Itinerary for September italy trip

The Milan station is huge. It’s also about the hottest place on the planet in late June, but I digress. I’d doubt that I could make a 6 minute connection without running, unless you can be assured that your ongoing train is on a very close platform to the one where you got off the prior train.

We’re going to Italy in September, too, but farther south. And we were in the Cinque Terre last year - really troubled by the massive crowds - way more than on our previous visit. I hope you enjoy the Cinque Terre, but be prepared for tons of other visitors. Restaurant reservations will be advisable, if not mandatory.

Welcome to the forum!
We need a bit more info to give the best advice.

Who is in your travel party? Are you experienced travelers?

Where are you looking for train tix?
Use the official train sites so you can see all of your options.
https://www.trenitalia.com/content/tcom/en.html
https://www.italotreno.it/en

Where exactly are you staying in Lake Como and in Cinque Terre? Which towns?
I think the trip from Dolomites to CT is going to be longer than you think.

As an experienced traveler I would not feel comfortable with a 6 min change- just can’t move that fast anymore!
If the connection is to a regional train and you miss it then you can take the next regional train with your ticket.
But I would look for a longer connection.

With dates and destinations we could help you figure that out.

The Dolomites are stunning! You will enjoy your stay in Kastelruth(Castelrotto in Italian.) Beautiful hiking with unbelievable views. You will enjoy Lake Como too, with it’s villages and views of the Alps. Then you will be dropped into the mobs and hordes of tourists in the Cinque Terre in a busy time of the year. Perhaps you should rethink the Cinque Terre until another trip at a less busy time. You could replace the Cinque Terre with the Piemonte, a beautiful nearby region filled with vineyards and charm.

Our travel party is two seniors, and two 35 year old woman. This will be our first trip to Italy and our previous other travel experience was to Ireland a few years ago. Our plans are to go to Lake Como on September 19, then Kastleruth, dolamites and then arrive at the Cinque Terre on September 27. We were planning on staying at Vernazza in the Cinque Terre for three nights. Do you think it will still be busy there at the end of September? We are planning on taking the trains for most of the trip but we were thinking of hiring a private driver for a few transfers. Any recommendations on how to find Private drivers. ? After our time in the Cinque Terre we are meeting up with friends and staying a week in Tuscany at a private estate. From there we are flying to Croatia for one week to Premosten. We are greatful for any advice and recommendations. Thanks

Certainly looks like your travel group enjoys the great outdoors, and you have selected some beautiful areas to explore. Must say that it is rare that we have posts from first time visitors to Italy that are not including any of Rome, Florence or Venice in their itineraries.
As for your initial question, personally I think that 4 people, including 2 seniors, with baggage, planning to make a 6-minute train connection at Milano Centrale is quite “pazzo”, meaning crazy. But, different strokes for different folks, right?

I don't see how you get from Lake Como to Kastleruth/Castelrotto or from there to Vernazza n 5-6 hours. Figure you'll use up most of a day getting from one to the other and don't try for tight train connections.

You are as likely to find mobs of tourists in the CT at the end of September as an earlier. It depends a lot on how many cruise ships are in nearby ports each day. OTOH, I believe that the better hiking is on trails that are not favored by the day-trippers and perhaps if you head out early and get back fairly late, you will miss most or all of them

don't see how you get from Lake Como to Kastleruth/Castelrotto or
from there to Vernazza n 5-6 hours.

Agree.

Bus from Castelrotto to Bolzano 45 min
Bolzano to Vernazza is at least 3 changes-
Best/shortest option I see on 9/27 is Fast train from Bolzano- 8:45 to Milano Centrale then change to IC to Levanto then change to Regional to Vernazza arriving at 3:15 for a total train trip of 6.5 hours - plus the time on bus from Castelrotto- IF bus runs that early in am to make that train in Bolzano.

Still not clear where in Como you plan to stay but assuming Varenna that trip is at least 2 changes, more likely 3 then the bus from Bolzano to Castelrotto makes the entire trip about 7 hours.

For private drivers here are 2 recommendations. They will be expensive given the distances you need to cover but with 4 travelers it might be worth it. Would certainly save time and wear and tear!

https://connectotransfers.com -- they do more than just airport transfers
www.mydaytrip.com

hey hey linda
your trip sounds great but.... wishing and hoping is great but reality of how far the places you want to be, the time it takes on a train, if a private driver $$$$$$$ one way and he's to get back to original departure spot.
like others mentioned, i think it's more hours on traveling days than you really think, plus timing of transfer is too short.
many people want to travel now days and get out of their cocoons after 2+ years, there doesn't seem to be shoulder seasons anymore. september/october is so so busy with harvest time/fall weather, many cruise ships with stops in cinque terre with thousands/hoardes of people as day trippers. crowded trains, restaurants, cafes, streets/alleys/stores/shops packed to the gills, it's butt to butt social distancing and all on time limits to get back on their ships before sailing away.
after these stops, enjoy your quiet time at friends estate, what part of tuscany, sit back & relax with a glass of wine and the beauty of the area, mingling, talking, having meals together.
then to beautiful croatia, we had a cruise stop at split and just loved that area what several hours we had there.
good luck on everything, have a great time and do come back to let us know how you did.
aloha

Travel time between locations as mentioned might not be realistic. Personally, I like to travel in one direction so going from Lake Como east to the Dolomites than back west to CT doesn't make sense.

As much as I've tried the Lake Como to CT doesn't work. I love both those places but for me it's one or the other as they are not easily connected. But if I had to ... I'd prefer - CT to Lake Como to Dolomites and fly home from Venice.

Dolomites in September might be chilly depending on when in September so I might fly into Venice... Dolomites, Lake Como then CT.

Thanks so much for all your advice. At this point we have some definites . Fly to Milan, September 18th . Take train to varenna for 4 nights. Head to kastleruth for 4 nights . After that we have 3 nights before we stay in Tuscany at Agrivilla pini for two nights. From there we meet our friends for a week in Tuscany approximately 40 miles from sienna and then we fly to split and stay at a house in Croatia for one more week. Any suggestions of what to do for the three nights between kastleruth and Tuscany? My daughter will spend those 3 days with us before they head off on there own to Croatia. When we were in Ireland we hired drivers 3 different days and found it very relaxing and lots of fun . That being said we are willing to spend the big bucks for one or two days . Appreciate all your thoughts .

I would spend those 3 nights in Florence. All of your other locations are lovely for sure but that would be a bit too much "relaxing" for me. I'd want to spend time in a city- see some art, churches, museums, history, etc.

It looks like Agrivilla Pini is near San Gimignanamo. How are you getting there? There is no train service.

Will you rent a car for your time in countryside 40 miles from Siena? How will you get to/from this villa? Where exactly this?

From where are you flying to Split? I assume Florence?

You've definitely got some transportation issues to work out.

Flights to Split might be hard to come by in the off season. We had to fly from Vienna to Split when we went the month of May pre-covid. I agree with staying in Florence ... it is a beautiful city with lots to do.