10 - 11 Days in Tuscany & nearby - Planned itinerary


New member
Need your help please...I'm planning my 30th anniversary in October 10'.

Want to visit in 10-12 nights: Cinque Terre, Florence, Pisa, Lucca, Sienna + a few Tuscan Hill towns. How would you organize it in terms of night stays? What hill towns would you recommend? What itinerary would you follow?

Thank you!


Well-known member
10-11 Days Holiday in Tuscany

Dear R2RO,

first of all, let me make my best wishes for your anniversary :D

You intend to visit many beautiful places and cities in Tuscany. I personally suggest you plan your stay as follows:

3 days/2 nights in Cinque Terre - you have enough time to visit all small towns of Cinque Terre and enjoying the seaside. For more information on what to see you can read our post Weekend at Cinque Terre.

5 days/4 nights in Florence - it's a good base for day-trips to Pisa and Lucca. You also have time to visit Florence and its major museums and monuments. I suggest you book tickets for Uffizi Gallery and Academy Gallery in advance. I also recommend you visit most of Florence churches (Santa Maria Novella, Santa Croce and San Marco), because they really deserve a visit.

4 days/3 nights in Chianti - the Chianti region is one of the most beautiful region in Tuscany. There many places to see and things to do. I suggest you stay closer to Siena so that you can easily visit it and then go around Chianti. I also recommend you visit San Gimignano and Monteriggioni, two beautiful medieval towns. In Chianti you can also enjoy some wine tastings. For more suggestions you can read the article Discover Chianti.

If you intend heading to Rome, and since you have 2 days left, I strongly suggest you discover Maremma, in southern Tuscany. I personally love it :D. It's the ideal place to relax and experience the other side of Tuscany.

In this forum you can also find more suggestions and ideas to plan your holiday in Tuscany.

I hope this helps and don't hesitate to ask any other question


New member
Hola Valentina:

Thank you so much for your advise.

This is what I have been thinking:

Fly into Pisa and stay there for 1 night.
Train to Cinque Terre - 2 nights
Train to Florence (Stop in Lucca just to visit) - Stay 3 nights
Rent a car and drive to Siena with stops in San Gimignano - stay 2 nights in Siena
Visit San Galgano and drive to Montalcino - stay 2 nights
Visit Montepulciano and drive to Cortona - stay 1 night
Drive to Florence - return home

What do you think?

Grazie Mille!!!



The Tuscan Expert ;-)
Staff member
ciao R2R0,

Your itinerary as you've planned it also works out really well, it sounds like a good plan to see Siena and the area to the south of it. You can include Chianti if you wish it on any day you're in Florence or Siena as a short day trip.

San Galgano is beautiful so I highly support your decision to include it! :)

Enjoy planning the anniversary trip, it sounds like it will be wonderful!


Well-known member
Plan for 10 - 11 Days in Tuscany

Dear R2R0,

I agree with Lourdes. The itinerary you planned works really well :D

I also think that San Galgano is a great choice. It's really beautiful and magic.

Since you are at the border with Maremma, I suggest you find the time to visit the city of Massa Marittima. It has a beautiful marble dome and great landscapes. Also Monticiano and Roccastrada deserve a visit.

I'm sure you'll enjoy your trip!

Don't hesitate to ask any further question :D


New member
Similar trip with a few extra days

a 25th anniversary, we will arrive in Florence September 25 and leave October 10th.

We want to stay in Florence 4 nights. Travel the countryside 7 days and end our trip in Cinque Terre for a few days.

I was thinking to rent a car only for the country side. Staying in Montepulciano
and just outside of Siena. Then day trips from those two places.

The above is helpful. Can you expand for someone with more time?


The Tuscan Expert ;-)
Staff member
sounds like a wonderful trip!

Ciao szarate,

A 25th anniversary celebration in Tuscany sounds wonderfully romantic, I am sure you will both love it!!

Have you been to Italy before? I think the plan you have of where to stay for most of your vacation already sounds really good, I endorse the 4 nights in Florence so that you have enough time to enjoy it going at a good pace rather than trying to cram everything into less time. There is lots to see in Florence - from the cathedral, baptistery and bell tower (I suggest a climb up to the dome or up the bell tower, you get an amazing view of Florence from there - don't do it the first day, but rather after you've been around sightseeing at least a day so that you can enjoy picking out where you've already been, it is a lot of fun!), Piazza della Signoria, the Palazzo Vecchio, the Uffizi and Accademia as well as all the churches -- there is a lot to see and you also want to take the time to enjoy your meals, eat lots of gelato and enjoy being in Florence for such a special occasion.

You definitely don't need a car while in Florence but it would be really convenient once you leave into Tuscany - it would give you the freedom to move around as you please and not depend on bus schedules -- although there are some places easily reachable by train and you could do those before you get the car, such as Pisa or Lucca.

The 7 days in Tuscany could be divided between a few days in the Chianti area (2-3 days) so that you can visit the hilltowns in Chianti and do wine tastings. You should also visit San Gimignano. This is all in the area between Florence and Siena.

The other 3-4 days you should move further south, to below Siena. If you stay in Montepulciano you can easily visit the Valdorcia towns on one day, Cortona and Sansepolcro on another, Arezzo as well. Somewhere in between visit Siena too of course!

You could head west toward the seaside for at least 2-3 days in the Maremma area near Grosseto before going up to Cinque Terre (2 days) which is no longer Tuscany but Liguria.
The reason I say this is so that you can enjoy the flat sandy beaches and beautiful wild landscape that Tuscany offers in this area. There are wonderful wine routes here and the "cities of tufo", the hilltowns sitting and carved into the tuft rock of the area as well as the beautiful National Park of the Maremma along the coast.
The Cinque Terre (literally a translation of "five lands") are on the rocky cliffs right on the water, no sandy beaches aside from a stretch in Monterosso and are very romantic but also expect crowds. They are no longer a "secret" and so many people go there sometimes you walk in line along the trails.

Hope you're enjoying planning your trip - let me know if you want any additional ideas!


New member
szarate continued

OK Thinking 25-27th in florence. 28-30 San Gimignano. Oct 1 - 3 Montepulciano. 5-6 Maremma (?) And 7-9 Cinque Terre. Fly out on the 10th from Florence. Is this too much for the time? Obviously we will be making all the day trips as mentioned before. Can we really do both Maremma and Cinque Terre comfortable?

Also do you have an opinion of Hotel Pescille outside of San Gimignano?


Well-known member
10-11 days in Tuscany

Dear szarate,

I think you have a good plan :D

Although I noticed that you are missing October 4th in your planning. Does it mean that you are going to stay in Maremma from October 4th to 6th?

Anyway I would like to suggest you spend at least 3 days in Maremma, because it's really worth visiting. I would say stay there from October 4th to 7th and then leave to Cinque Terre. For a special day out in Maremma I strongly suggest you go to Saturnia thermal baths and enjoy a full day of relax.

Driving from Grosseto to Rapallo (Cinque Terre) is about 3 hours and you can easily do it in one day.

Regarding spending the last night in Cinque Terre it depends from your flight schedule. At what time is your flight? If it's in the morning it's probably better if you spend your last night in Florence.

I'm sorry to say that I don't know anything about Hotel Pescille near San Gimignano. Here you can find a list to accommodations in San Gimignano, if you haven't booked the hotel yet.

Well, I hope these suggestions helped you planning your holiday in Tuscany :D