Syros is the island that surprises almost everyone who visits it for the first time. As the administrative capital of the Cyclades and home to the magnificent neoclassical city of Ermoupoli, it carries a weight of history, culture and sophistication that sets it apart from every other island in the archipelago. The grand marble streets, the opera house, the Catholic hilltop of Ano Syros and the buzzing harbour make Ermoupoli feel like a proper city rather than a holiday destination. But beneath that urbane exterior, Syros also hides one of the most quietly exciting small scale wine cultures in the entire Cyclades.
The island has not always been associated with fine wine, and that is exactly what makes discovering it here so rewarding. The northern region of Apano Meria is considered one of the oldest vine growing areas in Europe, where generations of Syrians have terrace farmed the steep, rocky hillsides to cultivate vines that express something completely their own. The rare local variety known as Serifiotiko, alongside Assyrtiko, Monemvasia, Mandilaria and Black Aidani, all grow here under the same fierce Aegean winds and bright volcanic sun that have shaped Cycladic wine for thousands of years. The wineries on Syros are small, passionate and deeply personal. Coming here to explore wine is not about ticking boxes on a famous tasting circuit. It is about discovering something genuine, intimate and utterly of this extraordinary place. These are the five best experiences waiting for you.
Table of Contents
1. Chatzakis Winery
Overall Information
Chatzakis Winery is the most well known and most celebrated wine producer on Syros, and the story behind it is exactly the kind of story that makes small independent winemaking so compelling. Oenologist Nikos Chatzakis spent years working in larger commercial wineries before following his heart back to Syros and establishing his own boutique domaine in 2011. His goal was clear from the very beginning: to produce wines that honestly reflect the place they come from, with a genuine respect for nature and the authentic character of each variety. The winery is located in the San Michalis village within the Apano Meria region, one of the oldest vine growing territories in Europe, at the top of a sunlit hill framed by the Catholic chapel of Saint Benedict. From this vantage point, the views across the Cyclades are simply extraordinary. The range of wines Nikos produces is exceptionally interesting, spanning a crisp mineral Assyrtiko labelled San ta Maratha, the fruity and approachable Fabrica White made from Monemvasia and Kountoura, a fresh Fabrica Red made from Mandilaria, a Black Aidani rosé and a genuinely special limited production varietal wine from the rare local Serifiotiko grape, called The Sheriff Fatman. Each wine is bottled largely by hand, and the care invested in every label is evident in every sip.
Location
Chatzakis Winery is located in San Michalis village in the Apano Meria area, the northern part of Syros, 841 00, Greece. The winery sits at the top of a hill surrounded by the typical Aegean landscape of sunbaked stone, wild figs and scrubland, with only the sound of the wind and the birds for company. Looking west from the hilltop you can see the islands of Gyaros, Kea and Kythnos shimmering across the water. Looking east, the houses of Andros, Tinos and Mykonos are visible on a clear day. There is also a second point of access through the Langadas area of Talanta, just south of the road connecting Galissas to Ermoupoli, which is where the winery stores and offices are based.
How to Get There
From Ermoupoli, the capital of Syros, driving to Apano Meria takes approximately thirty minutes along the northern road that winds up through the interior of the island. Hire cars and scooters are available from several rental companies in Ermoupoli, and this is by far the most practical way to reach the winery. The road passes through some of the most dramatic and quietly beautiful scenery on the island, including the cluster of traditional villages that make up the Apano Meria region. Several guided wine trail tours departing from Ermoupoli include Chatzakis Winery as part of their itinerary, and these are an excellent option if you would rather not drive yourself. Public buses run to the northern villages from Ermoupoli during the summer season, though the frequency is limited and a taxi from the main square is a more reliable and comfortable option for a dedicated winery visit.
Services and Experiences
Chatzakis Winery offers guided wine tasting experiences in a setting that is completely unlike anything you will find at a commercial operation. Visits are by appointment, and the team warmly welcomes small groups for a tour of the vineyard and a tasting of five wines paired with a small selection of local cheese bites that genuinely enhance each pour. The tasting takes place in the open air, surrounded by vines and with those extraordinary panoramic views of the Cycladic islands spread out in every direction. The focus throughout is on education as much as pleasure. Nikos speaks about his approach to each wine with the quiet confidence of someone who has thought deeply about every decision made in the vineyard and the cellar. The bottles produced here are also available at wine shops across Syros and selected outlets in Athens, but tasting them in this setting, on the hillside where they were made, is a genuinely different and more moving experience. Booking well in advance during the summer months is essential, as the intimate capacity means availability is genuinely limited.
