Advice for first-time Italy 2 week itinerary

First, I would flip it. Into Venice and home from Rome. It is far easier to fly home from Rome than Venice.

Your selection of places to visit is fine, although you do have many places for the time involved. Arrival and departure days are pretty much to devoted to transit. At least Rome and Venice merit more time, I think. I agree that flying into Venice and out of Rome is generally better. Easier to recover from jet lag, and adapt to Italy, in no-auto Venice than in quite congested and fast-paced Rome.
Does your first itinerary reflect several 1-night stays in a row? That can be very hectic, plus you can use up a lot of time unpacking, re-packing, checking in and out, etc. Your family will move at the speed of the slowest one. Especially with a car, those various towns in Umbria and Tuscany can be visited from one central town or even an agriturismo in the beautiful countryside, eliminating the need for the 1-night stays.
Also, you’ll need to do some research about rental vehicles. Can you rent a car big enough for 5 adults plus baggage (does your family pack light and small, or big and heavy?), or will you need some kind of bigger vehicle, which can be much more expensive, also can be hard to drive in towns and to park in tight spaces. You really don’t need or even want to drive in Rome, Venice, inside Florence, or in the Cinque Terre. Maybe just rent for the more rural areas. Be sure to check out some of the details of driving in Italy, such as ZTLs, IDP for each driver, etc.

Itinerary 1 has too many one-nighters. I prefer #2, with more days in each stop. If it were me (and it isn't, of course,) I'd skip Cinque Terre and add the extra days to Florence and Venice.

Have a great trip; I suspect we'll be seeing more of you on the Forum. Welcome, by the way.

As a frequent traveler to Italy I think you have too many towns on your itin. for 15 days. You are a large group and could reduce your visits exclude CT this trip at least. The areas u wish to visit are a blockbuster of sights and experiences it would be ashame to rush through. I just returned from Venice in Sept. and it was my 5th visit. I barely duplicated anything, there is just a lot to see.
Oh this time I finally took a gondola ride! Anyway just give a little more thought to your pace.

Itinerary #1 seems quite busy, and I wonder whether you realize that both Orvieto and Assisi are sight-rich and ideally would be full-day destinations if not longer. It appears that you'll have only a few hours in each. A few of the others (including Spoleto) I haven't visited; they may be short on allotted time as well.

You're planning a lot of in-transit sightseeing. It's seriously risky to park a car with suitcases or other belongings visible inside it. Parking lots near tourist attractions are happy hunting grounds for thieves. I'm not sure you can find a vehicle that will hold so many people and their luggage in a closed compartment.

I think the Umbria/Tuscany portion of your #1 trip would be very challenging without a car. Your #2 trip could be accomplished without a car.

See flights from SEA into Venice and out of Rome on www.skyscanner.com. Drop CT which you do not have time for; plus there are transportation issues. On the driving portion I suggest you spend 3 nights in one location; this area in Southern Tuscany is hard to beat for scenery and places to explore:

https:/…valdorcia.html

I prefer to stay in a town, vs in a villa or farmhouse out in the sticks. Read this about driving in Italy and restrictions involved [ZTLs]; avoid leaving anything of value in a car when parked:

http://driventoit.blogspot.com/

The idea is to drive directly to a hotel and drop off bags before doing any sightseeing. Visiting towns you will park outside and walk in. We arrange our cars by calling up the broker Autoeurope; get zero- deductible collision, which covers any damage to the body of the vehicle. They will recommend the best agency based on your particular situation [big vehicle concerns]; possibly where the car is being returned.

Leaving Florence take a taxi to Via Palagio degli Spini, the complex near the airport; much better chance of getting the large vehicle. It's a 1.5 hour drive to the place I mentioned [one reason for flying into Venice vs Rome]. Chiusi is a very popular place to drop a Hertz car [closest to the station, all closed Sunday] and take a train to Rome. Or you can drive to Rome, probably to the Termini Station.

For 15 nights, one distribution might be car 3 nights, Venice, Florence and Rome 4 each.

Thank you all for your thoughtful responses. I would summarize the general consensus thusly:

1. Fly into Venice and out of Rome, as opposed to into Rome and out of Venice: I did look into this, and prices were comparable. However, I liked the short then long flight into Rome, versus the long then short flight into Venice, at least for the flights that I saw. I will weight these considerations.

2. Tuscany/Umbria roadtrip component: Base yourself in one place, rather than one-stops. Duly noted. I would then lean toward staying in a town like Siena. The original thought was to reduce round-trip day-tripping. The point regarding car theft, as well as car size, are also noted. For all these reasons, it may be wise to reduce the duration of the trip involving rented car.

