As we enter sweater weather, most travel plans center on getting to a ski resort or back home for some form of winter-holiday-extravaganza. Point being, there aren’t many of us making travel plans the week before Thanksgiving for May, but there should be. Not only are you likely to get a great price on tickets, you also give yourself a sliver of sunlight to help you make it through frigid weather, dark days, and those obligatory family functions.
We asked Samantha and Ryan Looney of Our Travel Passport to turn us on to a great destination to book right now, and they couldn’t say enough good things about Grecian islands. The Looneys have visited more than 20 countries together, but they’ve been back to Greece multiple times. They’ve flown to islands, sailed to into their ports, ferried between them, and even chartered a boat to take them to a different island every night for a full week. But with 6,000 Greek land masses punctuating the Aegean and Ionian Seas, we needed them to get detailed. The vagabonding duo was happy to name their three favorites. Read on to see what they have to say.
RECOMMENDATION 1: Visit Milos
Samantha: Our favorite Greek Island is Milos. It’s definitely not as popular or touristy which is why we love it so much. But it’s becoming a lot more popular.
Ryan: Yeah with Instagram and everything, it’s getting more exposure.
Samantha: It has this stunning beach that’s made of volcanic ash. It’s called Sarakiniko and it seriously looks like you’re on the moon. If there was a beach on the moon that’s what it would look like.
Ryan: It feels out of this world. The island itself is not very big, so we rent ATVs and we go all around it. July and August are the high season, and we’ve been in both May and September. So on various vacations, we’ve had the entire beach to ourselves. Or there were like one or two other people there.
Samantha: There’s also a lot of beaches. As opposed to Santorini, which doesn’t really have as many beaches, so it’s harder to get that lay out, relax on the beach experience. On Milos, there’s a lot of really beautiful, different, unique beaches. We’re beach people, so we love going to beaches. That’s part of why we love it so much, too.
Ryan: There’s a lot of cliffs to jump off. And the food is really cheap.
Samantha: Yeah, and it’s just really delicious.
Ryan: You don’t get any cruise ships that go there, or at least not major ones. So, the tourist prices are still about $10 per plate.
Samantha: For like a giant plate with a lot of food.
Ryan: You can get a meal for like $3-$5.
Ryan: We’ve been to some exciting places — islands in the Caribbean, Bora Bora, French Polynesia — but when people ask us our favorite place, it’s these islands without a doubt. There are amazing for travelers because there’s so much to do. There’s so much to see. It’s affordable, and it —
Samantha: It has its own unique charm. It has a charm that you can’t get anywhere else. There’s nowhere else in the world with white houses and blue domes next to a cliff dive, so it’s just really unique and magical that way.
Ryan: After the third time in 16 months we said, “We’re going to need to build a house on one of these islands kinda like Mamma Mia! vibes.
Samantha: I feel that’s one of the things about Milos that we love is it really feels very like laid back and traditional and you could just live there forever. It feels like the island that Mamma Mia! was built on. It’s not, but it feels like that same vibe of you just hop on your ATV or your moped and you go to the bakery in the morning and then you go for a swim in the afternoon and you all sing and dance and live happily ever after!
Ryan: With that said, Milos doesn’t have any properties that make you feel pampered round the clock. I think they’re building one right now, but there aren’t any five-star resorts. There’s a lot of four-star boutique hotels that are great, but you’re going to have to do some exploring on your own if you’re going to experience the island. If you’re comfortable with that, it’s a great place. If not, then Santorini, Mykonos and other islands like that —
Samantha: They have more like luxury five-star experiences. If you really want like an authentic, explore on your own, feel what it’s like to live in Greece kinda experience, those smaller islands they really make that.
RECOMMENDATION 2: Visit Syros
Ryan: Syros is one of our new exciting favorite islands that we discovered on this trip. It is part of the Cyclades —
Samantha: So is Milos.
Ryan Looney: Milos is as well, but Milos has this white building built into the cliff kinda vibe, with the turquoise shutters. Syros has a lot more colorful looking, like yellow, and blue, and red. It almost, it feels like Italy, it feels like you’re pulling up to Positano or –
Samantha: Or even like the south of France. It feels much more European than Greek if that makes sense? Even though Greece is part of Europe.
Ryan: It’s more Mediterranean. Everyone thinks Greece is Mediterranean, but Syros is on the Agean, and it’s just full of cafes and a lot of old men sitting out at restaurants late into the night, and –
Samantha: And it has much more of that like stone color to it, than the typical white and blue that you see with Greece, so it’s just really beautiful in a different and less traditionally Greek way. And also, the water there is super crystal-clear blue, which in Milos is really clear blue too. I feel like all over Greece is that way, and it’s really just so beautiful.
