Help with Italy Itinerary & airfare questions

Florence: I would break up your Tours so you are touring one day, wondering around and doing your on day then next, then touring again. Waking up two days in a row early to meet a tour can make your feel like your go-go-go all the time. We used Walks of Italy for our Florence tour, BUT only 3 hours and Walkabout Florence for our all day Tuscany day. Look into both and see if these fit your idea of fun.

I would cut a few days (3) out of Rome and base in Sorrento for 3 days to see the Amalfi Coast and you can also visit Pompeii.

Airfare I think you can do much better than $1500.00 PP RT that is on the high end. I would look for $700.00-$900.00. Aer Lingus has a great rate as does Air Canada, just keep your eye on it and sign up for that email service I told you about.

June=HOT! But nice long days...what a beautiful time to see Amalfi!

No one can predict airfare trends for the summer of 2019. Airfares have gone done in the last few years significantly (the Euro was also very week vs. the dollar for a while which probably helped). Airfares may stay about the same by then or may go up a lot - or down.

Personally, I wouldn't worry much about the airfare yet. $1,500 pp RT is probably very adequate but if it goes up to $1,700 will you cancel your whole trip? I doubt it.

"How early should I buy my airline tickets?" is a preference question like "What's your favorite flavor of ice cream?" You'll get passionate answers for early and for later. You'll just have to decide for yourself. Just understand the pros and cons of buying early vs. later. If you buy early, fares may go up after you buy and you'll congratulate yourself - or go down and you'll kick yourself. (But try not to.) But if something happens and you have to cancel or postpone your trip and you bought the ticket 6+ months ahead, then what? (Many people have trip insurance, but it doesn't cover everything that might happen.) Airlines also change their schedules sometimes closer to departure day; you might buy tickets for what look like excellent flights that wind up getting changed to a tight connection or something.

(If you haven't guessed, I tend to wait and not buy early.)

Don't worry too much about missing your flight out of Rome. Just plan to arrive early enough so you have plenty of time. I would never avoid Rome just for that reason.

Is Florence really the best place to fly into for you? (Or out of?) It's not a big airport for international flights from North America. Check fares for next May (to get an idea what they might be in 2019). If you can get good flights into Florence, without lots of connections and a decent fare, sounds fine to me. But you might find cheaper fares into Pisa or Rome. (There are a very few direct trains a day between Rome's Fiumicino airport and Florence FYI.) Use Google Flights and see what your flight options would probably be in 2019, based on next May. If flying to Florence means an extra flight connection or a much higher fare, I'd rather fly to Rome if that's better and just take the train to Florence instead of the extra flight.

I wouldn't overthink or overplan your itinerary. You've already done lots of planning. One thing I've learned is to try to be flexible. Things may not work out as planned and you may wish to change something when you get there. I see some people planning their itineraries to the HOUR on various days and I think that's kind of silly - sounds like less of a vacation than a march. If you have a lot of days in each city, you shouldn't have to worry too much about museums not open while you are in town or something.

Another possible day-trip from Florence would be Lucca.

Another possible day-trip from Rome would be Orvieto. If you're interested in antiquities, Ostia Antica is easy to reach from Rome.

I share your dislike of hotel changes, but with the amount of time you have, I'd spend at least two nights on or near the Amalfi Coast if I wanted to see that area. The trip from Rome will be long and rushed, with (I assume) no time to do any rural walking.

For your flights, start monitoring fares late next summer or early next fall. Checking every day isn't too frequent. You could even check out fares this year from time to time. The idea is to get an idea of what the typical price is for your travel period so you can jump on any unusually low fares that pop up. In recent years there has been considerable variation from week to week and even from day to day, but you're not in a good position to take advantages of the buying opportunities if you can't immediately recognize a good deal.

I like to use Google Flights, but there are other options. You can check round trips from your origin to "Italy" and see what the fares look like to Rome, Pisa, Florence, etc. From my origin Rome and Milan are nearly always the cheapest options, but it may be different from your home airport. It's great to be able to fly into the first city you want to visit and fly home from your last city. Having to make rail connections at the beginning or end of your trip is often not terribly expensive in Italy, but it wastes time. That may not be so critical on your arrival day since you may be jet-lagged and sleep-deprived anyway, but to have to give up a chunk of your last full day to relocate to your departure city is unfortunate. Sometimes it's the sane thing to do, though, because of huge cost savings.

