Best and Worst Greek Islands to Visit in the Fall

I had always heard that early fall was the best time to visit the Greek Islands. By mid-September, the majority of travelers have traveled home. The islands are still open and operating but with much fewer tourists. 

I visited nearly all the main Greek Islands at the end of September. The weather was perfect, and I have to say, all but one island was a pleasant surprise. 

Here is my complete ranking of the best and worst Greek Islands to visit in the fall: 

default

#1 Ios

Ios was not on my radar at all before traveling to Greece. In fact, I probably had never even heard of it. In the summer, the island is popular for young adults, specifically from Ireland, to come party. During that season, it is known to be loud & grungy with a heavy party scene. 

However, once university picks back up for students in the fall, the island is abandoned by all the 18-20-year-olds and becomes the biggest hidden gem of the Greek Islands. It’s one of the cheapest islands, with the best beaches and incredible Greek Cuisine. My only regret is not staying longer in this hidden paradise. 

In the shoulder season, many beach clubs offer free access to their beach chairs by purchasing any food or beverage. This works incredibly well when glasses of prosecco are an affordable 7 Euro. 

When you visit, I have three recommendations: 

• Eat dinner at Lord Byron. Make a reservation & order the feta cheese appetizer. The restaurant is funky, fun, and the food some of the best I had on any island. 
• Grab an after-dinner cocktail at Ios Blue Bar. If you like espresso martinis, you must try their take on the drink. 
• Catch the sunset at the Church of Panagia Gremniotissa. Best spot on the island and walkable from the main town. 

#2 Naxos

I had a friend who visited Greece multiple times and praised Naxos as one of her favorite islands. The moment I arrived, I knew it would also be one of mine. It has beautiful narrow alleyways filled with cobblestone and hidden bars you could wander lost until the early morning hours. They say when you’re perusing the alleys and find something you want to buy, get it then. There’s no promise you’ll ever find that shop again. 

One of the best parts about Naxos is its affordability. It is by far the cheapest island with some of the best food. On Mykonos, one is lucky to pay 18 Euros for a cocktail, while here in Naxos, you can sip Mai Tai after Mai Tai for 6 Euros. 

I really enjoyed how it felt lively but not overcrowded. Even in the fall, there were plenty of places to go out and enjoy the nightlife. It felt like the perfect amount of people. 

My recommendations in Naxos: 

• Grab cocktails at Diogenes Cafe. They offer 99 cocktails that are all 6 Euros each. This was with inflation pricing in 2023! 
• Climb Mount Zas (Zues). This is the highest point in the Cyclades and is heavily tied to Greek mythology. The hike is only 5km round-trip with just over 390m of elevation gain (1300ft.)
• Dinner at Flamingo for sunset. I don’t think there is a bad item on the menu. Members of our group got the Lamb Kleftiko, Swordfish, and pasta, all of which were delicious. 

#3 Thirasia

You’ve probably never heard of this island, and I hadn’t either. It was actually fate how we ended up here. During this trip, we used a sailboat to get from island to island, and bad weather blew us into this port for two nights. It’s located directly across the crater from Santorini, but it couldn’t be more different. If Santorini is on your list, Thirasia is a short 20-minute boat ride away and feels like a completely different world. 

During our entire day on Thirasia, we only ran into two other tourists, a German couple at a remote supermarket. Other than that, we were the only non-locals on the island the entire day. It was quite funny to stand on the rim and look over at Oia, knowing there were thousands of tourists there, while we sat alone at a restaurant with an incredible view just a few kilometers away. 

But the best of Thirasia is a little winery in the middle of nowhere. Our skipper had told us about it, and when we were walking in its direction, we wondered if we had somehow gone astray. But showing up, we found that it was just a hidden oasis. It’s called Mikra Thira Winery, and it is the best winery I have been to in the entire world. Our group of 8 stayed for over four hours, and we were the only ones there the entire time. Again, this is only a 20-minute boat ride from the most popular island in all of Greece. 

Thirasia is probably one of the last authentic Greek Islands in existence. When talking to locals, they said they wanted more tourists, which is why I’m including the island in this piece. I just hope it keeps its character and never becomes too popular. 

#4 Milos

It was incredibly hard for me to rank my favorite islands. If I’m being honest, Ios, Naxos, Thirasia, and Milos were all favorites in different ways. 

Milos is by far the most naturally stunning island and the one I looked the most forward to visiting. If I were to go back and sail Greece again, I would sail around Milos. It has the most incredible coastline, with the most insanely blue water I’ve ever seen. If you’re a nature lover, you can’t miss this place. 

