Northern Italy and Tuscany

Could you add numbers of days to each stop? (I realize you say 3-5, but it helps to visualize a trip if that detail is explicit--for example, are you staying in Paris 3-5 days twice, that part is not clear?)

Notes about Cinque Terre versus coastal Tuscany: I vastly prefer the Maremma coast, but Giglio might be too quiet in October. If you don't mind that, no worries--just something to consider. In October, you can get rain in CT, which makes flexibility in your schedule a plus.

No train to the Dolomites. Bus, car. Amazing
mountains! Culture is a mixture of Italian and Austrian. Consider staying in Ortisei at the wonderful family owned and run Hotel Grones. We drove there via Lake Garda.
Note: Florence is in Tuscany.
After several nights in Florence, rent a car and go to a Tuscan village or town. Stay there at least five nights. We usually stay a week.
It is better to calculate time by nights, not days.
Example: Three nights = 2 days
Your title for this post says Northern Italy and Tuscany which is a good focus. Then you add Sorrento and the Amalfi Coast which are in Southern Italy. We didn’t go south of Rome until our 8th trip to Italy and have seen a lot of the areas in the south including Sicily, Puglia, Sorrento. I suggest taking your nights given to the Amalfi Coast and Sorrento to the North of Italy itinerary. Then give the South of Italy more time on a future trip. You also had skipped Naples. Lots more to see in the south next trip!

Thank you for your replies.

Arriving in Paris Aug 31 - Sept 3
Milan Sept 3 - 6
Venice Sept 6-10
Rome Sept 10-16
Amalfi Praiano Sept 16-21
Sorrento 21-23 (visit Pompi Naples)
Florence Sept 23-28
Tuscany (Pienza) Sept 28-Oct 2
Cinque Terre Oct 2-6 take train back to Milan
Fly to Paris Oct 7 fly home 10th

Can we take the train from Milan to Verona and car, bus or taxi to Bolzano?

Arriving in Paris Aug 31 - Sept 3 Milan Sept 3 - 6 Venice Sept 6-10
Rome Sept 10-16 Amalfi Praiano Sept 16-21 Sorrento 21-23 (visit
Pompi Naples) Florence Sept 23-28 Tuscany (Pienza) Sept 28-Oct 2
Cinque Terre Oct 2-6 take train back to Milan Fly to Paris Oct 7 fly
home 10th Can we take the train from Milan to Verona and car, bus or
taxi to Bolzano?

Thank you for adding that detail!
I am not familiar with the Dolomites, so I'll have to leave that to others. I think with the amount of time you have, the lakes would be a better fit than the mountains, but if you get the transport sorted, it could work for a brief peek.
Now that I see it is earlier in October, I would feel less nervous about rain in Cinque Terre (of course one never knows, but early October is less risky than mid to late October). I am pretty hard core about avoiding crowds, so I always support alternatives to Cinque Terre. If you get the urge to swap for Maremma, feel free to ask questions.

You could take the train Verona to Bolzano, then other destination(s) by bus.

As to the Dolomites and ease of access, Bolzano is an excellent jumping off point so yes, take the train there then go on to the Val Gardena where things are still open and active in Sept. (I recommend earlier rather than later in the month, though. By early October last year it was getting pretty quiet and some buses stopped running.)

We always take a taxi from Bolzano these days (about Euro 90 to Ortisei last year) but there is a bus. LMK if you seriously need a recommendation on a taxi company.

Don’t go if you don’t have at least 4 nights to spend. It’s a bit of a journey to get to and from and no one I’ve met ever said they wish they’d spent less time!

Thanks for all the great advice. I think I have it figured out less time in Milan and instead go to the Dolomites. Hotel Grones is sold out unfortunately but looks like there are a lot of other places. Beautiful area. We are also going to spend more time in Tuscany outside of Florence and visit Maremma instead of Cinque Terre. We have rented a B&B in Pienza out in the beautiful countryside and will rent a car. When I said northern Italy that was the only part of the trip I needed direction on. Rome and Amalfi Coast are set along with Florence. We will do some side trips out of those areas. There is never enough time but a trip back hopefully to finish the southern part of Italy. How about taking a ferry to I sola del Giglio? I am assuming if I extend our stay in the Tuscany area like Pienza we can travel to the Maremma area from there it appears to be a little over an hour drive. Thanks again!

I would stay somewhere in the Maremma after Pienza. Ferries to Giglio leave from Porto Santo Stefano. Porto Ercole is cute, but I liked Orbetello because it was close to the mainland, so I could do day trips in either direction without so much driving. Google Maps says it is 15 minutes from Orbetello to Porto Santo Stefano, but I recall it feeling much longer--the road is very curvy.
https://www.giglioinfo.it/giglio-island/isola-del-giglio-ferries.php
There are plenty of options on the mainland as well--Pitigliano is gorgeous (be sure to check out the vie cave near Sovana/Sorano). Massa Marittima is charming. Many people go ga-ga over Saturnia hots prings, but it was too crowded for me. Maybe you could luck out in October.
If you were going to Cinque Terre for hiking, the hiking in Ucellina park is marvelous.

There’s a train to Bolzano and then a bus to Kastelruth. It looks like about 4 hr 30 minutes from Venice. We’re going there by train in October for 3 nights. See https://www.dolomites.org/alpe-di-siusi-seiser-alm/ for info on what you might like to do. We plan to take the gondola and lifts up and walk / hike in the upper meadows if the weather is halfway nice. We’re also going to Lake Como and Lake Maggiore each for 3 nights. Trains from each place is not direct but at least I won’t have to drive and worry about parking.
I use Google maps to get an idea of what trains & buses to take but it’s too early to book. Check out Sudtirol Alto Adige bus pass for free train and bus transport in the Dolomite area if you’re staying in Kastelruth. Our hotel offers it as do most others.

We are planning to stay in Bolzano. There are a number of trains going from Milan to Bolzano each day. I think we need to switch trains in Verona . I need to do some more checking. But since we only have 2 full days in the Dolomites I thought we could base in Bolzano and take the Gondola and or bus to get further into the Dolomites. We to to Venice next via train. Thanks for all the information I will check it out. To an earlier post we are skipping Cinque and spending more time in the Tuscany area and we will plan on also going to the Maremma.

We are landing in Milan at the Malpensa Airport at 1:30 on Sept 3rd. How do we get to the Porta Garibaldi Train Station from the airport and is two hours enough time to get from the airport to Porta Garibaldi? Thank you.

I'm not sure about the Florence to Tuscany and Tuscany to CT.... Tuscany is a region and Florence and. CT are towns in Tuscany. I was very disappointed in CT. I recommend going for 2 -3 nights max. Then return if you want.
Have a wonderful trip

Lorie

Your itinerary looks a lot like the one I just did with my wife for our 30th. We share your enthusiasm for getting a lot of places out of a trip.

We did 2 nights in Bellagio, and we were absolutely blown away by the scenic beauty that's the combo of Alpine mountains next to water. Sat for hours just gazing at the vista. The Dolomites also look wonderful, but without the water. Depends if you'd rather hike, or chill out drinking spritzes and renting a boat for a little cruise.

We had 2 nights in Sorrento, 1 night on Capri, then 2 on the Amalfi Coast. All were lovely, but Capri and the Amalfi Coast are simply jaw-dropping. Sorrento has nice views but was mainly useful for easy access by train to Pompeii. The pebble beaches are wonderful, and our hotel pool was brilliant too, but both lose their appeal quickly once the sun gets behind the mountains after 4 or so, probably earlier in October. Capri's the only place on the southern coast where you see the sunset.