Timeline for a relaxed honeymoon

For 2 weeks, I would not choose more then 3 places. Remember the time it takes to check in and out of hotels, get to train station, and travel, etc. Especially, on a honeymoon. I was Soooo stressed, lol! I think trying to see Amalfi, Rome, Florence, and Venice, would be too much travel time. Not visiting time.

A lot of people suggest flying into Venice, stay 2-3 nights, get over jet lag, then do Florence and Rome. Fly home from from Rome. I know you said you have been there, but, ask your wife to be, what she would like!!

Going to Amalfi would be time consuming, travel wise. But, if you skipped another town (Florence or Rome) and flew out of Naples, you could do it. But, take it from a female, Don't skip Venice :) Plan your next trip instead!

BTW, if you are going this May (2016) get reservations ASAP, no matter where you are going!!

If by 2 weeks you mean 14 nights on the ground, then I think you could visit all four - Amalfi coast, Rome, Florence and Venice. It would work best if you could fly into Naples and home from Venice or vice versa. Amalfi coast - 4 nights, Rome - 4 nights, Florence - 3 nights, and Venice - 3 nights. It would be a bit more relaxing to limit it to three and since Venice is the outlier you might want to drop that and save it for another trip - Venice would be perfect for an anniversary trip.

Thank you all for the responses so far. I just wanted to clarify a few points to make it easier. This will be May 2017, so no worries there.
Also, I figure all 4 is unrealistic, and maybe 3 is even not the best plan, but I wanted to get an idea on each location individually. I should've also mentioned that the Almalfi is a definite, but the other 3 are optional.

Remember the time it takes to check in and out of hotels, get to train station, and travel, etc.

I'll echo this advice! Even though Rome to Florence, for example, is only around 1.5 hours by train you need to check out of your hotel, get to Roma Termini ahead of the train, get to your hotel in Florence and drop your bags. If you leave after breakfast at 8:30am, it will be almost lunch time by the time you're out and about in Florence. And this is for a relatively short trip, no changes. Ravello to Rome will take substantially longer (I'd recommend Sorrento instead, BTW, beautiful town). Figure each time you change locales it costs you almost half the day at least, often well into the afternoon. So an optimistic "3 nites" on the planner really means an afternoon (in which you might be a little tired) and then 2 days.

If you're looking for a relaxed pace, I'd go with 3 places. Leave some Italy to visit on your anniversaries! It also gives time for serendipity and to work around the weather. With a couple of nights per locale, even if there is 1 or 2 days of rain or clouds at a given stop you still have a good chance of sun. And maybe you hear of some festival in town or run into people who tell you about a great daytrip they did; with a couple of days per place you'll have the chance to go w/o sacrificing your plans the way you'd need to with only 2 full days in town.

As for Venice, the most important advice here is to ask your bride! That said, if you want a charming city with canals, friendly locals, nice restaurants, great museums, then let me suggest Amsterdam on a future trip. I don't really see the charm of Venice, a once-proud city that is a shell of its former self (seriously -- many of the buildings on canals are empty since its expensive to live in Venice and many jobs outside of tourism have left). But that's just me...

One other suggestion is instead of the coast and cities, how about a city, coast, and Tuscany/Umbria? Stay in a hilltown (Perugia is a nice sized one, you can go a lot smaller if you want like Cortona or Spello) and visit wineries or other hilltowns during the day with a rented car, then enjoy a quiet dinner that makes you think you're living back in the Middle Ages.

I think any 3 of your options would be lovely. The Amalfi area will have you moving between small towns. For Venice you'd probably be mostly in that city itself but with a good bit of time on the water; side-trips to places like Verona are available if you have time. Rome and Florence feel quite different to me, and I'm sure you know what I mean because you've been to both. Which sounds most appealing to your future wife: the large, bustling city with a lot of classical sights, or the smaller but also touristy city that's more art-intensive? There are side-trips available from either, but she might be more interested in the Tuscan hill towns.

Since the Amalfi area is definite, I'd tend to include Rome so I could mentally check off two major southern Italian sights. Either Venice or Florence would be a bit more convenient to include in a future trip to Switzerland or Austria. But with the fast trains, it doesn't really make much difference.

Fly into Naples

Curreri Viaggi bus to Sorrento.

Stay in Sorrento 5 nights.
Much better transportation options.

Train, Circumvesuvian to Naples Central.
Or ferry from Sorrento then Alibus to Central.
Train to Florence. About 21/2 hrs.
4 nights Florence and Tuscany.

Train, to Rome.
4 nights.

Fly from Rome.

Other option would be to fly into Florence and home from Naples.

You asked which one you should add to the Amalfi Coast - Venice, Florence, or Rome. That's like asking which city a visitor to the US should see if they can only choose one - San Francisco, New Orleans, or New York. They are all very worthwhile, and VERY different. So, no one can really choose for you, as everyone will have their favorite and less favorite.

Read as much about each one as you can, and see which one calls to you. Or watch videos - Rick's on these three cities are only a few years old, and he has multiple ones on each city, here (scroll down and click Italy): https://www.ricksteves.com/watch-read-listen/video/tv-show

Kayak.com (EDIT: these are for 2016 prices! I just re-read your second post that you are looking at 2017, but these still give you an idea that the flights should be affordable)

May 16 to 31 Lufthansa USD$1195 pp (you lose a day travelling to Italy
San Diego to Venice
Naples to San Diego

14 nights total, with suggested itinerary if it were me
Venice 3
Florence 3+/-
Rome 4+/-
Sorrento 4+/-

The travel between each location is average 2+ hours by train which is easy. The relaxation is not by how many days you spend in any one place but how much (or little) you do each day. With your experience in Florence and Rome, just pick fewer things to do each day to keep it relaxed.

