loves nothing more than helping travellers plan their best trips and fulfil their travel dreams.

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