If you tell us your point of origin in the US, some folks here may have tips for good flight possibilities. [Never mind--I overlooked the reference to LAX in the initial post.]

You might want to go in May if at all possible. There are fewer crowds, it is not as not and airfares are cheaper.
We flew Norwegian Air Shuttle into Gatwick and visited a relative. Then we took a EasyJet flight (cheap)/into Pisa. The train ride over to Florence was just over an hour.from their train station.
A long weekend was long enough in Florence for us. We rented a car and moved 45/minutes south in an agriturismo for 4 days. Day trips were made to hilltowns like Volterra, Certaldo, and San Gimignano. We took a long day trip by car up to Venice one day. We then drove down to Orvieto and spent one night before returning our rental car and taking the train into Rome.
It is hard to tell the best time to buy the airline flight. I would be shooting for prices far under $1500. There are some great airfares being offered presenty--depending on where you are flying to/from.

@Letizia Thank you so much for the recommendation to put days between to break up the "tour" dates. Really good suggestion! I'll do that :) And $700-$900 from LAX would be a dream! From your lips to Gods ears I hope haha. I'll check out those two airlines you suggested when it gets closer.

@AndrewH. Thank you for your thorough comment. Its so true I tend to over plan and obsess just in general and my husband tells me we need to just go with the flow on this one. It's like a fine line between worrying that if I just go with the flow I might miss out on an experience we both would love. But your right I want to just enjoy the experience and not over plan. I think we would want to book a little later to try and grab a good deal but have enough time to book an Airbnb. Now that @Letizia has told me how much we could save I'll just wait until I see a deal and play it by ear.

We are pretty flexible in our jobs should we try and go during a different season when it's not so busy and HOT? I was thinking May wouldn't be too bad but maybe I'm just kidding myself. I don't want to go when the weather is bad or its too cold so winter is out. I'm a Southern California girl I don't do too well with cold and I'd like it to be good weather for our trip to Italy if possible.

When is everyone's favorite time to visit Italy weather and busy wise?

This looks great to me! I support less hopping around. That means more time getting to know fewer places in more depth.

There are lots of great places in Italy! The “big 3” for a first time are Rome, Florence, and Venice. Often followed by Tuscan wine areas and Pompeii. You have a lot of this. Venice is the most “missing” and you can see it next trip.

Rome’s airport is a 45 minute cab from the center. Not awful as far as big city airports go. It doesn’t really matter, but I like into Florence and out if Rome because Rome is just easier once you’ve adjusted to Italy a bit. But if you can get a better deal or direct flight, either is good.

Don’t know about Pisa vs Florence airports

Booking varies so much. Start looking now just to get an idea of prices. Once you have a feel then buy whenever you see a rate you like. I usually buy early - 6-8 months and find great fares then. Some people will advise waiting but I don’t like the risk, plus if you book early you get the best choice of seats. $1500 is more than enough from the East and Midwest. It’s high for big markets like Chicago and NY where I tend to spend $1000. LAX is big, but fartheraway, my guess $1500 will be more than enough.

@acraven 2 nights in Amalfi Coast would be amazing. I'll see if my husband will take a "weekend trip" from Rome with me to stay in Positano for a few nights. Great suggestion. We can use the $442 it would have cost to book that day trip to the Amalfi Coast and use it for an air bnb maybe. Great suggestion! Thank you. Do you think the weather would be nice there if we went in May?

@David I'm leaning more towards going in May before the summer crowds. Thank you for the suggestion :)

@Mira YES less hopping would be best for us! We want what you described "getting to know places more in depth" then spending a day in each place and ultimately missing out in the end. Im thinking booking flights 6-8 months in advance would make me feel safer. We will probably do 6 months out.

Thank you everyone for your input it's very valuable. I welcome as many tips as possible :)

Ocsurfergirl, from one planner to another, I figured I'd let you know what has been working for me. I couldn't have a trip coming up and not research, as I need to have ideas on what to see and don't want to waste time on sites that we're not interested in, so I would be stressing if I didn't research. What I've gotten better at is that I do the research on what interests us, and put things in 'A' and 'B' categories. 'A' category is for things I think we really want to try and see, and I have the 'B' items in case we get bored and need something else to do. But when I'm looking at the days, I really try not to over plan each day, as some of the best memories we have are 'unplanned' things that have happened because we were just walking around, sitting having a drink, etc.

