from Florence to Naxos?

You can fly Pisa to Athens and then fly to Naxos.

Check skyscanner.com for options

Where is your return flight back to San Francisco? Athens? Or somewhere in Italy?

We haven’t figured out the return flight to SFO yet either. : ) Seems like Athens probably makes the most sense? Ferry to there from Naxos. Spend a night or two in Athens before flying home?
I’m very open to other suggestions. Thanks!

You have to think strategically when you have such a short time. Skyscanner shows June 2020 flights nonstop from Florence to Santorini dep 2pm land 5:20pm starting at $306 -- not cheap, but the Pisa-athens-Naxos route probably wouldn't be that much less, & consider the time & hassle to get to Pisa!

• SANTORINI - I would suggest a VERY short stop in Santorini (40 hrs; 1.5 days, 2 nights)... stay at a rimside-view hotel in Firostephani (just N. of Fira town, walkable to sights but unknown & bypassed by tour mobs!) -- many of these offer free transfer from Airport. Each night find cafes in Firostephani or Fira to enjoy Sunset -- AVOID Oia for this. In AM, 8:30 get bus to Oia for 90 mins of wandering & photos before cruise crowds jampack the lanes, then leave. On AM of day 3, take 10:45am ChampionJet ferry, large catamaran with open back deck for caldera view on departure, arrives Naxos (yay!) by noon.
• NAXOS - for short stay, I advise staying at a hotel right ON the sands at St. George Beach, directly adjacent to Naxos town. It's a win-win, seaview from your balcony, easy 10-15 min stroll by water to all town attractions; cafes, shops, museums, winding maze-y lanes up to Kastro -- yet beach is serene at night, sit at cafes on sand under the stars. I go there in June, so I know. Try to spend at lesast 4 nights there, and DON'T Ferry to mainland... it eats up much of a day & you can't spare the time... TIP: book Naxos flights EARLY - the small modern turboprops(only 3 per day) fill up Months ahead of time. If you sign up for Aegean "newsletter" (really, just e-mail alerts) - https://en.aegeanair.com/newsletter/ - You'll see any price breaks if available (but don't wait past Jan-early Feb).

• ATHENS - Short stay? Book in Plaka area, or u waste precious time on loong hot walks or $$ taxis. Even if u have "points" don't be tempted by big chain hotels almost all are far way from landmarks. This "tiny url" - http://tinyurl.com/heq6edp - is booking.com's filtered site (showing how close places are to Acropolis)- go to MAP VIEW & Choose lodgings less than 1 mile from Acropolis. If you can get a late-morning flight, you could have afternoon for sightseeing (Acropolis is GREAT from 5-7:30, crowds are gone & ruins turn gold in sunset. Next day, do a free walking tour, go to Acropolis Museum, do "walk-by" viewing of Temple of Zeus, etc.

My suggestions will cost a substantial amount in transport but as the old saying goes, if you don't have time, you must spend money. My scenario is an attempt to provide you with maximum time ON the ground, enjoying Greece, and minimize the hours on planes, ferries, busses, etc.

I really appreciate your detailed suggestions Janet. We've been to Santorini (pre-kids) and don't feel a need to see it again. I was only thinking of it as a place to fly to from Italy and then ferry to Naxos. I wasn't aware there are direct flights to Naxos other than from Athens. We want to maximize our days spent on Naxos rather than island hopping.

But those flights are a bit pricey. So one other question (opening a can of worms).... Are there any beach areas in Italy, Spain or Portgual that have "similar" beauty, ocean/beach fun and relaxed vibe that Naxos has for a family?

I spent about five days in Naxos, two by design, three by freak of nature when constant gale force winds stopped the ferries from running (in early September). I loved the place! Renting a car and getting out of the main part of town was extremely affordable - about $35 for the day. We drove to other towns and visited the Kouros in situ. Food was amazing. Went to a concert - with amazing musicians playing authentic songs on authentic Greek instruments. Townspeople were lovely to us. Our hotel owners went above and beyond the call of duty to make sure we were on the first ferry that was able to depart the island so that I didn't miss my flight to the US from Athens - going to the ticket office after midnight to reserve our spots and get our tickets while we were sleeping. Very walkable main town. Lots of people were able to fly out of the small airport, although reservations/seats sold out quickly. Truly one of the best places to visit!

jd, I did not state that there were flights to/from Naxos anywhere but Athens... I was speaking of flight from Naxos to mainland. Frankly, if you want to find better island/beach options in different countries, you will need to go to forums for those countries ... you won't find many experts here who favor those countries over greece.

In Italy, try Puglia or Cinque Terre. Maybe even Amalfi Coast but I don’t know if it would be as family friendly and much more expensive than Naxos.

Sorry Janet, I misread your post saying the flight was from Florence to Santorini, not Florence to Naxos.

There may also be flights from Bologna to Athens.

Thanks for the suggestions. It's hard to plan this piece this far in advance since many airlines don't yet seem to have their full flight schedules for late-June 2020. But we also want to nail down our hotel reservations in Naxos ASAP.

One option that looks like the timing might work for us would be to take the train from Florence to Rome airport, and then fly direct from Rome to Santorini. Then spend the night in Santorini. And then ferry next day to Naxos.

Coming back, we could fly from Naxos to Athens, spend a night or two there and then fly home.