QUESTION: Pompeii and Positano in One Day from Sorrento

It may be logistically possible ( 'doable'), but doubtful if enjoyable.

With CT on your itinerary, it is needless to try to do your 'Day2' proposal

so should we just cut Positano out,

yes

I would say not only Day 2, but Day 3 also looks problematic. Dinner in Capri with a plan to be in Rome to sleep that night ?????? for outbound flight in the morning ????? No way.

You basically have one full day in Sorrento given that the day before and day after include getting there from Rome and getting back to Rome. You can't see Sorrento, Pompeii, Capri, and Positano in that time. This is completely unrealistic.

You plan on having dinner in Capri yet planning to be in Rome later that night? Are you aware that dinner in Italy is typically eaten late, often around 9 or 10. The last ferry is at 19:40 and takes 1hr 20mins. Add on travel to the train station, train to Naples then train to Rome it makes for a very long day. In order to catch the last ferry you'll be eating dinner very early, many places may not be open at that time so my preference would be a late leisurely lunch. Personally I would forego Capri and devote more time to Pompeii, it certainly requires more than a couple of hours to do it any sort of justice.

You also mention the sunset in Positano after dinner. Sunset in April in Naples is around 19:45, Italians are eating dinner way after that time so you might struggle to find a decent restaurant open at the time you want dinner or else......"when in Rome".

Are you aware that dinner in Italy is typically eaten late, often
around 9 or 10.

We eat dinner in Italy earlier than that, no later than 7:00 or even earlier, depending on the day, and while a fair number of restaurants don't open until 7-8, we haven't had problems finding a place to eat. But no, I don't think yours is a workable itinerary. If Capri is a must, it would be more rushed than I'd prefer but you could do this:

Option 1:
Day 1 - early train from Rome to Naples, Circumvesuviana to Pompeii (check your bags at the excavation) and then to Sorrento.

Day 2: Capri. As the last ferry may be returning to Sorrento on the early side, settle for a nice lunch.
Check ferry schedules here: this could change in a little in April but currently the last one leaves Capri at 18:45.

http://www.sorrentoinsider.com/en/ferry-schedule?from=capri&to=sorrento

Day 3: Get up, have breakfast, check out, have your hotel store your luggage, explore a little of Sorrento. Trains back to Naples and Rome in the mid-to-later afternoon.

You could also do it the other way around, going directly to Sorrento on Day 1 and doing Pompeii on your way back to Rome. I just don't see being able to get Positano in there unless you skip Capri.

Haven't been to Capri, but if there is a historical bone in any of your bodies, I'm going with Pompei on Day 2 instead of Capri in Kathy's otherwise-sane plan. I think stopping in Pompei on Day 1 on the way to Sorrento could be exhausting, and needs a day dedicated to it. But that's just me...

April's still not quite warm weather time on the peninsula and could be a mite chilly or downright cold. Now, Pompei would have pretty much the same weather but if sunny but cool/cold, Pompei to my way of thinking would be better than Capri. If it's raining, neither is a good choice!

OR...keep both plans at the ready depending on weather forecasts.

BTW, Sorrento restaurants are better than most re: eating a little bit earlier, and some (I'm thinking Il Leone Rosso right by the Sorrento train/bus station) stay open all day.

Check out a private car tour, for example, Simply Amalfi. They can pick you up in Sorrento, drive all the way around the peninsula stopping for the world’s most beautiful views and in Positano, Amalfi and Ravello, with time for a great lunch. In the early afternoon, you will take a scenic drive to Pompeii where a professional guide will show you around for two hours. You will then get a ride back to your hotel in Sorrento in time for passagiatta and dinner! This is an 8-9 hour tour that goes at a relaxing pace, and has the advantage of an experienced driver on that crazy road, who knows all the great stops, and you never have to figure out where to park or wait for a bus. Capris is to many people, an overrated tourist trap, filled with cruise ship passengers, and in an inconvenient location.

Day 1 is doable. Day 2 and 3 looks more like a race against the clock than vacation. To Positano by bus, back by boat in the case you leave Pompeii out. Or Pompeii without Positano. To see Pompeii and hike Mt.Vesuvius in one day is probably not realistic. Day 3 I think is doable but more race than vacation.

I think stopping in Pompei on Day 1 on the way to Sorrento could be
exhausting, and needs a day dedicated to it. But that's just me...

Jay, i'm with you there but then, we spent FAR more time at Pompeii than most tourists do (and it was my 2nd time). If one doesn't have as deep an interest in the place, then maybe 3 hours or so is enough? I guess that's not uncommon for a lot of visitors. It's just tough as we had more time in Sorrento, Pompeii and Capri that our OP has to work with.

Thanks everyone for all your suggestions, tips, and insight!! Will take everything into consideration.

Totally forgot about the late dinners in Italy. It's been 2 years since I've last been and completely forgot about it!
(Note: I went in July 2016 and have never been south of Rome)

Definitely will dedicate one day to Pompeii, and see where the rest of the day takes us (back to Sorrento most likely). Will check out tour options for easier travel/less hassle.

From what I've read from everyone's comments, I sense the majority prefers Positano/Amalfi Coast over Capri. Any other pros/cons for both? Or which you all prefer over the other and why? Also what is the weather like in early April and will this play a factor in which to visit over the other? No one in my group is desperate to go swimming or the beach so no worries on that aspect.

Thank you all! I appreciate all your insight

-Emily