A boat is the most romantic way to see Greece: no check-in times, no crowds at breakfast, just the two of you, a quiet bay and a different sunset every evening. These are five places where it works best.
Sailing as a couple at a glance
Best months: June and September, for warm sea, long evenings and fewer boats
Boat: a monohull for the sailing, a small catamaran for space and comfort
Pace: short sails, long lunches, one lazy day
Good for: honeymoons, anniversaries, or just time together
Three of these islands, Kea, Serifos and Milos, are on my Cyclades sailing week, and Paxos and Antipaxos are on the Ionian sailing week. Syros fits easily into a Cyclades route.
1. Syros: an elegant harbour town and sunset in Kini
Ermoupoli, the capital of the Cyclades, is a surprise: marble squares, neoclassical mansions and a small opera house modelled on La Scala. In the Vaporia quarter, below the blue-domed church of Agios Nikolaos, the old captains’ houses go straight down to the sea, and people swim off the rocks between them.
Walk up through the lanes to Ano Syros, the medieval village on the hill, for the view over the harbour. On the west coast, the bay of Kini faces the sunset.
The waterfront of Ermoupoli on Syros.
Skipper’s note: Syros is one of the best places in the Cyclades to provision, with real shops, bakeries and a fish market. Stock the boat here before heading to the smaller islands.
2. Paxos and Antipaxos: green coves and turquoise water
In the Ionian, Paxos is small, green and covered in olive trees. Gaios, the main village, sits on a narrow channel behind two small islets. Lakka, in the north, curves around a shallow, sheltered bay, and little Loggos has a handful of tavernas on the water. The west coast is all cliffs and sea caves, best seen from the boat on a calm morning.
A short sail south, Antipaxos has some of the clearest water in Greece. Its beaches, Voutoumi and Vrika, look almost tropical.
Sailboats by the sea caves on the west coast of Paxos.
Skipper’s note: The day boats from Corfu and Parga reach Antipaxos around midday. Be there early in the morning, or stay on in the late afternoon, and you’ll have the bay almost to yourselves.
3. Kea: a quiet escape close to Athens
Kea is the first island of the Cyclades, a few hours’ sail from the mainland, and still feels undiscovered. Vourkari is a small harbour with a row of cafés and bars on the water, in one of the most sheltered bays of the Cyclades. Up the hill, the village of Ioulida climbs the slopes, and a short walk leads to the Lion of Kea, carved into the rock more than 2,500 years ago.
On the south-west coast, Koundouros has clear water and quiet coves for an afternoon swim.
Vourkari harbour on Kea, with yachts at anchor.
Skipper’s note: Starting from Lavrio, Kea is only a couple of hours away, an easy first sail. From the Athens marinas it is a longer first day, but worth it: you arrive feeling you have left the city far behind.
4. Serifos: slow island life and a white Chora
Serifos is the island for slowing down. From the port of Livadi, the white houses of the Chora tumble down a steep hill above you. Go up in the late afternoon, wander the lanes and stay for sunset in the little square. Back below, the sandy beach of Psili Ammos is a short ride from the port.
The windmills and white houses of Serifos Chora.
Skipper’s note: Take a taxi up to the Chora and walk back down to the harbour in the cool of the evening. It is all downhill, and the view is with you the whole way.
5. Milos: sea caves, white rocks and sunset in Plaka
Milos is often the highlight of a Cyclades week. Sarakiniko’s white volcanic rocks look like the moon. Kleftiko, on the south-west coast, is a maze of white rock arches and caves best reached by sea, which makes it the perfect place to arrive by boat. In the evening, watch the sun go down from the Kastro above Plaka, then have dinner in the village.
Don’t miss Klima, a fishing village of brightly painted boathouses right on the water.
The white rock arches of Kleftiko on Milos, best reached by sea.
Skipper’s note: Arrive at Kleftiko early, before the excursion boats come in late in the morning. It is sheltered in a northerly wind. Treat it as a swim-and-lunch stop and spend the night elsewhere, and skip it if there is any swell from the south.
Closer to Athens: Poros and Hydra
If you have less time, the Saronic Gulf is romantic too. Sailing into Poros through the narrow channel at sunset is unforgettable, and Hydra, with no cars and its stone mansions around the harbour, feels like another century. Read the Poros sailing guide and the Saronic Gulf guide.
Sunset from the deck: the best seat on any island.
Tips for a romantic sailing week
Choose the right boat. A monohull of 11–13 metres is plenty for two. If comfort matters more than sailing, a small catamaran gives you more space. See Catamaran vs Monohull.
Time for yourselves. A good skipper knows when to be your guide and when to give you space. Say at the start that you would like time on your own.
Nights at anchor. Mix harbour nights with nights at anchor. Dinner on deck under the stars, with no one else around, is the highlight of most couples’ trips.
Plan for sunsets. Ask your skipper to time the day so you are at a west-facing bay or a harbour with a view by evening.
Bring something to celebrate. A bottle of local wine from the island, chilled in the boat’s fridge, for the evening you will remember.
Two on the bow, under sail.
Questions couples ask
Is a sailing holiday a good idea for a honeymoon?
Yes. Your own boat, a different island every day and nights in quiet bays make it one of the most private ways to see Greece.
Can we sail with only two people on board?
Yes. Many couples sail with just a skipper. The boat is all yours.
Which area is most romantic?
For white villages and dramatic sunsets, the Cyclades. For green coves and calm water, the Ionian. For a shorter trip close to Athens, the Saronic Gulf.
When is the best time for couples?
June and September: warm sea, long evenings and fewer boats in the bays.
Keep reading
How to plan your first sailing holiday · a step-by-step guide
Catamaran vs Monohull · which boat suits two
Sailing Poros · the most beautiful arrival in the Saronic