Upcoming Three Week Trip

Four nights is perfect for Athens.

3 days in Athens isn't too long. It's not just a city with the Acropolis and a few other archaeological sites.
Even 6 days wouldn't be too long.

Regarding live music, there are a few restaurants where you can listen to live music in the Psyrri district or in Plaka. But real traditional Greek music, for example Rebetiko (Greek blues) like this:

https://www.youtube.com/watch?v=Me0YYa1WxQs

is played in other places such as "Ο Αγγελος" (The angel). in the Echarchia neighborhood.

https://maps.app.goo.gl/xXQKsEVyhbo5DuWeA

Or the Marathonitis tavern in the Pangrati neighborhood.

https://maps.app.goo.gl/GJq7JWpjKaUTUm7u8

Four nights is not too long in Athens. For a fancy dinner, go to Botrini’s. We had a reservation for there in January, before our planned trip got canceled, but will certainly go there on the next trip. For a very nice, although not overly fancy, dine at Mani Mani. If you ride the Athens Metro. be especially alert for pickpockets and thieves.

On the Peloponnese, be certain to stop at Nemea, for its ancient stadium, other fascinating ruins, and fine museum. Another daytrip from Nafplio, besides Epidaurus, is Mycenae. Farther south, the walled village of Monemvasia is worth at least a night’s stay. It was magical. The Mani could be more than just “somewhat” relaxing… plan on at least three nights.

You’ll want at least five nights on Crete. We had three weeks just on Crete in 2019, renting a car and touring east and south, besides the two cities you mention. In Iraklio, have dinner at Ippokampus. In Hania, we had dinner at Semiramus, in the old Jewish quarter, accompanied by music. You can also wander at the east end of the harbor, and pick from among the many restaurants for the one most appealing.

I've been to the Peloponnese twice and have a third trip scheduled for this April as there is so much to see, do and experience there.

You could spend weeks there and still not see it all.

Filled with history, villages, mountains, coastlines, beaches, great food and welcoming locals and lots more.

You have three locations mentioned for your three weeks.

Figure a minimum of 2 days in Athens with 3 better and nothing wrong with 4 either. There's more to Athens than most people think.

It's possible you could split the Peloponnese with Naxos and Crete but I think that won't give you much time for the Peloponnese and Crete as both are large areas and could take weeks each to fully experience.

Naxos is very nice but the last time I was there was way back in 2013 when it still wasn't "discovered" by tourists. Not sure how things are there now tourist-wise. Still worth looking into especially when you are there in April as it's way before the main tourist season.

If you plan properly and can find good schedules to get from one location to another (which can eat up time) it's do-able

If I had to chose I would cut either the Peloponnese or Crete and spend as much time as possible on one plus do Naxos.

However, do what's best for you.

If interested you can read my trip report of my last trip to the Peloponnese with photos. It may help make decisions on your plans for your trip.

https://www.tripadvisor.com/ShowTopic-g189483-i1277-k14200587-Peloponnese_Trip_Report_Sept_25_Oct_12-Peloponnese.html

Are flights booked?
It's easy for me to say because I haven't been to Naxos, but you could so easily fill all of your time in the Peloponnese. If I was going to do one island, it would be Crete.
My trip was 11 days in Nafplio (visited Epidaurus and Mycene, Nemea en route), Kardamyli (stopped at Mystras, did some hiking), and Stemnitsa (hiking). We topped at Messene en route, which was amazing. The Bradt Guide is great.

Is this trip in 2024? If so, you’re leaving in 2 weeks, and you must finalize your decisions & book hotels ASAP.

I assume you have already booked your flight from Crete to US. Is it all on one ticket, with a stopover in Athens? If it’s 2 tickets — one from Crete to Athens, another from Athens to US — most Greek travelers recommend returning to Athens the day before, in case of flight delays from the island. That would cut your time in Crete to 4 nights. So I think you should skip Naxos. You could easily spend your whole 3 weeks on Crete — so much to see & do. Search this forum for ideas — there are lots of Crete travelers.

Thank you all for your feedback. It was immensely helpful!