Toronto to Lamezia Terme - 14 Days

Lamezia Terme is in the far south, so I would forget Venice for this trip. Get a book on Calabria and decide what you would like to see and do there, but I would only go as far north as Rome.

Agree on Rome as a northern limit... and even that could be a stretch as there are so many sights in southern Italy:
- the Naples-Amalfi Coast region (incl. Capri, Pompeii...) deserves 4 fast-paced days as a minimum, preferably 5
- Matera is otherworldy, and neighboring Puglia is very interesting (Alberobello, Ostuni, also Lecce but that's becoming out of the way), that's another 4 fast-paced days
- I'm then leaving 3-4 days for Rome, and 1-2 days for travel times (you'll want to sleep close to Lamezia Terme before you leave).
I admit I've never been to Calabria, so maybe I'm missing must-sees there.

If you are really getting that great of a deal, you could just fly/take trains all over the country, but I would make my dream the toe of the boot and possibly dip into Sicily as well.

You have created quite a challenge.

Venice and Rome being your top wishes, your choice of airport, is not ideal. I understand budgets are not unlimited, but I suspect when ALL the costs of getting to from your desired destinations, the flight savings may evaporate. Fuel and tolls will be significant. Parking while in Rome and Venice will not be cheap, and all the while the meter is running for the rental car. I would suggest you look at using trains to get from place to place.

I think a more basic examination needs to happen on deciding on which is more important. Going to the wished for Venice and Rome, or getting the cheapest flight to an inconvenient locale..
Your time has value. Getting from Lamezia Terme will take a whole day on each end of you trip, even if only getting to/from Rome.

While not a perfect comparison, your routing is like flying from Dallas to Calgary, so you can visit Toronto and Montreal, because the fare is less.

Is it possible to fly out from Venice or Rome to save the long trek back and still realize some cost savings?

Personally I would make lodging reservations ahead. You probably could find lodging on a drop in basis, but I suspect it will be and the far ends of the spectrum

There's a risk involved in not booking hotels in advance, especially for a budget traveler. Occasionally, you have a choice of paying much more than expected for a hotel room or eliminating a planned-on destination. I am currently relaxing in a nice (but not special) room costing me about $850 for 5 nights (about triple my average) because there's some sort of important futbol (soccer) game in Valencia that soaked up all the inexpensive rooms and sharply increased the rates for the few remaining options. How will you feel if something like that happens to you? Eliminating Rome will not be an option, will it?

I appreciate all the awesome feedback, but have a few more questions.

Missing Rome/Vatican is out of the question as that is truly the only point of absolute interest to my wife (although she does want to see the entire country).

It seems I am narrowing down the trip quickly, which will make the lodging conversation easier to manage.
Revised route - comments?

The following is the mapped route:
Lamezia Terme (Fly In/Out)
Positano
Naples (Optional)
Rome
Vatican City (Mandatory)
Florence
Arezzo (Business stop - hour drive from Florence)

Bologna (Optional)
Venice (Optional)

Google maps shows the total trip to be only 17 hours. I have driven from Toronto to Florida (24 hours) without issue in two days and is where I reference my driving tolerance. I have no idea how to compare the two driving exercises, nor can I assess the accuracy of the time suggested by Google.

https://www.google.com/maps/dir/Venice,+Metropolitan+City+of+Venice,+Italy/Bologna/52100+Arezzo,+Province+of+Arezzo,+Italy/Florence/Vatican+City/Rome,+Metropolitan+City+of+Rome,+Italy/Naples,+Metropolitan+City+of+Naples,+Italy/84017+Positano,+Province+of+Salerno,+Italy/Lamezia+Terme/@43.6457743,11.2023121,10z/data=!4m56!4m55!1m5!1m1!1s0x477eb1daf1d63d89:0x7ba3c6f0bd92102f!2m2!1d12.3155151!2d45.4408474!1m5!1m1!1s0x477fd498e951c40b:0xa2e17c015ba49441!2m2!1d11.3426162!2d44.494887!1m5!1m1!1s0x132bed72f3fda815:0xf846f1b18734dc08!2m2!1d11.8796336!2d43.4632839!1m5!1m1!1s0x132a56a680d2d6ad:0x93d57917efc72a03!2m2!1d11.2558136!2d43.7695604!1m5!1m1!1s0x1325890a57d42d3d:0x94f9ab23a7eb0!2m2!1d12.453389!2d41.902916!1m5!1m1!1s0x132f6196f9928ebb:0xb90f770693656e38!2m2!1d12.4963655!2d41.9027835!1m5!1m1!1s0x133b084f6a6c7e99:0x3df52cc13b78191d!2m2!1d14.26812!2d40.8517983!1m5!1m1!1s0x133b9768a710d21b:0x8cde0b2863cede31!2m2!1d14.4849812!2d40.6280528!1m5!1m1!1s0x133fe50fc4431e61:0xc887d98b39eafc22!2m2!1d16.3092719!2d38.962912!3e0

sat,

A few thoughts.....

As you mentioned Lamezia Terme, I assume you're planning to book a flight with Air Transat? If that's the case, I believe Air Transat also flies from Toronto to Rome and Venice. Perhaps you could arrange open-jaw flights inbound Rome and outbound Venice (or vice versa).

To answer your questions.....

• Using a rental car will not be the quickest or most efficient way to get around. The high speed trains which travel at up to 300 km/h would be a better use of your limited holiday time. It's important to note that for driving in Italy, each driver listed on the rental form must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. These are valid for one year, and easily obtained at any CAA/AAA office (two Passport-sized photos required, which may be provided by the issuing office). Failure to produce an IDP if requested can result in fines on the spot! Have a look at https://it.usembassy.gov/u-s-citizen-services/local-resources-of-u-s-citizens/transportation-driving/ for more information on I.D.P's and driving in Italy.

You may also want to have a look at some of the other posts here concerning the dreaded Zona Traffico Limitato (limited traffic) areas that are becoming increasingly prevalent in many Italian towns & cities especially Florence, which is almost saturated with automated ZTL cameras. EACH PASS through one of the automated Cameras will result in a €100+ ticket, which you won't know about until several months after you return home!

• For travel in September, I would highly recommend reserving hotels in advance. That's often a busy travel time in Italy, and pre-booking will give you more flexibility in terms of the area of each city you stay in and the price range. There are lots of good hotel suggestions in the RS Italy guidebook.

With the revised itinerary, focused on cities + the Amalfi Coast where driving is a pain, I would strongly suggest no car.
The following is doable:
Lamezia -> train to Salerno (2.5 hours) -> Amalfi Coast (4 nights incl. Pompeii day trip; Sorrento is most convenient base)
Amalfi Coast -> train Naples (1-2 nights suggested) -> train Rome (4 nights)
Rome -> train Arezzo (if you must; not sure if you need to stop for the night)
Arezzo -> train to Venice, 3.5 hours (if Venice is your dream, skip Florence and Bologna) (4 nights)
Venice -> fly to Lamezia terme (direct from treviso, or via Rome, or long, long train ride (7hr+ or overnight)) -> night in Lamezia probably needed