tell me I'm crazy

You don't say when you are traveling, but I have found that that feeling of being overwhelmed ebbs and flows. At first it feels like you are drowning. Put your research down for a time, then come back to it. The more familiar you become, the easier it gets, but it does take time. Remember, you are doing everything you would be paying a travel agent with years of experience to do.

I just returned from my dream Italian adventure. From my first day in Rome, I realized that I did not dedicate enough time to each city. I spent morning, afternoon and evening running around trying to see everything. I saw a lot...problem is this....I had little "linger time." My realization is that no matter what, I would not be able to see everything that I wanted to experience in Italy. I love history, art, and a wine enthusiast and love music and dancing. That said, moving forward if someone asked my advice about going to Italy ... what should I see?? I would say this. How long do you plan on being in Italy? If two weeks, pick two of your favorite or most desired destinations. If three weeks, pick three. Spend a week in each but take linger time. Italy has it all...love, religion, music, art..it has it all, why not wallow in it while you can. Don't spread your time too thinly so you can see more. This is just my opinion from my recent experience. I am now planning on returning next spring so I can catch up with my "linger time." Have fun and do slow down!

Nope, you're not crazy.
This is the "age old" recurring dilemma here: more time in fewer places OR less time in more places.
Trip planning can be fun but also challenging and, as you have said, even stressful. Because you're planning some things that you haven't done before.

There are advantages and disadvantages of both choices: more time in fewer places OR less time in more places.
At least you're not even close to doing what some travelers write in here about (fewer now than a few years ago), where they were planning to see Paris in a day, "the south of France" in a day, and basically one region per day.
They were ignoring, or not aware of, travel time, checking into the hotel, unpacking, packing up in the morning. You're obviously not guilty of that.
It's easy to say it's a matter of the traveler's preference, but how do you know what is right for you when you're doing something for the first time, such as being in a new area.

As you've already figured out, if you spend less time in more places, you may wear yourself out--in fact, you mentioned that you're already worn out by planning the logistics of the "less time in more places" option.
But, if you spend more time in fewer places, then you'll have to settle for not seeing some places on your list.
It's commonly said that you should assume you'll go back, but for many of us that may or may not be the case. Europe is a big place.

As I said, the recurring dilemma. Someone else's preference may not be right for you. Somehow, you have to choose.

If you haven't driven in Italy, one thing worth cranking into your decision-making process is: many American travelers find that driving a car through the larger Italian towns and cities is surprisingly stressful to a number of drivers. At least some travelers would say that, unlike here, renting a car there is not the easy, affordable and obvious choice that it is here.
You can get to Lake Como by train, and a car does you no good if you want to see the usual villages around the lake.
And you definitely don't want to drive into or around the main touristic sights of Florence by car.
But some other places on your list can't be efficiently seen without a car.
So you have dilemmas or choices there, as well: where to drive and where not to drive.

Jay,
I'll second the thought that you're not crazy - yet! The planning process is somewhat stressful indeed and as Kent pointed out there are any number of factors to consider. Italy is very different in that public transportation to most of the major places is pretty good so the need for a car is far more limited. Based on the bit I know I would suggest your current plan, which spans nearly tip to toe, is a bit ambitious and there will indeed be little time for lingering. Lingering is part of what makes Italy fun. Could I make the suggestion that you plan time to linger? What I have started to do in such planning is to have some "we have to be at the museum at this time" and then allow for room in between to walk slowly, hang out with a cup tea or just sit and people watch for a bit as we move along to perhaps the next place or perhaps just free-flow it, "we're here and around here are these options; any of them sound interesting to go visit?" Its hard to get me inside on nice days so if its a lovely day or a gross, rainy day, its easier to be flexible.
FWIW I'm headed to the Tuscany area in about a month and find myself stressing out already about parking a car that is somewhat mandated given that we're staying on an isolated farm....public transportation is the way to go if possible!
Safe travels and lots of fun to you!

My planning has evolved over many years of experience, and I still screw it up from time to time.

First I would check trenitalia.com for train schedules and fares; you don't say when you are going, but you can purchase tickets up to 119 days before travel. You will at least have an idea of how long the trips take, how many connections you have to make, and perhaps the cost (if it's more than 119 days out or a regionale train is involved, pick a date within seven days of the day you check the website, preferably the same day of the week that you plan to actually travel). Note that Sunday (festivi) services may be less frequent than weekdays (feriale).

I like to travel early in the day and get to my destination. Lots of people prefer to leave their luggage at the hotel or train station on checkout day, sightsee in the morning, take an afternoon train, and arrive at their destination in time for dinner, or later. Travel can be a stressor (cancelled or delayed trains, traffic detours if you are driving), so I like to get it out of the way. Then I have the afternoon for sightseeing and maybe taking an orientation walk around the city.

With four areas in 14 nights, you will be moving pretty quickly. You might want to switch out Amalfi Coast for Cinque Terre (I can't believe I'm suggesting this), depending on time of year. Personally I would try to get to the Amalfi Coast.

You don't mention Rome or Naples, but you will be changing trains in both if you go to the Amalfi Coast. I have had very happy stays in the Amalfi area (especially Ravello and Praiano) on a 2-night stay.

First of all heed Robertos' advice and drive to Sorrento. October on the AC is not congested. We have

been in October, and you definitely save time by driving yourself. Just be aware you will probably have to

pay for parking. I use Via Michlin for driving directions, but you will have to add time to their estimates.

Here is the bus schedule, look closely at how long it takes between towns.

http://www.theamalficoast.net/orari_sita_bus_timetables.html.

As Zoe said, sometimes the best layed plans go awry . Think you will have a wonderful trip.

To add to Sherry's comments about lingering time, I have always found it most enjoyable to pick an activity or site to see in the early part of the day. The rest day it's great to stroll a new neighborhood, wandering into shops and galleries, then "linger" for a late lunch in a café, people watching and enjoying the local cuisine and wine. A short nap back at the hotel is refreshing before a late dinner and a little more strolling. My family and I have vacationed like this since our kids were little, and it's a great balance between educational, inspiring and interesting sightseeing, and enjoying a little laid back cultural enrichment.

Enjoy your trip!