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A few questions about the Amalfi Coast (in May)

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Good morning

Tickets are bought, let the planning begin.

I am spending nine nights on the Amalfi Coast in mid-May. I have three guidebooks (two centered around hiking, and one (gasp) is Rick Steves. Don't judge! This is my first time to the Amalfi Coast and he always has a decent high level overview of things to see and do for first timers. The other two are the Cicerone hiking guide and the Sunflower Landscapes series (hiking). I'll probably get one more guidebook before I set out. Or not, maybe the internet can fill in the gaps.

I am tentatively thinking of the first three nights on Capri (land at 1230 PM, probably arrive at my hotel around 4 PM) and have to find a hotel there.

Q: Should I look to Capri or Anacapri for my three nights? Where am I most likely to have things to do or see in the evenings - even if it's just people watching at a cafe with a glass of wine? I am hoping to do at least one hike while I am on Capri.

Q: Blue grotto: must do/do not miss it, or, don't lose sleep over it?

The next five nights will be Positano, most likely.

Q: Although I have hiking guidebooks, spending one day with a local guide for hiking would be useful. At least until I get the lay of the land. Bonus if this person collects you at your hotel. Any recos?

Q: So far I'm thinking "no car". Even a tiny 500. Will I regret this? The main reason it would be nice is for exploring (of course) and finding the trail heads. I am hoping to do at least two hikes while I am in Positano. The Pathway of the Gods would be one of them. I imagine a full day will be taken with Pompeii and Herculaneum, from Positano, and a second day with Paestum (which I'll combine with other sightseeing). That only leave two other days, really, to do any kind of hiking.

Q: With no car, I am likely to hire a driver for one full day of sightseeing. If you had a driver for a full day, how would you spend that particular day? Can I do Pompeii etc easily enough by public transport and thus save the driver for something else directly along the coast?

My flight home from Naples leaves at 130 PM. What I think this means is that I could be anywhere along the Amalfi Coast and be just fine with making it to the airport on time. Regardless of where I am, I will have a driver take me to the airport. No public transportation.

Q: I'm not convinced either way on spending my last night in Naples. Since my flight is in the afternoon, I could even spend the last night in Sorrento (and, if I got there early enough, visit Pompeii on that day, the day before I leave, and not even attempt it from Positano, although it would mean little time in Sorrento itself). Would you definitely spend 24 hours in Naples (knowing that you will go back if you miss it this time) or would you spend your last full day and night in Sorrento? I'm starting to lean to Sorrento and make this entirely a non-city trip.

Thank you!

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