First time trip Oct 2024 flight plan

I almost always try to use open jaws flights. It always saves time and sometimes money (and to me time is worth more than a small additional cost) I look at Skyscanner for flights and then book directly with the Airline. Unlike many in the US, I don't have alternate airports to look at for other cheaper/more convenient flight options as I fly out of Toronto. It looks like you are still undecided about where you want to go so maybe research a bit more before buying flights. In/out of Rome/Venice or vice versa is a popular option as it covers the typical first time itinerary (Rome-Florence-Venice) but everyone has their own preferences. Others may give you feedback about Cinque Terre at the end of October. Tuscany is beautiful in October. And personally not a fan of Milan unless heading to Piedmont wine region or the Italian lakes.

Fly into Rome and spend a couple of days there. Then catch the fast train up to Venice, come back to Florence and on over to the Cinque Terre (via La Spezia) from Florence. Then take a fast train through Rome to Naples. I'd go on to Sorrento from there--to the Amalfi Coast. Then back to Rome for the remainder of your time.

I would skip Milan as it's out of the way. Catch it your next trip on your way to Lake Como and the Alps.

Thanks daisyscan and David for your prompt responses.
The reason I mentioned Milan because I'm hoping to find more flights with less prices for the returning flight to SFO.
I really like David's suggestion, Google flights gave me better flight time and price for SFO-Rome round trip.
Since I'll visit CT, so I think I'd skip Amalfi. I'd like to spend a couple days in small hill towns, San Gimignano, or Voltera, or Orvieto, don't know yet , will seek your advice next. I'd really like to visit Alberobello area, but running out of days :-)
daisyscan raised the weather question for CT at third week of October, could other people please give me your experience.

Given the time of the year your trip is, I see an open jaw routing of in to Venice and home from Rome something to be considered.

Venice-Milan-CT-Florence-Naples-Rome. This puts you at CT in the earlier part of Oct., to improve your odds of better weather.

Depending on what you find for airfare you could do Venice-Milan-CT-Florence-Rome-Naples, but I suspect flying home from Rome may be cheaper, even when adding in the cost to get back to Rome from Naples.

We arrived in Monterosso 11/4/23 - it was raining lightly, but progressed to a torrential downpour by evening. Sun was out the next day, but violent waves pounded the shore for the next two days.

I believe all of the blue trails were closed at that point. They had also received rain late in October, which had resulted in a few of the blue trails being closed at that time.

We're were able to visit three villages and did the low hike through vineyards. It was a challenge finding dinner on a very quiet Monday evening,

With the surf so violent, no boats were in the water - we had hoped to hire a private boat to sail along the coast, which reportedly provides the best CT views.

I would suggest, if you have the most economical and convenient flights as round trip, landing and leaving IMMEDIATELY. You are already on the move, so why not save a complete hotel change and start off far away and work your way back?

Regarding October weather...no guarantee.... but I was staying in Chiavari (a bit North of Cinque Terre) for the entire month of October 2022 and it was beautiful...folks were still on the beach! Hoping for same weather luck this year...fingers crossed.

Have you considered flying into Milan and back from Naples? That would give you a fairly straight line of travel to avoid losing time back-tracking. Just food for thought.

Hi, I found good flights into Venice and out of Naples and would like your feedback for my draft plan. Hopefully, weather in CT second week of Oct will be less risky:-)
Thanks so much.
10/3: arrive in Venice 6:55pm
10/4,5,6: in Venice
10/7: train to Florence
10/8,9,10: in Florence with day trip to Siena
10/11: train to Pisa, store luggage for the day's visit, then go on to CT
10/12,13 : in CT, or should stay here for 3 days?
10/14: train CT to Orvieto. if transportation takes too long here, maybe skip Orvieto and visit 1 more day trip to San G. or Volterra from Florence
10/15: in Orvieto
10/16,17,18,19: Rome
10/20: train to Naples
10/21,22,23: in Naples with 1 day trip to Pompeii
10/24/ fly home at 12:35 pm

10/11: train to Pisa, store luggage for the day's visit, then go on to CT
10/12,13 : in CT, or should stay here for 3 days?

Yes, 3 nights (2.5 days) is the sweet spot for CT. 2.5 days gives you enough time thoroughly visit each town, to take the ferry to see the coast from the sea and to do some hiking between towns.

on 10/14 & 15 I'm not sure what you mean by "if transportation takes too long here, maybe skip Orvieto and visit 1 more day trip to San G. or Volterra from Florence" On the 14th if the transportation to Orvieto takes too long what will you do and where will you be on the 15th? IMO it's better to just go to Rome, put your bags away, and then do Orvieto as a daytrip from Rome. It's just a one hour or so train ride, lots of trains per day, and you can see everything there is to see in a half-day or so. If you love it stay longer in the day and catch a later train back, if not then leave earlier.

