Sorrento is the easiest base on the bay. It has a walkable old centre, a harbour with boats to Capri, a train station for Pompeii and Naples, and buses for the Amalfi Drive. Capri is a short crossing away, the Amalfi villages are a day trip along a famous road, and Pompeii is about half an hour by train. The catch for a November visit is that this is low season: many boats run reduced timetables or stop, the Blue Grotto is often closed, some hotels and beach clubs have shut for the winter, and the days are short. A good plan keeps every outdoor day flexible and has an indoor backup.
What to book ahead
Very little needs to be booked months in advance in November, which is the great advantage of the season. Book your hotel early, because several of the best properties close for winter and the choice narrows. Book the Amalfi Coast day trip and your Pompeii visit for dates a few days out, once you can see the forecast, and keep them refundable. A cooking class is worth reserving for a weekend evening. Villa San Michele and the Gardens of Augustus are walk-up sights with short winter hours, so they need timing rather than booking, though an entry ticket for the villa saves queuing at the gate.
Getting around
In Sorrento you can walk almost everywhere, and the Sorrento lift links the town to the port. For Pompeii, Herculaneum and Naples, take the Circumvesuviana train from the station, which runs frequently and costs little. For the Amalfi Coast, a guided day trip avoids driving the narrow cliff road, and local buses also run along it. For Capri, boats and hydrofoils leave from the Sorrento port, but timetables thin in winter and rough sea cancels sailings, so check the day before and leave slack at both ends. On the island, a funicular links Marina Grande with Capri town, and buses climb to Anacapri.
How many days
Three nights is the minimum to see Sorrento, one Capri day and one more day trip. Four to five nights lets you add Pompeii and the Amalfi Coast without a rush, and gives you a spare day for weather. If you have only two nights, choose one island or coast day and spend the rest in Sorrento.
Where the headline sights fit
Give Capri a full day. Cross early, take the chairlift up Monte Solaro in Anacapri if it is running and the sky is clear, visit Villa San Michele in the late morning, then take the bus back to Capri town for the Gardens of Augustus before the afternoon boat. A boat circuit of the island is a good alternative if the sea is calm, and the Blue Grotto is a bonus if it happens to be open. The Amalfi Coast trip takes a whole day as well, leaving in the morning and returning at dusk, so do not pair it with anything else. Pompeii is a half day on its own and works well on a day when the forecast is poor for the sea.
Rainy and rough-sea days
Keep the cooking class, the lemon grove tasting and the old town for the days when the sea or the road is unreliable. The lemon grove visit takes under an hour, so it slots into a gap, and the cooking class fills an afternoon. Sorrento itself is open all winter, and its Villa Comunale terrace and lanes are rewarding even in grey light.
A simple three-day plan
Day one, arrive and walk the old town and Marina Grande, with a limoncello tasting before dinner. Day two, Capri, with Anacapri, the villa and the gardens, checking the boats the night before. Day three, Pompeii in the morning by train and a cooking class in the evening. Add the Amalfi Coast on day four if you have it. Swap days freely depending on the forecast.
Practical tips
Pack layers and a waterproof jacket, because wind on the water and at the summit is cold. Wear shoes with grip, since stone paving is slippery in rain. Carry some cash for small purchases and entrance fees on Capri. Check opening times on the day, as winter hours change and many places close on Tuesdays. The Italian lunch hour can be long, and some restaurants close between lunch and dinner, so plan meals around it. Finally, accept that the sea decides: the best low-season trips are the ones with a spare day built in.
