Sorrento or Positano?

We were there last October. The water was very rough, so unfortunately our private boat tour was cancelled. We stayed in Sorrento and loved it. We were unable to get to Positano, so I have no opinion on staying there. We were able to take the ferry to Amalfi one day. Very touristy and crowded by the cathedral so we walked up and out of town and had a lovely quiet lunch. The beach in Amalfi was small, but lovely and I put my feet in the water. No one was swimming. Wherever you stay in that area will be magical.

Probably too cold. I liked Sorrento for its affordability and nighttime atmosphere.

I have stayed in Sorrento, Positano and Amalfi. My least favorite was Positano, a cute town when viewed from the roadway or ferry. If I wanted to stay on the coast, I would return to Amalfi. It’s small and I found it to be laid back and convenient for bus or ferry transportation to explore the coast. Realize that Sorrento is not on the Amalfi Coast but it is a charming city with a lot to do and see. Which to use as a base is more down to your particular travel style.

What do you want to do/see while there?

Sorrento has the best transportation connections. For example, you easily can get to Pompei, Amalfi, and Ravello. A day for Capri would also be a good choice.
Positano is very hilly and steep. It’s filled with shops featuring expensive clothing and other products aimed at well-heeled tourists. There was so little of interrst there that we left after half a day. Even if the water were warm enough for swimming, the beach is not very attractive.l

Thank you for all the comments, so very helpful! I grew up sailing and would like to experience the coast from the water. Beginning to think Sorrento would provide more water day trips.

Our group of 5 spent 8 days/7 nights on the Amalfi Coast with Positano as a home base in early May. As others have said, it is very hilly and you must be at a minimum level of fitness to enjoy any town on the Amalfi coast since they are all pretty vertical. That said, we felt that Positano was a perfect central base point particularly for boat tours which left regularly from the small pier. We went swimming from the private boat we arranged, but did not go to the local beach. The boat tours went to Capri as well as Amalfi Town, Ravello and Minori both on the water and on land (separate tours). The food and nightlife in Positano was outstanding, and the "vibe" was very laid back and casual. From Positano, we took the above day trips so we were not actually in Positano that much except to sleep, so it worked for us. I recommend going a little further south to Paestum as well to see the amazing archeological park with the Greek temples and ruins zones; they are remarkably well preserved. Then, within 2 miles of that we stopped at a Buffalo farm and enjoyed a tour showing how they make buffalo mozzarella. We hired drivers to get us to each of the Amalfi coast towns, and felt that it was a good investment, although somewhat pricey. You don't want to personally drive on the Amalfi coast unless you have nerves of steel and don't mind the dozens of scooters and pedestrians crossing the tight road in front of you. That, and lack of parking anywhere made the decision to hire drivers practical.

We also visited Sorrento for a day trip when leaving Positano on the way to Naples airport and it was delightful as well. From there, we visited Pompeii the next day which is a must-see. Sorrento is probably a lot less expensive then Positano, with perhaps some more hotel options, but for us the central location and beauty of Positano made our trip really special. Have fun!

Now that we have a tiny bit of your interests, we can say that Sorrento has more ferry departures and can handle larger boats, which is better in shoulder season water conditions. Is your sailing experience in a lake, or in the open ocean?

You have not asked about private guided small boat tours, or self-crewed rentals. Or the qualifications for renting them uncrewed. Wind and waves can be quite high in the area. Some seasonal businesses may start to shut down in October, but Sorrento has higher activity all year.

Positano has more physical charm and glamor, but has hundreds of stair steps, and tends towards higher prices. It takes hours to "get" somewhere from Positano at low cost. We spent five nights in Sorrento for daytrips, and it worked well. (Late May, very hot) Positano has small, sheltered pebble beaches. Sorrento has one public beach, very small, and sandwiched between two smellable marinas.