2nd Trip to Italy - Recommendations?

Your biggest issue is that you want to go to two places in opposite directions, Tuscany and Amalfi coast. Hmmm...I think, having been to Italy 3 times, that I'd save Amalfi for another time, and use my time more efficiently:
Fly into Rome (arriving in morning?) but don't stay there yet, go directly to Tuscany. You can rent a car and drive. After 4 very relaxing nights, drive to La Spezia and turn the car in, and spend some time in Cinque Terre, which has similar views to Amalfi. Then you can either go to Florence (which you basically will pass by to get to Rome anyway), or go directly back to Rome for a couple of nights.

You don't say what month you are going, and you will be told that CT is way too crowded, but we loved it, stayed in a romantic apartment with balcony overlooking the beach in Vernazza. It is especially romantic early and late (nap in the afternoon! what a luxury for new parents!). We found Amalfi coast to be every bit as crowded as CT (we went both in September/October), but we did not visit Pompeii etc, just soaked in our surroundings.
Have fun planning!

Most here will say to put all of your Rome nights together and in your case I agree.
I’d head to Sorrento first for 4 nights since it is new to you
Then train to Florence/Tuscany for 4 nights then finish with 2 nights in Rome. Those 2 nights together will be more usable than splitting them and Sorrento is a nice place to get over jet lag.
If you can swing 11 nights add 1 to Tuscany
Maybe spend 2 nights in Florence as arrival day there is just a half day then pick a base in Tuscany for 3.
A rental car in Tuscany would be useful. Pick it up as you leave Florence you can drop somewhere like Orvieto or Chiusi and catch train to Rome

I see your proposed itinerary, and then I also come back to your comment “we are beyond stressed”. Since you will probably be returning another year, I would highly recommend taking your itinerary and cut the number of locations in half. Enjoy the locations, savor the ambiance, linger at a cafe with a beverage, etc. Another day in Rome to see highlights could easily be 5 more days to see highlights! Otherwise, you will return back home and feel tired that this “time out” vacation was hectic going at your normal pace. (This is written from personal experience.)

If you have time in Rome, I recommend the Villa Borghese for the most beautiful statues and pleasant, uncrowded atmosphere. Timed tickets with limited admittance allows you to really see the items on display. Buy your tickets online in advance.

Will you have a car? A stop in Orvieto during your travel between Florence and Rome would be a nice addition. I don't know when you are going, but we have been twice in April and the crowds were not a problem at all.

Enjoy!

FThanks for the replies! We will be going in February or early March, when it’s not so darn busy.

(1). Joan: I do know we will do Amalfi and Tuscany, but thanks for the suggestion and voicing your concerns with that approach. We went from Milan, to Venice, to Florence, to Rome and back to Milan last time, so we understand the time required on the train and we are okay with that because we want to see atleast 3 different areas.

(2). Christine: Going straight to Sorrento is a great idea! We’ll do that if we can make an early morning Rome arrival!

(3). Jean: As to stress, that is current stress. This trip will be in February/early March 2020. Many months from now, and we actually enjoy the trains and seeing different towns. We are 29, so we enjoy the “constant moving” idea of traveling. We got bored of Santorini after 2 days! Hah. We definitely prefer to squeeze atleast three locations into each trip. Type of three always works for us!

(4). Joanne: Great suggestion! We absolutely want to go there while in Rome!

Hi there, Matt, and congrats to you and the Mrs. for passing both bar and baby!

This trip will be in February/early March 2019.

LOL, stress speaking there? I think you meant 2020 unless you're traveling in Mr. Peabody's Wayback Machine. :O)

Amalfi Coast in late Feb./early March? While a great idea going on the off season to miss the high-season crowds, weather is going to be a crapshoot and there's not much to do there when Mother Nature throws a hissy fit. The ferries also don't run to Positano, Amalfi or some other locations in the winter (they will to Capri from Sorrento as long as the sea isn't too rough) if that makes a difference. SITA buses will be operating as normal. With 4 nights/3 days to work with, you'd want to keep the itinerary loose enough to shuffle your sightseeing according to sun or showers.

Kathy:

Maybe a little! :)

Running on an hour of sleep after a long night with an eight week old boy! He is 100% worth it though!

And yes, the weather is a crapshoot. We went early March in 2017, and it was perfect during the day and chilly in evening and early morning. It’s just the nature of traveling at that time I suppose. Worth the trade off in my opinion!

We went to Naxos in October and had the island to ourselves! It’s hard to beat that - and hopefully renting a car around Sorrento in the dead season would let us avoid some Amalfi traffic!

