Sorrento for 5 days-must sees to visit?

Must-see depends on your interests. For me Pompeii, Herculaneum and the Archeological Museum in Naples were must-sees. And I'll pick Capri over the Amalfi Coast any day of the week. We spent 12 days in Sorrento in April. Here's a link to my Trip Report if you think it might be helpful. https://community.ricksteves.com/travel-forum/trip-reports/trip-report-2-weeks-of-day-trips-from-sorrento

To get from Naples to Sorrento we thought the Circumvesuviana train was fine, but some of this forum prefer to spend considerably more for the convenience of a private driver.

https://community.ricksteves.com/travel-forum/trip-reports/venice-lake-como-sorrento-amalfi-coast-with-lots-of-rain

Above is our Trip Report from this past May. I'm sure you'll have better weather than we did. Allan's Trip Report is a comprehensive review of the area.

I was very naive regarding the congestion in the area, the lack of efficient transplantation modes, and how crowded every area was. There is no fast and efficient way to get anywhere. I did like staying in Sorrento.

The regional train was very packed, we had to stand for the hour train ride from Pompeii to Sorrento, and was very hot in May. We met folks on the train who had to stand all the way from Naples to Sorrento. The schedule was more of a suggestion.

We used Aldo Limos for transportation from Naples to Sorrento, around 100 €, took almost two hours because of the traffic. Aldo is based in Sorrento, and has an office right off the plaza. ( See my TR.) I highly recommend Aldo, and Christine, in the office, is a Brit, so communication was easy.

Mondo, recommended by RS, does shared transportation services, along with shared tours.

The SITA buses along the AC are packed with probably a hundred people at each stop trying to get on.

The Positano ferries are really affected by bad weather, and the dock was knocked out when we were there. All the ferries are impacted by rough weather and can be canceled.

Have a great trip, but be prepared for the logistical challenges of moving through the area.
Safe travels.

We were in Sorrento in 2017. We hired a driver to take us from Naples train station to Pompeii. That was one of my lifelong bucket list items and I think it is a must see. We did a private guide in Pompeii through Context. It was incredible. I would also recommend taking a boat to Capri. It is magical. Explore the island and town. Take a dip in the water if the temperature is good at that time of year. See the blue grotto and some caves. Walk around Sorrento and just be inquisitive - go in shops, talk to people, try a restaurant in a whim. Finally, go to Ravello. It’s close to Positano (which you should also experience), but we felt it was less “cheesy - touristy”. Beautiful views and they may even have some great music going on when you’re there.

As Allen said, what you would enjoy seeing/doing depends on your interests. It's difficult, maybe even unhelpful, to make recommendations for someone we haven't met! Capri? Sure, we enjoyed our stay on the island but where one poster thought the Blue Grotto was a must-do, that one was a must-avoid for us - we preferred, say, trekking around the island to scenic spots and Roman ruins - so we're all different. Pompeii? That one was high on our gotta-do list and we did just fine without a guide or driver so again, different strokes! :O) What can you tell us about yourselves?

As well, how to get to your B&B can depend on exactly where it's located. For instance, our hotel was an easy walk from Sorrento's Circumvesuviana train station but other accommodations may involve a public bus or taxi to reach from the station or from the port, especially if a larger luggage is involved. So which B&B are you staying at so we can look up the location?

Are you flying into Naples, and are you also flying OUT of Naples? If you have a morning flight out, it's often recommended to stay IN Naples the night before. If flying into/out of Naples, there is coach (bus) service from the airport to Sorrento and vice versa.

https://www.curreriviaggi.it/en/naples-airport-shuttle

There is a lot to see in the area, so naturally your “must sees” my differ. Pompeii and Herculaneum are both once-in-a-lifetime kind of places imo. You should spend a day in Naples, and see the Archaeological Museum and Capella San Servo. These sights (along with transport from Naples to your accommodations) are best served by the Circumvesuviana train. It gets a lot of grief, but it is the cheapest, most frequent and efficient way to get around the Bay of Naples. Just be mindful of your luggage and valuables. Thousands of people take this train everyday and are fine.

I’m with the other poster, in that as a daytrip, I might pick Capri over the AC. Still, a ferry into Amalfi (and past Positano with its damaged dock) is an unbeatable experience. With either route, get as early a jump as possible to stay ahead of the crowds. Taking a bus from Amalfi up to Ravello may make for a more hectic day, but Ravello is gorgeous and was a particular highlight for me. I would recommend taking the ferry over the bus traveling to and from Amalfi.

There’s no need to budget time for Sorrento itself. There’s not really anything to “see” there, but it does make for an excellent and relaxing home base. You’ll explore all of it with a couple evening strolls.

Also, any recommendations on getting from Naples to our B&B in Sorrento?

Does your landlord not have any suggestions?