Need help - first time exploring the Amalfi coast

We only had three nights and stayed in Atrani. We didn't see a whole lot (going back for 5 nights is on my to do list). We really enjoyed Ravello. If you like walks, we did the walk down from Ravello to Atrani, and tho it was a bit hard on the knees (lots of downhill/stairs) it was lovely.

Where are you going before/after Positano? EG - if you are coming from Naples area, you may be best to do Pompeii before hitting Positano. Or when leaving depending on where you are going when you leave. When we went, we flew into Naples, spent the night, and went to Pompeii on our way to the coast. When we were leaving the coast, we stopping into Naples again to see the Arch. Museum.

On a previous trip, we did a day trip from Rome and did Herculaneum and went to the top of Mt Vesuvius - that was pretty cool - again, a bit strenuous - loosely packed dirt/soil/rocks made the journey taxing. But Mt Vesu was a highlight for sure.

Some people will book a trip to Paestum (prob via Walks of Italy, or you could use a service like Sorrento Silver Star Cars - we used them for a driving tour of the coast and it was the highlight of the trip for my mom) and also see the mozzarella 'farms'. We didn't have time, but it is a def do on our next visit.

We used Positano as a base for a week in September. We picked up a brochure in the visitor's information center for a tour of Pompeii that picked us up at our apartment and included a guide at Pompeii for 60 euros each. Our pickup was at 3PM so we missed a lot of the huge crowds in Pompeii. We took the ferry to Capri and had lunch at the town Anacapri which is away from the busy tourist area accessible by the tram. Another day we went the Amalfi town and walked to Atrani for lunch in the square. We did not go to Ravello but our driver who took us back to Naples to the train station said it was a beautiful town and we were sad to have missed it. Take time to enjoy the beach one day!! FYI....there is no way to get around Positano and explore its' nooks and crannies without walking up and down hill but depending on your fitness level, and your knees, we found that walking the streets was easier than the steps but it was the long way around. Maybe a combination of steps and streets or steps down and street up???

The car service we used for transfer to and from Naples train station was Simply Almalfi. They also offer tours if you are interested. The drivers were very personable and gave us lot of great information while driving us back and forth. Katherine was your contact and was very prompt in getting back to us. Several of the car services provided in the Rick Steves' book did not reply to our initial emails.

Except for seasonal ferries, Positano is not well situated for ambitious day trips-unless you have a car service. Sorrento is not as pretty, but we were glad we slept there. It's a matter of opinion. In fact, we paid over 200 Euros for an eight hour car and driver to visit Positano, Amalfi, and Ravello, because surface transit on the AC is so crowded and sluggish, especially May to October.

I am not sure, but I think the ferries would be running in May. They are very convenient and economically.

1. Do a day trip to Capri. We did 5 different hikes on the island and stayed away from the crowds - the views are spectacular on the paths !

2. Hike the Path of the Gods - we stayed in Positano and took the bus up to Nocelle, hiked down to Praiano, rode the bus to Amalfi, and took the ferry back to Positano - great day !

3. Do a cooking class in Ravello with Mama Agata - just a delightful day and her giant lemon cake is to die for !

Definitely try to visit Ravello, you can take the bus easily.

Ferries stop in various combinations of towns, including Minori (Pasticceria Sal de Riso), Amalfi, Positano, Sorrento, Capri, and some others.

You can take the bus to Salerno and then the train to Paestum, but it will be a long day.

We stayed in both Positano and Sorrento.
I greatly preferred and my wife even more so Positano over Sorrento but there is no denying Sorrento is better logistically and also for day trips elsewhere.
If you only have 5 nights and no other time to do it, I think you should plan a day trip to Pompeii but from Positano your best option would be a pricey private car type service to do so.
The day trip to Capri is a must! Assuming the ferry is running which it should be it is easy to reach from Positano. An overnight there would be a nice bonus to see the town after the tourist leave and it is so breathtakingly beautiful that I would love to stay there ; transporting any luggage is an issue though and unless you can add nights I don't think you have enough time to overnight there and also take a day for Pompeii within your 5 night window.
Make sure to take the chair lift in Ana Capri, you can choose to hike down or take the chair lift back down if you don't care for hiking.
Ravello is also an absolute must, easy to do on same day as you visit Amalfi. That is a good full day (Amalfi and Ravello from Positano via the scenic bus or bus one way and take the ferry one way to Amalfi - Ravello is above Amalfi and not on the sea so only reachable by bus from Amalfi)
The best meals we had in the Amalfi Coast were in Ravello, this small town seems to really take pride in high quality food!
The SITA bus is very easy to navigate, cheap and a very scenic fun ride. it does get crowded so some patience is needed sometimes to wait for the next uncrowded bus.

We enjoyed in Positano one of the services that pick you up from Positano and take you to their house/restaurant high above the town. Is a price fixed multiple course home cooked meal of high quality and you will not leave hungry. The view is great and value is very high especially with the free car ride. Sorry I don't recall the name but ask at your hotel they will know, it is definitely not a place the locals eat but very homey / family owned authentic feeling.

Ravello is a wonderful day trip from Positano. I really enjoyed the Villa Cimbrone and the food at the restaurant there was superb (and in a wonderful, quiet, relaxing atmosphere). If you'd like to take a cooking class, I walked by a sign for Villa Maria cooking school http://www.cookingravello.com/en/ (and I watched people picking eggplants and tomatoes for their class).

And when you take the boat to Capri and head up to Anacapri - I enjoyed an appetizer at the Villa San Michele cafe. And you must stop in and view the majolica tiles at the Chiesa di San Michele. Stunning! It would be nice to stay one night on Capri. That way you could experience it after the tourist crowds left. I was fortunate to arrive from the mainland early in the morning and by early afternoon I wanted to leave - hordes of tourists in the main town of Capri. Not my cup of tea. But maybe in May it will be different. I was there in September.

Pompeii is a definite must. I wasn't too excited ahead of time about my visit there, but with the right guide, it is amazing. And then it would be great if you could follow your visit up with a trip to the museum in Naples that houses original frescoes, etc. from Pompeii. This is really a special treat.

Have a great trip!

We had a couple of good meals at C'era una Volta last year. Nothing fancy, but well prepared and reasonably priced for Positano.