3 nights in Capri

Any hiking?

Yes, and probably the best thing to do on the island, IMHO! We did quite a number of these and enjoyed them very much:

https://www.capri.com/en/traveller-search?todo%5B%5D=nature&all=1

Ignore the touts/prices for guided hiking tours: you don't need them.. Get a map of the island at the visitor center in Capri town when you arrive. The hike out to Villa Jovis was one of our favorites, although most of it is on narrow, paved residential lanes and not dirt paths.

It is difficult to overemphasis how much of Capri is pedestrian-only, and hilly. Public busses cover little of the island and are microscopic with long lines to board. Taxicabs cannot reach every spot on the island. If you have big luggage, I would consider that in selecting a hotel. (We didn't sleep on Capri.) You are not going to tumble out of bed and be at a snorkel boat ten minutes later. Time of year makes a big difference is fierce crowds - you didn't give the month. Long advance booking is advisable. Ferry boats vary in size, but some carry hundreds of passengers.

Thanks Kathy for the recommendations. It is good to know about the transportation. We will be there in early may this year looking at May 8-10th nights. how bad are the crowds then? Would all of our water stuff need to be booked in advance? we will have one big piece of luggage each so I guess staying somewhere close to where the ferry drops us off or in main part of town would be best?

There is porter service (fee) available at the docks for moving luggage to the hotels, and the hotels usually offer that service (usually) for an extra fee as well. From the Capri tourism site:

https://www.capri.com/en/getting-here

"The first thing we suggest you do is drop off your bags with one of
the porter services on the pier.

If your hotel is in Capri, we recommend having the luggage porter
service transport your bags directly to your room. The service will
cost from €5-12 per bag (depending upon where your hotel is located),
which can seem expensive until you consider having to drag bags
through the narrow and steep lanes on Capri to begin your vacation...

To reach the Piazzetta, you can take the funicular (which departs
directly opposite the pier; the ticket office is to the right) or one
of Capri's open-top taxis. The fare for a ride between the port and
the Piazzetta is about €17 (my note: taxis do not go into or past the
little Capri town Piazzetta).

If your hotel is located in Anacapri, you should take a taxi with your
bags. The fare from Marina Grande to Anacapri begins at €25 plus extra
luggage fees. Otherwise, above the funicular ticket window you'll find
the stop for bus routes to Anacapri, which run often. The alternative
is to take the funicular and then the Capri-Anacapri bus. Most of the
hotels on Anacapri offer free or economic shuttle services between the
port and the hotel: inquire directly with your hotel."

Be cautious not to take very large suitcases or pack them so heavily that you can't manage them easily by yourself...which you're going to have to do on and off trains in Italy, up/down flights of stairs at hotels (unless yours has a lift), etc.

We didn't do any "water stuff" so I'm no help there, sorry. I'm guessing the water will be pretty chilly in early May but some folks have higher tolerances for that than others.

We stayed in AnaCapri in 2012 at the Hotel San Michele. I'm not a big one for romance and that sort of thing but sitting on the terrace with a glass of wine, watching the sun go down over the Bay of Naples is pretty sublime.

Kathy is being kind saying the water will be "chilly". Average water temps will be betweeen 62-68 in May.
With this in mind are you sure you want to spend 3 nights on the island?

As for views, the higher you go on the island, the better the view.

We stayed at the Weber Ambassador Hotel overlooking Marina Piccolo, on the quieter side of the island. Relatively lower rates, even when we splurged on a large terraced room. Their van will pick you and your luggage up at the pier to drive you to their location. The hotel has a free shuttle van which can take you into/from the town center during your stay. It is touristy, but seeing the Blue Grotto was fun, and I was glad I did not back out of the tour.

Gerri. I think we could do it in two nights but it may be rushed. We want to do a boat tours and do some hiking and just seeing the town. May even do a one day ferry trip to Positano. Does that sound ok for 3 nights?