Ryan: We were shocked at how uncrowded it was for such a gorgeous place. We’ve never seen it on Instagram. Actually, before we started this interview, I was like “Do we say Syros? I don’t wanna expose it to the whole world and let everyone know about it.” We were really shocked at how uncrowded it was. Because of that, it is really authentic. You can feel the lifestyle of the people. One side of the main town, the port of Syros, is just lined with ladders going into the bay. Every little cove has several ladders, and the locals on their way home from work put their backpacks on the side and change into their bathing suits and hop in for a nighttime –
Samantha: A quick fix.
Ryan: In the ocean and float on their back for a while in the salty Agean and then they’ll just kinda dry off and continue on their way. It was really cool to see that, and we’re like “I wish we did that.”
Samantha: It feels like a very calm island lifestyle. You wake up in the morning, and there are a few people out maybe at the coffee shop and the bakeries are all getting ready and opening and it smells like fresh bread and pastries and then people are hopping into the ocean before they go off to work. It’s such a cool, laidback lifestyle.
RECOMMENDATION 3: Visit Santorini
Ryan: Number three on our list is Santorini, and it sounds a little cliché because that is, to me, the most popular island in Greece, if not Europe [he’s right].
Samantha: But you can’t go to Greece and not go to Santorini.
Ryan: It’s absolutely iconic for all the right reasons. The island is a caldera from an old Jurassic volcano that’s actually still active, and you can go out to the center of it. On the outer ring of the caldera is where the towns sit on the cliff. That’s where you see the pictures of the white buildings on these cliffs and every hotel basically has an infinity pool going out to the center of the caldera with the ocean in the middle. Because of that, it attracts a lot of cruise ships, and it gets crowded and is a little bit more expensive.
Samantha: So my tip for that would be wake up at sunrise and go out and explore and get as much time to yourself as you can before those cruise ships show up around 9 or 10. Then you have all morning to enjoy the island to yourself and then relax at your hotel and enjoy the views during the day while everybody else is out exploring. Again, at night it dies down as people get back on the cruise ships. Then, you can enjoy the sunset and the sparkling city on the hill over the ocean at night. There really is nowhere else with sunsets quite like in Greece. The sunsets are truly stunning and they’re iconic for a reason. It is definitely worth it to watch the sunset every single night because it is breathtaking.
Ryan: I think something that makes these sunsets too cool in Santorini — and you’ll get a similar experience in other islands — is that the islands are so close in proximity to one another that you generally get a little silhouette of another island in front of the sunset and it makes for a really cool view and pictures as well. Santorini is cool. There’s a lot to do, but it’s one of those places where you can go and relax in a pool, explore the charming little town, and you can have a pretty Greek experience.
Those are our top three islands. I’d say the best way to see them is both from land and sea. You’ll get a whole different experience in Milos. Most of the beaches and caverns and volcanic formations and caves aren’t accessible from the land, so you need to go out on the ocean or go on a boat and see it from that angle. For example, in Santorini to see the buildings up in the cliff is different from being in the buildings up on the cliff.
Samantha: Yeah, in Milos I definitely recommend doing a tour of these old pirate coves. It is really cool and really unique. You can’t get there any way other than by boat. In Santorini, we would suggest doing a sunset cruise tour. It picks you up at 3:00 pm, so it’s not really a sunset. Then, it takes you all around the caldera and stops right in front of where the sun sets in Amoudi Bay. You just watch the sunset from the ocean, and it’s just a whole different experience. It’s so beautiful, looking right into the water and watching the sunset right into the horizon that way.
BONUS ADVICE: Start Planning Now
Ryan: You can’t go year-round.
Samantha: In the winter time, everything shuts down. Even the people who live on the island will go to the mainland for winter time because the weather’s not great. When I say winter, I’m talking about probably November through March.
Ryan: The season for Santorini, for example, is probably the longest of all the islands, and that’s like April through October. But in April and October, you’re going to get a little more wind and the water’s going to be pretty chilly. In the Aegean Sea, the water doesn’t ever get that warm. July and August will be comfortable, but in June and September and May, we call it refreshing on a hot day.
Samantha: No it’s pretty chilly.
Ryan: In Milos, it’s even shorter. It’s basically May through September because I think they deal with more waves and storms during the low season.
Samantha: But when you go in the low season (like if you go like April, May, and then October, September), it’s cheaper. The hotel prices are different for the low season versus the middle of summer high season. If you are looking for a cheaper Greek experience, then definitely go in the low season. It’s worth it.
Ryan: The driver in Milos said that it’s great in the winter, but she loves the summer as well. So if you stayed local, maybe it still stays nice, but you’re not going to spend as much time at the beach.
Samantha: It’s also probably harder to get flights and ferries to the island during the winter time because even in the off-season there’s only one flight a day to some of these islands or two flights a week or something like that from these islands in the low season. Then in the high season, there might be three or four a day or two or three a day, so that might be a challenge if you’re trying to go in the winter.
Samantha: Now is the time to start planning your trip for the next high season.
Ryan: I think the first time we went, we found really cheap flights, in December. Yeah, we bought them in December, and we purchased them for May. We got flights for like $350 to Athens round-trip from LA, and then to the island, it’s like around $50, or you can take the ferries.