March/April Honeymoon

Sounds like a wonderful itinerary, and lucky you to have 3 weeks!

A friend recently stayed on Capri itself and loved it. However, getting on & off the island might make it inconvenient to visit your other Amalfi area destinations. Have you considered staying in the town of Pompeii? I stayed there years ago and it was nice.

You can YouTube various towns and villages and get a sense of how "drab" or charming they are before you decide. Also assess how central they are to serve as a home base so you don't have to pack up and change hotels too often.

Best wishes on your wedding!

I had a lovely time near Sorrento in early April. It seemed to me a perfect time to visit.

Looks like a good plan.

I was in Sorrento in February and enjoyed it. If you want day trips to visit the surroundings, Sorrento is the only place to stay. It is well-connected by ferry to Capri (if you decide to go there . . . ), by train to Pompeii and Herculaneum and Naples (the Archaeology Museum is a must-see) and by bus to Ravello, Positano, etc.

Also check flights into Milan and out of Rome. That may be more kind to your budget and it's closer to Venice than Rome is. Also check the possibility of flying home from Naples. Also take into account the cost of the train if you don't fly into Rome. Today the train from Rome to Venice is €84/pp (and 3H 45M); the train from Milan is €44 (and 2.5 hrs).

Lastly count nights, not days. You'll use about 1/2 day each time you move. If you don't fly into Venice, you'll use a good part of your first day just getting there, so to have 3 full days in Venice, you need 4 nights there. Going to/from Sorrento will also take a lot of time. Even Venice to Florence will use several hours - packing, getting to the train station, finding your Florence hotel, checking in.

the price difference seems to be 200+ pp

I presume this is USD.
Cheapest train tickets from Fiumicino Aeroporto to Venezia S. Lucia are around 90 USD (for 2 persons), but you have to commit to a specific time, so you need a couple hours buffer time in the airport; The train trip is 4 - 5 hours. To save 310 USD you spend 2 x 7 hours = 22 USD per Vacation hour. That is your decision, but to me vacation time is more valuable than that :-)

That's a good point; I hadn't thought about the buffer time in case a plane is running late to be able to catch a train. Though I was looking on the trenitalia website and was seeing Rome->Venice train tickets for ~50 euros pp if we book well in advance, am I missing something there?

How close to the trip do you recommend booking flights? I read some things online that said to book just 6-8 weeks out, but that scares me a bit how close that is cutting in. I've been looking at the search engines but haven't gotten a good sense of what the low point of flights will be (flying SFO-> italy).

I'm finding SFO->Milan -->Rome that are the same price as roundtrip to Rome, that may be my best bet.

I've been doing more research on the Napoli region, and here is a new thought. Let me know what you all think.
Will be coming from Tuscany region - take a train from Florence to Naples (~3 hours)
Leave luggage at train station storage in Naples, spend the afternoon exploring the city
Evening ferry to Ischia, spend 1-2 nights on the island. Looks like an interesting alternative to Capri and has more character than Sorrento. Hiking, horseback riding, thermal pools.
Ferry to Sorrento, spend another 1-2 nights there, with day trips to Pompeii and possibly Positano/Amalfi
Then back to Rome for the end of the trip

The problem with buying train tickets in advance for a train after landing is that it's a gamble. How comfortable are you with risk? If you are late for the train, you lose the money you paid and you have to buy full-fare tickets for the next train.

What could make you late for the train? Your flight could be held up by a mechanical problem or by weather. You could circle the skies, waiting to land. You could land and sit on the tarmac waiting for a parking spot. You could have a long wait in line at passport control. If you are checking bags, you may have a lenghy wait at the carousel. Then you have to take a train from the airport to the city station. In my (limited) experience, the trains between Fiumicino and Rome Termini are regular and on time (and run about every 1/2 hour), but the ones between Malpensa and Milan Centrale are less frequent and less reliable.

When you take into account the price of a train ticket and the extra time travelling from Rome to Venice, I would have no hesitation paying $200 more.

Sorrento is less seasonal than the other places you mention, and has superior transport connections. Granted Positano is more spectacular, but Sorrento still has its own charm.

Organise your Sorrento time like this ...
Day #1 Tuscany to Sorrento (4 nights)
Day #2 Capri
Day #3 Pompeii & Herculaneum
Day #4 Positano
Day #5 Sorrento to Rome (via stop in Naples)

Congrats, and what a wonderful honeymoon you will have. Enjoy.

First, splurge on the extra $200 pp for air into Venice. Not only do you have train costs, but the risk of the plane being late,ball that extra time to get there....you are wasting valuable time to save a little. You will be kicking yourselves when you land.

As far as the Amalfi Coast, Sorrento isn't on the AC, but a good central location. However, I really think you are doing yourself a disservice by not staying at least one night in Positano. After the crowds leave, it is just magical to dine with that view and wander around with no crowds. I would go to Positano first, for two nights...and ferry over to Capri...doesn't take long. Then, go to Sorrento for 2 nights and visit Pompeii and Sorrento.

Thanks for all the input. Good to know about Milan being more challenging than Rome in terms of train timing, will keep a close eye on the open jaw tickets.

No one has commented at all in Ischia - is Capri more worth our time? Ischia too complicated with ferries in early April? I was definitely interested in the thermal springs and views of Ischia and a bit put off but the tourist craze of Capris, but it's always hard to tell what to put value on without actually knowing the place at that time of year.