Honeymoon Itinerary recommendations

You have three bases (Tuscany, Campagna, and Rome). On a honeymoon, with less than 2 weeks, on a first trip to Italy, I'd stick to two bases. You're probably thinking that seeing more places will give you a richer and more varied experience, while in reality, it's more likely to give you tension and frustration, as you will be spending much of your time getting from place to place instead of savoring the places you're actually in. More than most places, enjoying Italy is about savoring it, not about dashing around and checking sights off a list.

Rules of thumb:
1) The day of arrival is often a jet-lagged haze. It's particularly risky to drive on the day of arrival, but you also don't want to plan anything prepaid and expensive, or anything indoors too long.
2) The day of departure is taken up with getting to the airport. So, unless you have a very late departure, you cannot do any "sightseeing" on this day.
3) Every time you change places, you lose at least a half day (I do see that you have accounted for this). In addition, it takes some time to get acclimated to a new place. When you're on a tour, the guide can take you places right away, so you hit the ground running right after arrival in a new place. When you're on your own, it takes longer.

I know some of this may sound harsh, but I think most here would agree. We want you to actually enjoy your trip, not come back feeling you need a "vacation after the vacation"!

I agree! It has so much travel time with very short stays in worthwhile places. Skip southern Italy and spend more relaxing, wine touring time in Tuscany. I had never heard of San Cascisno and have been to Tuscany four times. It may be fine. Perhaps stay in one of the Chianti villages? Panzano, Greve, Radda, Castellina?

This is for a honeymoon in May??? And you still don’t have plans pinned down with accomodation reservations made??? Yikes! Whatever you decide, I would hop to it!!

Agree with the others. Through this would technically "work," most want a slightly slower pace on a honeymoon. If that's not you, that's okay, but definitely consider the travel time required.
Are flights set? I would try to do cities first and outdoor pursuits last, for warmer weather.
Where are you flying from? You may not want to drive upon arrival if it's after an overnight flight.

Your itinerary is at odds with your stated goal of relaxing.

Given your stated goals, perhaps skip Florence and add those nights to your stay in San Casciano.

Do not do Capri and the Amalfi Coast as separate stays. Too much moving around.
Stay in Sorrento and day trip to Capri if you must, OR stay 3 nights in Capri and add a night to Rome.

IMO there are no “half days.” When you say three nights 2.5 “full” days really it is 2 full days. Each transfer day it is suddenly 3pm before you get around to doing anything. By the time you get up (guessing you don’t want to be up at 6am evryday), breakfast, pack, get out the door, get to the next place, check in, get oriented, have lunch, the day is mostly gone. Just your Amalfi Coast to Rome transfer, unless you leave extraordinarily early, it will be 2pm or later before you are ready to sightsee. And somewhere along the way you will probably need to do laundry.

Congratulations on your upcoming wedding! We honeymooned in Italy a few years ago in late April/early May and had a wonderful time. I definitely agree with the others on condensing your trip. I think an extra night or two in Florence would be time well spent.

We spent three nights in Orvieto (a very charming place between Florence and Rome) and absolutely loved our time there. More of the stunning views you’re looking for. If you decide to drop southern Italy, maybe you could spend a couple of your extra days here.

We also day tripped to Tivoli to Villa d’Este. It has lovely gardens and was a refreshing break from the hub bub of Rome.

Happy planning! :)

Thank you all for your responses and recommendations. My wife and I just took a lot of this into consideration and restructured itinerary to be more beneficial to our time spent in our opinion. we know the travel day from tuscany to Southern Italy will be time consuming, but we are willing and committed to doing that as it is something we really want to do and see. We’ve condensed capri/AC and extended Tuscany/Florence by 1 day.....

1. Arrive and stay right in city of Florence for 3 nights to avoid traveling again upon arrival and jet lag. 1/2 day to relax and explore city a bit at leisure. 1 day city of Florence. 1 day trip to Lucca and more Florence city time.
2. Then travel via rental car to either Chianti/San Gimignano for 3 nights. Along the drive to destination hit Antinori winery. 1 day would be day trip to Siena. 2nd day would be Wine/Food tour. We want to see San Gimignano so if Chianti was our base we would make the Winery Tour incorporate that... Or vice versa if we stay in or around San Gimignano as base then we would take Winery Tour day through Chianti....
3. Return rental car back to Florence and take Train direct to Naples. (We understand long 6hrs ish of travel but we are willing to do it). Ferry to Sorrento. Sorrento base for 3 nights. 1 day trip to Capri. 1 full day of exploring AC via boat tour probably.
   Leave Sorrento back to Rome to finish trip. 3.5 days/4 nights in Rome.