Great suggestions and points! Thank you!

True that Sorrento is not a worthwhile destination for those months with the ferries not running. Naples of course is a marvelous city, and if combined with Tuscany IMO it is better to do Tuscany first. You have time for 3 stops, so this would work well.

In and out of the same airport it is expedient to head somewhere directly and stay in that city last. The drive from FCO to Southern Tuscany takes around 2.5 hours:

https://www.wanderingitaly.com/maps/valdorcia.html

If impaired after the overnight flight, it would be wise to stay overnight in the seaside town of Fiumicino and get an early start in the AM. You would want to return the car in Chiusi and take the train to Naples. Hertz [closed Sunday] is a half block from the station; first train to Naples at 10:54 [change in Rome], direct at 11:45. Train time from Naples to Rome is 70 minutes.

Running up to Florence and Cinque Terre IMO would be extremely foolish, adding an additional stop [which you don't have time for] and lots of additional travel time.

If within your budget, given the month I would suspect no trouble getting a room at the Locanda de San Francesco in Montepulciano [later on it gets filled]. See booking.com. Seven rooms with views of the valley, good breakfast and a wine bar downstairs. Parking a few steps away, right near the outlet road. No ZTL issue as they will report your plate number to the authorities. Good restaurants down the street, or drive down the hill to the highly-rated La Grotta by the San Biagio church.

1) I only read down (through) to ChristineH's comments (about the 3rd down?) and thought she had a great plan - if you really want to go south AND north.

2) along the lines of others - you will run out of time and won't be able to see all the stuff you listed (in the Amalfi/Sorrento area, for sure) - but that's OK. Prioritize the things and relax and enjoy the time and skip the lower priority (to you) stuff!

Matt- I just re-read your post and realized you have a lot on your list for Sorrento & Amalfi areas. (Sorrento is not on Amalfi coast). Given that I’d say give that night #11 to Sorrento/Amalfi, or if you want an overnight in Naples use it there before/after train to Rome.

then travel to Sorrento for 3-4 nights and enjoy Pompeii, Mt. Vesuvius, Naples, perhaps travel to Capri for a half day, and of course enjoy the Amalfi Coast!<<

We just spent 4 nights in Sorrento, 2 in Amalfi, 1 in Ravello and 2 in Salerno- our days were full.

4 nights in Sorrento is 3.5 days
Naples is a full day or a half day and a night.
Pompeii is at least a half day. Did you want to climb Vesuvius or just see? If climbing- that’s at least another half day.
Capri is a full day- we didn’t care much for Capri but loved the boat trip around the island. Weather permitting!

Amalfi/Positano/Ravello-well you are out of days.
I'd put Capri bottom of the list and plan a day trip by bus along the Amalfi coast. RS has detailed info in his guidebook.
We liked Amalfi and Ravello very much, Positano-not so much. Very pretty from the sea, etc but not much more than high end shopping. YMMV

and hopefully renting a car around Sorrento in the dead season would let us avoid some Amalfi traffic!<<

Not sure how renting a car avoids traffic- you are the traffic! I would not want to be driving in Sorrento/Amalfi/Naples. Talk about stress. Take the bus or splurge and get a private driver for a day- then you can both enjoy the wild ride and scenery.

(I would get car in Tuscany)
We loved Montepulciano. Stayed at Palazzo Carletti and will again on our next visit.
https://www.palazzocarletti.it/en

Sorrento in February - I did it, had mixed weather and loved it. If you can work it out, February 14 is their town saint's day, with a morning procession, a festive atmosphere and a market for at least a couple days before and after. With or without the 14th, you can ferry to Capri (though service is suspended in bad seas), take the local Circumvesuviana commuter train to Pompeii, Herculaneum and Naples and ride the bus to the Amalfi Coast towns. In February, there were more locals than tourists in Sorrento and all the shops and (good) restaurants were open, and the town is charming after dark. If you stay in Sorrento, you don't need and won't want a car. If you really want to rent a car for the Amalfi Coast, you are much better off basing in Salerno. Before you do that, read about my experience here. Driving the AC is not easy; I have had a lot of experience driving similar roads along the California coast and in the mountains.

Instead of spending your first night in Rome, spend it in Naples (unless your flight lands late in the day). You may have time to see a little of the city (the RS self-guided walk is good) and have dinner on your first day. Next day, see the Archaeology Museum (it's a wow) and take the Circumvesuviana to Sorrento (you could stop at Pompeii on the way - there's luggage storage at the sight).

