Kythira

In the Meteora region, we stayed at the Hotel Doupiani and got a room with a balcony and fabulous view. It’s in Kastraki, the smaller of the 2 towns, and we loved it. Unfortunately, my husband got sick earlier(probably in the crowds at Delphi), and they couldn’t have been nicer. And what a fabulous buffet breakfast!
https://www.doupianihouse.gr

I was able to book my flights (using points) last weekend! Just in time too, because the point cost has gone up and availability of flights has gone down. So arrival and departure dates are set; everything else is able to be changed, but here's what I've settled on for the time being:

Days 1-3 Travel (arrive Athens 7am)
Days 4-7 Athens
Day 8 Pick up car, drive to Meteora
Day 9 Meteora (booked a room at Hotel Doupani)
Day 10 Drive to Delphi
Day 11 Delphi
Day 12 Drive to Nafplio
Days 13-16 Nafplio and day trips (Mycenae, Mystras)
Day 17 Ferry to Naxos
Days 18-21 Naxos
Day 22 Fly to Athens
Day 23 Return Home

I've kept the island at the end of the trip because it's worth it to me to spend that extra night in Athens in order to hopefully to have warmer weather while I'm in the Cyclades. I also switched from Paros to Naxos after seeing the price difference in accommodations between the two islands. I had a slight preference for Paros, but lodging options there are about twice the price of similar options in Naxos! I'm actually really excited about Naxos, now that I'm looking into it more.

Right now I'm debating between staying in Chora or near Agios Prokopios/Agia Anna. I'm leaning toward Agios Prokopios/Agia Anna with the thought that since the rest of the trip will involve lots of moving around and driving, I'd like to stay in a place with a balcony/patio and sea views, where it would be nice to hang out if I want to stay put and slow down for a couple of days. I don't mind taking a bus into town or around the island if I want to be more active.

For Naxos, consider the Hotel Grotta. Glorious views, an astonishingly generous and tasty breakfast buffet, and the kindest most helpful staff imaginable. Easy walk to downtown Chora.

Your plan sounds very good. I assume you'll ditch the car in Athens or Piraeus? I'm curious about your journey to Greece - is it really 3 days?

About accommodation on the islands (or anywhere in Greece), a lot of smaller places won't show their availability for spring until next year so that may distort the prices you're seeing. But there's nothing to stop you reviewing your Paros vs Naxos decision next year if you want to.

Enjoy yourself!

*** “However, another of my reasons for leaving the island until the end of the trip is that temperatures will likely get a bit warmer over the three weeks. Originally I was thinking late April-mid May, but now I'm considering using more points to go early-mid May - either way, I'll have warmer weather in Paros if I leave it to the end of the trip.” ***

That’s more than likely true, but not a given. I used to do my trips to Paros and Naxos in mid-May, but the weather is not dependable that time of year. Once while on Antiparos in a very chilly mid-May I was told by a local you should have been here in April, the weather was warm then this year. Another time, when getting off the ferry in Naxos, also in mid-May, I was met at the docks by the owner of the small hotel I was staying at. The first word out of his mouth when I got off the ferry was κρύος (krios) which is the Greek word for cold. He wasn’t kidding, but it did get warmer while I was there.

kja Hotel Grotta is a couple hundred more than other options I have bookmarked, but the breakfast and view look amazing, so I will keep it on the list.

dreamon The travel to Greece isn't 3 full days, but it does span over three days. I leave late at night on a redeye to Boston, then a long layover, and then an afternoon flight to Athens, landing about 7am on the third day. It's going to be brutal, but I'm limiting myself to staying within the Delta points I have so that my flight is "free." That's a compromise I'm willing to make in order to afford the hotels for a three week trip. Also, good point about some hotels not having availability yet. I've made refundable bookings for most places, but I've also bookmarked some interesting properties that don't yet show availability.

Heimdaall May was the latest flights I could afford while staying within my point balance (ideally I would have gone in late May or June), so I'll just cross my fingers and hope for the best with the weather! Seoul at the end of my trip in May this year was chillier than expected; luckily we had better weather at the beginning of the trip earlier in the month.

I reckon May is perfect in Greece as the weather is warm but not yet so hot and the wildflowers are wonderful (especially late April/early May). Of course it can vary a bit from year to year and depending on where you go.

For budget, outside of Athens we typically paid about 55-75eu a night for two (often with either breakfast or a kitchenette) and had fantastic accommodation.

Hello all. I've been working on my May 2026 Greece itinerary, and I have two questions I'd love for people to weigh in on.

1. I will be traveling from Nafplio to Naxos to Athens. Since I will be driving from Nafplio and I will need to return a car, it makes the most sense to take an afternoon flight from Athens to Naxos. (Car rental prices to/from the airport are much lower than pick up/drop up in Piraeus.) I'd like to have the Greek ferry experience, so ideally I'll return to Athens from Naxos via ferry. I'd overnight in Athens and then fly out at 1pm the next day to return home. I know that with potential strikes and weather it's not advised to plan ferries and flights the same day. Is taking an early ferry the day before enough of a buffer ot still too much of a risk?

2. I'm planning to visit Hydra, and I'm trying to weigh the pros and cons of doing it as a day trip vs staying overnight. I'd love to be there overnight, but that does mean one more hotel switch, and I'm not seeing many hotel options at the moment. I'm not sure if it's still too early to book or if more places require more than 1 night.

The overnight option would look like this:

• Athens (4) -> Meteora (2) -> Delphi (2)
• Delphi -> leave car in Ermioni, afternoon ferry to Hydra -> overnight Hydra
• Hydra -> late afternoon ferry to Ermioni -> drive to Nafplio
• Nafplio
• Mystras (Nafplio)
• Epidaurus & Mycenae (Nafplio)
• Nafplio to Athens -> Naxos (5)

The day trip option would look like this:

• Athens (4) -> Meteora (2) -> Delphi (2)
• Delphi -> Acrocorinth & Ancient Corinth -> Nafplio
• Nafplio
• Mystras (Nafplio)
• Hydra (Nafplio)
• Epidaurus & Mycenae (Nafplio)
• Nafplio to Athens -> Naxos (5)

You may take a afternoon flight from ATH to NAX or you may reach the airport in early evening, go by train or metro to Piraeus (about 1 hr jouney), sleep at Port Square Hotel (a few steps from the pier of Naxos bound ferries) and leave Piraeus the next morning at 7.25 by slow ferry Blue Star 1.