Sorrento & Varenna in 14 days

The other possibility is we do a multi-city so into Rome & out of Milan. The issue I have with that is we are fly into & out of Boston and there are no direct flights to Milan. I prefer non-stop when possible.

That is a personal preference choice of train travel vs a change at an airport. No right/wrong answer. The key thing is to be in the departure city the night before, which it appears is your plan.

The rest of the trip looks good. What are the "couple of restaurants" in Florence?

Both Sorrento and Varenna are remote from Rome. You have to sleep in Rome the night before your departure. Don't you like Rome enough to enjoy a night or two there again? You clearly know Italy and are thus entitled to your preferences. But it's a long distance each way, north and south. I like Florence, but I would repeat it only for art and villas, not for dining. Restaurants in Europe do endure in a way they don't in the US, but it seems ... unusual ... to me. Opinion! I mean, I've never had better pizza than I had in Reggio Emilia, but I wouldn't go back just for that. (And never had worse pizza than in Florence!) (The pizza in Naples is different, but also pretty good.)

You can do Pompeii from either southern location. Don't you want to visit Capri or Ischia? It's not that far from Sorrento. Sorrento will be busy by the middle of May, and it will be hot and sunny. I needed A/C in Sorrento, last week of May. Note that Sorrento is a cliffside, post-war resort town, with one sandy beach, located between the two marinas - odor of diesel fuel. I don't mean "don't go to Sorrento", just "don't over-romanticize it." We found our five nights there (for daytrip convenience) well-spent. We hired a car service for 8 hours on the Amalfi Coast, and went to Capri one day, really nice. Skipped the Blue Grotto with no regrets.

We spent 11 days in Sorrento in April, here's the link to the Trip Report if you're interested https://community.ricksteves.com/travel-forum/trip-reports/trip-report-2-weeks-of-day-trips-from-sorrento. Assuming you have an overnight flight to Rome, I'd recommend you consider not going all the way to Sorrento straight after your flight because it makes for a long day. If we had a do-over we would have stayed in Rome for a night. We could have done a private driver, but I wasn't willing to spend that kind of money as we were quoted about €600 on average.

Pompeii is closer to Sorrento, however it's not difficult to get to from Naples either. I would recommend a trip to the Archeological Museum in Naples as a follow-up to Pompeii. We actually spent 4 days exploring the various Vesuvius eruption locations. We started with a 2 hour tour of Pompeii and then wandered for 3 more hours. Another day we visited Naples and the museum, a third day was Herculaneum and then a 2nd day at Pompeii to see the areas we missed that first day. After Pompeii we headed to Oplontis which is a spectacular villa also buried by the eruption.

Sorrento is a convenient location to see Pompeii and also make daytrips to the Amalfi Coast and Capri.

Joe32F - when he was last in Florence it was a long time ago and either the Mercato wasn't there then or he doesn't remember it - not sure which. There are some dishes there that I would like to have again. The other is Ciro and Sons had this Pasta and Pear dish that I still dream of. It was this little purse like pasta filled with cheese & pear. Oh my - so good. From what I have read it is a popular regional dish. As I had it in May 2019 I'm hoping I can find it again. There were others but those are my 2 main things. The food in Florence was so good. He & I would both pick the train over flying. We both love the train.

Tim yes if we fly out of Rome we would stay overnight. I love Rome but he does not so I was trying to minimize our time. I expect to visit Italy often solo in the future years and since this particular trip is both of us it needs to appeal to both of us.

Allan I already have your trip report book marked a long with several others that have been shared recently. I really appreciate folks who do trip reports! You & Tim both mentioned day trips. Yes Sorrento is meant to be a quiet and nice base for visiting the region including Capri etc. Once I have the number of nights sleeping in each town I'll go back and do another itinerary. Italy is one of those countries I don't go into thinking it will be my last time there so I don't stress if I don't do everything on my wish list. I expect to be back both with him and solo.

The answer to this question is probably in something I have bookmarked. We do want to go to the Archeological Museum in Naples and I strongly want to have Napoli pizza. Considering his strong feelings towards Rome (which I attribute to being the last place he visited and was tired) I am concerned he won't like the chaos of Naples. Still - to me it seems like if we do a day trip we may as well stay for 2 nights and try to get to know it a little. It could take us by surprise in a good way. What do forum members think?

Do not overlook the Farnese Marbles in the Naples museum.

I am concerned he won't like the chaos of Naples. Still - to me it
seems like if we do a day trip we may as well stay for 2 nights and
try to get to know it a little. It could take us by surprise in a good
way. What do forum members think?

