Help - 21 day honeymoon - Itinerary flexibility

April/May is early for the Dolomites and most lifts to higher altitudes will not be open. Save it for a summer trip in the future.

I know I am more extreme than many here, but I believe in itineraries based on the right place(s) at the right time. I doubt that late April is the right time for the Dolomites (which are great in mid-summer when most of the rest of Italy is broiling). When you have too many potential destinations, I think it makes a lot of sense to use weather as a culling factor.

I am not knowledgeable about spring conditions in Lake Como or the Amalfi Coast, but I would guess the likeliest unfortunate weather on Lake Como early in you trip would be chilly rain, whereas you might have excessive heat in the Amalfi area toward the end of your time in Italy. Which would bother you more?

I absolutely loved Lake Como when we visited Italy last August. It was not part of my original plan, but for us, flying from the west coast, Milan had the best connections and air fare. From Milan, it made sense to take the train (approximately 60 minutes) to Lake Como. It ended up being one of the favorite parts of our trip and I think it would be a very romantic honeymoon destination. However, it was about a 3 1/2 hour train trip to get from Varenna to Florence, so that might be a factor.

If you decide on Naples/Amalfi Coast and unless you can find a great airfare/reasonable departure time from Naples, I suggest going there directly from Tuscany, visiting Rome last and flying out of Rome. The weather in Italy in late April and first half of May is ususally transitional, so you're likely to encounter a mix of warm/cool and wet/dry days. For example, in Florence this year late April was quite nice (Easter brunch was outside on a terrace) but much of May was fairly cool. I doubt that it would be uncomfortably hot or cold anywhere except maybe the Dolomites if you were to visit there at the beginning of your trip. Pack clothing you can layer to accomodate fluctuations in the Spring weather.

The multiple night stays are good. You might, however, be short changing Venice which is a great place to start a honeymoon. Three nights there only gives you two full days and part of a jet lagged arrival day. Personally I'd add two nights to Venice to not only do it justice, but to have time for a day trip to Verona or Padua. Where the extra nights come from are up to you and the bride to be. Just food for thought. Love long and prosper.

The revision looks perfect--I don't see any room to add anything else. What is the question?

Thanks all for the comments and steering me toward right place, right time, right amt of time. My (updated ) question is which of the following seems like the best for a first trip to Italy? We are young and like to keep moving. We probably won't make it back to Italy for a long time so trying to balance relaxation with seeing the most.

4 nights - Venice
3 nights - Lake Como (~May 1)
3 nights - Cinque Terra
3 nights - Florence
2 nights - Tuscany
5 nights - Rome

4 nights - Venice
3 nights - Florence
4 nights - Tuscany
4 nights - Naples/Amalfi
5 nights - Rome

4 nights - Venice
3 nights - Lake Como
4 nights - Florence (add in another day trip)
4 nights - Tuscany
5 nights - Rome

4 nights - Venice
3 nights - Lake Como (~May 1)
3 nights - Cinque Terra
3 nights - Florence
2 nights - Tuscany
5 nights - Rome
I feel like that one has too much moving around (especially CT to Florence), and I have weather concerns for Lake Como. I would not bother with two nights in Tuscany--it's not really enough time to settle in and relax, so I would add those days elsewhere.

4 nights - Venice
3 nights - Florence
4 nights - Tuscany
4 nights - Naples/Amalfi
5 nights - Rome
This one looks perfect! Though I would consider moving one night from Rome to Naples and the AC depending on what you have on your agendas for both.

4 nights - Venice
3 nights - Lake Como
4 nights - Florence (add in another day trip)
4 nights - Tuscany
5 nights - Rome
I don't know about weather in April at Lake Como, but May on the Amalfi Coast is super--that gives #2 the edge to me.

I'll agree with valadephia...

4 nights - Venice.
3 nights - Florence.
4 nights - Tuscany.
4 nights - Naples/Amalfi.
5 nights - Rome.

This one looks perfect! Though I would consider moving one night from Rome to Naples and the AC depending on what you have on your agendas for both.

Much easier to return home from Rome, better selection of flights. 3 times easier to reach the airport.

My thought is:

4 nights - Venice
3 nights - Lake Como
4 nights - Florence (add in another day trip)
4 nights - Tuscany
5 nights - Rome

My reasoning is that the fewer times you change locations the better. A lot of time (at least 1/2 to 3/4 day) is forever lost each time you move.

We are now looking for help with AC. We are planning on all 5 nights in Sorrento--to make a base and venture to Positano, Mt Vesuvius/Pompei, Capri, Amalfi. Or should we split it up with another spot in AC?

Thanks so much everyone for your strategic and helpful comments! We are going with:

4 nights - Venice
3 nights - Florence
3 nights - Tuscany countryside
5 nights - Amalfi Coast
5 nights - Rome

Sounds like a very good plan to me. I don't like moving around too much so I'd stay put in Sorrento which is charming in the evenings and has very good restaurants for dinner.

If you want one base for those places, Sorrento would be most convenient. However, I would look at photos and mull over the logistics. You can visit Capri from the Amalfi Coast, and you can see Pompeii en route (would work better the day you depart for Rome). I thought just seeing Vesuvius from afar was sufficient, but if you want to see it up close then you should probably stay in Sorrento.