Planning a two week long trip to Italy- Could use some guidance

I don’t think it makes a difference at that time of the year weather wise, but if it is your first trip to Italy you should start in the north so you can become more accustomed to Italy before visiting chaotic but wonderful Naples.

I would start south and worth north because of the weather. However, you should research your flight options to see what is available going in both directions. There could be a significant difference in cost, or you could run into a painfully early departure time on the return trip (common though not universal from Venice; I don't know about Milan). I haven't checked the rail schedule, but I think it might be possible to make either Lake Como or Venice your last stop, though Lake Como is closer to Malpensa Airport.

However, I think trying to squeeze all those places into a 2-week trip is going to mean you are short on time everywhere. You need considerably longer than 2 weeks for that itinerary. For me, these would be about the mininum times I'd want at your destinations:

Lake Como: 3 nights (if the first stop; maybe could squeeze to 2 nights if the last stop)
Venice: 3 nights
Florence: 3 or 4 nights
Tuscany: Add 1 night to Florence
Rome: 4 nights
Naples: 1 night (I spent 7 nights there)
Positano: 3 nights (the minimum needed to have "a few days" there, assuming 2 qualifies as "a few")

As you can see, that adds up to 17 or 18 nights, and it doesn't give you even one full day in Naples.

I suggest your trim down your list. 7 locations in 14 days means you will be relocating every other day. Each move takes up half a day or more.

So either Florence/Tuscany, Rome, Naples and Positano ( skipping Milan/ Lake Como and Venice), or Milan/Como, Venice, and Florence/Tuscany ( skipping Rome and further south).

I second the notion to cut down the list. In addition, part of the charm of Italy is small towns like Pisa or Siena. I would stick with Florence and Venice and some towns in the north like Siena. If you did 4 Days in Venice, 4 days in Florence, you would have 4-6 more days for small towns. Do the north on one trip, the south on another.

I'll vote with the others that your itinerary would have you spending time in transit + checking and out of hotels that could be better spent sightseeing: too many locations in too few days. 2 nights in any location = 1.5 days sightseeing; 3 nights = 2,5; etc.

Along with other suggestions for a trimmed itinerary would be Lake Como>Venice>Florence/Tuscany> Rome. Fly into Milan and go directly to, say, Varenna; fly out of Rome. Then again, which locations to include depends on which of them are top of your list. Will your two weeks include your travel days on each end? It makes a difference.

As well, what are your interests? What do you most want to see/do on this trip?

If you go to 7 locations, you will spend at least 3 1/2 days of your trip checking in and out of hotels and traveling to your new location. Even in my thirties, I would have found visiting that many locations on my own(tours are different because someone else is handling all the logistics in the most efficient manner) in 2 weeks to be exhausting. Figure out your priorities and give a reasonable amount of time to those locations.

At the risk of a penalty flag for 'piling on' I will join with the others that you have too many places for your time frame.

Given the time of year and total time, direction of travel, for weather concerns, is of no significance

Hi Dennis,

My recommendation would be to fly into Venice - 2 nights.
Florence - 4 nights. Take 1 or 2 day-trip tours of the Tuscany small towns and/or a wine tour, etc.
Salerno - 1 night.

Positano - 3 nights. (Amalfi may be less expensive.)
Rome - 4 nights. Fly home from Rome.

So, you would purchase a multi-city airline ticket.

I didn’t include Lake Como because you also have Positano as a water destination. You really don’t have time for both. If you would rather go to Lake Como than Positano, drop Salerno & Positano. Fly into Venice or Milan. Cover those two destinations and then head to Florence. And end in Rome. My preference would be to fly into Milan and go to Lake Como - a nice place to get over jet lag. And add your Salerno day to Venice. Venice is so special!

So that option would be to fly into Milan and go directly to Lake Como - 3 nights.
Venice - 3 nights.
Florence - 4 nights. Take 1 or 2 day-trip tours of the Tuscany small towns and/or a wine tour, etc.
Rome - 4 nights. Fly home from Rome.

All of these options can be done by train.

The last option that Jean suggested is the same as I was going to suggest. Really four locations -Lake Como, Venice, Florence, and Rome-is ideal for two weeks. lake Como is a great place to get over jet lag (having done it).

