First ever trip to Italy

I don't worry so much about airlines, though I do avoid Aeroflot and Turkish -- but the latter only because of a long layover in Istanbul (the airline itself is great). I would definitely poll for recent Alitalia experiences. They may be worth the risk for a really great fare. It is not really that long of a flight.
Consider strongly your itinerary--are you trying to get open jaw (multi city) flights? The schedule is what I consider above all else--what time i leave, how long of a layover, and what time I depart. Cross reference that with cost to find the best choice.

Use kayak.com and buy the cheapest/most convenient fare/itinerary. Airlines don’t really matter anymore.

Alitalia's premium economy is fine, but the airline's fate is in constant flux. The Italian government and various companies like Delta and the Italian train service are trying to put a rescue package together. We've recently taken Iberia, with a stop in Madrid, and Lufthansa, with a layover in Munich. Prices for both can be decent, even for premium. British Air also has decent prices, but there's Heathrow to deal with. And they're frequently late, so making the connection flying back to NY can be dicey. Whatever you do, don't take Norwegian--they're unreliable, long delays and cancellations are frequent, and they've been running cruddy charter flights to Rome on decrepit planes with no entertainment and broken equipment.

My concern with Alitalia is its financial situation. Many airlines are in trouble at present (e.g. Norwegian), and Alitalia is one of them. Some would argue that the company is too politically important for the Italian gov't to let it fail, but May 2020 is a long time away... I'd take the risk for a 2019 booking, but not this far ahead.

Also,
- it is not "obvious" that Alitalia will be cheaper; May 2020 fares are not available yet anyway.
- you might be able to save with a connection in Europe. Your luggage follows through, if it's a single booking. Only worth it if the saving is significant (several hundred $)
- premium economy is not worth it on every airline, check reviews carefully. Actually, I'd rather recommend flying business to Europe (night flight), and regular Economy back. That can mean booking two one-way fares, which is not an issue.

Hi Mir,

Alitalia may be a little iffy for reliability right now. I am not 100% sure of this.

I fly out of Logan. Check out British Airways. They do connect through Heathrow of course - a very, very big and busy airport. But, Newark and JFK are just as crazy, lol!

American Airlines and Iberia code share with BA, so check out their sites too. But, I've found American to be more in fare compared to BA and Iberia a wee bit higher at times.

However you go, I suggest that you look into "open jaw" tickets, wherein you fly into one city (ie Venice) and out of another city (ie Rome). I almost never fly in and out of the same European city any more, and I travel on a tight budget. Generally, it's no more expensive to fly open jaw than it is to fly roundtrip in and out of the same city. Also, I usually check flights on kayak and probably travelocity or expedia, to just see what's available, then go to the airlines' own sites to do the actual booking. Finally, you might want to look at "packages" on both expedia.com and travelocity.com. These two are BIG companies, with long, mostly dependable track records, and have both given me great customer service when there was a question or change needed in my itineraries. I just last month saved almost $1,000 booking a Delta (going)/Air France (returning) flight package with four nights in Rome. If you'd like to discuss more the pros and cons of booking through a travel website (like expedia or travelocity), let me know.

mir1329, are you familiar with codesharing? If not beware that flights that have a Delta flight number, whether booked through Delta or on a third party site like Expedia, might actually be on an Alitalia airplane. I dont know who United's partners to Italy are (KLM, Lufthansa?) but they can also be on codeshared flights.

It's your second sentence that caught my eye and prompted me to jump in. I have no suggestions about airlines BUT I have learned that the first thing you don't need to do is get flights. The first thing you need to do is figure out a basic itinerary. Then you'll know which airport/s to fly into and out of. The major airports are Rome, Milan, Venice and Naples. Generally flying open-jaw (into one city and out of another) is more efficient and costs about the same. Here's the thing. . . say you want to see the top 3 - Rome, Florence and Venice. If you lock into a round-trip ticket to Rome you will find that you're going to spend a lot of money and time on a train to get back to Rome from Venice. So you may initially think you're saving money on a bargain flight and end up wasting nearly a whole day and spending more money.

How flexible are you with the length of your trip? On my first trip to Italy I arbitrarily decided that I wanted 12 days in Italy and booked tickets. I then had a lot of headaches trying to fit in everything I wanted to see and do. If I'd planned out my itinerary first, I'd have seen that adding 1 more day would have made a huge difference.