And what I've also gotten better about is that if we don't get to all the things I hoped for, I don't focus on what I might have missed, I make sure to enjoy what I am seeing!

I think the odds are pretty good that you'll have nice weather on the Amalfi Coast in May (especially late in the month), but there are just no guarantees. A couple of years ago I flew into Rome on May 25. The temperature was pleasant, but I got rained on fairly heavily on two of my four days in Rome. They weren't all-day downpours, but enough that I needed to seek cover; I wouldn't have been happy hiking in that weather. Then I headed up to Orvieto (about an hour north of Rome), where I was told that the weather had been unseasonably cool up until shortly before I landed in Italy. From then on I baked, week after week, until late September. I had two brief respites when I traveled north of Berlin and into the Dolomites. You just never know.

I suggest looking at the historical monthly temperature graphs on wunderground.com. They show hour-by-hour data for most major locations, and you can check every May for at least the last ten years. Take a look at the range of what you might experience. To me, that's much more useful than a single "average high" and "average low".

Particularly since you're from southern California, you need to be aware that in the shoulder season, Italy is neither SoCal nor southern Florida. Rome is at the same latitude as NYC, though the winters are much milder. But mid-summer in much of Italy can be really, really unpleasant.

With THAT much time, I would do 3 bases - Florence/Tuscany, Amalfi Coast, and Rome.

You should have no problem getting a good airfare from LAX but you'd do better if you have some flexibility to fly off-season (in May as opposed to June, if possible). An off-season non-stop fare from Norwegian Air to Rome can be as low as $500 or so. And it's easy to take a train to Florence from Rome, if need be.

I share your dislike of hotel changes, but with the amount of time you
have, I'd spend at least two nights on or near the Amalfi Coast if I
wanted to see that area. The trip from Rome will be long and rushed,
with (I assume) no time to do any rural walking.

With the amount of time you have, I'll go along with the recommendation to shift a few days from Rome to the Amalfi Coast. We don't like to move too often either but the AC is just far enough away, and you have just enough time, to warrant the transfer to a third location. There's also too much in that area to begin to cover in one short (by the time you subtract transit time) day. I'd just return to nearer Rome the evening before your flight home as the AC can be a pain to travel from if having to make a morning plane.

Seriously, consider R/T LAX-FCO.
On arrival day head to Florence. As mentioned above, there are two direct trains that connect FCO to Florence. Or taxi to Roma Termini and connect to hourly trains there.

My next suggestion is on day (7), train Florence-Naples-Sorrento. Around 4 hours Spend 3 nights. Though not technically the AC, it gives you the best transportation options.

On day (10), train Naples-Rome. 1H10m. Spend 6 nights. This puts you in your departure city so there's no need to rush back or do a 1night stay.
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As others suggested, I think it's a good idea for you to fly roundtrip to Rome. I input some random dates in May for Norwegian Air (leaving the 16th, coming back the 30th), the nonstop roundtrip airfare came out to $580/person, I know that this is for 2018 and you won't be leaving until 2019. Norwegian Air is a budget carrier, so the price does not include food, checked luggage and seat reservations, you will have to pay extra $180 for the above benefits. I'll be flying them in February from Oakland to Rome (I prefer to travel during the low season), I got the tickets for $420 roundtrip, without all the frills. I've learned how to pack light from all the great suggestions that I learned from this website.

My personal favorite time for Italy is September to mid-October. The weather, generally, is glorious all over the Country, crowds and prices are lower as it is fringe season. September is a wonderful time for the Amalfi Coast.

You've already received great advice (use Weather Underground to check historic temperatures, Google flights to check/monitor prices, spread out your long tour days). The only point I'd add is that you never know what NEW flight options might arise in the next two years. For example, Norwegian and Wow are making a push to add routes to Europe - because you are in LAX you are most likely to benefit from this (not so much in the rainy Northwest). And I completely agree with going in May. I know you're a SoCal girl, but I was in Rome in very early May and it was hot and super miserable (humid, no breeze, no ocean to cool you).

PS I'm a planner too - in initial stages of my 2020 trip planning (before I even go on my 2018 trip).