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Need help with Itinerary

My three friends and I are planning a trip to Greece/Italy (Amalfi Coast) from May 1 to May 17, 2019. Our dilemma is where to begin the trip. Tentatively, here is where we're at:

1) May 1st fly to Athens - spend 3 nights
2) Fly from Athens to Santorini- spend 4 nights
3) Fly from Santorini to Naples - spend 4 nights in Sorrento, followed by 4 nights in Positano
4)Fly home from either Naples or Rome

Maybe it's a bit early to be looking, but multi-city tickets from Chi- Athens, then Naples (or Rome) back to Chicago are quite expensive if the Chi-Athens leg is to be direct. I'm also having a hard time with the Santorini to Naples leg. It doesn't seem like there are a lot of options. Flying from Athens to Santorini is not a problem, but that Santorini to Naples piece is a problem.
Regardless of where we start I'm beginning to think that it makes sense to buy a round trip ticket Athens-Santorini on one of the European airlines such as Ryanair. I was hoping to not have more than 4 flights total, but.......

Has anyone done a similar itinerary? Any suggestions? Would it be better to flip flop the two countries? I appreciate any input. Thanks!

Posted by
585 posts

Look at Aegean Airlines or Alitalia for flights to Naples. You may find you still have to do a stopover in Athens......Don’t think it makes a difference which country you start in. I did once fly from Venice to Crete by Alitalia and had to change to Aegean for the flight to Crete.....

Posted by
2489 posts

First of all, consider whether you really want to visit Greece and the Amalfi coast in one trip. I spent 10 days on Amalfi coast two years and and 14 days in Greece this May/June.

But if you do, a few comments.

This May, we flew to Athens via Newark and then bought separate tickets on Aegean air. My adult children ended up on Ryan Air because of the time they arrived (8:45 pm Turkish Air flight and Ryan Air has a 11 pm flight) but Ryan Air was more than Aegean air so I would check Aegean Air first. I also like Aegean Air better. You also might be able to buy a ticket from Athens to Naples (or maybe from Santorini, although I doubt it).

I would consider going first to Santorini and then to Athens. Santorini is mostly about the view and that is easier to appreciate jet lagged than Athens. We spent 3 nights in Santorini and I thought that was about right. We hiked from Oia to Fira one day and explored the island the second.

We spent 2 nights in Sorrento--climbed Mt. Vesuvius one day and visited Pompay the second. Think about what you want to do with four nights. We could have spent 3 nights there I think. Sorrento is charming but not that big, but we had very little time there because we were busy day tripping.

Positano is nothing but steps and really seems to mostly be about shopping. We spent one day at the beach, which is rocky but you will be there pretty early for that. We stayed two nights in Positano and two nights in Amalfi town and if I had to do it over I would have stayed in Amalfi town the whole time and made a day trip to Positano. I liked Amafi town a lot better and you can reach other towns easier. Now the disadvantage of that is Amafi town is further from Naples. But regardless, you are going to need to be back in Naples the night before your flight.

We flew out of Naples to Frankfort and then back to the U.S.


Posted by
186 posts

I have done a similar trip:

Fly to Santorini first (via Athens, or however you can cheaply; rec. Aegean Air)
Then go to Athens when you are better rested and can walk/sight see
Fly to Rome or Naples from Athens (whichever is cheaper)
Directly take the train or bus to Sorrento (either is easy to do) and enjoy your time between there and Positano
Bus or train back to Naples or Rome (whichever is cheaper) and fly back home.