Five nights will go quickly in Southern Italy. As charming as Ravello is, it is not the most convenient location unless you don't plan on visiting the neighboring villages. From Positano you can easily visit surrounding towns. I stayed in the neighboring town of Amalfi. We loved the Hotel Floridiana. No views, but the sleeping rooms and breakfast room were lovely. Excellent value and service. http://www.hotelfloridiana.it/ There are also many good restaurants in Amalfi.

We spent four nights on Capri and I would have enjoyed more. We stayed at La Minerva http://www.laminervacapri.com/en/rooms. Worth the upgrade to a patio room (although you didn't mention your budget).

I think you'll get plenty of advice on this board on where to stay, but my vote would be Amalfi as it is easy to get to Ravello and Positano. We were able to get a hydrofoil from Capri to Positano or Amalfi (I can't remember which), so I would image Capri could be a day trip.

We fell in love with Amalfi. From there, it's super easy to visit Ravelo and Positano, and there are boats to Capri.

I agree that Ravelo is really not convenient as a base. The bus service is a not punctual and I would have felt stranded up there!

Positano is beautiful, but I was glad we went for a few hours and came back to beautiful Amalfi.

And Capri, beautiful, but overcrowded most of the day. The nights however, are splendid, if in a high-class facelift sort of way!

If I might add, take a look at Ischia. Besides Amalfi, it's the place we preferred in our whole Southern Italy trip. Beautiful island, great food, kind people, and... volcanic spas everywhere... Ahhhh, heaven.

Pictures here : http://jojomart.shutterfly.com/

And you can read my trip report for more info!

You will have a WONDERFUL time either way.

Positano or Amalfi would be the most convenient for reaching other nearby areas.

Both Capri and Ravello are too isolated as a base location.
The other options all have relative merits---you must choose for you.

It is so hard to choose as all these places sound amazing. Im going to add that these 5 days will take place before my husband and I head to Fiesole/Firenze Florence for a wedding that we are both in. This will take place from a Wed night-Sat morning. We will be busy those days, so we were thinking a relaxing start to our trip would be great. This is another reason why the isolated locations arent sounding too bad. It will allow us to truly relax if that is what we choose.

I loved both Ravello and Capri - for a night or 2 at most each. I agree with the majority - I think it makes most sense to stay in Positano or Amalfi. You can still just relax if that's what you want, but to choose to spend 5 days in a place that is not a convenient base for the area really doesn't make much sense to me.

For a different point of view:

Were I going back to the Amafli for an experience of food, wine and living in the culture, I would pick Ravello. For Italians, the truly enjoyable experience of that part of Italy is to relax in a beautiful villa or apartment for several days in a row. Ravello has one or two very good restaurants that serve local food, and if you walk up hill to Serra, you can find a genuine regional culture and restaurant unaffected by mass tourism.

If what you really want to do is a lot of touristing to Capri and other towns, getting on and off buses and ferries, then of course you want to stay in Positano or Amalfi (the town) so you can be early to get on line.

But if you want to experience of a sliver of what Italians experience when they go to the area to relax, and have little intention of doing anything but enjoy the views and the food, and take a few walks and that's it, then Ravello will -- obviously -- get you away from the tourist scrum. Once the daytrippers from Positano have left, you'll have the place to yourselves.

It's a great hideaway for people who know how to enteretain themselves in a beautiful setting and who want some real peace far from the madding crowds.

If you think you will get antsy without a lot of shops around and ways to keep moving, you should book elsewhere.

Another question I have is would you pick Capri over Ischia? With only 5 days i'm really trying to make the best possible choice. I feel like I can't go too wrong with any choice, but its so nice to hear advice and suggestions from others who have traveled to the areas. I appreciate it!

I think the answer to that question depends on your tolerance for tourists -- and what kind -- vs. your desire for the drop dead gorgeous views that have made Capri so famous. Also, some people head to Ischia to avail themselves of the many spas, resorts and thermal waters, so if that would be a huge treat for you, only Ischia offers that.

Capri proper is absolutely overrun with tourists by day. At night, its just you and your fellow tourists, however many the hotels can handle. The slightly more remote Anacapri sees far fewer daytrippers, but some people aren't prepared for the remoteness and would rather be around more restaurants, even if it means more tourists.

It is just really hard to advise someone else -- although plenty of people will try to twist your arm into repeating their trip (for reasons the rest of us can't figure out). The mass tourist impact in Capri and Positano is significant, likewise in the Amafli, and it touches everything, including the restaurants. Ischia gets a lot of German and British tourists, and has less of the picture postcard views that most people are looking for.

Some people really want to avoid the mass tourist impact, and so they head to lovely little towns like Minori or Cetara or Paestrum, or Serra right above Ravello. But they are consciously trading away the most sought after views by night for the better food, the more tranquil ambience, the more Italian feel (and the marginally lower prices).

Obviously many people could give a rat's behind about sharing views with many fellow tourists. They would hate to travel so far and not see Capri, or not stay right in Positano. I am pretty sure that if you are determined and choose wisely, you can find hidey-holes even in the most famous mega-tourist destinations, and relax if you want to. Many people don't find anything negative about these places.

You can get a wider range of impressions if you also read hotel reviews on Tripadvisor for places like Minori or various towns in Ischia, or Anacapri. People will talk about their preference for one spot over another, and maybe you'll see some reflections of what you are looking for.

By the way, I'm not sure I've picked up on when you are traveling. Between July and August, the famous tourist spots are jam-packed. In other months, things are little less hectic and low season is very calm.

Sorry for my typo -- Paestum.