I am constantly surprised by people who suggest traveling by rail to another destination on the day of arrival. I fly from the East Coast and even traveling Business class and getting some sleep, the LAST thing I want to do on arrival is to travel on. Could me my age (late 60s) but I need at least one night to acclimate.

I would also ask Dennis if you have traveled to Italy before? Booked and taken trains in Italy before? How much luggage are you bringing (pls say one carryon per person). I am assuming you are traveling via public transport?

With those questions, I would ask how often you want to pack up and travel vs staying in one place for a few days. I would also suggest you determine what it is you want to do/see? Most travel writers and sites say Rome is a must-see. Well I saw and was underwhelmed because ruins and churchy things do not excite me. But wandering the "streets" of Venice is something I could do day after day after day. Florence gives me my arty fix as limited as my fix is. But I love Florence because of its walkability and the connections with greater Tuscany and the food and/or wine tours.

I also love Como but I would not consider landing in Italy, train to Como and Ferry to other towns on the lake. If I had visited before, I might be OK with this but not as a first timer, jet lagged and uncertain about what the heck I got myself into.

I also loved Sorrento but getting there is a PIA. Positano seems to be a "click the box" stop for many. I don't think you should add southern Italy to this trip. Fly into Florence, train to Venice, train to Como and back to MIlan for flight home.

I am sure many would disagree but that is my 2 cents.

cbrochu30, our worst one was flying from Seattle to Amsterdam to Zurich (Comfort Plus seats), and immediately taking FOUR trains after we arrived in Zurich to get up into the mountains at Wengen! But it was so worth it to wake up the next day with those stunning views from our bedroom and balcony.

Think of this trip as your first of two to Italy. Figure out geographically and pacing-wise what makes sense. Travel days are a necessary waste of time so don’t move around too much. Build in purposeful down time in the middle. So…

Maybe choose north vs south?

This trip: VCE-Florence-Tuscany-Como-MXP
3+2+6+3 nights

Next trip:FCO-Umbria-Amalfi Coast-NAP
4+4+4 nights

Thank you all for responding. I think I have a pretty good idea of what to do. One thing was clear from all the responses is that we cant see all what we want to see in two weeks. So we will plan this all over again and curtail our list. For those who asked yes this is our first trip to Italy.
Thank you again for your responses.
Dennis

Planning any trip is usually an iterative process involving a lot of prioritization. No matter how much time we have, it's never enough. Sometimes places you want to see are closed on the day you'd like to see them, requiring significant itinerary changes. Been there, done that many times. 🥴

I totally agree with everyone who's said that you really have 2 (I'll add or more) trips outlined. For me every trip starts with what I want to see or do in the locations I think I want to go and how much time it will take to do that. Keeping the in-country travel time in mind, the rule of thumb is that 2 nights in a location are needed to have one day to visit it. For me, at least 2 nights in a place are mandatory. So when someone asked about what you're counting as 2 weeks, I immediately wondered if your travel days from the US to Italy and return are inside that 2 weeks or if you actually have 2 weeks on the ground in Italy. Like that person said, it makes a difference.

You are very smart to be starting your trip planning now. Not being sure of how much research you've already done, I'm recommending the following resources to help with your planning.

1. The Travel Tips right here on the RS website: https://www.ricksteves.com/travel-tips
   These are helpful for anyone planning a trip to Europe, especially if they haven't been there or to the specific country they plan to visit before.

2. The various topical forums related to those tips under Tips & Trip Reports like the ones on Packing, Transportation and Best Walking Shoes for Travel.

3. The RS Explore Europe section for Italy: https://www.ricksteves.com/europe/italy
   The details there may help with setting priorities, for this trip to Italy and the many others you'll want to make in the future. Spoiler alert -- you will want to return again and agaiin.

4. The Beginner's Guide to Train Travel in Italy from the Man in Seat 61: https://www.seat61.com/train-travel-in-italy.htm I've traveled by train in Italy many times and particularly love the fast and comfortable Freccia trains. Even using them takes some time, but typically they are faster than flying.