2. OuSyra Winery
Overall Information
OuSyra Winery is one of the most charming and distinctive wine stories in the entire Cyclades, and not just because of the wines themselves. The winery was founded by Scotsman Edward Maitland-Makgill-Crichton, who came to Syros, fell in love with both the island and a Greek woman named Eileen, and decided to make it his home and his life’s work. The name OuSyra comes from Ousyra, the name given to the island of Syros by its first inhabitants, the Phoenicians, meaning happiness. That sense of joy and personal commitment runs through everything at this small, family run estate in Chroussa on the southern part of the island. Edward and Eileen farm their ungrafted Serifiotiko vineyard with the kind of hands on attention that only a small family operation can provide. The winery produces a range of terroir driven wines from rare indigenous Cycladic varieties including Serifiotiko and Assyrtiko, along with a beautiful limited production rosé called Les Contours D’OuSyra that is available exclusively at the winery in very small quantities. This is exactly the kind of intimate, personal wine story that makes exploring the smaller Cycladic islands so deeply rewarding.
Location
OuSyra Winery is located in Chroussa, a small traditional village on the southern part of Syros, 841 00, Greece. Chroussa is a quiet and largely undiscovered corner of the island, far from the tourist bustle of Ermoupoli and surrounded by the natural landscape of rocky hillsides and terraced vineyards that characterise the more rural parts of Syros. The ungrafted Serifiotiko vineyard, which forms the centrepiece of the tasting experience, is one of the most genuinely special vineyard sites you can stand in anywhere in the Cyclades.
How to Get There
From Ermoupoli, the drive to Chroussa takes approximately twenty minutes by hire car or scooter along the southern road out of the city. OuSyra Winery is a family run operation and visits are strictly by advance booking only. The team is clear that advance booking is essential to avoid disappointment. The simplest way to make a reservation is through the winery’s website at ousyrawinery.com or by contacting them directly on their phone number, which is listed there. Once your booking is confirmed, the team will provide precise directions to the property. Given that Chroussa is a small village and not always clearly signposted on all navigation systems, having direct contact with the winery before you set out will save you any confusion and ensure your arrival goes smoothly.
Services and Experiences
OuSyra Winery offers a tasting experience that includes a tour of the winery itself and a tasting amongst the vines at the ungrafted Serifiotiko vineyard, which is one of the most memorable and atmospheric settings available for a wine tasting anywhere in the Cyclades. The duration of a tasting is approximately one and a half hours, giving you ample time to understand the story behind each wine and to ask the questions that naturally arise when you are standing in a vineyard surrounded by vines that predate the phylloxera epidemic. Pricing is set at 30 euros per person for a group of two, reducing to 25 euros per person for groups of three or more. The wines tasted include the OuSyra Serifiotiko and OuSyra Assyrtiko from the main range, alongside the exceptionally limited rosé Les Contours D’OuSyra when available. Bottles can be purchased directly at the winery. It is worth noting that OuSyra also operates a separate restaurant and bar in Ermoupoli under the same name, at Klonos and Kiparissou Stefanou, 84100, Syros, open daily from 6pm except on Wednesdays. The restaurant serves Cycladic cuisine and naturally features the winery’s own wines prominently on the drinks list, making it a wonderful way to end an evening in the city after a day exploring the vineyards.
3. Parakopois Winery
Overall Information
Parakopois Winery is one of the newest and most exciting wine experiences available on Syros, and it represents the growing ambition of the island’s wine culture with great clarity. This small family winery has been crafting wines from indigenous Cycladic varieties with a focus on authenticity, local character and genuine hospitality that immediately sets it apart as a must visit destination for any wine lover exploring the island. The winery takes its name and its identity from a deep connection to the Syros terroir, and the wines it produces reflect that connection with honesty and care. The range includes Nissou Methi White Dry wine, Nissou Methi Rosé, the Single white dry wine, the Ambito aged dessert wine made from dried grapes and the Onore dessert wine, each one crafted from indigenous varieties that tell the story of the land they came from. The name Nissou Methi itself translates as the intoxication of the island, which is an entirely fitting description of the experience that awaits you when you visit. This is a place that takes wine seriously without ever losing its sense of warmth and pleasure.
Location
Parakopois Winery is located on Syros, 841 00, Greece, in the island’s interior. The winery is set within the characteristic Cycladic landscape of terraced vineyards, rocky outcrops and wide open skies, and the setting immediately communicates the remoteness and authenticity that the wines themselves seek to express. The surrounding countryside is quiet, unhurried and genuinely beautiful, offering a complete contrast to the elegance and activity of Ermoupoli just a short drive away.
