Italy Itinerary Suggestions (2 weeks)

Looks fine, I’d just work on fleshing out the Montalcino part, as those transfers and private day trips can be pricey, but you have tons of time to refine it. Monterosso to Rome is fairly easy by train but I’d definitely splash out to avoid the Florence to CT train.
There are much better beach locations than CT, but not as many with such excellent train service. Did you choose it for the hiking? Or just for coastal scenery?

Would love suggestions on alternate beach towns!

CT fit the bill with sandy/organized beach. Love the idea of hiking while there (we generally squeeze in hike or bike ride on our trips), but honestly it is not a must. I landed on it because I was having such trouble researching beach spots.

Private transfers will be expensive - especially over long distances - is there any reason you're aggressively avoiding the available train system? With the exception of Montalcino your destinations are all served well by trains. If you're happy with the cost to convenience ratio then that's fine - it's your trip.

You might look just further north of CT to towns like Sestri Levante or the smaller Moneglia. All these beach towns are connected by the old trails and the areas between them are protected. So walks in the wilderness with ocean views are standard and they are all connected by train so you can hike one way and take the train back to your town when you're done.
The section from Sestri Levante to Moneglia is a more challenging section: https://www.wikiloc.com/hiking-trails/moneglia-sestri-levante-81993367 but there are a lot of options.

If you do end up traveling by train to or past La Spezia/CT look for an "Intercity" train if you can find one. They let you reserves seats and even have first class. It's not much but it will only be as crowded as the number of seats.

Have a great trip,
=Tod

Do not mind train travel - like the private transfer option so we can do some stops in between and not worry about luggage. (ie stopping in Montapulciano on the way to Montalcino; San Grimingnoa on the way to Florence; Pisa on the way to Cinque Terre. We may end up shifting to train travel if we need to tighten the budget.

I will definitely research the beach alternatives you have listed, thank you!

Just some things to ponder—how up for a stop will you feel on arrival? I’ve had some lovely drivers on my travels, but you may or may not be up for that after an overnight flight, and your driver may or may not be the entertaining sort.
Other than Pisa, most places are pretty safe to leave your stuff in your car, but of course it’s better to do loops when you can just in case.
Luckily June is usually not terribly crowded on the coast, but I’d avoid Cinque Terre unless you especially wanted to see it and/or hike. The beach there is really not much to write home about, but I can’t think of any stellar ones that would not require a car .

All your destinations except for Montalcino are best reached by train.

I presume you are writing from North America. I also presume you are not old and are also in good shape (with a teenage girl, probably your daughter, and willing to hike at the 5 Terre). So my guess is that at home in North America you do drive a car, I can understand the reluctance to drive in cities like Rome or Florence, or even at the 5 Terre, where the train is a much better option, but why can’t you rent a car for the Val D’Orcia (Montalcino)? You could pick up a car at Avis-Budget in Chiusi, 200 yards from the train station, which is very close to the Val D’Orcia, keep it while there and return it in Chiusi or Siena. Keeping luggage in the trunk is not an issue if you visit those towns after dropping off your luggage at your accommodations. Montepulciano and Pienza are just minutes away, San Gimignano is also less than 1.5 hour drive from Montalcino.

Then from Chiusi or Siena, after returning the car, you can proceed the rest of your trip by train. Visiting Pisa with luggage on the way between Florence and the 5 Terre by train is not an issue either. You can leave your luggage at the Pisa Centrale station, which has a luggage storage (“Deposito Bagagli” in Italian), visit the city for a few hours, then retrieve your luggage at the end of your visit to proceed to Monterosso (or wherever on the Ligurian Riviera) by train.

A private drive from Rome to Montalcino, one way only, will cost you in excess of $500. Then while in Montalcino what are you going to do? You need a car to get around. It’s a rural area, and there are no taxicabs, so you need to prebook private transfers for each day trip, and each will cost you hundreds of euro.

Below are some transportation info resources.
Train schedules and prices:
www.trenitalia.com
Use Italian names for stations
FIUMICINO AEROPORTO
ROMA TERMINI
CHIUSI-CHIANCIANO
FIRENZE SANTA MARIA NOVELLA
PISA CENTRALE
MONTEROSSO

Rental car options:
www.autoeurope.com
If picking up in Chiusi, Avis-Budget is the only option.

Have you priced out all of these transfers? All the stops will add significantly to the cost if you use something like daytrip.com.
Who knows how much those prices will increase by June 2028.

I’m aware how much they cost. I’m aware how inflation works. We will also not need a car in Montalcino with what we have planned. We also do not want to be irresponsible and drive when we have had wine to drink. As I said nonnegotiable.

I’m simply asking if there are suggestions for alternate routes to what I have listed. Just want to get ideas to compare. Even other suggestions outside the Tuscan region.

Choose the Region you desire:
https://www.villagesitaly.com/regioni/tuscany/
https://borghipiubelliditalia.it/en/toscana/

If a rental car is non negotiable, take a train from Rome to Chiusi-Chianciano, then book a private car transfer to take you at the station and drive you to your accommodations.

There are several private drivers in the Montalcino area. Google “NCC Montalcino” and several options will come up. NCC stands for Noleggio Con Conducente (Car Hire with Driver) and is the official designation for private car transfers (limo type service) in Italy. If you book one based in Montalcino, it will probably be best. He can certainly pick you up at the Chiusi Chianciano Terme station. There are numerous trains from the Rome FIUMICINO AIRPORT to Chiusi-Chianciano T.. you will need to change trains at Roma Tiburtina.

Something else to consider could be Lake Garda. There are some lovely beach clubs and resort properties and some are well-served by public transportation. Sirmione could be one option. We spent a very nice relaxing day at a low-key beach club called Lido Galeazzi. Sirmione’s city center gets very crowded, but there are a lot of places to stay just outside of it that would be an easy walk or bus ride.

Lazise or Garda might be another to consider. Not accessible by train but it does have a ferry and bus.

We stayed on Desenzano and really loved it, but it did not have many close beach options. We took the train there easily to/from Verona.

Sirmione looks gorgeous! Thank you for the recommendation - I'll have to look into this further! I was thinking of coming up with an alternate itinerary that included Venice to give to my daughter/husband to get their input between the two and this would work beautifully with that.