Honeymoon: Amalfi Coast or Greek Islands

I think you should stick with Italy, for all of the reasons you cited. Save Greece for an anniversary trip when it will be easier.
Plus, seaside weather in October is fleeting, I would not waste a second in transit.
Share where you will be in Puglia. You can craft an Italy trip with ease I assure you.
If you have your heart set on Greece, I would still tweak it--you can try to find out what direct flights will be available from Bari or Brindisi in October, or you can look at the ferry schedules and go to a different part of Greece.

Ok, thank you. I think you're right. I just find myself saddened by abandoning the work I've already done, but with any luck we can go another time.
We will be in Ceglie Messapica from September 25-October 2nd. I forgot to mention that I've booked an airbnb in Matera for the week after that, after hearing raves about it here. We likely won't stay for an entire week, so maybe 3 or 4 nights there and then back to Bari or Brindisi for our flight out and some time by the sea.
Then to Amalfi. I guess Sorrento is the place to start? Then to Amalfi town with a stop in Positano? A lot of people here seem to think that staying in Positano isn't worth it. I've heard good things about Ravello, but maybe not as a home base?
Depending on when we leave Puglia we have about 8-10 days to spend in the Amalfi area. One of those days is also a milestone birthday for me, so we're willing to maybe splurge for a night or two somewhere special.
Thank you for your help!

Side note: I have the RS Italy guide book and Puglia isn't in it AT ALL. Is it a different book or does he just not go there?

One thought I had was to stay at one of the luxury masseria in Puglia, but it sounds like you think you will have had your fill of Puglia. Another thought was the Gargano Peninsula, north of Bari, as it has a slight resemblance to the Amalfi coast without the crowds. But you did mention possibly being bored, and there is not much to do near there in terms of sightseeing, just gorgeous nature.
So, I think stopping en route at Matera, then heading over to the Amalfi Coast sounds wonderful.
Sorrento just does not do it for me--I think it is a good place to stay if you want to do a lot of day trips in both directions, as you can visit Naples, Pompeii, Capri, and the Amalfi Coast from there.
It sounds like you will have a rental car, so when you arrive from Matera, you can drop it at Sorrento or Salerno, or even Naples airport, but I would not drive into Naples proper.
First, figure out what day trips you want to do, then sort out if you will be staying in Naples any (your last night might be prudent depending on departure flight). But I would encourage you to stay on the actual Amalfi Coast, in any of the villages with ferry service (see the Travelmar website for schedules), or stay on one of the islands, Capri, Procida, Ischia.
If you are worried about weather, stay close to Salerno, as then you can access the mainland for day trips fairly easily if you get rain. congrats!

RE Guide Books: check the Blue Guide and Lonely Planet

We have a small VRBO home booked on the Amalfi Coast for the 4th week of October. It is located near the town of Atrani, so close to both Amalfi Town and Ravello. The home is beautiful and I've been so impressed with the owner. He and I have been in communication with each other for over a year, since we were scheduled to stay in April of 2020 but of course had to cancel that plan. The home has stunning sea views and the reviews on VRBO are outstanding. According to the booking calendar, it's still available the first two weeks of Oct. I think it would make a perfect honeymoon stay! I'll send you a link in a private message.

You're right to be concerned about what the weather can do to ferry schedules in the Cyclades. When we were there several years ago, choppy water caused the cancellation of our fast ferry ride from the mainland to Santorini. It wasn't stormy or rainy weather, just high waves. We could still get there on the regular ferry, but it took 8 hours instead of under 4.

Just wanted to say we absolutely love Sorrento. It’s charming, beautiful, friendly, easily walkable and perfect as a transportation hub. Been many times and my adult son is taking his girlfriend there on 6/24 (after Paris). Sorrento is not technically the AC but the AC starts right next to Sorrento and looks the same as the Sorrento coast. It’s splitting hairs to say it’s not the AC.

We love Hotel La Tonnarella in Sorrento. You can get rooms with a private terrace, balcony, or patio. It’s a charming hotel on the cliff overlooking Sorrento (10 min walk to downtown) with mind blowing views of the Bay of Naples, Capri, Naples, Mt Vesuvius. Lots of public terraces, flowers, a very good restaurant, great buffet breakfast, and a private beach for relaxing and swimming in the Med.

From Sorrento, day trips to Positano, Amalfi, Capri, Naples, Pompeii, Herculaneum and Mt Vesuvius are fun and easy by boat, train or bus.

Hi,

congratulations on your upcoming wedding! I have visited Italy several times, and had a beautiful Greek Island cruise. If you have two weeks after the wedding, I would either spend all of it in Italy, or do the majority in Italy and then visit Mykonos and Santorini before heading home. They are both beautiful in their own way, without a lot of 'have to do' items, since you will be on your honeymoon. In Italy, I really recommend from Puglia visiting the Almafi Coast, then Capri and follow it up with the five beautiful little towns in Cinque Terre, also known as the Italian Riviera. I also found Venice and the hill towns of Tuscany to be very romantic - Sienna, San Giamaniano (bad spelling), and other quaint towns. If you are into wine you might really enjoy the vast number of wineries among the hill towns. All the places I have mentioned are slow moving and great for a relaxing and beautiful and romantic honeymoon. Wishing you all the best!

A bit more regarding Rick’s guidebooks - he generally features what he’s determined to be the “best” of a country. I imagine he’s been to a lot of places, and maybe thoroughly enjoyed them, but for one reason or another hasn’t even mentioned them in his guidebooks. His books from 20 years ago used to say, “Don’t be fooled because my books are thinner than others. My readers like them that way.” But his books have slowly gotten bigger and thicker. His Spain book used to not have Cordoba, but now it’s a major destination in more recent editions. And if you go someplace that’s not in his book, you’ll see very few people there toting around a Rick Steves guidebook. He’s deliberate about what makes his books and what is excluded, but there are a lot of fantastic parts of Europe that don’t get covered (yet) by Rick.

Thank you all so much!

I would suggest you think seriously about whether you want to spend essentially all your time (which seems to be at least 3 weeks) in seaside towns. I understand wanting to relax on a honeymoon, but I'd want to mix it up a bit with some city sightseeing. I love picturesque towns and villages, but I find that the fifth one doesn't have the same "wow" factor as the first.

There are speed/hydrofoil boats and overnight boats that depart from Brindisi to Corfu, a Greek Island, that you could look into for a short visit.

https://www.directferries.com/brindisi_corfu_ferry.htm

https://www.rome2rio.com/s/Brindisi/Corfu