Planning a first trip go North or South??

The Big 3 in Italy, for travelers with 14 days on the ground, is Rome, Venice, and Florence.
Of course, it's your trip, so you can see anything you want, consistent with the amount of time you have>

Tuscany and Umbria are lovely open-space locations. So is the south. The big 3 are big cities, wonderful museums, GREAT architecture and lots of people.

Down below Naples you will see the trullis, strange little cone-shaped buildings in and around Alberobello. The city of Bari has a beautiful harbor. There is something magical about the south of Italy ..... but you must beware of pickpockets and thievery. Just be cautious. Most of the music we Americans think of as "Italian" music is from the south.

And, of course, Sicily is gorgeous.

Have a wonderful trip. You will be going back again because there is so much beauty to be seen

Perhaps fly into Rome and explore, then take the train to Orvieto and rent a car to explore Tuscany and Umbria. You could find an agriturisimo in this region and explore different areas by car each day (small towns, wine tasting, etc) Then if you want to go do Venice, head there for the last couple days and fly home from there.

For your first trip, I would stay in the north-central part of Italy, start in Venice (3 nights), take a few days in the Dolomites (3 nights), visit Tuscany (Montalcino would be fine) and take a daytrip to Siena (3 nights), then Assisi (1 night) and finally Rome (4 nights). That would take 14 nights. You could substitute Cinque Terre for the Dolomites. You could also squeeze in a daytrip to Florence from Montalcino but it's a lot of travel time roundtrip in one day. I think you can skip Florence if you are not into art and museums, and put in Assisi if you are looking for some Catholic spiritual sites (go to the Hermitage for sure, it's out in the country just a few kilometers from Assisi).

In Rome, some churches that you may find interesting are Santa Pressede, Santa Costanza built over catacombs, San Giovanni in Laterano with the Scala Sancta across the street, San Clemente for a church built over a pagan shrine, and Santa Sabina (one of the oldest churches in Rome, great views from the garden next to the church).

moreno,

My suggestion would be to focus on the north of Italy for this first trip, starting in Venice. Just to clarify, you have 16 days for this trip?

While you're not fans of large cities, Venice is very unique and well worth at least one visit (IMO). There are numerous photo op's there! Florence is also a marvelous and historic city and as a photographer I'm sure you'll also find lots of subject matter there. If you don't want another city stay, you could stay outside of Florence in an Agriturismo and just day-trip there. Add some time in Siena, Orvieto or perhaps the Cinque Terre and finish your trip in Rome.

There are some potentially expensive "caveats to be aware of in Italy, both with rental cars and with public transit. The main issues with rental cars include the need for EACH driver to have an International Driver's Permit, possibility of violating ZTL (limited traffic) areas which exist in many towns (hefty fines), parking, high fuel costs, tolls, speed traps including the automated Traffic Tutor system and automated fuel pumps which may ONLY accept "Chip & PIN" credit cards at unattended locations. Issues with trains and other public transit include the need to validate (time & date stamp) tickets for Regionale trains, buses, Metro, etc. (again, hefty fines). On the faster trains such as the Freccia high speed, seat reservations are compulsory and these are specific to train, date and departure time. If a passenger boards a train for which they don't have reservations, again hefty fines which are collected on the spot!

Ken,
No they have 14 days, that's 16 days minus 2 travel days at both ends. That's what they're saying in the OP.

Kent,

Thanks for the clarification.

Zoe's nailed it again! There's nothing I could add.

Find the quiet Venice - up before dawn to watch sunrise over the lagoon from St. Mark's Square, wander the back canals,

Zoe gave you some good ideas.
You have 14 nights on the ground.
Fly to Venice
Venice 2 nights.
Rent car as you leave Venice
Dolomites mountains (Ortisei): 2 nights
Lake Garda (Malcesine or Riva or anywhere on north lake): 2 nights
Drive down to Tuscany agriturismo near Siena: 5 nights (day trips to wherever, incl Florence, Assisi, etc)
Drive to Rome return car in Rome near Tiburtina station upon arrival
Rome: 3 nights
Fly home from Rome FCO

Adjust nights as you see fit, but spend at least 2 nights in the same place. One nighters are time waster because of the time involved in checking in and out of hotels with related packing.

If you want to do 2 nights at the Cinque Terre, skip lake Garda and go there after Tuscany. Return the car in La Spezia, near Cinque Terre, and stay without a car the rest of trip. From the Cinque Terre go to Rome by train (3.5+ hours, no changes)

Thank you to everyone that has responded, it seems staying North will be the way to go this first trip!! We will definitely do Rome and Venice and hit some in between spots. I like the idea of flying into one and out the other, definitely makes more sense! I am so grateful you took the time to respond and I'm sure I'll be posting again with more questions throughout this planning process!

Since the northern half of Italy is generally more visited, you'll find lots more tourist information published, and of course Rick Steves' Italy guidebook is the place I would start. Instead of a standard museum setting, would you enjoy seeing art in it's original location in palaces and churches? Venice is especially good for that. Remember that you can escape crowds in Venice just by venturing a couple of "blocks" off the main, signed tourist route.

I think that tourism works like this: if you haven't been to Italy at all, go to Rome, Venice, Florence, Siena. then come back and "dig deeper" on a repeat journey.

I don't think your first visit should be spent getting way off the tourist path, agriturismo, etc. That's not to say you should exhaust every large touristy center first, but at least spend a trip getting acquainted with the land so you are conversant in the atmosphere and history of the place.

This isn't Italy-specific advice I'm giving, just a general philosophy of traveling.
Enjoy!