When to buy airfare and Italy/Greece itinerary suggestions

In your other post you bring up the possibility of staring n Greece, which I think is a good idea, particularly the island(s) first, then Athens and then move onto Italy.

To that end I would suggest getting your flights done sooner rather than later. Open jaw (aka multi-city) Denver to Greek Island and home from Milan. Get a separate flight Athens to Rome. I would skip CT and focus on Rome, Florence and Lake Como, and be back to Milan for the flight home. Trying to do 4 places in Italy will just have you running in/out of train stations

My $0.02

I agree with Joe about starting in Greece. From there I would fly to Rome or Milan, and end in Milan or Rome, whichever works best for flights home. Two nights in Rome really isn’t enough. Save CT for off season. Add those nights to Rome. Don’t under estimate the impact of crowds and heat on what you can accomplish. It can be brutal at that time. Get ac.

I've always purchased airline tickets about a year in advance and never regretted it.

Go to a website like skyscanner and they will provide updates as to when ticket prices change, but at this point you may want to go ahead and buy as soon as something seems "average" or reasonable.

I will concur the heat and crowds add another element to stress, fatigue, and how long it takes to do things.

I bought our tickets for Rome flying out of Milan back in September. We are flying out of San Francisco on 6/17. I couldn’t afford to go if I bought tickets now. Buy tickets now! My wife is a teacher so we have to travel in high season as well. It will definitely be hot 🥵.

hey hey freeburg.chris
my own opinion is this schedule is too much traveling with trains and planes. spending time packing/unpacking, getting to airport/station, waiting, plus check-in to hotels are between 2-4pm. unless you can get early check-in or dropping off luggage without lugging around on uneven pavement/cobblestones until check-in. been there done that, no fun.
jet lag on your first morning is REAL, you are traveling during busy & crowded high season, HOT HOT HOT, waiting in lines to get into attractions (skip the line does not mean you skip security). you have one full day in rome and what do you plan to see, next morning out by 10-11am. i would leave out cinque terre and add to rome. you got the tourists and cruise ships passengers all bombarding the area until the day trippers leave in afternoon. how many cruise ships are in port, maybe 2 to 4, which means thousands,
why travel all the way to milan to get a flight to athens? isn't there another airport you can fly from?
athens and the greek islands will be HOT. crowded and very busy. regular travelers and cruise ships. the places you have listed you want to see is what the whole planet wants to see and travel summer time with families. we travel once during summer and will never do it again, but understand why with you guys. just be really prepared for crowds and heat, get A/C!!!
we had a cruise stop at santorini, didn't like it. was so so crowded, rude people pushing and shoving, shops/restaurants on overload packed. we walked down a back alley, stopped so my friend bought a large gorgeous decorated pottery to ship back to states, found small mom & pop restaurant overlooking caldera with about 5 people and just loved that atmosphere.
loved mykonos and corfu, did private taxi tour shared with passengers we met on cruise critic to cut cost.
so many different islands to choose from, but if santorini is a must for fiance, happy life. congratulations on wedding.
don't wanna seem like deloris downer, i think you should concentrate on either italy or greece. you will just be on the go go go, with little time to relax like others have said.
you could go to the italian riviera, lago di garda (lake garda), we loved this lake near verona. no matter what beach place you decide, so many others will want the same thing. make sure where you want to go before buying airfare, get multi-city. prices will seem high and they are, if it feels good to buy go for it and don't look back. so many people are shocked at the costs, prices of everything has gotten so high on everything here, there and everywhere. hotels, condo/airbnb's/ walking and food tours, rental cars, fees. always look at your airline ticket to see if it changes/cancels, with shortage of pilots/crews, planes, changing airports always be on the up & up. it's stressful but you have enough with the wedding, it takes alot to plan but i like planning and does you good to know what's ahead of you and not go blindsided like i've seen many people do.
greektravel.com
matt barrett's guide if you want to read about it. lots of info from the travel posters here, good, bad, and ugly. good luck
aloha

I would buy now and book directly with the airline. Prices are unlikely to drop from here, there will be no warning when they change, and when they rise, they will won't go down until after the summer season..

Thank you everyone for your feedback. I am grateful for how helpful everyone is!

We narrowed our focus and simplified quite a bit. We are still doing both Greece & Italy, but flying straight into Santorini for 3 nights, possibly a second island for 3 nights, Athens for 3 nights, and then 5 nights in Florence and 3 nights in Rome.

I am looking for excursion recommendations from Florence. I have read good things about Siena, Tours by Roberto and Castello del Tribbio. We would love to spend at least a day in Tuscan countryside. So, 2 days exploring the city in Florence, 1 day to Siena and 1 day of wineries/agriturismo. Are there other recommendations or things to keep in mind?

I am looking for recommendations for Rome neighborhoods. I have read good things about Trastivere, Piazza Navona, Campo De Fiori. I see lots of places around Monti, Prati, and Trevi. I am still getting to know the neighborhoods. What are people's reactions? Are these too far?

For Rome, we plan to do 1 day in the Vatican City and 1 day around city center. We would like a quiet night's sleep, A/C, and private bathroom for under $100-150/night (breakfast provided is not as important to us). We love to walk and so I think we want to be close to the action, but away from overly tourist areas. (Quiet + Walkability may be an oxymoron, I know we are the tourists!)

We found a place with a private balcony in Florence, which is very exciting. I think this may not be as important for us in Rome, but a great view would certainly be a plus.

Thanks again for all your help! I love the community!