Late September - Early October Italy Trip Recommendations

Have you ruled out using a car? I don't know the Dolomites area or the Lakes areas so cannot advise on comparison. I do however think you should look carefully at timing for your trip. It may be a little tight for all on your list. You could fly into Milan, take train immediately to Venice. How many days did you want to spend there? If Tuscany in the middle is a must too, then your time is getting pretty short since you have to then get to the AC and then get back to Milan on your next to last day. Twelve nights is a great amount of time(!), but you still have to use it well. How much time did you want on the Amalfi Coast, and what all did you have on your list for there?
If you have any of those questions answered already, let us know, but otherwise I'd just spend a bit more time mulling over you possibilities and fleshing it out. I'm into scenery too and often plan hiking trips--you still get plenty of cultural enrichment, so no worries about that

we aren't necessarily against using a car, but didn't know how big of a must it was. we are hoping for 2-3 days in each place, but getting back to Milan in time for our flight might prove to be difficult. I want mu husband to see as much as we can (I've been to Italy once before and hit most of the big touristy spots) but I also want to experience some new places and don't want to feel rushed! Feeling very torn on what is "worth it" and what isnt.

hey hey hannah
is this trip like next month???
sept/oct is busy months and not shoulder season anymore. its harvest time/festivals all over the country. everywhere you are hoping to go and see will have many many people wanting to see and do the same thing as you and husband want.
check out lake garda, we stayed in bardolino right on the lake, early oct for annual wine festival. small villages around the lake, boat rides across the lake or up to top and back,
duetigarage.com
due a guided tour of lake with a guide driver
lakegardatravel.net
read about different towns, things to see and do, tours with getyourguide
why not give milan a chance to visit, plus lots of fashion is here
veloleo.com
sightseeing tour in a rickshaw
saveur.com
milan being most underated food city, many dishes are made with rice since it's a rice growing region
pasticceriamarchesi.com
find this bakery/candy shop sit and enjoy
tripsavvy.com/ galleria vittorio emanuele II
bbc.com/ travel milan italy's lost city of canals
wheremilan.com
automotive museum collection (alfa romero museum right outside of town)
aloha

Hopefully others will chime in on the Dolomites, but I would think very hard about moving so much. A few days is fine for Venice--few give it more than that. A few days is fine for one place in Tuscany (btw, a car is pretty much a must for the rural hill town experience in Tuscany), but I would definitely not travel all the way to the Amalfi coast to spend anything less than three full days (four nights). That goes double if you want to do hiking, an island day trip, see Pompeii.
When you come up with an itinerary, be sure to look at the actual train times (write them on the itinerary!) and build in the time to check in/out, get to train stations, plus a little fudge room for getting lost (we all do it). Even after many trips, I still write it out day by day as that is the only way I can visualize my time. If I see a lot of travel time, I know I need to cut back on something.
I'd much rather skip something than rush through something and feel shortchanged and exhausted. You can always save the Amalfi Coast for a future trip--there is lovely scenery in the north, too. The only mistake travelers really seem to make is rushing. I would try to make the most of a good fare to Milan, good luck!

Our family of four (including our 20 and 22 year old daughter and son) spent 14 nights in Italy earlier this year. We stayed in 4 different cities and even our “kids” said they would have preferred to spend a longer time in fewer places. I suggest choosing 3 places at the most. We used the high speed trains and loved it, but travel consumes a day; especially considering some of the distances you are looking to cover. I agree with the other post that suggested going to Venice the first day, but take into account some things. Are you staying on the island (which I recommend)? If you fly into Malpensa, after navigating customs (which was not a hassle but the lines were LONG) you are looking at a roughly 1/2 hour train from the airport to Milano Centrale, then you will get on another train to Venice and you are dealing with your luggage as well. We limited ourselves to one carry on suitcase and one back pack per person. Frankly, it’s easy, but after a long haul flight to me, it would be a lot. Then, if you are staying on the island, you have the transfer from the train to what was, when we were there, very full vaporettos; unless you are willing to pay handsomely for a water taxi. Regardless of what you do, you will be in Italy which is one of the most incredible countries I have visited and will likely have a wonderful experience that will simply inspire you to plan your next trip.

If you’re dead set on going to the Amalfi Coast then I highly suggest paying the change fee/fair difference to fly in or out of Naples for that leg of your trip. By the time you pay for train tickets and private transfer to get to the Amalfi coast you’re going to pay that much anyway. Save yourself the time.

That being said, as others have said this is still high travel season. I am going during your same time frame and have been planning for a year. Pickings are fairly slim on the Amalfi coast. All of my usual places are booked. The Dolomites are very worth getting a car and going there. You could stay in Ortisei and hike Seceda one day and Alpe di Siuisi another.

Can you change flights at all?
Would make a lot more sense to fly in to or out of Naples given your need to see Amalfi coast. That adds a whole lot of travel time on a rather short trip.

Honestly if you do have to keep flights in/out of Milan I would drop Amalfi this trip.
( a 2 night stay anywhere is really just 1.5 days, you lose at least a half a day when you change location)

Fly to MIlan
Go straight to:
Dolomites or Lake Como or Lake Garda or Lake Maggiore 3 nights (I'd pick one of the lakes, less travel time)
Venice 3 nights
Tuscany 4 nights- you will need a car unless you plan to stay in Florence and day trip
Back to Milan - 2 nights
Fly home

If Amalfi is a MUST then you might check into flying from Milan to Naples and start there, working your way north.

After reading these comments, perhaps your Husband may see that adding the Amalfi Coast doesn’t work in the number of days you have. Save it for a trip focused on Southern Italy.

We land in Milan Sept 14, leave from Firenza Oct 4.