3. Skip Cinque Terre and/or Venice: If I had to skip one, it would likely be CT, per general priorities of my travel party.

Follow-up questions:
4. How would you cluster five days in Tuscany and Umbria? Here is an itinerary I developed based on the concept of basing oneself in Siena and Assisi.

Day 1: Siena

Day 2: Daytrip: Siena to San Gimignano

Day 3: (Rent a car) Daytrip: Siena to Montepulciano

Day 4: Transit form Siena to Assisi, spend day in Assisi

Day 5: Daytrip: Assisi to Orvieto (return car)

Day 6: Train: Assisi to Rome

Thank you again,
Mark

Daytripping from Assisi to Orvieto, heading back to Assisi for the night, and then taking a train to Rome the next day means quite a lot of extra time on trains. I think you'll lose more time that way than you would by changing hotels and spending a night in Orvieto, though I hate one-night hotel stays.

Take a look at the train times on the easy-to-use Deutsche Bahn website.

... I liked the short then long flight into Rome, versus the long then short flight into Venice, .... BUT what you will not like is the 4am trip to the Venice airport to catch a connecting flight to somewhere else in Europe for your direct flight home. And you might have to wait two or three hours at connecting airport to make sure you make the connection. However, in Rome you can a nice breakfast in the AM, short trip to the airport at a reasonable time -- 8, 9am, to catch a noon direct flight home. Check your return schedules. Your arrival day is shot in part because of jet lag so a short flight into Venice is really not going to make much difference. You will sleep some.

I agree with Frank on the reasons that flying into Venice is easier than flying out of Venice, having been to Italy 4 times in last 6 years (since retirement), with another trip planned for 2020. We have done it both ways and have varied our itinerary each time to avoid squeezing in too many sights in each trip - except Venice, which we've visited each time, from 2 to 4 days. It has been my favorite city - I am not into big cities, but being 'car free' makes the vibe different and we focus on a different sestiere each time. We usually add one other 'main' destination, and enjoy driving through scenic areas from Venice and before the next big stop (e.g., through Dolomites before heading south to Florence or through Tuscany en route to Rome, but ditch the car before going into city). As far as long flight then short flight, I find that easier to do - with long flight first, I get it done before getting tired; then it's easy to tolerate short flight after a break, even if the trip is getting long. Besides that last connection, add in the time to get to a hotel so you can crash a while, so last half of trip is more equal if the flight if shorter.

I agree on the suggestion about flying into Venice and out of Rome, due to the early-morning departures. Also, one of the best European experiences that I have enjoyed is taking a water taxi from the airport to our hotel in Venice, it's simply wonderful, and what better way to start your trip in Italy.

If your parents don't really like big cities, then there's no rule that you have to visit Venice and Florence and Rome all in one trip (as awesome as each of them is). You could stay a bit north and leave off Rome, or skip Florence and only visit Venice and Rome. I would leave in Venice because, due to no cars, it feels like a smaller city. But you might want to visit there in Springtime, given the issues they are having currently in Venice.

I like the Cinque Terre, but if you go in October, there's a slightly higher chance of having not so good weather, and Cinque Terre in the rainy is not so fun. I also like Siena, but parking there is a hassle, though you can park outside the city and just walk to your hotel (it's small enough that it's easy to do). I actually like staying in San Gimignano; the daytrip people leave by the evening, and the town is much quieter then. And lots of good restaurants in San Gimignano, especially for its size.

I would suggest you have at least two 3-night stays in smaller towns in Tuscany and/or Umbria (or more). And start thinking of your trip in terms of the number of nights instead of days, it will making the planning and scheduling where you stay each night a little easier. I also would say that you have a lot of short stays, especially with a group of your size. Not that it's a huge group, but the delay factor seems to increase exponentially with each additional person in a group.

I did fly out of Venice and it required a stay at the airport in Verona. WE decided to spend our last day in Venice and travel to the Verona airport , leaving Venice around 5. I was to nervous trusting transportation at 4AM in Venice. I assumed arriving at the train station there would be a simple bus that stopped at all the airport hotels. There is a very large bay of multiple busses and no one to help us, late hours and no English available. No ticket office, just buy your ticket at the Tabac inside the train station. I can't remember how we finally determined which bus but it was not an airport shuttle. We were dropped of in the middle of a highway round about, very unnerving, but we could see our hotel. Fly out of Rome!