If this was my trip I'd redo 10/12-14 to stay in CT all 3 days since there's a lot to see in the area. Not just CT but Lerici, Portovenere, Santa Margherita Ligure, etc. (but skip Portofino). In October not sure how good the weather will be, but these days October seems to be the new September. Then I'd go down to Rome and do Orvieto as a daytrip as described above.

Also since you're 1st time travelers to Italy I'm going to recommend Sorrento over Naples. Some people love Naples but it's a gritty city with some not-so-nice parts, and while we didn't constantly feel like we were walking down a dark alley at nite it didn't give us the warm and fuzzy feeling that things are safe here. That's Sorrento. Perhaps see Naples on a daytrip from Sorrento to visit the archeological museum and have a great pizza. If your flight is 11:30am or later you can take a bus from Sorrento to the airport the day of your flight.

Thanks so much for your feedbacks.
Please check my new version:
10/3: arrive in Venice 6:55pm
10/4,5,6: in Venice - 3 days
10/7: train to Florence
10/8,9,10,11: 4 days in Florence incl 1 day trip to Siena and 1 day trip to San G. or any other good hill town
10/12: trans to Pisa, store luggage and spend the day visit Pisa , then go on to CT
10/13,14,15: in CT - 3 days
10/16: trans to Rome
10/17,18,19,20: Rome - 4 days
10/21: trans to Naples
10/22: Pompeii
10/23 or 10/24/ fly home from Naples
I'd really like to visit Alberobello 1 day and Matera 1 day instead of the 3 days in Tuscany area and Naples because I think this is also my last time to Italy due to my age, but don't know how to fit in.
Really like to get your feedbacks.
Thanks so much.

Hi,
I replaced CT with AC, which is closer to Naples, my return flight, and add 1 more day to the trip.
10/2: arrive in Venice 6:55pm
10/3,4,5: in Venice - 3 days
10/6: train to Florence
10/7,8,9,10: 4 days in Florence incl 1 day trip to Siena and 1 day trip to San G. or any other good hill town
10/11: trans to Rome
10/12,13,14,15: Rome - 4 days
10/16: trans to Bari, then Alberobello
10/17: in Alberobello 1 day
10/18: trans to Matera
10/19: in Matera 1 day
10/20: trans to Salerno
10/21: Pompeii day trip
10/22,23: Almafi coast day trip
10/24/ fly home from Naples
What's the weather and the crowd like CT in mid October vs AC during third week?
Is it easy to use train or bus from Bari-Alberobello-Matera-Salerno? or just taxi from Alberobello-Matera?
Is Salerno a good home base for Pompeii and AC, and close enough to bus or train to Naples for 12:35 flight?
Really appreciate your feedbacks so I can go ahead with booking.
Thanks so much.

Salerno is good as long as you know that the train trip to Pompeii can be direct to the farther station away from the front of the ruins, or involving a change to the commuter train to backtrack into Naples first. I am also unsure of the ferry availability in the end of October, I bet most likely they won't be running so you would be subject to buses, which aren't for the faint of stomach on the twisty roads. I would also, for your peace of mind, find out how much a driver would be to the Naples airport from Salerno, as there might be multiple legs of travel from Salerno to the airport unless you catch the airport bus (not even sure if it still is in existence?) to take the stress out of it.

I know that when I went to CT in the beginning of November it was rainy and gross (and I haven't taken the effort to go back to see it on a sunny day haha). You might have slightly better chances of nice weather on the AC.

Maybe do this so you’re in Naples the night before your flight.

10/20: trans to Salerno
10/21,22: Almafi coast day trip
10/23: trans to Naples, day trip to Pompeii
10/24/ fly home from Naples

It's always risky to traveling to the airport on the day of your outbound flight, whether by driver or train. The infrastructure in the area has been sadly neglected, and is very congested. Roads have traffic accidents, trains go on strike and have delays. I'd strongly advise being in your airport town the night before.
I agree, you don't need both the CT and Amalfi Coast, so you are wise choosing one. Southern Italy MAY have better weather on October, but again, check the ferry schedule .
You have obviously done a lot of research, and it's fun watching your plans evolve as plan in earnest.
Safe travels.

Thanks so much for your prompt responses which shed more light into my research and planning.
Matera to Salerno travels is much better to Sorrento , and Naples day trip to Pompeii seems easier to visit the archeology site compared to from Salerno. Therefore, I think Marco's suggestion may work best for us, who don't have prior experience in Italy.
Matera to Salerno and day trips to AC from here.
Then move to Naples to day trip to Pompeii and be there the night before the return flight home.
Do you think I get this right?

Or should I trans from Matera to Sorrento and day trips to AC and Pompeii from Sorrento
Then at the end of the last day trip, trans to Naples to fly back the next day.