Positano Recommendations

It would be wonderful if you could spend at least one night on Capri. I assume you are traveling to Capri independently. Head out of Capri Town to the Giardini Agosto to see the beautiful views. Then walk from there along the coast to Punta Tragara. The whole walk is in a pedestrian zone with stunning views. There should be way fewer tourist crowds in this area. We stayed there and loved the experience.We stopped by Positano for a day and enjoyed a seaside lunch so can’t much regarding it. Lots of steps to get down to the beach area.

Ravello is lovely
Walk out to Villa Cimbrone for the fantastic view

Thank you so much for your recommendations.

We loved hiking the Path of Gods. Not everyone's cup of tea but the views are outstanding.

It sounds like your travel is not "budget". I mention that because it's also possible to visit Pompeii by public transportation, and they have a baggage check for luggage in that case. However, when Positano is your destination (rather than, say, Sorrento or Salerno), it makes sense to use a car service. Naturally, it costs money to have a driver sit and wait for a multi-hour visit. (Pompeii is very large.) I recommend dinner reservations, and lunch reservations for any well-known restaurant.

This area is very busy in June, and quite hot. Because Positano has only one two-lane road through it, your mobility will be slightly restricted. And because Positano can accomodate only smaller ferries than the larger ports, I would prioritize getting ferry tickets you want in advance. (I have not slept in Positano, however. So no personal experience with that.) It makes sense to use a beach club (not sure whether that is an actual facility, or if you mean "a guy who rents chairs on the beach") to reduce the sense of crowding.

I am not suggesting that Positano is not an upscale experience. It certainly still is. But it's a different definition of luxury than Hedge Fund Dudes use in the USA. The beaches in town are small and pebbled, and the water can be cold. Certainly the beaches around Boston tend to be "better" (... "different", if you like ....) than those on most of the AC. Have you checked your hotel location? Positano can have many, many vertical steps between some locations. I am not familiar with its (vigorous) summer nightlife, since we only visited in daylight.

Rather than saying you "must" sleep on Capri, I would just say that it's a different experience than the mainland. Capri is quite large, hilly, and mostly pedestrianized. So you should prepare for several miles of walking if you want to experience much of the island. We skipped the Blue Grotto, and were not sorry we did. It's a time-sucker, for a very limited experience. Alas, you will also find Capri crowded.

Thank you all for you assistance.

I realize the private driver for Pompeii is an added expense, but seemed to be the best way for us to "fit" in Pompeii on the travel day from Florence and get to Positano. Seemed better for our family to do Pompeii on this day rather than head out again from Positano on another day.
We are staying in an Air BB in Positano.
Will definitely add hiking the Path of Gods to the list - great suggestion that I think the whole family will enjoy.

Thank you again for input.
I have found this forum very helpful in trip planning.

We stayed in Positano for 3 nights. There are some beautiful areas to walk within Positano for some great views. You can walk along Via Positanesi d'America to the right of the ferry boat stalls to Fornillo Beach. Spiaggia Grande is a larger beach. I am not sure how clean the water is to actually swim in. Dinner at Hotel Eden Roc - Adama and Eva Ristorante at sunset was lovely with the lights of the town and sea view below. Other picturesque streets are Viale Positea, Via Cristoforo Columbo, and Via Mulini. There are a lot of steps in Positano, but the higher you go the more magnificent the view.

We got Travelmar ferry tickets online in advance to Amalfi and then went to the booth by the Positano ferry docks to have them print the boarding passes 30 minutes before and lined up to get the upper deck seats. We took the ferry from Positano to Amalfi town which offered breathtaking views from the sea. From Amalfi we took the open air City Sightseeing bus up to Ravello where you can see Villa Rufolo and/or Villa Cimbroni.

We also stayed in Sorrento and went to Capri by ferry from Sorrento. I think you will have an amazing trip!

Thank you so much for those great ideas!

If you need a guide for Path of the Gods, we used Zia Lucy. She's wonderful. I know some people do it on their own but it's definitely safer with a guide. I walked it with my daughter and son-in law. It's not a hard hike but lots of loose stones.

there's a vlogger named Nicki Positano who lives there (obviously) and hikes constantly, check our her work on Youtube and she has friends who could guide for you.

another good resource is her friend Elizabeth who owns the Blue Star boat company

https://www.bluestarpositano.it/english.htm

thank you again for your suggestions! I appreciate the help

Hey, a little late to respond, but...

I did a sunset cruise with this company way back in 2015: https://www.cassiopea-positano.com/en/sunset-cruises/

It was great. They allowed us to add a stop at a village along the coast for dinner. Pricey meal, but it was amazing.

If ancient temples are of interest, consider a visit to Paestum.

Also... I agree that hiking the Path of the Gods is worthwhile. Like others, a friend and I did this hike with a guide but many do it without a guide.