Family trip to Italy

Hi. Appreciate your informative explanation of places to visit. Could you suggest an itinerary for me and my family (mother, 2 sisters, 4 yr old and myself) from 8-26 June, starting from Rome? I plan to stay 4-5 days in Rome, 2-3 days in Siena, 2-3 days in Florence, a day trip to Pisa or should we stay a night, 3 days in Venice and 2days in Milan. I’m not sure of how to travel throughout italy. Should I drive to the various cities? This is my first time and I would really appreciate advice for travel route and accommodation etc. especially with my child. Hope you could help. Thanks



Hi Kavita, thanks for liking my blog an d for dropping me a note.

I think that you allocated a reasonable amount of time to the different cities you plan to visit, with enough time to enjoy them and to accommodate to the needs of a small child. Maybe you can consider spending a little more time in the Tuscany country side. Anyways, I’ll send you a mail tomorrow with the usual “must sees” in each one of the destinations you mention.
Concerning Pisa, it can be easily visited with a day trip from Florence, you may need an overnight stay only in case you decide to visit also Lucca (beautiful town, but not in your itinerary).
Concerning driving in Italy, the only place where a car could really be useful is Tuscany, all the other places can be easily (and conveniently) reached by train. Actually, you don’t want to have a car in Rome and Florence, since the city center is closed to private cars, and of course you don’t need it in Venice!
Concerning Milan (which is the town where I leave…), do you have any specific reason to spend there 2 days? Alternatively, you could try to spend one nigh on Como Lake, maybe Bellagio.
By the way, I’m I correct to assume that you will land in Rome and leave from Milan? This will have an impact on the logistics.
Last question, concerning accommodation: which kind of budget per day did you have in mind?
Just let me have these info (+ anything else that comes to your mind), so that I can fine tune my answer.
Hi JP,
I appreciate all your ideas. I thought I should enlighten you with a spreadsheet of my holiday plans. I found great joy in planning and mapping out the route of my journey through your wonderful picturesque country. Btw, we visit italy to celebrate my birthday in June! What else could I ask for.
This is the highlights, my detailed spreadsheet and word document analyses routes, times, sights, tours, distances etc… You will be impressed. I’ve learnt so much about italy in the one week of study. Thanks to you!
8-12 June:airport transfer $50-60 euro. Rome apt at via goito. Rome private tours Sylvia 3, 3 hr days at eur$175 per tour. Dinners, lunches on spreadsheet (tbc).
Rome-montalcino (M)
Pick car from Roma termini at 11am 12 June.
3hr scenic drive to M.
12-15 June (Siena,chianti,) agristurismo in M-3 nights, Brunello wines.
15june- drive from M to Florence (2hr)
Leave car at public car park near at (Borgia allegri, Firenze)
15/16 June drive to Pisa (1 hr) for day trip or around the countryside of Florence. Return car by 1700 hr 16 June.
Florence tour 17, 18 June mornings. tours 35 euro pp( min 5, max10).
19 June at 12.30pm– train to Venice
Reach at 2.30pm Santa Lucia train station, vaporetta water (taxi) to hotel palazzo.
20,21 June- private tour of doge’s palace, basilica, grand canal, gondola ride etc 2 mornings 10/11-1 pm(2-3 hrs)
22 June- Venice to cadenabbia, como. checkout time? Still deciding.
TRAIN OR TAXI? Or drive?
It’s a long journey. Train toMilan-2hr 30 min, taxi from Milan euro $170 tocadenabbia.22-25 June- Cadenabbia, lake Como.
3 nights in a historical mansion with a pool.

June 25-26 Milan – hotel?

26 checkout- shuttle to airport? Check with hotel or apt.

So thought this was a more appropriate plan to spend quality time in places I would prefer.
I would spend some time shopping too so I’ll take some time for that activity too. Any preferred places in Milan?
I appreciate all your efforts. When you are in singapore I’ll do the same. If you are in the area pls let me know; italy or singapore.
Hi Kavita, apologies for the late reply. You’re right, I’m impressed! I think you gained a really good level of understanding of how to plan a trip to Italy!

Some tips:
– You are travelling with your very young daughter: try to add moments she can enjoy as much as you do. Rome has a lot of parks, such as Villa Borghese, where to have he playing and relaxing. Bring her on top of Altare della Patria (the “type writer” in Piazza Venezia) for nice sights on Rome; there are short cruises on the Tiber river that she would enjoy as well. One wonderful place, that you could visit the day you rent a car, is wonderfull Villa D’Este in Tivoli ( it’s a renaissance park with dozens of fantastic fountains, 1 hour from Rome. My son loves it!
– Mind the distances: actually your apartment is a little far from the center of town, so plan your visits accordingly (you won’t be able to come back to your apartment for resting at mid day – laying down in a park could be an option. Actually, when yo visit the Roman Forum, consider that the nice part is not the one you see from Fori Imperiali avenue, but the garden on top of it (“orti farnesiani”), accessible with the same ticket. Again, nice place to rest and to let your little girl relax and play
– DO RESERVE Colosseum and Vatican museum visits! Queues are terrible
– Here is a great resource for travelling with kids in Italy:
– Shopping in Milan: for massive, cheap shopping, consider spending a day in a designer outlet such as Serravalle Scrivia ( or Fox Town, which is actually in Swiss, just after the border ( They both organize shuttle from Milan.
– You don’t (necessarily) need to take a taxi to Cadenabbia: take there is a train from Milan to Como (one hour) and then the Ferry Boat, depending if you are full of suitcases
– 3 days on Como lake may be a bit too much, I would spend 2 days there, and one more day in Tuscany
– Travel light! June is warm in Italy, you don’t need to bring too many things (and you need free space for your souvenirs!)
– Tuscany: there are tons of things to see, and Val D’Orcia is beautiful. Have a look at my many posts (just published a new one on Florence), and get back to me if you need additional infos. Consider sleeping in a castle (there’s a post about it), nice experience for your kid. Try Castello di Spedaletto, it features also a pool, good for your daughter (there a post about it)
– Venice: have a look at my “Venice with kids” post.
Write me back if you need more infos.


Would you like a personalized Italian trip advice? Just go to my page “Free Travel Advice“!


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