Tuscany in 5 days


Hi. I am dedicating 5 days of my Italy honeymoon to Tuscany but it seems that there are so many places to see and everyone I asked had different opinions about each place. We will be driving...

Definately Florence - I was thinking a day and a half

After that, I am torn - there are so many cute places that people recommend visiting. I don't care for shopping at all. I love medieval architecture. Also, I am planning to hit a lot of museums in Rome so I would not be interested as much in Tuscany museums. I want nature and architecture. I would also definately want to do a wine tour. Can you please help me with the other 3.5 days I have? Where should I go and what should I see?

I heard mixed reviews about Pisa. On the other hand, San Gimignano sounds like my ideal place. I appreciate any advice.

Thank you,


Well-known member
Spending 5 days in Tuscany

Dear laris1284,

congratulations for your wedding! :D

I can understand your doubts about what to see in Tuscany, since there are so many things worth to be visited. I agree with you about spending 1 day and half in Florence, even though I recommend you visit at least a couple of museums. I know that you are going to visit lots of museums in Rome, but museums in Florence aren't the same of Rome. I strongly recommend you visit the Uffizi Gallery, displaying some of the most beautiful works of Renaissance such as the Birth of Venus and the Spring by Botticelli just to name the most famous works. Then you can decide to visit either the Academy Gallery, displaying the original of Michelangelo's David or Pitti Palace, where there are several museums, such as the Palatine Gallery.

About Pisa you can spend half day, so that you have plenty of time to visit Piazza dei Miracoli, where the Leaning Tower stands.

For the other days 3 days and half I suggest you visit the Chianti region, Siena, San Gimignano, Monteriggioni and maybe Certaldo.
Chianti is famous for the Chianti wine production and for the beautiful landscapes that are spotted by medieval fortresses and castles, as well as nice towns and villages. I suggest you read the article One day in Chianti to find more information. I also suggest you add to your itinerary the medieval town of Barberino Val d'Elsa, since you like medieval architecture ;) Furthermore you'll have the opportunity to do wine tastings in Chianti. Along the way you will find many farms offering wine tastings and cellars tours.

After a day in Chianti I recommend you spend one day visiting three beautiful medieval cities that are San Gimignano, Monteriggioni and Certaldo. As you said, probably San Gimignano is your ideal place. It is the typical medieval town enclosed in big walls. Its peculiarity are the high towers designing its unmistakable skyline. Have a look at some pictures of San Gimignano to have a better idea. Then you have to visit Monteriggioni, a medieval fortress, and Certaldo, whose upper historical center is really charming. Both these towns have typical medieval architectures and I'm sure you'll like them :)

On your last day in Tuscany I suggest you spend the whole day in Siena, that is the medieval city par excellence, as Florence is the cradle of Renaissance. I don't know if you like medieval painting, but I recommend you visit the Civic Museum in Piazza del Campo, displaying several masterpieces.

I finally recommend you read other threads in this forum and the article about spending 5 days in Tuscany to find more ideas and suggestions for you vacation.

Well I hope I gave you some good ideas for planning your 5 days in Tuscany! :D Don't hesitate to ask any further question and to share your experience.


Just one more question - should I stay in Florence or somewhere else in Tuscany in order to be able to visit all the above sites? What location would be most convenient? We are driving so I wouldn't need proximity to public transportation.

Thank you!!!!!!


Well-known member
Accommodation in Tuscany

Dear laris1284,

I'm happy to know you find our forum helpful :D

If you want to spend 5 days in the same location I then suggest you find an accommodation in Chianti, that is located between Florence and Siena.

Since you are on your honey moon I'd like to suggest you Villa il Poggiale that is a romantic B&B in Chianti set in a Renaissance Villa, and Romitorio di Serelle, a Chianti farmhouse set in a medieval hermitage.

I hope it helps. Come back any time :D
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Amalfi Coast

Thank you, Valentina. I really appreciate your recommendations.

I was wondering if I could also get your advice on another part of Italy - I will also be visiting Amalfi Coast. I have already figured out what I want to visit - Capri, Pompei, Herculanum, Naples and just driving down Amalfi Coast.

Where would you recommend I stay in order to be able to access all my desitations? Many sites recommends Sorrento and many Positano. As a result, I am torn between the two.

Thank you.



Well-known member
Where to stay between Sorrento and Positano

Dear Larisa,

we are specialized in Tuscany and we generally don't have many information about the rest of Italy. But in this case you were lucky, since my boyfriend is from Naples ;)

Sorrento is centrally located and well-connected by public transportation to other main destinations thanks to the Transvesuviana. On the other hand Positano is more fashionable, but you can have more trouble moving around by public transportation, both to get there and around.

So I suggest you stay in Sorrento, because it's going to be easier for moving around. In fact, I suggest you don't drive at all and use public transportation in the area. Traffic in Naples and in the Costiera Amalfitana (Amalfi Coast) is terrible and can be dangerous. I'm telling you this not to scare you, but because I've been there and that is how I've experienced it.

I hope these suggestions will help you deciding where to stay :D