Thank you all very much. You've all offered great information and it will definitely be put to good use in ultimately making a decision.

As several of you mentioned, it's really about what we (let's be honest, she) wants to see. So, I told her that sometime soon I'd make bruschetta and set out an antipasti and make some pasta, open a few bottles of nice Italian wine, and create a Hulu playlist of Rick's travels to each of these locations. She can write down her thoughts on each of the locations and hopefully that will help us decide which locations make the cut and which ones will need to wait until next time. Regardless, I'm sure it'll be a great trip.

You recognize that for a relaxing honeymoon you don't want to be trying to rush and see everything.
I assume you and your new bride are going to want to sleep in some mornings and have a few relaxed days mixed in with some site seeing without a schedule to adhere to.

Right now I am in a travel stage when I want to rush around and pack the day but I do this knowingly I will return more tired than relaxed. Have also been in stages when I just want to leave my regular life behind and veg on a beach for a week.

My point being your plan is rushed even though you don't want it to be.
For a relaxing honeymoon for 2 weeks you would seriously be at the limit of relaxing just doing Rome and the Amalfi Coast. Yes you could always see some Florence highlights by doing a day trip from Rome but personally recommend you completely forget about Venice and Florence.
Rome 5 nights
Sorrento 4 nights
Ravello 4 nights
Have a 14th night ; add it to Rome and then maybe that 1 day trip to Florence also makes more sense.
Helps if you can fly into Rome and out of Naples otherwise you may be losing a day in the AC and be forced to stay the last night back in Rome.
For your 5 year anniversary you can plan a much more packed return visit more sites in Italy (1 or 2 year anniversary if you can swing it)

For a honeymoon i'd skip Rome. Go back there on another trip.

I'd do Venice, Florence (Tuscany) and Amalfi. You can fly into Venice and out of Naples. 3-4 days in each city.

Good advice. And something to add (and maybe pass on to other travelers), I will be using miles to book our tickets. The great thing about doing this is that (at least with American) it looks at things as 2 one way trips, period. It doesn't matter how many legs of the trip there are, or whether you're flying into an out of the same airport. So, San Diego to Rome, 30k miles. New York to Rome, 30k miles. San Diego to Naples, 30k miles, it doesn't matter. Same thing with the return, so use this to your advantage. My thought is to fly San Diego to Naples (yes, there will definitely be stops in between, but they don't cost any more), then take a train to wherever else, and fly out of that city (Florence or Venice) straight back to San Diego. Again, there will be connections, but by using miles, those connections do not have any additional cost.

... create a Hulu playlist of Rick's travels to each of these locations.

RS shows are great. I'd also recommend the shows by Samantha Brown and Rudy Maxa. Your local library may have other travel shows.

hanzosbm: good to know regarding American miles.
For West Coast to Europe that is quite a bargain in miles. I imagine an East Coast person could use that to advantage if going to Hawaii or Alaska in much the same way.
I think a couple of others are that way also but not all. From what I recall United is the same.
Sometimes the layovers are brutal though with award flights that offer this system.
Some use a mileage based system and levy taxes and fuel surcharges per stop (ex. British Airways) ; some others based the mileage needed on the cost of the flight itself (ex. Jet Blue)

The good thing about using miles is almost every single airline allows you to book each one way for half the price of a round trip making these type of fly in X city and fly out of Y plans work much better with miles than cash.
The only brand/alliance I know of that does not allow that is the Skypass alliance which has some big brands in it and only allows for round trip award flights, I have access to with Korean Air miles but that lack of one ways makes it less useful than others.

In your case definitely saves time to fly into one and out another. In some cases your options are limited flying out of small airports like Florence and/or could have really bad layovers though compared to Milan, Rome, Venice, etc...

Take your time and enjoy the cities you will visit! I suggest to stay 4 days in Rome and 4 days in Florence, you won't see everything, but you will enjoy the best landmarks of the two cities. Venice may be 3 days. You can also think to reach the Chianti region or the countryside near Florence (Castelfalfi, Volpaia in Chianti, Radda in Chianti, Montefioralle, Montaione). If you want to discover some legendary territory I suggest Lunigiana and the area between Castelfalfi and Montaione, close to Villa Ciggiano, you will find many path (like Via Francigena) to enjoy nature and have some relax.
And what about Perugia? Umbria is a delightful region and Perugia is a "must" to see. Reserve a day for Perugia and Trasimeno lake.
Hope you will enjoy Italy!

I took my wife to Italy for our honeymoon. It was her first trip to Italy and my third. We spent 3 nights in Venice, four nights in Florence and 5 nights in Rome. We had ample time to relax and do whatever we wanted. Since you are going to Amalfi Coast, I would just sub out Rome for the AC. If you are using miles for flights, I highly recommend trying to get business class, at least for the outbound flight. It's a long way from SD to Naples! You should be able to get some sleep. For the return flight, you will probably be awake and not really need a bed. Are you aware of the changes coming to the AA award chart? The miles required for most awards is going up and the off-peak dates are being shortened.

For your flight search, I recommend using the British Airways website. This will pick up other airlines in the OneWorld alliance better than the AA site. It looks like your flight from SD would have to go through either LAX, Chicago, Philly or New York. I would search the long-haul route and find something suitable, then call AA to book it all the way through.

If you do end up flying into Naples and making Sorrento or Ravello your first stop, ask your hotel what it would cost to have a driver pick you up at the Naples airport and drive you to your hotel. They have contacts and can make the arrangements.

There is nothing like seeing a driver holding a card with your name on it after a long flight. Will be a little pricey, but a perfect way to start a honeymoon.