If I remove a night from Capri then I would add it to another city and do 4 nights in either Venice or Lake Como?

If you add Positano, that will give you a good option if you've seen and done everything on Capri without changing locations.

Kathy is being kind saying the water will be "chilly".

LOL, Gerri. You are being kind not telling me I'm nuts for softpeddling the chill factor. :O)

So after learning a little more about capri I'm beginning to worry that 3 nights there may be too much time for all that we had planned. We wanted to see the island and do a boat tour, do some hiking/chairlift, and see the grotto. However, I think almafi and positano would be neat to visit as well. Can we do day trips to these places from capri or would it be better to spend two nights in sorrento instead of one and go to these places from there and then only do 2 nights in capri?

I have tried searching ferry’s does anyone know if a ferry runs from Capri to Positano to do like a one day trip?

http://www.positano.com/en/ferry-schedule?from=capri&to=positano

Looks like it’s not common to go from Capri to Positano but other way around. I will try to stay in Sorrento one more night so we can do busses to almighty and postano

The Blue Grotto is not always accessible; it is weather-dependent. And be sure you understand about the you-have-to-pay-twice bit.

We spend 5 nights in Capri at the end of May. We found a villa on vbro equidistant from marina picolo and the piazzetta (the main square in Capri town). We hiked, swam, did a boat tour, drank prosecco every dinner. The villa had a swing that would overlook the blue Mediterranean sea. My daughter who is five now still talks about it a year later. The flowers in May were sublime. 3 nights too much? I don't think so.

We used this service for the boat:
http://www.giannisboat.com/

I got a lot of ideas from:
https://www.capri.com/

If you are a strong swimmer and the sea is calm, you can swim in the Blue Grotto early morning or evening. I would not recommend the visit during the day, as the lines are very long.

From the website www.capri.com....

"Can I swim inside the grotto?
Visitors are not allowed to swim into the grotto or dive from rowboats to swim inside the cavern. Many visitors wait until after 5:30 p.m. when the rowboats leave and the ticket office closes to swim inside. This is illegal and dangerous, as the high waves can slam swimmers against the stone of the low cave mouth."

We did this walk when we were on Capri a few years ago: https://www.capri.com/en/e/towers-and-forts-2

It is a stunning walk with views to die for., and we saw, perhaps, three or four others making the same hike. However it's not for people with any sort of mobility issues, some parts of the path are a bit treacherous. We started near the Blue Grotto and ended at Punta Carena, where there is a lighthouse and a snack shack, where we drank our fill of water and beer before we got on the bus back to Anacapri. A highlight of our trip.

Enjoy!
DD

How long did this hike take you? Was it an all day thing?

Deidre, we did the same hike! It was fabulous! We got a map at the tourist office on the Piazzatta the day before. I thought the trail markers not always obvious, but with a map it was easy.

I can’t remember how long it took... I want to say less than 3 hours. We swam at the blue grotto at 7am for 10min. We were on the trail by 7:30am. Took the bus back to Anacapri from the light house. We were visiting the Villa St Michelle before 10am. The crowds were just showing up.

But my favorite hike on Capri was on the via Pizzolugo, all the way down to the restaurant Da Luigi. Best pesto pumpkin pie I ever had:)

We stayed on a pedestrian pathway that runs between Punta di Tragara and Giardini di Augusto on the southern coast of the island. Beautiful views including of the famous rocks, Faraglioni. It was always pleasant in this area. The Giardini get a lot of visitors but the pathways are lovely and uncrowded. The ciews from tne Giardini are breathtaking. We would venture to the town center after day trippers had left.
We used the porterage service for our luggage when we got off the ferry and was at the hotel before we arrived. The hotel checked every day to see when the boats would go out and we were lucky on our last day there.. Rough seas mean they are canceled.
We took a bus to Anacapri and it was very crowded too, and it was September.
We stayed at family owned La Minerva, one of our most favorite hotel experiences ever.

One of our favorite hikes was to Arco Naturale - beautiful walk !