Getting to Anafi on a sunny early June morning was just monumental for my love to this place. A same-day work trip from Santorini found me on Chora’s main square and its jaw dropping view to the south of the Aegean Sea. Most importantly, it introduced me to the warm-hearted and lightly-spoken people of Anafi.
Drawn from its political past during the 1920s to 1940s when Anafi served as a remote place of internal exile for political dissidents, communists and trade unionists, the island still retains a leftist character and one that shouts freedom. Evolving from a 1970s hippie and naturist haven on Roukounas Beach, the island naturally fostered an inclusive, laid-back atmosphere over the decades – especially after the pandemic when it started becoming a popular gay, alternative scene. Today, it attracts a very international crowd that can get really busy during August.
Back to my first day here, I still remember meeting the mayor Iakovos Roussos who welcomed me to this haven. Dressed in a causal t-shirt and work overalls, I found him running errands around his pantry shop whilst offering me a coffee from the coffee-place next door. “The next time you come, plan a few more hours and we’ll go for fish“. Luckily, I returned only a few weeks later, but still haven’t gotten around having that fish!
What struck me most was that Anafi doesn’t try to impress anyone. There are no designer boutiques, no beach clubs competing over DJs, no rush to become the next Cycladic hotspot. Instead, life revolves around long conversations, lazy swims, spontaneous dinners and evenings that rarely go according to plan. However, given the few options around this tiny island, everyone follows the same schedule more or less. And food, unsurprisingly, becomes part of that rhythm.
Just outside Chora, Margarita combines one of Anafi’s finest sunset views with a kitchen that celebrates the wider Aegean. Much of the menu revolves around exceptional raw ingredients sourced from neighbouring islands, transformed into beautifully understated dishes that allow every ingredient to speak for itself. It’s the sort of place where dinner naturally stretches into a second bottle of wine. A few steps further down towards Kleisidi beach, Pig & the Mule has become the island’s unofficial living room. Whether you’re stopping for excellent coffee, a laid-back drink or one of the best hummus plates you’ll find anywhere in the Cyclades, it effortlessly captures Anafi’s relaxed pace. The accompanying small plates make it dangerously easy to lose an entire afternoon. A few people work remotely as it has one of the best WiFi spots in the island; luckily these are just a few.
At Astrahan, founded by the island’s own winemaker, Greek flavours are approached with remarkable delicacy. Fresh local ingredients meet international techniques, while impeccably prepared raw fish often steals the show. Pair everything with one of the estate’s wines and you’ll quickly understand why so many visitors end up returning more than once during their stay. In fact, Stefanos was the head chef at Margarita for a few years before venturing on his own. So he definitely knows a thing or two about great food.
For something far livelier and more traditional, Armenaki delivers exactly the kind of Greek island evening you secretly hope to stumble upon. Tables fill with generous seafood, excellent pasta dishes and local wine before the musicians arrive. As the night unfolds, traditional folk songs turn into spontaneous dancing, strangers become table companions and leaving before midnight suddenly feels impossible. This is the classic Greek folk live music scene, dubbed with tasty dishes all around.
If you’re seeking for more adventure, it’s wise to budget a hike up to Monolithos. Getting to the monastery at the foot of the hill is the easy bit – going uphill on foot on a 1h15min trail is the challenge. Most visitors tend to start a couple of hours before sunset as the views from the Church of Theotokos Kalamiotissa are one of a kind. At 480m above sea level, everything becomes magical, especially as the sunset hues paint a beautiful picture.
And then there’s Madres bar. There are no opening hours. No reservations. No Instagram announcements (for the most part of it). Instead, everyone simply looks towards the building. If the single light above the roof is on, word quietly spreads through Chora. Sometime after 3am, groups slowly make their way downhill, music begins, drinks start flowing and another unforgettable Anafi night takes shape. Some mornings end there just as the first light appears over the Aegean.
When it comes to where to stay, nothing captures the island’s understated luxury quite like Ypseli. Spacious suites, genuinely thoughtful service and architecture that melts into the landscape create the closest thing Anafi has to a boutique resort, without ever compromising the island’s wonderfully laid-back personality. It remains peaceful, intimate and refreshingly unpretentious – exactly as Anafi itself should be.
Perhaps that’s ultimately what makes Anafi so addictive. It isn’t trying to compete with Santorini or Mykonos. It doesn’t need to. Anafi simply remains itself: a little freer, a little slower and wonderfully unconcerned with what everyone else is doing. And maybe that’s exactly why so many who discover it quietly keep coming back.
See
- Chora – the island’s main settlement, sitting atop the hill with a rugged yet cute backdrop of whitewashed buildings and alleys.
- Monolith – one of the largest in Europe and the tallest one; takes a good hour’s hike to reach the top. The view during sunset (or sunrise) is mesmerising. Make sure you wear comfortable shoes walking up.
- Port – very small port which gets busy as the main ferry arrives early in the am (most of the day).
Swim
- Klisidi beach – easiest to get to and a few minutes from the port. Makes a great combo with coffee, drinks and nibbles at Pig & the Mule and/or Margarita.
- Katsouni beach – the best beach if you’re into relatively small coves. You can walk to it on a 10min trail after Klisidi beach.
- Roukounas beach – long sandy stretch with a distinctive nudist part too. Loupa bar at the back of it is great for a quick focaccia or drinks.
- Agioi Anargyroi beach – just below the Monolith with great views to it.
Stay
- Ypseli Anafi’s Hive – the best accommodation on the island with undeniably the best breakfast in town inspired by the three adjacent islands around Anafi.
Eat/Drink
- Margarita – the most famous restaurant of the island with some great views to the Aegean Sea, especially after 7pm. Menu changes daily.
- Astrahan – arguably the most sophisticated eatery of the island, located in the whitewashed alleys of Chora featuring a veranda with a view. Must have their chickpea with aubergine!
- Armenaki – traditional taverna setting with live Greek folk music almost every night. Try their fish and whatever else is fresh.
- The Mule & The Pig – the most laid back place around where people tend to stick around for a few hours once there. Makes a perfect combo with Kleisidi beach (or Katsouni for the more brave ones).
- Monolithos – groovy bar with great cocktails and the place where each night’s drinks start.
- Mill – head to Milos after 2am for a quick drink or more… this afterhours bar is still run by the same couple in the last few decades.
- Madres bar – visit after 3am and make sure you’re prepared for anything. The sunrise after 5am is sensational!