Weather is unpredictable. Plan to spend your time in rural Tuscany (or Umbria - just as nice) with options for places to see so that rain and gray skies don't put a damper on your trip. Or consider forgoing a car and staying in Bologna and daytripping by train to other towns - Parma, Modena, Ferrara, Padua, Ravenna . . .

God, I'd forgotten how much a 29-year-old can do in 1 week. Your itinerary exhausts me just reading it. I hope you have a wonderful trip.

HAH! This will be over the course of 10-12 days. There is certainly some "wiggle" room.

Thankfully, we enjoy the exploration aspect of travel more so than the "relaxation." A healthy mix of is essential, but we do enjoy the adventurous side of things.

matt,

Congratulations on passing the Bar exam!

I haven't worked through your Itinerary in any detail, but my first impression is that you're trying to cover too much ground in what is essentially a very short time frame. Is there any possibility you could add some time? February may be a bit chilly especially at nght, but early March will likely be a good time to travel although one never knows with the weather.

Thanks everyone, for your comments and suggestions. Perhaps we change Sorrento to Postiano?

Please hear me when I say this: We are not trying to cover EVERYTHING across each location. For example, spending time by the Amalfi Coast/Sorrento/Naples, we will be covering the highlights. We have taken the train across Italy multiple times and believe the 5hr ride from that area to Tuscany for another 4 nights is very doable.

All this being said, most travelers want to soak up as much time as they can in each area (so it seems to me) but we are limited in the 12 day period, and want to "squeeze" in atleast three areas. I understand we might not get the most out of the Amalfi Coast, Sorrento and Naples from 5 nights, but we okay with that, due to close proximity of those areas.

Hopefully this gives a bit more context behind our plans. Thanks again!

Matt- I am one here who does not really think you are trying to do too much.
Make the right choices with transportation and towns you stay in and it is doable.

When we do longer trips- 3 weeks or so- we tend to linger and spend 3/4/5 nights in locations with some 2 night stays mixed in.
This last trip was only 14 nights and we wanted to cover a lot.
Rome 3, Sorrento 4, Amalfi 2, Ravello 1, Salerno 2 Venice 2- it was fine- even that 1 night stay in Ravello was worthwhile. The 6 hour train ride to Venice was also a nice break- we napped, read, had a picnic lunch- it was nice be off our feet for a length of time

We didn't care much for Positano- there will be no ferries running so your only transportation is a bus or private driver. We took the bus from Amalfi to Positano got off at top of town and walked down. IMO nothing more than high end shopping, overpriced cafes. We spent about 3 hours there and that was plenty. Yes it is pretty but so are Amalfi and Ravello and Sorrento. Amalfi is a better choice as far as transportation and there are things to do in Amalfi. The town just felt more real to us- although still touristy it was not the same as Positano. We loved sitting on the piazza and just enjoying the view of the Duomo- it dominates the square- just beautiful, enjoyed happy hour there on both evenings. The duomo/cloister/museum is very well done and worth the 3euro fee. Go up to the cimitero- there is a lift. Visit the paper factory. Hike Path of Gods, head over to Atrani- just around the bend.
You can take the bus up to Ravello for the day - visit Villa Cimbrone- another beautiful sight- and the views are to die for.

Tip: We were traveling to Ravello for just 1 night but had our luggage. We scoped out the bus situation the day before and noticed all the buses were jam packed full with no space for luggage. There is a red City Sighteeing HOHO type bus that runs along the coast and also runs an open air bus from Amalfi to Ravello for 5 euros- picks up same spot as SITA bus. We decided to take that bus instead- the driver put our luggage on the bus for us and we were only 2 of the 6 people on that ride. It was great- open air- so nobody was getting sick (quite a few were sick on the bus to Positano). It dropped us just a few feet from the SITA bus stop. We did take SITA bus down from Ravello next am (where the guy across the aisle was puking out the window- sorry if TMI! ).
A taxi to Ravello from Amalfi is about 35euros so we felt we really had a bargain ride.

We liked Sorrento a lot- I would stay there again. Great base for all the sights, lots of very good restaurants. Find a hotel with a view.
We splurged and stayed at https://www.delavillesorrento.com- chose it for location, view and pool. Unfortunately we had a lot of rain while in Sorento so the pool wasn't used but the view was still wonderful. Really lovely very large room with a balcony, very good bkft. Easy flat walk to train/bus or into town. Lemon grove across the street.

It is your vacation- if you want the 3 locations- then do that. With a little one and a career beginning it might be a while til you get back to Italy! I have a 31 yr old daughter who is go go go - she would be fine with the "pace" of your trip.