I've been back for 6 weeks and I still can't decide what I think of Naples. It was well worth it to us for the museum alone and I think Naples is worth at least a day if for nothing else but for the experience. You may love it or you may hate it but I've never been any place like it.

I really like Art Nouveau architecture, so I spent a lot of time walking around Naples, in addition to hitting some of the traditional sights. I don't like setting up camp in an expensive place and day tripping to less expensive spots, so I appreciated the comparatively low cost of sleeping and eating Naples as well.

Just wanted to thank everyone for the advise & tips. We chatted last night and agreed to spending the 1st night in Rome rather than directly to Sorrento. We also agreed on 2 nights in Naples. I read him what you wrote Allan and we chuckled. Travel is an adventure!
And we also decided that we would be open to flying out of Milan with a stop if it made life easier.

Now the watch for those dates to open up for sale and then pricing starts! Thank you again.

Since you seem to be open to a gleeful and ironic look at Naples, here's a discussion I didn't participate in:
https://community.ricksteves.com/travel-forum/trip-reports/surviving-naples

We certainly had no trouble in Naples, although strong air conditioning and sealed double windows cover a multitude of sins. I am troubled (as I was in Athens) by people parking on sidewalks and endangering pedestrians.

We also agreed on 2 nights in Naples. I read him what you wrote Allan
and we chuckled. Travel is an adventure!

Travel is an adventure and Naples is the jungle.

https://community.ricksteves.com/travel-forum/trip-reports/venice-lake-como-sorrento-amalfi-coast-with-lots-of-rain

Attached is our Trip Report from this past May. The rain we received was certainly unusual, and I'm wishing good weather to you.
I would also suggest flying out of Milan. It's not a large airport and we had no problems a few years back. Or- go to Venice and see if there are any decent connections, altho there can be problems getting to that airport early in the morning.
I was very disappointed with the Amalfi Coast. This trip had been canceled a few times, so maybe my expectations were too high? And the rain didn't help. But the traffic, congestion, diesel smell from the roads, and lack of any efficient mode of transportation, public or private, ruined the vibe for me. I hated sitting in traffic and the crowded regional trains. I know, I sound like a grump. I actually liked staying in Sorrento. But I hated how difficult it was to move around. I guess I just like northern Italy more than the south.
But I wish you safe and wonderful travels, with lots of ☀️!

We were just in Sorrento and Naples in May so I thought I would share some of the things that worked out really well for our trip:
1. We used AldoLimos for both a private transfer from the Naples airport to our Sorrento Hotel and for a one day tour of Ravello, Almafi and the countryside to our hotel in Positano. I highly recommend them. We had great tour guides, it took the stress out of a crazy area for travel (the long lines to the packed SITA buses) and the countryside meal at a winery was a highlight of our trip.
2. We hired Gaetano Manfredi for a tour of Pompeii and Herculaneum. Gaetano arranged for us to private transportation from Sorrento to the sites and back, lunch in Pompeii and did our tour in Pompeii and arranged for a private tour guide in Herculaneum. It may have been a little pricey but we thought it was well worth the cost.

3. We did the small group tour of Capri that left from the small marina in Sorrento run by MBS Blu Charter Boat tours. You can sign up on Trip Advisor or from their website. There were 10 of us on the boat which worked out really well. Weather prevented us from touring the blue grotto, but we were taken to about six other sites along the Capri coast, plus a swimming spot which we all enjoyed. We went to the small marina in Capri where for $20 per person they arranged for all our transportation needs via a private bus. Seeing people fight over the cabs and the long lines to the municipal buses, we were glad we did it. We were initally taken to Anacapri which was nice. Some of us rode the lift and others toured the town. From there we went to Capri (the town) which was frankly a zoo. I was glad to have the short visit, but I enjoyed the nature beauty of the island much better.
4. In Sorrento we stayed at the Grand Hotel De La Ville Sorrento which I highly recommend. The hotel has two pools with one of them on the terrace with beautiful coastline views. Since we were traveling for a month, I needed a day just to hang out by the poll and relax which worked out very nicely at this hotel. The second pool is in a garden so if you wanted a quiet spot, it was available. The location was good because we could easily walk into the main areas of the town but avoid the noise and crazy chaos that was happening in May. The only thing I didn't like about the hotel was that it hosted tour groups so at breakfast you would see a large number of people leave at once and frankly, they all looked sad. (I am not a giant tour group kind of traveler). The service was excellent and the tour groups did not affect it.
5. Try to get a reservation to Restaurante Bagni Defino. It is right on the water with great seafood. We had them grill the local sea bass which they filet at our table with a wonderful sauce. Plus it was our anniversary and they sent over a bottle of champagne and made us feel very special. If your May is like our May,, be sure to have reservation for dinner while in Sorrento. It was so much more crowded than I expected.
6. Naples. I was worried about the craziness of Naples so I followed a forum suggestion and booked us at the Hotel Rex on the water. The hotel is simple but had good AC. I think this location worked out well for us. We could get to the Museum and found great pizza nearby.

