Sorrento - Early June

Question: does your airbnb host know how late you'll be arriving (however you end up getting there)? It's going to be midnight at best. Where is this accommodation?

Houston>Paris>Naples>Sorrento>airbnb at midnight or so with two small children....That's a pretty brutal itinerary.

Yes, fortunately the Airbnb host is very understanding and flexible. It was the best we could do flight wise....

Sorrento to Pompeii is very easy on the commuter train which has a stop by Pompeii's entrance. Guides are available to hire at the entrance of Pompeii.
We paid a driver to take two of us from Sorrento to the Naples Airport and it was around 115E two years ago.
Restaurants:
Sorrento: Bagni Delfino, down at Marina Grande, seafood, on the water and Ristorante Pizzeria Tasso.
Capri: Would this be for lunch, a day trip? Or are you staying on Capri too and want dinner recommendations?

Regarding the pizza chef, don't do it! Neapolitan pizzas taste the way they do because they are cooked in an oven which produced dry heat at temperatures in excess of 600 degrees. Your AirB&B property will have a dinky stove that can't reach these temperatures and it will be too small. Enjoy your Italian pies in situ, in the Pizzeria where they are born.

For Pompeii, hop on the Circumvesuviana and you are there in a half hour. If you want a guide, hook up with one when you get to the Scavi.

Beaches aren't the same in Italy as they are in other parts of the world. The Italians generally travel to seaside areas and then rent beach chairs and umbrellas to use while they contemplate the beauty of the water and the warmth of the sunshine. The owners/operators of the umbrellas generally control who is going to be enjoying them, and some of the more coveted areas are reserved for years in advance. As you indicate, there really isn't much of a beach in Sorrento and the beachy areas are composed mostly of man made breakwaters. I would suspect that these areas are expensive to rent, and would not know how to reserve a space unless it is controlled by my hotel. I am not saying there isn't good sand in Italy (I am doing a beach vacation myself this year on Ischia, one of the islands in the Bay of Naples, where there is lots of sand) but I suspect that your hotel pool would be a much better sunning and swimming experience than the rocky surfaces between Marina Grande and Marina Piccola.

For transfer from the airport try this company,

http://www.sorrentosilverstar.com/contact-us.html

For 2, I think the cost was €110 one way. Several here have used them.

For a boat tour, my daughter and friends have use this company. Their summer pricing is not up yet.

https://www.youknowboat.com/en/anacapri-and-capri-boat-tour-from-sorrento-winter-edition/

I agree with the poster above, if your B&B doesn't have a pizza oven, go out for it.

Weather - we are from Houston...it's hot and humid here. ALL. THE. TIME. I have read several posts about unbearable "heat" in June in this part of Italy....how hot is it really? Will it be just a normal weather day since we are used to heat and humidity at home?

If you do outdoor activities at home in the June-Aug time frame, then Sorrento in early June will pose no hardship, weatherwise.

Have you gotten yourself a good, current guide book to help address your other questions?

Have you asked your landlord about transport options for your late arrival?

No, haven't gotten a guidebook all though I have read over many travel blogs and articles about the area. I guess I was looking for some real world personal reccomendations.

I asked the Airbnb host about transportation arrangements, and he said he could assist with that....but I was wondering what the standard fare would run for a Sorrento to Naples airport run....and for 9 people and luggage, most of the quotes I am getting are for 2 vehicles...which is fine if that's the way it needs to be done....but one larger vehicle would be ideal.

Lanna, the company I referenced above has a 16 passenger van. If you fill out their form asking for a quote they should get back to you in 24 hours. Right now it's around 16:00 there.

I guess I was looking for some real world personal reccomendations.

The problem with that, lanna, is that everyone's interests/abilities are different so must-do's are all over the place. Best to spend some time with a guidebook and local tourism sites to see what appeals to your group. Skip the touts on the website for tours as they aren't really necessary in many cases.

https://www.sorrentoinsider.com
https://www.capri.net

Boat tours:
I haven't used this outfit but it was highly recommended to me by someone who had, and I passed it along to another couple. They LOVED their tour so take a look?

https://www.giannisboat.com
https://www.giannisboat.com/en/tour-sorrento

Note that they will put together a custom tour from Sorrento for groups of 10-12. Personally, I would decline the optional Blue Grotto piece as if there's tourist trap on Capri, IMHO, it's that one. And however you do it, a day of private boat excursion is going to be expensive.

Hiking:
We did some nice hiking on Capri that kids could definitely do but I don't think as you'll have enough time for much of that if in conjunction with a boat tour.

Pompeii:
Yes, just take the Circumvesuviana to the Pompei Scavi - Villa dei Misteri stop and hire a guide at the entrance if you'd prefer a tour versus exploring on your own. The scavi, BTW, is HUGE.

https://www.sorrentoinsider.com/en/naples-to-sorrento-train-schedule

I don't know if you've found a transfer yet, but you might see if this company is less expensive.

http://www.easypickup.it/ENG/prenotazione_andata.html

Hope this helps.

We used topexcursionsorrento.com for transfers. Excellent! Giovanni is the owner.