My fiance and I will be taking our honeymoon in Italy ( July 2012 ) - We'll be in the country for 12 nights. Here's what we're thinking:

Fly into Venice ( 2 nights )
train to Florence ( 4 nights ) 2 in Florence and 2 in either Chianti or Siena?? We would like to stay in a farmhouse or at a vineyard while in Chianti or Siena.

Now here's the question on what to do from Chianti or Siena.

We'd either do Cinque de Terre, portofino etc ( northern italian riviera ) for 4 nights then to Rome for 2 nights and fly out of Rome.

Or go from Chianti / Siena to Rome for 2 nights then to Amalfi / Positano for 4 nights then fly out from somewhere down south.

We're torn between Amalfi and Cinque de terre and which one is a must see? That portion of our trip would be the relaxation period in a higher end hotel.

Always welcome Fodorites feedback!

If you have only 12 nights (and it's your honeymoon!), I would suggest covering less ground and really enjoy la dolce vita.

With the jetlag and all, I really don't think you would have time to really appreciate Venice in 2 nights. It's quite a magical place.

Perhaps 4 nights in Venice, then 4 nights in Florence, maybe 3 nights in a chic countryside hotel with a daytrip to cinque terre if you feel like it, and 3 nights in Rome. Rome is a fantastic city (my favourite in Europe). 2 nights is not enough in my opinion.

Enjoy! You'll love Italy.

Two night stays are tough. Just when you get in the groove, you are leaving. Transport and packing eats up a lot of time. Plus, you will be jet lagged your first day in Venice. And Rome certainly requires more than 2 days. I understand the desire to see a lot of places, but you really see more with more time in fewer places. I highly suggest paring down your own must sees to fewer places. You can go back!

There is no denying Cinque Terre is beautiful, and if you like hiking then it doesn't get more convenient. However--and this is a big but--it was dreadfully crowded in May, so July will be a fresh hell. Also, if you want high end then Amalfi will be your place.

If you do opt for Amalfi, read my trip report. We were there a few weeks ago and enjoyed it a lot. But again, less travel = more dolce vita!

Agreed on the comments above. Less is more in my opinion, especially if you want to be able to slow down a bit.

Cinque Terre is beautiful, and I would highly recommend it (on a later trip). If luxury is what you want, however, you will be very hard pressed to find it there.

I think heading south of Rome would result in way too much travel.

Think about 4 nights in Venice, train to Florence for 3 nights, rent a car and spend 3 nights in the country (look around Montepulciano/Pienza), and last two nights in Rome. You'll want more time in Rome (and Florence, I'm sure), but this is managable and the route is compact and directionally correct the whole time.

Congrats on your nuptials, btw.

Thank you for the quick responses, and keep them coming!

Any suggestions on the easiest / cheapest airports to book one way flights from? We're headed from Boston.

Check with a travel agent to get the best combination/price. The prices can vary so wildly, it's hard to tell!

Cannot repeat enough the advice to make fewer, longer stops.

July is height of the tourist season, so Venice and Florence will be very busy and airfares will be expensive. This changes constantly, but one couple in our group last week flew Boston-Madrid-Bologna and paid less than any of us who flew directly to Italy or through the usual gateways like Frankfort.

And try to get direct flights if you don't want to live my recent nightmare of late flights, missed connections and lost baggages!

My last reply goes against Ackislander's comment... Keep in mind that sometimes it may be cheaper, but to lose one whole day in an airport sucks!

I think you want open jaw flights, not one way, right? (Or do you mean within Italy?)
I use kayak.com.

We just returned from a 11 night trip if you count your departure night as one night- 5 nights in Rome, three nights in Positano and two nights in Naples. There was not enough time anywhere. Rome was the best but we still did not see everything that we wanted to see so I suggest you focus your trip on a few places and hope that you can return later. Don't forget that you will lose time travelling from place to place. Have a great honeymoon.

When looking at travel sites (expedia, travelocity, etc.) you want to select the multi-city option when looking at flights, not one-way. Very important difference. Multi-city flights cost the same (give or take) than stanard round trip into and out of the same city.

For the trip you're thinking about you want multi-city for sure. Don't needlessly double back to an originating airport. Even if it saves you a few bucks think about the time and the cost of getting back there.

How about 3 nights in Venice, then renting a car and driving to the country (we can discuss where later) for 4 or 5 nights, with day trips to crowded and hot Florence? Then the rest of your time on the Amalfi Coast. I highly recommend the Hotel Poseidon in Positano for an upscale honeymoon destination. It's not full out over the top unaffordable luxury, but it is damn nice, and there is a swimming pool.

You can always fly into Venice and look at flying out from Genoa or maybe Pisa. That way you could see Venice, Florence and stay in Portofino for a few days of high end luxe. I love the Hotel Spendido and the Splendido Mare. From Portofino you can grab the train and go to Cinque Terre for a day.

On our honeymoon we did 3 countries and 5 cities, I am still exhausted from that trip and that was in 2002. Less places more time.
All the best!