Honeymoon 2 weeks, late April-early May 2016 Florence, Rome, Amalfi/Positano/ or Cinque?

Congratulations on your upcoming wedding and your choice of Italy for your honeymoon. Italy is a wonderland.

You have identified the Most challenging aspect of going to Italy: with so many choices, how to choose where to go.

To Americans a 2 week vacation seems like a lengthy vacation, but the time will go quickly. you likely will use at least 2 days in transport there and back. That leaves you with, max, 12 days to be used on your destinations. If you want to go to stay put you will have 12 glorious days. If you wish to experience 2 locations, you will lose at least part of a day on logistics: packing up & checking out of your hotel, going to train station/airport, arriving and checking in at your new lodging. This might leave you with 6 days in 1 location and 5 in another. The more locations you decide on the shorter your stay in each location. There is the inevitable challenge of seeing as much as possible and yet ensuring you aren't rushing around too much.

I personally would probably choose 2 Places as I like to savor the destinations rather than moving around but other people prefer a different pace. I would probably spend 5 days in Rome (you mention your husbands interest in Rome ..so many fascinating historical sights), 1 part day in transport, and 3-4 days in Florence ( if you are interested in art ), with perhaps a day trip or two.(Assisi, Lucca). Last year we spent 3 days in Padova (20 minutes by train to Venice and a delightful low key, walkable, ancient town), 2 nights in Orvieto (Tuscany beautiful scenery, 1 hour from Rome), and 6 nights in Rome. For us, the timing allowed us to experience each location ( finding a favorite coffee shop or bakery, recognizing how to walk from one place to another)---but because we like to stay more than 2 nights, my destinations were limited. I never experienced Florence! Or Sorrento! Or Lucca! Or Positano! Ah, Italy. ( remember you can fly "open jaw, flying into one city and out of another which saves time;a round-trip is not needed ). Enjoy your trip!

What, no Venice??? Personally, I would go to Venice over Milan. It is very romantic. With 2 weeks you could easily do Venice (fly into), Florence, Cinque Terre, and Rome (leave from). I know you said you didn't want to change hotels much, but the travel distance on the fast trains is not that bad.

But, given your original idea, you could do Florence 4-5 nights, with a day trips to Siena and Pisa/Lucca.
Cinque Terre 2-3 nights, then Rome 4-5 nights, with a day trip to Orvieto.

As far as time of year, one can never predict weather. It may be a little cool, it may rain, who knows for sure.

Congratulations and happy planning!

Lake Como (3 nts) >> Cinque Terre (3 nts) >> Florence (4 nts) >> Rome (4 nts)
or
Venice (3 nts) >> Cinque Terre (3 nts) >> Florence (4 nts) >> Rome (4 nts)
or
Florence+Tuscany (5 nts) >> Amalfi Coast (5 nts) >> Rome (4 nts)

What time to go? Overall I would definitely say May, however if you are set on swimming in the sea then go in September.

Thank you all greatly for you insight, we will be finalizing our plans today and you have all helped us greatly with you input helping us narrow down our points of interest. I appreciate it, we are very excited to spend some time in Italia!!

I agree...Venice is just do romantic...please don't leave that off your list.

I think late April/early May is an absolutely optimum time to travel to Italy. Almost everything is open, without the tourist hordes that will come by the end of May. Weather should be perfect, actually warm the farther south you go.

Fly into Venice (or Milan if it's easier logistically but then train to Venezia), and out of Rome or Naples. The air is the first thing to book--everything else will fall into place after that.

So let's say you have 12 nights. If you roughly figured 3 nights each in Venice, Florence, Rome & Sorrento/Ravello on the Amalfi Coast, you wouldn't be wrong. It would give you a good overview, albeit a tad rushed, but train travel for this itinerary would be efficient. Oh, and remember that this time of year on the A.C. will be spectacular, again without the hype you're talking about because it's just before high season. I would take it over the C.T.

More of a slow-to-medium-cook version would be fly into Milan, train to Florence, 5 nights there with daytrips to Siena or other destinations in Tuscany, do your cooking class, etc. Then...your husband wants to experience Rome but you want to lie on the beach, too. I have to think you want to hit the A.C. next for 3 nights, then finish up with 4 nights in Rome, flying out of Roma Fiumicino.

As stated upthread, you think 2 weeks is a lot, but it's not. The more time you get, the better. Before I traveled there, I heard that phrase 'Italy is to be savored', and thought it BS. Uh, it's a very accurate statement.

Enjoy your planning!