Your itineary looks great. I think you have enough days spaced apart to make it no such rushed. Like you I was worried about connections since we had to do it, and it turned out not to be a big deal for our flight back to the US.

We also used Aldo Limos and were very happy with their services and drivers.

Thanks everyone for their advice. We've been discussing this trip more and now leaning towards not staying in Naples but visiting from Sorrento. We can then decide if we want to go back on a future trip for a longer visit. We are also considering splitting our time South between Sorrento and Amalfi. Not sure that is the right thing to do or not. I've read lots of posts about people waiting a long time for buses plus I think seeing a place at night when day trippers are gone can show you a completely different place. If it helps we are not shoppers. In fact I'm even wondering if Positano would be enjoyable since we are not shoppers. It seems like everything I read about it only mentions shopping.

I'd also love to somehow fit in Stresa but it just may not happen this trip as I don't want to feel rushed. If we split up our time between Sorrento and Amalfi does it matter which one do first? Right now I'm thinking something like this:

May 11th - arrive FCO stay in Rome (we would be leaving Boston on the 10th rather than the 11th as posted originally)
May 12th - sleep Amalfi town 3 nights (visit Positano, Ravello, is Paestum better from here or Sorrento?)
May 15th - sleep Sorrento 3 nights (visit Naples, Pompeii, Capri)
May 18th - sleep Florence 2 nights (he doesn't want less than 2 nights here. We both really love Florence.)
May 20th - sleep Stresa 3 nights
May 23rd - sleep Varenna 2 nights - not sure on this. We'll either add time to Sorrento/Amalfi and just do Varenna or split it like this. At the moment I'm unable to decide for sure. I don't like fast travel but would like to see Stresa. Hard to find that balance.
May 25th - sleep Milan or Rome for 1 night before departure on May 26th.

Definitely go to Paestum (if you go) from Amalfi. The bus routes break there, Sorrento-Positano-Amalfi; then Amalfi-Salerno (and the train to Paestum in Salerno.) Paestum is almost impractical from Sorrento, although there is a high season ferry to Salerno, maybe. You can check on ferries from Amalfi, but you need a backup in case of high winds. With the Salerno-Amalfi area reported congested, this location is better also for Paestum. We gave up on Paestum from Sorrento-daytrip.

Remember you are staying in Sorrento for transit connections. Otherwise it's a perfectly nice postwar, purpose-built, reinforced-concrete (mostly) town. Lovely cliffside setting, only one tiny, public beach in Sorrento, located between two diesel-fuel odor marinas. Just for reference, not a "warning." Extra street closings each night for the Passeggiata. Many restaurants. Many souvenir shops.

Thanks Tim - that description you gave of Sorrento is also why staying in Amalfi town is appealing to us. It's a base - hopefully pleasant base but a base nonetheless.

I was amazed how much I disliked the Amalfi Coast and the craziness and crowding- and this was just this May, which is no longer shoulder season. The traffic, congestion, crowds, car horns, diesel smells just undid any sense of beauty. There is no efficient way to get anywhere in Southern Italy. Private drivers are nice, but still sitting in traffic. It took us two hours by Private driver to get from Naples train station to our sorrento hotel.

To me, Northern Italy is equally beautiful and just not so congested. Lake Como was relaxing and scenic and not uncomfortably crowded in May. I don't know Stresa, but there are glowing reviews here, making me want to visit.

I would decrease your time in the south and increase your time in northern Italy. Just my humble opinion.
Have a great trip!

Thanks Pat. I found put today I have a coworker in our London office who is on the Amalfi coast right now. His girlfriend surprised him with the trip for his birthday. I think he comes back Wednesday or Thursday & I'm looking forward to hearing where they stayed, activities & how they liked it.

It looks beautiful but reading about people vomiting on the buses & the transportation woes sounds very unappealing. My SO & I don't get to vacation together super often for various reasons & as the planner I want it to be nice. I don't expect perfect but ....