One week- Florence and ?

Cinque Terre should be great (I'm heading there in a few weeks). If you fly home from there, best airport is Pisa. Milan is also a good choice because the train goes directly from Cinque Terre to Milan. Regardless it will be a bit of a journey so factor that into your plans. And start reserving accommodations because the good choices are booking up.
Alternatively Siena and southern Tuscany would be good.
Have a wonderful time!

Hi Jen -
Congratulations on your anniversary! So what about this....

If you fly out of either Milan or Rome, you're going to need to spend the evening before departure in ether city. Also, you may end up staying in Rome/Milan on arrival day if your flight gets in really late so you really only have a partial day Sunday - Friday to work with, returning to Rome or onto Milan on sometime Saturday.

What if you got a nice apartment in Florence for the duration and day-tripped from there? It's a great base for any number of those, and you could settle in nicely without having to do any packing up and moving around. Siena, Lucca, Pisa, Fiesole and some others are easily reached, and the week would allow you flexibility to shuffle itineraries based on weather or just what you felt like doing on any given day.

You could also choose to spend a couple of nights in Siena or Lucca. I'm avoiding suggestions for the Cinque Terre because snagging a hotel at this late date could be a challenge: it books up pretty far ahead of high season. It may not be impossible but, well, it promises to be more difficult than not.

While Cinque Terre would certainly satisfy your jones for being near the water, if that is not a priority, I might suggest after 3 nights in Florence, to take a train to Orvieto in Umbria (2 hrs). It's a beautiful hilltown with a fantastic cathedral. The town's somewhat discovered now, but maybe you can find an estate or agriturismo in the valley to stay. We were there last month, and in late winter it was serene and magical. From one of the overlooks to the valley below, I saw this estate with a tower that I have been told is a monastery-turned-hotel. Maybe you can do something like that, and then visit the town during the day.

Stay there 2 nights, then since you're flying out of Rome, you might as well finish up there--a 1 hour train ride. Nothing wrong with the Eternal City!

I'll ditto Jay's good suggestions as well. Orvieto would be on the way back to Rome, and even though you've been to the Eternal City before, I'm very sure there are many things still to see that you didn't last time.

You have some great options to choose from!

OK, I think you have 7 days (Sunday thru Saturday). Day 1 (Sunday) - jet lag recuperation (Florence, jump fast train up to Florence on arrival in Rome and relax (if that is too much stay in Rome, perhaps a day trip to Ostia Antica, then Florence early Monday morning).

Then 4 nights (S,M,T,W) in Florence (3 full days M,T,W), so it is now Thursday morning. Take the train to Piombino (3 hours from SMN).

2 nights here (Th,Fri) enjoy the town and the water.

Saturday, train to FCO airport and spend the night, depart for USA.

This is probably totally different than you were expecting. But, it is something to consider.

Happy Anniversary.

Lots of options.
Consider a day in Siena, perhaps another day in Pisa and Lucca. There are many wonderful small cities in Umbria like Assisi, Perugia, and Orvieto that you might consider.

Fantastic! Well now I'm gettting excited instead of overwhelmed. I did read about excessive crowds in Cinque Terre and assumed I should not go there. I will look at flights and trains today and see what works. Thanks for taking the time to respond, this is so helpful!

Do all of you think Sorrento is too much traveling for a 2 night stay?
A friend of mine asked if I would make a stop there for her. It would be nice but really not necessary if too difficult. It looks beautiful when I google. do I fly or train to Naples then take a ferry? Or hire a car?

We stayed in Sorrento for a few days in 2008. While the town is pretty and the setting is nice, it did not seem as "authentic" as some other towns in Italy. The main attraction seemed to be shopping.

We stayed in Sorrento for a few days in 2008. While the town is pretty and the setting is nice, it did not seem as "authentic" as some other towns in Italy. The main attraction seemed to be shopping.

We spent an entire 10 day vacation in Florence in 2005, and took day trips to Siena and Fiesole. San Gimignano is another good choice for a day trip.

I would listen to the posters regarding staying in Florence or even Piombino before I would go to Sorrento.

One truly needs 3-5 nights on the Coast to enjoy it. There is just a bit more travel involved to get there to leave so quickly.

But if it calls to you, go for it ! Again, check lodging in all of your possibilities soon - that may make your decision !

Ok. I think I will make this "easy" (for now). I am booking my flight in and out of Rome. Staying in Florence 5-6 nights, last night or 2 in Rome. Now to find a nice AirBNB for the week!
Thanks again to all!