Cinque Terre and/or Venice in October as an addition to our 7 days in Tuscany?

Where to fly into and out of depends on where you are starting and ending your trip. It also depends on what options exist from your starting point, and how much extra time you are willing to spend to save money (if one airport is cheaper, but farther from your area of interest).

Florence (code FLR) and Pisa (PSA) are the main airports in Tuscany. For Florence, Bologna (BLQ) is also close enough to consider.

Pisa and Genoa (GOA) are the closest airports to the Cinque Terre. If you're searching for Genoa, it's often easiest to put in the full city name; putting in GOA often gets Goa, India!

Venice has its own airport (VCE), but flights departing Venice that are making a connection in Europe to go to the US often leave at very early hours. Getting to VCE early in the morning can be expensive or time-consuming. Therefore, it's often easier to start a trip at VCE than to end one there. However, at certain times of year, there are nonstop flights from VCE to Philadelphia (on American) and JFK (on Delta) and Newark (on United) that leave later.

Pisa gets nonstop flights from JFK for a few months a year. Otherwise, to get to any of these other cities besides Venice, you'll have to change somewhere in Europe.

Note that Milan has recently had much better prices from the US than any of the airports I listed above. Nonstop flights from the US got to Malpensa (MXP); flights that connect in Europe can go to either Malpensa or Linate (LIN). However, you must balance the savings against the extra time and money it will take you to get to Tuscany or Venice or the Cinque Terre from the Milan airports.

The city of Rome is only 90 minutes from Florence by very frequent trains, but from Rome's airport FCO you must allow at least another hour. Even so, it can work also, depending on your itinerary.

Open-jaw flights (into one airport and out of another) work very well for Italy; for instance, into Venice and out of Pisa. To find these flights, choose "multi city" or "multiple destinations" on Kayak, Google Flights, etc. These are usually much cheaper than two one-way flights.

Thanks Harold for all the flight information, it looks like that may be helpful! My biggest question is do we add on Cinque Terre or Venice or both being that October may be rainy season?

If you only can choose one, I would choose Venice. If the weather were to turn bad, I would rather be in Venice than the Cinque Terre. Venice is an amazing city. When we visited the Cinque Terre, we had great weather. I wondered at the time how different the experience would have been in bad weather. In Venice, there are many more things to do inside. I read an article that suggested Venice might be uninhabitable by the year 2100. With global warming, I would rather experience Venice now rather than later.

Another vote for Venice: there's just nothing like it.

Venice and Cinque Terre are completely different places and experiences. Venice, a powerful maritime economy (once, anyway), a thousand years of history, conflict, trade, bloodshed. Cinque Terre, a thousand years of back breaking horticulture, invasion by pirates, scratching a living from slopes that almost seem vertical, living on fish and olives.

Both are pretty special places.

we went to the CT on 5 October 2015 for 10 days. It rained the first day in the CT (we stayed at Moneglia) and there was no rain there for the next week or so, it rained up and down the coast but not in the CT. We then went to Lucca and had two days out of 4 with pretty significant rain. I guess it is luck of the draw, but for us the weather was great in the CT villages in early October. We were able to use ferrys on two days so the ocean was also calm on those days. Clearly if you are a hiker trails along the CT will be difficult if it rains. We did the hike to Portofino from Santa Margherita in the rain our first day and the trail handled it really well, so you can find hikes in the rain if you check around. Have a blast!

Btw the two, Venice takes my vote. October is kind of late in the season for a location like the Cinque Terre. October is the rainiest month of the year, especially the second half. You are going during the first half, therefore you have a better chance to have ok weather, nevertheless it's a risky month to make reservations at the Cinque Terre. If it happens to be rainy when you are there, you'd be wasting your time. The Cinque Terre would not be enjoyable with rain.

If this were my trip, I would fly into VCE and spend the first 2 or 3 nights in Venice. Then I would move to Tuscany. You don't specify where in Tuscany you will be based and whether you will have a car at that location. If by Tuscany you mean Florence, then a car is not recommended, if it's a place in the countryside or in a small town, then a car is really a must.

If you go directly to a countryside location after Venice, I suggest to rent a car in Venice and drive there directly. If you plan to spend a few nights in Florence first, then take the train to Florence, spend a few nights there, then rent a car in Florence.

Leave the Cinque Terre as an option for a day trip from your Tuscan location if the weather permits. If you have a car you can drive to Levanto in about 2.5 hours and to La Spezia in about 2 hours. From either you can take a train to the Cinque Terre in minutes. Both towns have parking at the train station. If you travel by train, then the trip is a bit longer with a couple of changes (generally Pisa and La Spezia). The train trip from Florence is about 2.5-3 hours each way.

To return home you should look for a flight from either Florence (FLR) or Pisa (PSA).

All the above airports (VCE, FLR, PSA) do not have direct flights from the US in October, so you will have to connect in some European hub. The only exception might be VCE, which I think has a Delta flight to JFK year around.

Thank you so much to everyone for all of your recommendations!!!