Lastly, if you are planning to spend time in Venice (I think everyone should, but I'm in love with the city so I'm biased), I recommend flying into Venice and starting your trip there. Venice is low-key, it's the best place to get over jetlag and soak up the atmosphere. Rome, on the other hand, is a big, bustling metropolis with major sights, making it difficult to tackle when you're walking around in a haze until you've adjusted. Or if you want to go to one of the northern lakes, like Como, Milan is where you should land.

You're lucky you'll have choices - I think you can find non-stop flights to all the major Italian airports.

Happy planning!

Stan has a point, but in my experience code-shared flights are so noted in the descriptions where possible "solutions" are listed. The print may be small, but the code-share company name and flight number are right there next to the name and flight number of the airline company that is taking the booking. At least that's been my experience.

Don't forget the "lesser" cities--for example, I've gotten great fares into Pisa. But Chani makes a great point--share your plans and we can offer suggestions. So many people buy cheap fares to Milan and then have no interest in the north.
Someone else mentioned avoiding Heathrow, and that is something I try to do as well, but that is really the only one I would go out of my way (or budget) to get around.

Oooh. I also avoid changing planes in CDG, Paris. Crazy big chaotic airport!

I use Google Flights as my primary air trans search, your bookings are directly through the airline and you can track the price progression/history. Airlines don't really matter, there's only a handful of US carriers that fly to Europe, just be aware of what airlines hub out of what airports Newark (United), JFK (Delta, AA) and more importantly who their code share/alliance partners are: United (Star Alliance: Lufthansa, Swiss, Air Canada, etc), American (One World: British Air, Finair, Iberia, etc) Delta (Sky Team: Air France, KLM, etc)

I usually fly Lufthansa in/out of Italy, mainly because they have newer airplanes than United and SFO is a UA/Star Alliance hub so, greater frequency of flights.

As others have pointed out, most important is to dial-in where you want to go, then figure out the dates, then start your air search. Basic first timer trip to Italy is Venice, Florence, Rome, knock-out the big three, fly into one, and out the other and you'll have plenty of reasons to return for a follow-up trip.

Omg thank you for all the replies, I really appreciate! You all gave me some great points. Especially the open jaw tickets! We are going for 3 plus weeks and want to see Venice, Cinque de Terre, Florence, Rome and Amalfi coast. Starting up north then ending up in Rome or the Amalfi Coast/ Positano...as I said still in beginning planning stages. Any and all suggestions are welcome and very helpful..... thank you again!

Bravo--you've actually got time for all that (some try to squeeze it into half that time, which is just sad)! That would be Naples for the outbound flight, ideally, but if Rome works better, you can take a train from Florence to Naples or Salerno for the Amalfi coast and save Rome for last.

I think what Chani brings up above about having your itinerary nailed down BEFORE you book flights can't be stressed enough.
I see so many here asking for itinerary advice- they have already booked flights to/from locations that are not necessarily where they want to visit, they got a "good deal" on a roundtrip, etc.
Open jaw is almost always the best way to go. Otherwise you are going to spend extra time and money working out an itinerary that gets you back to your departure location.

If you know you have 21 days- is that 20 nights or 21 nights? you can start now firming up a really great itinerary that makes sense logistically and cost-wise.
Every single time we have gone to Europe- 21 nights, 24 nights, 17 nights etc- I always wish I had a few more nights! I know that once I book my flights I am locked in and it's always worked out ok, but just make sure you don't book til you know exactly where you want to go and how you want to get there.

We found flying in to Venice and out of Rome was just perfect. Venice is great as an entry to Italy, lovely place to get over jet lag.
This next trip we are actually doing opposite into Rome/out of Venice but I feel OK with it since we've been there before. I know I can deal with getting to Venice airport for departure- which can be a hassle.

As for flights- since you have JFK and EWR as options you should be able to find decent flights to and from. We prefer nonstop to our destination- no worries about losing luggage or missing connecting flights. We prefer the same for return but I am more willing to take a connecting flight home if we have to. I suspect most flights from JFK or EWR do go directly to Europe- but if you have a layover anywhere before your Italy destination make sure it is really the best deal.
My daughter was recently stranded in Iceland (got a cheap flight, mom!) and narrowly missed a very very important conference in Frankfurt
She ended up flying into Brussels from Rejkavik then had to train to Frankfurt- so ridiculous and cost her $$$ and 2 nights with no sleep.

You can start now monitoring flights but you have months til you need to pull the trigger on booking anything. Book directly with the airline, not expedia or whatever.

And don't hesitate to ask for help or advise here while you are working out your itinerary- there are so many great travelers with excellent advice here. Every one of our trips has ben enhanced by things I picked up here on this forum.