September Itinerary Check – Lisbon, Seville, Santorini, and Athens

Is it doable? Yes. Would I recommend doing it? No. But it is your trip.

A couple of things to consider:
What’s your Plan B if the flight is cancelled on that Wednesday? Since Santorini is your most expensive location, you don’t want to lose a day there. Could you do your itinerary in reverse, instead, to mitigate the risk? Greece, then Spain, then Portugal.

Then the other thing is to look at the amount of time you will be devoting to transportation, including waiting time, taxis, etc. i move often, but I won’t go over an average of 1.5 hours/day for the trip total. Even a “quick flight” is hours when all of the waits, etc. are counted.

For Sevilla, I stayed at the Casa del Poeta Hotel last time for a change, and it’s beautiful. They have a gorgeous center courtyard and have a 30-minute classical guitar in the evenings to relax with a glass of wine, etc. and enjoy the Spanish ambiance.

A 2-night stay in Naxos means you’ll only have one full day there, which is barely more than a layover between two flights or trains. You’re better off extending your stay in Santorini or Athens and skipping Naxos, as it requires at least 4 nights to even scratch the surface.

Hopping all over Europe in two weeks wouldn’t be my choice either, with such brief stays in far flung countries that each deserve much more, but as noted, it’s your trip. As you like wine tourism the obvious choice for Seville would be a daytrip to Jerez for sherry bodegas as that’s what’s special and unique to Andalusia.

I agree with the majority of posters.... stick to one country. Greece. Seeing two cultures/countries in such a short amount of time gives you not much more than a taste with a lot of moving around. Many years ago we did 10 days of Greece and then stopped in France on the way back to the States for a week. It was our worst trip ( and we have made dozens) to Europe. Greece was magical but by the time we got to France we were tired and did not appreciate its beauty. Everything became a blur.

During our visit to Santorini we chose to stay at Lithies Traditional Homes which is located in Firostefani. We found that to be the perfect location for us, and their price point is well under your $600/night budget. I can recommend a terrific wine tasting accompanied with small plates at Venetsanos Winery, which overlooks the caldera. As mentioned, two nights in Naxos does not even begin to scratch the surface. What do you consider "the major sites" in Athens? Two nights there only gives you one full day, so realistically, is that enough time to enjoy those? Don't underestimate the time it will take for that. Would you be open to spending another night in Santorini, and perhaps doing a private tour of the island, and then adding a 3rd night to Athens?

I agree with the other posters that you are doing too much moving around. You will be spending so much time traveling from place to place, checking in and out of hotels, etc.

I love Naxos but 2 nights is not worth all the moving around. I would either eliminate Naxos and add a night to Athens and/or Santorini, and then I would add the other night to Lisbon at the beginning of your trip. So fly to Lisbon one day earlier. There is a lot to see and do in Lisbon. This will give you the opportunity to visit Sintra for a day, if interested. And to get over jetlag.

OR eliminate Athens altogether since you don't seem that interested in Athens. Then add one of those nights to Naxos so you have at least 3 nights in Naxos. You will have to spend your last night near the Athens airport.

If you do keep Naxos in your itinerary, I think it is the most logical island to visit after Santorini. You can take the Blue Star Ferry, and the ride is 2 hours.

For Santorini, we enjoyed staying in Firostefani at the Blue Dolphin Suites. We had a lovely room with a balcony overlooking the caldera. Our room cost in May 2022 was $270 per night.

Thank you so much for taking the time to read through our itinerary and share such thoughtful feedback. We truly appreciate the detail and honesty in your responses.

We’ve taken your suggestions to heart and have revised our plans accordingly. In particular, we’ve simplified the itinerary, reduced the number of stops, and adjusted our island choices and timing to allow for a more relaxed pace and less time in transit.

We are also very grateful for the specific recommendations for accommodations and wine experiences, especially in Santorini and Seville. Those insights are incredibly helpful as we continue refining bookings. We would welcome any other wine experience suggestions in Lisbon, Sevilla or Santorini.

Thank you again for generously sharing your experience and perspective!