1) Select your cities right away. STRONGLY advise sticking with Milan, Venice, Dolomites ONLY. Maybe Tuscany. other cities: Ravenna (mosaics, Byzantine empire in Italy), Bologna (first university), Siena, Pisa, Firenza, Lake Como, Turin, Trieste. There are so many places in the Milan/Venice area that you can easily fill out 4-5 stops (which is what I would recommend)

2) Here is our trip:
3 nights Milan, 2 nights Ravenna, 2 nights Padova, 5 nights Turin (Salone del Gusto food and wine festival 9/22-9/26), Pisa 2 nights, Siena 2 nights, Firenza 4 nights and flight home

3) You need to pick out cities and get your accomodations immediately, unless your budget is a large one.

With a month to go in the busy season, is there a way you can delay or reschedule this trip? We started planning in May, and had all of our accommodations by June.

hey hey hannah
remember that check in to hotels are 2-4pm unless you have early checkin and checkout is 10-11am. few people ask what to do , rent hotel night before and inform you're coming next day or rent extra night departure day. ask if they have luggage hold, most do but make sure.
i would have you and your husband look at italian riviera to cinque terre for a coastal city to look at. much closer than amalfi and the time it takes for traveling. as paul says, if this trip is next month, you have to have a bigger budget with slim pickens, hoping not, for accomodations, train travel costs.
so many gorgeous places to see besides the ones that are always mentioned here.
@paul love your trip, sure you did lots of planning and it shows. we went to wine festival in bardolino on lake garda few years back and it was FABULOUS, go and enjoy
aloha

Princess: Our good friend of 40 years suggested the Salone del Gusto, and it looks like great fun.

One thing about Milan: Apparently the early evening custom of the apertivo includes a light buffet in many of the central city bars. We will do that.

My wife read a wonderful history of medieval life and I am almost done. Of course, much involves N Italy. It greatly helps to understand the history of the area. We are really looking forward to Ravenna.

Just a heads up, the last week in September is Fashion Week in Milan, so make reservations ahead of time.

After reading responses and truly looking at travel times between destinations, we think we are going to do Venice, Tuscany, Cinque de Terre and have a night or two buffer on either end of our trip in Milan (with maybe a day trip to Lake Como). Thank you all for your help! If anyone has recommendations for the listed locations please feel free to chime in.

You can get around that and maximize your time by heading off to CT or Venice on arrival. Once you have the Tuscany part a little further along, we can offer transport tips.

Three paths as options…

Option 1. Train Milan to Venice. 3 nites.

Flight Venice to Naples. 4 nites.

Train Naples to Florence (Tuscany). 4nights.

Train Florence to Milan. 1 nite.

Option 2. Flight Milan to Naples 4 Nites.

(Plus is you’re already at the airport. Minus continued travel, it will take time after flight to reach either Sorrento or the Amalfi coast.

Train Naples to Florence. 4 nites.

Train Florence to Milan. 1 nite.

Option 3. This one does not include the Amalfi coast, but cuts total travel time substantially.

Train Milan to Peschiera del Garda. 4 nites.
( ferries around the lake with many villages and walks/hikes) Verona is a 15 min train ride away.
Train Peschiera to Venice. 3 nites.
Train Venice to Florence. 4 nites.
Train Florence to Milan. 1 nite.

These all keep you on a circular path.

Edit: look at Ryan Air, Wizz Air and Easyjet for flights. Check carefully on a airlines baggage requirements, boarding pass and your arrival time for flights.

Just to reinforce the good advice you are getting, skip the Dolomites for two reasons: by late Sept the weather is getting undependable and it is just not worth it for two nights. Spend 4 or more to make the journey worthwhile and to ensure you can dodge a bad weather spell.

Revised trip sounds more do-able. Now you need to get busy finding accommodations.

I would spend 2 nights in Milan, take the short train ride to lake como, 2 nights. Train to Venice, 2 nights. Train to Orvieto (hill town in Umbria that is fantastic and on the main train line) 1 night. High speed train to Naples then the local train to Sorrento. Spend the rest of your time on the Almafi coast ( that would be my favorite area). Take high speed train from Naples back to Milan.

hey hey hannah
what are your dates for this trip, how many, budget, where exactly in tuscany and cinque terre, any do's and dont's about hotels ( bed size, mobility issues needing a lift/elevator, look at cancellation policies. your ending city should be milan so you are close to airport with worrying about train issues.
@paul
a customer from northern italy told us about festa dell uva on lake garda in bardolino. booked car and hotel at hotel nettuno on the lake. we arrived venice from SFO saturday, up early with rental car near train station and off we went.
about 2 hours, parked in front of hotel and the party started, last day of festival with fireworks over the lake till about midnight. we are early risers but not this morning. the maids had to wake us up at noon to get out!! LOL s_ _t, shower and shave and out the door in 30 minutes, we laugh till this day. back at venice with our bardolino wino to celebrate in our apartment with chacuterie tray. always an adventure.
another adventure was a prosecco tour with private guide through the gorgeous hills above venice. another fun time.
hope to hear back fro poster for dates to help them out.
aloha

Here's another option. I did this trip last fall: Flew into Venice (3 nights) train to Florence (3 nights) train to Pisa (quick stop to see the tower) then train to Cinque Terre (2 nights) train to Milan (2 nights). It was a whirlwind trip and physically demanding hauling our luggage up and down steps at each train station. My friend and I decided it was too much to do in one trip. We head back with our husbands in October and are doing Venice-Florence. We'll go back to do Cinque Terre - Milan another time. So, you could replace Amalfi Coast with Cinque Terre for a similar environment and views. I've done Rome - Sorrento - Amalfi Coast - Pompeii which makes a nice trip. If you're going to be at Amalfi you'd want to take advantage of seeing Sorrento, Isle of Capri, and Pompeii while you're there. I'd make that a separate trip.