I put Milos on my list about five years ago when I saw a picture on Instagram of Sarakinkos Beach. It is just one of the many incredible landscapes across the island. Milos has everything from sandy beaches to hundred-food rock cliffs and white-scree sand dunes. I was in awe the entire day we were there. 

When visiting Milos, you must go up to the Church of Panagia Korfiatissa for sunset. It is in the most scenic town on the island, perched high on a hill. When researching Milos, you may get recommendations to visit the IG-famous Utopia Cafe, which is close to the church. We went, and I will do you the favor to tell you it is not worth the stop or the hype. The cafe opens at 6:00 pm, and the line to get in starts around 5:00 pm. The view is pretty, but the church has a better one. The kicker is the service. It might have been because we were American, but it took 1 hour and 15 minutes for one round of cocktails, and the sun was already set by the time we got them. Many parties had been served and paid their bill by the time we got our first drinks. If you are European, it could be okay, but not recommended for Americans. I understand we aren’t always to easiest tourists, but I felt terrible for those in my group who were excited to try this place and left disappointed. 

#5 Paros

Paros is beautiful and wonderful if you go to the right places. We spent a day anchoring out in a bay and had the best day of our entire trip; however, I was a little let down on the shore in Naousa. In some ways, I loved the town. It was empty and we had entire streets to ourselves. On the other hand, it seemed as if most of the town had already shut down for the season. It’s located directly across from Naxos, which is why I was also sticker-shocked when cocktails on this island were double the price.

I can’t knock on Paros, though, because we spent most of our time here anchored out and living our best boat life. When I tell you the ocean here is incredible, I mean it, and that means I can’t give the island a fair rating. I’ve heard the best towns aren’t the port towns, and we only stopped in Naousa for a few hours. Next time I’m in Greece, I plan to spend more time here. 

#6 Santorini

I will admit I had some hesitations before traveling to Santorini. After all, it’s world-famous, and sometimes that can ruin a place. I had worried that the island would be crowded, expensive, and underwhelming. And although it was a bit expensive, I thoroughly enjoyed our stay here. It is a big enough island you can get away from the crowds, and Oia was more spectacular than any online photos show. There were a few important elements that I feel truly made our time there special: 

#1 We didn’t go to town during the day. Even in the slower fall season, there are typically 2-3 cruise ships in port every day. If I had one big recommendation for all the Greek Islands, it would be NEVER to see them by cruise ship. You are on each island during the busiest time, with tens of thousands of additional tourists. If there’s one thing that ruins these islands, it is cruise ships. Most cruises allow travelers to disembark between 9:00 am and 4:00 pm. I accidentally went to Oia once between these hours, and it was horrendous. Only go to Oia in the morning or evening. 

#2 Stay at a quiet, boutique resort. We stayed at the Amenilios Hotel, which was in Oia, roughly 500m from the start of the town's pedestrian walkways. Even during the day, when the streets were busy, our hotel was a quiet oasis. It had everything one would want: a pool, a bar, a restaurant, and beautiful views. It was never crowded, as the entire hotel only had 12 rooms. 

#3 Visit other parts of the island. It takes roughly 40 minutes to drive from one end of Santorini to the other, and the famous town of Oia is only one tiny portion. When avoiding town during the day, I recommend heading out to explore. There’s Vilchada Beach, which is a beautiful black sand beach on the south end of Santorini. You can get there via bus for under 4 USD each way. You can also make a day trip to the winery mentioned earlier over on Thirasia or visit one of the many other wineries in Santorini. If you like hiking, you cannot miss the rim hike from Oia to Fira. 

#7 Mykonos

Sigh. It really hurts me to say this, but after over a decade of travel and 40+ countries, Mykonos is the most disappointing place I’ve ever been to. It might’ve also been a mix of bad luck, but I really think every other Greek Island is worth visiting first.

A group of us went to grab cocktails, and we paid 125 Euros for five drinks. After being in Naxos with 6 Euro cocktails, this felt like a rip-off. In addition, the waiter demanded a 20 Euro tip on top of that. I asked him if we could leave it in cash, which he swiftly ignored and swiped the card.  We all left wide-eyed and a little confused. Again, this might have been bad luck, but it was called Scarpa Bar if you want to know a place to avoid. 

The cocktails could’ve been easily overlooked, but it just seemed the icing on the cake in Mykonos. Even in September, it was so incredibly crowded, and it was the last island we visited. After being in so many incredible places, Mykonos just seemed to miss the mark, and not have the sparkle the other islands had. 

I will leave and say this. Mykonos has an incredible gay community. If you are gay, I would recommend still visiting for this reason. I have never visited a place so open, welcoming, and encouraging to the gay community. It does have that, and it was wonderful to see.