I agree that there is an amount of travel and moving around. But we know that we wont have the opportunity to return for quite some years once starting a family and we are trying to fit these 3 areas all in to the same trip and make the best of it. Providing this is the structured final itinerary i guess recommendations based on staying either San G or Chiantia for our 3 nights. I believe we already determined it makes most sense to stay in or around Sorrento for 3 nights and only day trip to Capri. Again, thank you for all of your responses. Much appreciated.

Be aware, DUI in Italy is 0.05%---- most of US is 0.08%-0.10%, so when you do your winery tour, having a rental car may not be the best option.

Revised plan looks much better

If you are arriving by train, it would be more efficient to take the train to sorrento. Otherwise you have to get to the ferry dock. We took the ferry because we were staying in Naples near it. It is a closed vessel more like being in an airplane than a boat. And you then have to get up to the town of Sorrento once you arrive. We took the bus.

Congrats on your upcoming wedding! My husband and I will be in Italy the exact same time as you and your wife! We are just nailing down hotels this weekend and there are plenty options, so don't let the naysayers get to you. We are spending 1 week in Sicily and 1 in the Amalfi Coast (which includes 2 nights on Capri). Once we got going on our plans, we really realized 2 weeks was not a lot when covering Italy. He would hear nothing of my wishes to see Rome or Tuscany on this trip....and as much as it pains me to say it, he was rrrr-rrr-right :(

It's difficult to say what's right for other people when it comes to travel as you will learn, if you haven't already, everyone has a different opinion. And they are just that, an opinion. I would say for a honeymoon, it was right to pair it down to just a couple bases. In my opinion, from what my husband and I learned of ourselves and travel styles over the years, is that you might have too much time in Rome. BUT that depends on YOU. When we went to Greece 2 years ago we had 3 nights in Athens and we should have given up the 3rd and spent that on an extra night in the islands. We aren't musuem and history buffs. We like the natural beauty, food and wine. So as much as it will pain others to hear this...once you've seen some ruins and big cities, you start to feel like you've seen them all. We just weren't enjoying our last day as much as we did our first. But we could have stayed and stared into the blue waters while drinking wine for the next 10 years and enjoyed every minute of it.

Enjoy your planning! Hope you enjoy Italy and I'm praying we have excellent weather!

Megan

Does your May 11-24 dates include travel days? If they do, your itinerary would look more like this. Shorting your scheduled time in Rome.

May 11. Travel.

May 12 arrive Florence.

May 13. Florence.

May 14. Day trip Lucca. Train 1Hr17m.

May 15. Florence-Greve in Chianti. Rent car. 35m.
Look at both of these wineries/Agriturismo
Both have great wines and fabulous food. They're just a few miles apart.

https://www.vignamaggio.com/en/index

https://www.verrazzano.com/en/

May 16. Greve-Antinori winery. 35min. Antinori-San Gimignano. 40m. San Gimignano-Greve. 45 min.

May 17. Greve-Siena 45 min.

May 18. Rather than backtrack to Florence, you could drive directly to Sorrento. No train changes, no hauling luggage on and off trains, time is about the same without stops.

https://www.sorrentoinsider.com

May. 19. Sorrento-Capri. Be sure to check return ferry times.

May 20. Sorrento-Amalfi Coast. Ferry there, Bus back.

May 21. Sorrento-Rome. Circumvesuvian& train, 2/12-3 hrs.

May 22. Rome.

May 23. Rome.

May 24. Travel.

Since this is your first time driving in Italy, please read this and download their e-book for more rules of the road. Each driver will need an IDP, translation of your drivers license. Available at AAA $25.

Edit: forgot to add driving info.

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

From previous posts I have altered the beginning of my trip and added an extra day to Tuscany and we have decided to stay in San Gimignano for 3 nights. Had a question regarding transportation from Florence to San G, and then trips from San G. I think it is in our best interest to not have a rental car since parking seems not the easiest in San G, and since one of our day trips will be Wine tours which we will use a private guide for as to be able to enjoy the wines.
1. What is the best way to get from Florence to San Gimignano? We want to see the Antinori winery. Should we visit that along the way to San G or should we make that a stop in our Wine Tour itinerary?
2. WIne Tour - looking to tour through Chianti at a few places. Again maybe addding Antinori to this day. Recommendations on guides/tours that pick up in San G and do something like that. Maybe with a lunch/cooking class in the mix.

3. Day trip to Siena - assuming use public transportation and spend the full day there guiding ourselves as to not be stuck to a schedule and returning after sunset.
4. Most important question! - Day of departure we plan on leaving very early as to start our long travel day to Salerno as we are staying in Positano. It appears going back and taking the 8am train out of Florence is the quickest most reasonable option. If that is true, is there public transportation back that early or should i hire a private driver/taxi since we would need to leave by 630am I imagine?

For travel to/from San G. your choices are going to be a hire car or public transit. Most likely buses with several transfers. You may be able to contract with a local taxi driver for transport as well. Figure on 1:30 minutes from Florence and the same to Siena by bus.

Have a great trip!