How to Get There
The best way to reach Parakopois Winery is by hire car or scooter from Ermoupoli, which gives you the flexibility to arrive and depart at your own pace and to combine the visit with other explorations of the island’s interior. Reservations are necessary for all tastings, and the team can provide precise directions when you book. The winery’s website at parakopois.com has a booking form and full contact details. Several guided wine tour operators on Syros also include Parakopois in their curated wine trail experiences, which is a convenient alternative if you would rather travel with a local guide who knows the roads and the stories behind each producer. Taxis from Ermoupoli are readily available and the fare for a dedicated winery visit is very reasonable when shared among a small group.
Services and Experiences
Parakopois Winery offers two beautifully designed tasting packages, both of which deliver a genuine and personal insight into what makes Syros wine so special. The Basic Wine Tasting lasts approximately one and a half hours and covers three labels: the Nissou Methi White Dry wine, the Nissou Methi Rosé and the Onore dessert wine made from dried grapes. All three wines are accompanied by a platter of cold local delicacies, and the tasting is priced at 21 euros per adult. Children between the ages of six and eighteen are warmly welcomed at 10 euros each, participating with juice rather than wine, which is a genuinely thoughtful and family friendly touch. The Premium Wine Tasting lasts two hours and features three wines including the Single white dry wine, the Nissou Methi Rosé and the exceptional Ambito aged dessert wine, which is a limited production label of genuine rarity and quality. This premium experience is accompanied by a rich platter of local delicacies generous enough to serve as a light lunch or early dinner, and is priced at 30 euros per adult. Both packages have a maximum capacity of twenty people per reservation, keeping the atmosphere intimate and personal. The cancellation policy allows a full refund up to 48 hours before the reservation, giving guests flexibility in their planning. The winery is also happy to adjust platters for dietary requirements including vegan, vegetarian and food allergy needs, provided you notify them at the time of booking.
4. Dr Wine, Ermoupoli
Overall Information
Dr Wine is the wine bar that the food aware, wine curious crowd in Ermoupoli has made its own, and the reputation it has built is entirely deserved. Located in the backstreets of Ermoupoli, Syros’s magnificent neoclassical capital, Dr Wine is a wine and mezze restaurant that manages to feel both properly serious about wine and completely relaxed and welcoming at the same time. The wine list here draws from Cycladic producers and the best natural wine makers across Greece, with a genuine commitment to supporting small, artisan operations rather than the familiar commercial names. The creative small plates that accompany the wine list are equally well considered, built from fresh local ingredients and designed to complement rather than overshadow what is in the glass. This is the kind of wine bar where the person pouring your glass can tell you exactly who made it, where the grapes were grown and why it was chosen for the list, which is the surest sign that a wine bar is doing things the right way.
Location
Dr Wine is located in the backstreets of Ermoupoli, Syros, 841 00, Greece. Ermoupoli is one of the finest urban environments in the Cyclades, filled with grand neoclassical buildings, marble paved squares, elegant townhouses and the celebrated Apollo Theatre, one of the oldest opera houses in Greece. The backstreets where Dr Wine is located are quieter and more intimate than the busy harbour front, giving the bar an atmosphere that feels genuinely local and unhurried without being difficult to find for visitors exploring the city on foot.
How to Get There
Ermoupoli is the main port and capital of Syros, and all ferry services to the island arrive here. From the harbour, the old town and backstreets of Ermoupoli are within very easy walking distance. Dr Wine is best found on foot through the labyrinthine but endlessly fascinating streets of the city. A good map application on your phone will guide you there reliably, and the walk itself through Ermoupoli’s beautiful architecture is one of the genuine pleasures of being on Syros. Local taxi drivers will know Dr Wine well and can drop you at the entrance in just a few minutes from anywhere in the city centre. The bar opens in the evening and stays open late, making it an ideal destination after a day of exploring the island and the wineries.
Services and Experiences
Dr Wine operates as a wine and mezze restaurant, meaning the experience here is best enjoyed as a proper evening out rather than a quick drink. The wine list focuses on Cycladic and Greek natural producers, with a particular enthusiasm for small operations that are doing interesting things with indigenous varieties. Syros wines from Chatzakis and OuSyra both feature when available, alongside carefully chosen selections from Santorini, Paros, Naxos, Tinos and mainland Greece. The mezze menu is creative and ingredient led, with small plates designed for sharing and exploring across the table. The atmosphere in the evenings is convivial and intimate, drawing a mix of well travelled visitors and local residents who appreciate good wine and honest food without pretension. The service is knowledgeable and genuinely enthusiastic. This is one of those wine bars where a simple question about what to drink opens into a real conversation, which in the end is the best thing a good wine bar can offer.
