Italy choice

As much as I enjoyed the CT ( 3 crowd free days in April a few years ago, before the hordes decended), I would opt for the AC or Sorrento (or both). While undoubtedly touristy and crowded at that time of year, IMO there are more opportunities for more varied experiences and day trips.

Are you planning to spend the entire 2 weeks in one location?

Which might be the better choice could be dependent on where else you plan to go

Hope you like hot, because you will plenty of it at that time of the year.

Happy anniversary to you and yours!

Have you been to Italy before? Are you locked in to those dates?

We have been in Italy the first two weeks in August and it was brutal. This was back pre-air conditioning so that made it even worse. It was 103 in Rome when we were there.

While exploring CT for a few days might be nice, there's really not a lot to do. It has become pretty much a tourist trap with cheap souvenirs and bad fast food. It is not a good hub to use for exploring other areas. Who knows what it will be like in August 2021 (or if you'll even be able to go), but before Covid it had become a severely over touristed destination, especially with the hordes of cruise ship day trippers.

Of the two, I think the Amalfi coast is a better option, but again, transportation in the summer is a challenge. What are your goals? Are you art and history buffs? What draws you to Italy?

I would suggest checking historic temperatures for those two spots during your time frame. How do you handle the heat? If heat can be an issue, maybe check farther north of CT. But, responding to your question, I would vote for the Amalfi Coast. There are more options for day trips and tourists are spread a little thinner given there is more space. You can also hire a driver in the AC for a day or half day to travel rather than rely on the bus. Because we needed to get to Ravello from Positano on a certain day, we hired a driver for a half day. It was easy to get to Amalfi to Ravello and then take a ferry back to Positano. The point is, there are various connections allowing you freedom to choose where you want to stay.

Aren't you a wonderful husband! Personally I would look seriously at Sorrento as a home base. It is easy (well, it's also very crowded) to do day trips to Capri, Pompeii, Positano, Amalfi Town and even Naples. Sorrento also offers, at surprisingly reasonable prices, great food and shopping. There are also places to just sit and people watch, watch the sunset, enjoy the view of the Bay of Naples. I would suggest a hotel that offers views, quiet and relaxation so that you can find your balance between tourist and 'just enjoying life'. I spend about a week in Sorrento every year for the past maybe decade and a half. I have my favorite hotel - PM me and I'll sing its praises. Sorrento is my 'go to' place in Italy where I can just meld into the scenery and culture. I like me there.

It will be HOT!! Can you push it to October, less crowds and better temperatures. For 2 weeks, I'd do more. I'd fly into Venice and out of Rome and do Florence/Tuscany in-between, totally the train, not need a car. Florence has many day trips into Tuscany by great companies. Have you bought the RS Italy book? You'll learn tons in it. For what you asked, I'd base in Sorrento and do day trips to Amalfi with Sharedtours.com and take the train to Herculaneum (the RS Italy book tells you exactly how to do it and it is so easy, but 2 weeks is a lot for that area. Or - take a RS Venice, Florence, Rome tour and then take the train to Sorrento when the tour ends- We've done that and it was great. Then fly home from Naples.

most restaurants in those areas are family run and when the family goes on their annual August vacations entire restaurants and shops shut down.

I don't know what happens in the Cinque Terre area in August, but, family run or not, no restaurant on the Amalfi Coast would close during the most crowded weeks of the season. Some shops catering only to locals will be closed during the days before and after August 15, that's a national holiday, most of tourists' shops will close only on the 15th.

The Amalfi Coast restaurants have 4/5 months to make money for the all year, the magnificent starred 7 make money even in winter but they are an exception.

david,

Both areas have their charms but are somewhat different in character.

The Cinque Terre consists of five small towns along the Ligurian coast, and is more "informal" than the towns on the Amalfi Coast. Each of the five towns is slightly different, so you'll have to make a decision on which one of the five you want to stay in. While staying there you could visit a number of other popular resorts in the area such as Santa Margherita Ligure, Portofino or Porto Venere. If you'd rather just chill on the beaches, Monterosso would be a great spot to do that. Monterosso is the largest of the five and therefore has the best choice of hotels and other lodgings, and lots of nice restaurants. While the overcrowding has been a problem, at this point no one knows when those crowds might return.

The towns on the Amalfi Coast tend to have more of the "old world" posh feel to them, but they would also be a great place to stay. One thing to consider is that transportation in the south is not as well developed or easy as in the north. Sorrento is a great place to use as a "home base" as there are lots of nice hotels in all price ranges and lots of nice restaurants. If you decide to stay here, have a look at this hotel - https://ilnido.it/ . While it's not right in town, it has fantastic views. If you want a great restaurant for that special meal, post another note as I can recommend a perfect choice. Sorrento has rail, bus and boat service so it's easy to visit Naples, Pompeii, Capri or other locations. If you have a super large budget and want to splurge, you could have consider staying in Ravello, which has been a big favourite of "A-listers" for awhile. You could also have a look at Positano, however that doesn't have rail service so it's a bit more awkward to get to and from. This would be a perfect anniversary hotel in Positano (but not cheap) - https://sirenuse.it/en .

The WHO said today that the pandemic may last for another year, so it would probably be prudent not to make non-refundable bookings.

I would clearly go for the Amalfi Coast over CT.

Also, you are from CT so the heat may be more of an issue for you? We are from South Georgia and can handle the heat in Italy, just fine.

After a few trips to the AC, I realized that in the blazing heat of August, if you stay in Sorrento and spend time on your hotel terrace or by the pool facing Vesuvio and Naples, most likely you’ll be in the shade all day. On the other side of the mountain, in the Positano, Amalfi area, looking south, you’ll be baking in the sun all day.

Is this for a two-week stay in one place, or paired with other places? Please share that, plus reassure us about your heat tolerance.

if you stay in Sorrento and spend time on your hotel terrace or by the pool facing Vesuvio and Naples, most likely you’ll be in the shade all day.

There's always the chance when facing Vesuvio that it might get a lot hotter very rapidly. ;-)

Hi David, Amalfi Coast and Cinque terre are both wonderful. Maybe malfi Coast is more popular and expensive.
Regards