Beach/pool stops for our kids in October

In the Cinque Terre, Monterosso has a small sandy beach. I have been to Lake Como many times and don't recall any beaches. The upscale hotels have pools. Lake Garda has some beaches. Small beaches in Amalfi Coast.
You can rent villas with a pool in Tuscany. I can't imagine how you'd travel , especially with kids, in Tuscan countryside without a car.
Contact Karin at Chianti and More for rentals in Florence and Chianti region.

This place just 5km out of Siena has 6 pools, including one with a current and a waterfall. We loved it. You would need a car for this part.

http://www.mulinodiquercegrossa.it/

Please add the order of your planned stops, presuming you have already made reservations. How are we to know if your hotels are in town or not? Tuscany has stellar beaches, but i am not sure where to fit them in yet.

We fly into Milan

2 days in Lake Como
1 day Sienna/ Civita
2 days Cinque Terra or Tuscany
3 day Sorrento
3 days Rome
3 days Venice

Thanks for the website but is there a link to book?

October weather might be beach weather, but I wouldn't count on it. Travelling further south won't change your odds appreciably. Amalfi and Cinque Terre don't seem kid-oriented to me, but I like the Lake Garda idea. You can hit a beach on the lake if you're lucky and also visit Sirmione and Gardaland (https://www.gardaland.it/en/ ) an amusement park and aquarium that is very popular with Italians. (see the Gardaland schedule for Oct. open days).

We stayed in an apt in lake como that slept 5 , had washing machine and was a few blocks from the free sand beach. Pm me if you want me to look up the information. It was handy to train station slso

We tried to do this too as we are headed to Italy with our four kids (7,10,13,15) this July. After exhaustive research and attempts, we have decided not to try to make the beach work (our west coast idea of a beach is very different than what is in Italy, for the most part) but we have added a 4 day stop in an Agriturismo in Umbria. We are staying at http://www.geniuslociumbria.com/ - I can let you know how it goes, but making the beach work on our trip between Venice and Rome just didn't pan out.

Good luck!

October can be lovely for Americans to go to the beach, but the Italians will number few, if any. We have been in the Cinque Terre/Liguria in October when the weather was great but the beaches officially closed. Doesn;t mean you cannot swim, but there will be no services by October. Check with any lodging regarding pools. I have seen many that shut down in September.

Aaron the link to book is under contacts. It's an e-mail.

We are taking our kids, ages 9, 14 and 16, to Italy in two weeks. We wanted a beach stop, too, and felt like Cinque Terre was too far to reach for only a two-night stay. We opted instead for Lake Garda. It has several nice beaches, including some with sand, and we will be taking the ferry around the lake to visit various towns such as Sirmoine with its castle, and we will take the cable car to the top of Mount Baldo in Malcesine.

There are beaches up and down the Tuscany coastline. Sicily has amazing beaches. My friends who live in Italy say there's nothing to compare to the beaches in Sicily.

I travel to Campania and Lazio every year in late Sept. early Oct. usually can swim off of Capri or Positano first week of October...but last year was very cold and stormy...so check weather up to the minute you leave and even then...I would not invest too much luggage space on swim stuff. one suit and flip flops that double as slippers for everyone.

Milan to Venice into Tuscany then Rome then Naples with a flight out of Rome or Naples makes the most sense. BUT...

If you already booked flights and Milan arrival and Venice departure are fixed...then try this:
Skip Como....go directly to Florence from Milan it is a fast train ride. 2 hours

Nights 1-3 Florence ( not sure why you are not seeing Sienna as a day trip from Florence?)
Nights 4-6 Rome high speed train from Florence in 1.5 hours)
Nights 7-9 Sorrento...1 day will be full of visiting Pompeii and you must go to the Naples Archeological Museum to fully appreciate Pompeii...IMHO
It is a long train ride from Naples to Venice about 5 hours or more...
Nights 10-13 in Venice fly home
This means 4 places instead of 6 that many folks have recommended...with 5 people ( 3 kids) that is a ton of places...Florence as a base and Sorrento as a base give you opportunity to see many places while staying put in the hotel each night.

I see the Como visit as out of the way since you are ending in Venice...I would spend more time in Campania which has beaches and a southern charm..

If you book an accomodation with swimming pool, don't forget to ask if the pool is still open in october as most close by the end of september.

October isn't beach time in Italy. Not even pool time, unless the pool is under a roof.

I would also love any recommendations on where else in our itinerary
would be a good place to get a hotel/house with a pool.

Aaron, I see that you have Sorrento on your itinerary? We stayed at Hotel Antiche Mura, Sorrento, in early October a few years back and their pool was still open. It was quite warm during the day during our stay but then again, every season is different so it could be a roll of the dice!

It's that roll of the dice which has me thinking that it may be safer not to book a location JUST for a beach or pool? Booking a hotel with a pool in a location you're already intending to stay will minimize the disappointment should Mother Nature decide to be cranky.