5. Syros Wine Trails Experience
Overall Information
For those who want to explore the full breadth of Syros’s wine culture in a single guided experience, Syros Wine Trails is the answer. This dedicated wine tourism operation offers curated tours and guided experiences that take visitors through the most interesting vineyard and winery destinations on the island, combining wine tasting with the history, culture and landscapes of Syros in a way that no individual visit could replicate on its own. Syros Wine Trails was established specifically to introduce visitors to the authentic wine heritage of the island, which stretches back thousands of years in the Apano Meria region and which continues today through the passionate work of producers like Chatzakis and OuSyra. The team behind the operation is deeply knowledgeable about local wine culture and takes enormous pride in sharing it with the curious visitors who pass through Syros each year.
Location
Syros Wine Trails is based on Syros island, with tours covering the key wine producing areas including the Apano Meria region in the north, the Chroussa area in the south and the neoclassical streets of Ermoupoli itself. The island is compact enough that a well planned half day or full day tour can comfortably cover multiple producers and still leave time to enjoy the extraordinary beauty of the surroundings. The starting point for most tours is Ermoupoli, from where a vehicle picks you up and takes you through the island’s landscapes and wine stories in a way that feels effortless and thoroughly enjoyable.
How to Get There
Syros Wine Trails tours depart from Ermoupoli, which is accessible by frequent ferry services from Athens’s Piraeus port as well as from Mykonos, Paros, Naxos and other Cycladic islands. The crossing from Piraeus takes approximately three to four hours by standard ferry. The Syros Wine Trails website at syroswinetrails.gr provides full details of available tours, pricing and booking options. All tours require advance reservation, and booking ahead is particularly important during the busy July and August period when demand is highest. The team is also available to create bespoke private wine tour experiences for couples, small groups or corporate visits, which is a wonderful option if you want something tailored entirely to your interests.
Services and Experiences
Syros Wine Trails offers several distinct tour formats designed to suit different interests, time frames and group sizes. The signature Cheese and Wine Tour is one of the most popular, combining visits to local winemakers with an introduction to the extraordinary cheese making tradition of Syros, including the celebrated San Michali cheese, a hard yellow cheese with protected designation of origin status that is one of the finest artisan cheeses produced anywhere in Greece. Other tour formats focus specifically on the wine producers, taking in Chatzakis Winery, OuSyra and Parakopois with guided tastings at each stop accompanied by local food pairings. All tours include transport between stops so you can relax and enjoy the wines without worrying about driving. The guides speak English and are passionate and articulate about every aspect of Syros wine culture, from the ancient vine growing traditions of Apano Meria to the rare indigenous varieties being revived today. Tasting packages along the tour route cover between three and six wines per winery stop, always accompanied by local delicacies. Private tours can be arranged for groups of any size and can be customised to include specific wineries, foods and cultural sights at your request. Booking directly through the website is the most straightforward option, and the team responds promptly to enquiries.
Tips for Wine Lovers Visiting Syros
Syros is one of the most underrated wine destinations in the Cyclades, and that is precisely what makes visiting it so rewarding right now. The wine scene here is growing, ambitious and full of producers who are doing genuinely interesting things with some of the rarest grape varieties in Greece. Here is what to keep in mind before you go.
- Seek out Serifiotiko wherever you can. This rare indigenous Cycladic variety is grown and vinified on Syros by both Chatzakis and OuSyra, and it produces wines of genuine character and individuality. Tasting it is a privilege that very few wine drinkers outside the island have experienced.
- Book all winery visits well in advance. Chatzakis, OuSyra and Parakopois are all small family operations with limited tasting capacity. Arriving without a reservation, particularly in July and August, will almost certainly result in disappointment.
- Combine your wine visit with a food experience. Syros produces some of the finest artisan food products in the Cyclades, including the famous San Michali cheese and the beloved loukoumades, traditional honey doughnuts that have been made on the island for generations. The Cheese and Wine Tour offered by Syros Wine Trails is an exceptional way to experience both together.
- Spend an evening in Ermoupoli. This is one of the finest cities in Greece and its evening atmosphere, when the neoclassical buildings glow in the warm light and the marble squares fill with people, is one of the great pleasures of the Cyclades. Dr Wine and the OuSyra restaurant in the city centre are both outstanding choices for an evening of wine and food.
- The best time to visit Syros for wine experiences is between May and October, with the harvest season in late August and September being a particularly special time to be on the island.
- Look out for Assyrtiko, Serifiotiko, Monemvasia and Black Aidani on wine lists across the island. These are the varieties that belong to Syros and its surrounding Cycladic terroir, and they tell the story of this land better than any guidebook ever could.
Syros rewards those who look beyond the obvious. Its wine culture is not yet on every traveller’s radar, and that is the whole point. Come now, while the stories are still being told by the people who lived them, while the vineyards are still small enough to walk through with the winemaker beside you, and while a glass of Serifiotiko poured on a Cycladic hilltop at sunset still feels like a genuine discovery. That is the kind of wine experience that stays with you long after the taste has faded.