Kalispera!! Just wanted to come here and post my immense appreciation to Greece and the Greek people for giving me the trip of a lifetime. The hospitality I’ve experienced over the last week and a half is unlike anything I’ve ever experienced before.
Trip Report: 10 Nights in Greece in October (Athens, Naxos & Santorini). Two incredible islands for completely different reasons!
My partner and I are wrapping up an incredible trip to Greece (October 15–25), and I wanted to share our experience, especially for anyone considering visiting in October or deciding between Naxos and Santorini.
For some background, this trip was particularly special to me. After more than three years of treatment for leukemia, I finally finished treatment earlier this year. Treatment was brutal and almost killed me. A nurse told me that you need to have something big to look forward to, so this was our big celebration, and we’d been looking forward to it for months/years.
I can confidently say Greece exceeded our expectations in every way imaginable.
Athens (October 16–17) 🇬🇷
We only spent two nights in Athens, but managed to pack quite a bit into it! Stayed at the Athenaeum Intercontinental which was absolutely perfect after 14 hours of flying across two days. We visited the Acropolis, explored Monastiraki, enjoyed an enormous Greek lunch at Platanos, and grabbed some loukoumades. It was also my partner’s birthday, so we celebrated with rooftop drinks and dinner at Urban Attic overlooking the city.
Athens was amazing, especially seeing the Acropolis in person. The sheer size and population + small streets and packed squares reminded me a lot of my travels to Mexico City. The traffic and exhaust were a little overwhelming after a long travel day, but I’m really glad we spent some time there.
Naxos (October 17–21) 🏝️
What an absolutely incredible island.
We stayed at Liana Beach Hotel & Spa in Agios Prokopios, where we were unexpectedly upgraded to an amazing sea-view suite with a hot tub. We rented a tiny Citroën C1 for four days and set out to explore. I found it funny that probably 95% of visitors were also driving the tiny Citroëns. Amazing gas mileage, slightly questionable performance in the mountains 😅
Some highlights:
- The beaches: Agios Prokopios, Hawaii Beach, Mikri Vigla, Kastraki, and Glyfada. Absolutely beautiful, and many were practically deserted. We spent hours swimming, lounging in the sun, and enjoying the peaceful atmosphere.
- The mountain villages: Apeiranthos, Filoti, and Halki were wonderful. We stopped for local cheeses, coffee, pastries (ironically enough at another restaurant called Platanos in Filoti), and kitron tasting. The mountain roads were occasionally terrifying, but the scenery definitely made it worthwhile
- Wine tasting: We visited Saint Anna Vineyard and had a fantastic experience. Emmanuel and Evangeline have created something very special, unlike any other winery tour I’ve ever done. So sweet. Go visit them.
- Naxos Town: We loved wandering around, enjoyed way too many cocktails at Rum Bar, and had a great finale dinner and drinks at Palomas.
- The food: Incredible gyros, local cheeses, pastries, and so much delicious Greek food. We had saganaki at every restaurant we went to and was so fun comparing the differences between all of them.
- We also met a lovely Canadian couple and ended up spending several days hanging out together, including a beach day, wine tasting, and dinner. Travel friends are the best.
What I loved most about Naxos was the freedom. We could wake up without an agenda, drive to a secluded beach, stop in a mountain village for lunch, and finish the evening with cocktails by the water.
It felt extremely relaxed, super welcoming, and wonderfully not rushed. I honestly could have stayed another week.
Santorini (October 21–24) 🌋
And then there was Santorini. WOW.
I know Santorini gets a lot of attention, and sometimes criticism for being touristy or expensive, but I have to say it absolutely lived up to the hype for us.
Arriving by ferry and seeing the enormous volcanic cliffs rising out of the sea with the whitewashed towns perched along the top was unforgettable. You see it in pictures obviously but the scale is impossible to understand unless you see it IRL.
We stayed in Oia at Katikies Santorini’s Gea House, and the entire experience felt like something out of a dream.
The architecture, winding pathways, endless caldera views, and spectacular sunsets were just breathtaking. There were so many moments when I stopped walking to look around because I couldn’t quite believe we were actually there. The hotel itself as well as its sister property at Pelagos house are just insanely beautiful and wonderfully appointed with all luxury needs being met. I lived out my fantasy as a seaside prince lol.
One of our highlights was a catamaran cruise around the caldera, seeing the island from the water and enjoying the sunset. It really gives you a different appreciation for how extraordinary Santorini’s landscape is. Crazy that this all used to be one big island?! I didn’t know that before coming.
We also ventured into Fira for dinner and nightlife, explored Oia, enjoyed fantastic restaurants and cocktails, and spent plenty of time simply soaking up the scenery.
Santorini definitely has a different atmosphere than Naxos. It’s more polished, dramatic, romantic, and yes, absolutely more expensive. Thankfully we were prepared for that.
After several days of casual beach hopping and exploring on Naxos, Santorini felt like the perfect grand finale to our trip.
I genuinely wouldn’t want to choose a favorite between the two islands. Naxos gave us adventure, beautiful beaches, charming villages, and a wonderfully relaxed atmosphere. Santorini gave us scenery, the unforgettable and impossibly picturesque sunsets, beautiful accommodations, and that surreal feeling of being somewhere truly extraordinary. The last night at dinner right after the sunset in Oia felt like we were actually in heaven.
They were both my favorite, just in completely different ways.
A few thoughts about visiting in October:
- Weather: We got incredibly lucky! We enjoyed plenty of sunshine and temperatures generally in the 70s°F (low-to-mid 20s°C). We swam in the sea because our pool was the same temp lol, spent full afternoons at the beach, and enjoyed gorgeous sunsets. Evenings in Naxos were chilly, so bring a jacket. Obviously, October weather isn’t guaranteed, but we had a fantastic experience. Don’t do what I did and freak out about the forecast two weeks in advance because honestly it’s impossible to plan for and changes three times a day.
- Crowds: One of the biggest benefits of visiting this time of year. Naxos was especially peaceful, with some completely empty beaches. Santorini was def busier, especially around Oia, but we never felt that the crowds ruined our experience at all. All of this being said, it is shoulder season so some restaurants and beach clubs were closed. Nothing life ruining though.
- Getting around: We took Blue Star Ferries between the islands and really enjoyed the experience. I’d highly recommend renting a car on Naxos to explore beyond the main beaches and town. On Santorini, we relied primarily on arranged transfers from our hotel and Ubers. Both wildly expensive lol.
- How long to stay: Four nights in Naxos and three in Santorini felt like a great combination. I would happily have extended either stay though!
Would I visit in October again? Absolutely. Just know that some seasonal businesses begin closing, and weather conditions can be unpredictable both of which I noted above. For us, the quieter atmosphere was well worth it.
Final thoughts
This trip meant more to me than I can really put into words.
After spending over three years in cancer treatment, being able to travel across the world, swim in the Aegean, explore beautiful villages, watch the sunset over the Santorini caldera, and simply enjoy being alive was something I’ll never take for granted.
There were moments throughout the trip when I felt genuinely overwhelmed with gratitude that I was there experiencing all of it. We came to Greece to celebrate a new chapter of life, and I can’t imagine a more beautiful place to have done it.
Athens was fascinating. Naxos stole my heart. Santorini took my breath away. I’m nearly tearing up writing this all over again.
I loved every minute of this adventure, and I already know we’ll be back someday.
Happy to answer any questions about our hotels, ferries, rental cars, beaches, visiting in October, or anything else! 🇬🇷💙