First Timers in Italy in September

Positano is the opposite direction from Rome if Florence/Tuscany is next

And why in the world would you want to drive there?

The rest of itinerary is fine

Assuming you will use trains for most but Tuscany really needs a car ( not Florence)
Nor would you need or want a car in CT, Lake Como or Venice
Just an expensive headache.

Who is “we” and what time if year is this trip?
Helps if we have more info

Hi Kim -
The order of your trip looks good but yes, do remember that your travel days only count as partial days. In other words, 2 nights at Lake Como is 1.5 days and not 2, and you can't rely of the weather to cooperate for photos on that one full day. 4 nights is 3;5 in Venice; 3 nights in the CT is 2. 5 days. Oh, and please don't stay in La Spezia; stay in one of the 5 CT villages.

This concerns me:

My goal is to drive down to Positano for the day after Rome.

Positano is a long drive from Rome, especially if you intend to spend that night in Florence, You will spend much more time on the road than seeing any of the coast, and again, weather might not cooperate for few hours you would have. Also, traffic will be heavy and slow in the Amalfi region, and parking is scarce. I'd definitely scrap that plan and save the Amalfi Coast for a future trip when you can give that region the time it needs and deserves.

How are you intending to get around on this trip? You do understand that a car is not advised for any of the locations on your list aside from stays outside of Florence to explore parts of Tuscany? Trains are going to be your most efficient method of transport between the places on your list.

What time is your flight out of Venice? Normally these are early morning departures meaning you’ll need to sleep at an airport hotel the night before or take an expensive water taxi to get there. Most people prefer flying into Venice and out of Rome to avoid changing hotels.
Instead of five nights in Florence make it four and take a direct train to La Spezia (2h 30m) and store your luggage so you can sightsee. Afterwards take a direct train to one of the Cinque Terre towns (15 to 30-minutes) and sleep there for two nights. If you stay in Monterosso you’ll have one less train connection to get from the Cinque Terre to the Varenna-Esino station on Lake Como.
By subtracting two nights from your current itinerary you now have two nights to fit in Positano which you do not want to do as a day trip. The best way to do this (and less nerve racking) is to take a direct train from Rome’s Termini station to Salerno (3h 15m) and then a direct ferry to Positano (1h 15m). From Positano take a direct ferry to Salerno then a direct train to Florence’s SM Novella station (4h).

Did you already buy your plane tickets? Do you like the itinerary going south to north? Do you prefer to have warmer weather for the duration as Venice and Lake Como can be cooler than Rome towards the end of September. If your plane tickets have not been bought fly into Naples and hire a driver to take you to Positano for 2 nights. It will give you maybe 1.5 days. Take one day from Cinque Terre and one from Venice. If your tickets are already purchased. upon arrival in Rome train to Naples then on to Positano or possibly train to Salerno and ferry.

If you fly SAS out of O'Hare (looks like $700 flights available) you don't have to leave Venice until 11 am, so you can ignore comments about early morning departures from Venice.

I hope you are not planning on renting a car for the whole trip. Car would really be useful only for a couple of days in Tuscany, and a major headache the rest of the time. If your heart is set on a day in Positano, take a fast train to Salerno and hire a driver for a day.

I would skip Positano and when travelli g North after CT spend the night in Santa Margherita and continue on..quick ferry to Portofino. It too is the Italian Riviera.

IMO, one too many days in CT, 2 few days in Lake Como.

You say Tuscany/Florence, if museums are your bucket list items then plan at least 2 solid days in Florence.

Tip for CT - if you must go, stay in Monterosso al Mare. Use the ferry to traverse to other towns whenever possible as the train stations can become a mosh pit at times.

I agree with Linda
We are in Santa Margherita now and it is lovely
Very few tourists, haven’t seen any Americans
Very picturesque, beautiful buildings, a nice waterfront, great local food, fabulous views and a stunning church

Took ferry to Portofino today just 15 min ride and it was almost deserted

I’m sure it’s crowded in the summer but off season now is excellent
By contrast we spent barely 3 hours in Positano, walked down, had lunch
Couldn’t wait to leave

The views OF Positano from the water are much better than the views in town

And I will agree with Christine! Skip Positano. You will get your fill with Cinque Terre for this trip. Trying to squeeze in Positano will be exhausting. I would take a day off Venice and add to Lake Como.

Thank you everyone! This group is so informative, I always learn from your comments!

Our flight is already made but I wish I would've gone north to south instead of south to north. Great idea!

As for driving...we will only have a car for part of our trip...not in the cities. We will be taking trains in the cities.

Thanks again...my husband and I are so looking to our September trip! :)

Kim, as it's still not clear where you intend to have a car, you only need one for any Tuscan exploration outside of Florence. Not for the CT and not for Como. Hope you've scrapped the Positano idea!