Starting in Rome and ending in Venice through Tuscany


New member
We have planned this family vacation for so long and we are excited about our first trip to Italy.

Having spent 8 days between Barcelona and Athens, family of four - Two adults and two teenage girls will land in Rome on a Monday night in October. Have flights booked to return to the US on Tuesday the following week. So we have 8 nights / 7 days to spend in Italy. Below is our draft itinerary.

I have the following Questions:
1) Should we stay an extra night in Rome (Thursday night) and depart to Tuscany on Friday Morning?
Would miss a lot in Tuscany if we begin our trip to Tuscany until Friday?
2) If we leave Rome Thursday night, we still do not have a town where to stay on Saturday night. Can you give us a recommendation.

3) Sacrifice a night for Rome or for Tuscany?

Monday night till Thursday afternoon. Total two full days and a half to see key spots in Rome. Then pick up a rental car and head to Montepulciano on Thursday at 3PM.
Thursday night: Dinner and overnight at Montepulciano (have a hotel in town)
Friday:Sight see the town Friday morning. Then drive up to Pienza and Montalcino. Continue driving through the country roads and end up at Siena approximately in the evening.
Friday night: Spend the night at Siena (have a hotel near Il Campo)
Saturday day till noon or so: Sight see town center of Siena
Saturday PM: Drive up to SG?
Saturday Night: have no idea yet which town to spend the night. No hotel reservations. Any suggestions?
Sunday morning: Visit Florence for half a day
Sunday afternoon: drive to Venice
Sunday Night, Monday: Venice
Tuesday morning: depart to the US

Your advise is appreciated


The Tuscan Expert ;-)
Staff member
Ciao Titus,

I think your itinerary looks good, considering the whirlwind tour of Italy you're planning :) I'd generally recommend seeing less in order to see more - I think you'll be spending too much time in a car and not enough on the ground.
Just a morning in Florence? Can you skip Venice?? What time does your flight leave Rome on Tuesday? if it is really early morning, you might consider driving down from Venice on Monday and spending the last night in Rome so you won't be in a hurry to drive down.... when/what period are you coming?

So as far as your questions go, I'd go with what you have planned and leave Rome on Thursday and drive to Montepulciano, that way you can leave the following Montepulciano morning and start your tour through the Val d'Orcia to Pienza and Montalcino.

As far as Saturday night, I'd recommend staying at either Casolare di Libbiano or Palazzo Malaspina B&B - the first is near San Gimignano in the countryside, a beautiful B&B in a farmhouse while the other is in the charming medieval town of San Donato in Poggio. Both are good starting points to head into Florence the next day.

These are just my initial ideas - if you give me more feedback on when you're coming or whether you can change anything on the itinerary to slow down ;), I might be able to offer more suggestions! For example, drop Venice, spend more time in Florence and then also go see the Leaning Tower of Pisa which is in Tuscany ;-)


Well-known member
I just did Florence, Pisa and Rome in July. I recommend less time in Rome, and more time in Florence.
I wouldn't waste valuable time with the Vatican museum -- the crowds there made us miserable! We took an ancient Rome tour, which was AWESOME - it was a 5-hour tour with colosseum, Roman Forum, etc. You'd still have time to see the Pantheon, Piazza Novana, Trevi fountain, etc..

Half a day in Florence will only make you want MORE. Hotel Casci is wonderful -- a block from the Duomo, located in an old palace, and an outstanding breakfast (not just cappuccino and a roll, although they are available) and the people who run it are very friendly and speak English.


New member
Thanks Melany for your advise on Florence. I am leaning to spending less time in Rome and will consider spending a good day in Florence

Lourdez - Thanks. You are right, I need to give you additional data points. We return to the US from Venice. Flight leaves at 10:30 AM Tuesday October 08. In addition, I made some changes to our trip prior to arriving in Rome. As a result, we arrive in Rome Tuesday late night October 01. So we will begin our trip to Tuscany on Friday October 04.

Friday late afternoon drive to Montepulciano and overnight there
Saturday day drive through the Val d'Orcia, Pienza and Montalcino and overnight at Siena -
Sunday morning: drive up to Florence - spend all day here
I am still undecided whether to drive to Venice on Sunday afternoon or spend Sunday night in Florence proper or in a B&B near Florence?

Since we are leaving from Venice I figure we ought to have a taste of Venice. So even if we drive to Venice on Monday morning and overnite there, we would just have taset of it?

Tuesday morning: depart to the US from Venice


The Tuscan Expert ;-)
Staff member
Oh yes, knowing you're flying out of Venice definitely helps! :)
Also, that you're coming in early October also helps - weather should still be very good but also the big crowds of summer will start growing smaller. The Vatican museums seem to have gotten worse in how the handle visitors, according to Melany's feedback you hardly have any time at all to enjoy and see the Sistine Chapel. But if you can manage to fit it in, it would still be worthwhile.

The itinerary as you've modified it will work out well. Just keep in mind that you really are just tasting Italy in a week, since most people would dedicate at least 2 weeks to visit the same places you've included.

In order to not feel so rushed and see a little more of Florence, I'd definitely recommend you spend the night - you'll get to see the city in the evening and night, and then can head out to Venice the next day.
For lodging in Florence, take a look at

Remember to consider for Venice where/what to do with your car if you're intending on keeping it until you go to the airport on Tuesday morning... either stay on the land side of Venice and just take a train into the lagoon or drop off the car on Monday, stay in Venice proper but then arrange for a shuttle or taxi to the airport the next morning. You will get a good taste of Venice on that Monday as you'll have of Florence on Sunday.