Greece is one of the world’s most romantic destinations – and there’s no better way to explore it with your partner than on a sailing holiday. Here are 5 dreamy island escapes filled with sunshine, turquoise waters, and unforgettable moments.
1. Syros – Stroll through Ermoupoli & romantic sunsets
The capital of the Cyclades has a timeless charm.
📍 Walk around Vaporia, enjoy wine with a view, and dine by the sea during sunset.
2. Paxos & Antipaxos – The hidden gems of the Ionian
Small, lush islands with crystal-clear waters.
📍 Drop anchor in secluded bays, swim together in turquoise coves, and wander the quaint village of Gaios.
3. Kea – Peaceful escape close to Athens
Perfect for a romantic weekend or a short getaway.
📍 Relax in Koundouros, dine in Ioulida, and swim in serene beaches away from the crowds.
4. Serifos – Calm, authentic, and moonlit nights
The ultimate slow-living island of the Cyclades.
📍 Sunset walks in Chora, cocktails in the square, and night swims in Psili Ammos.
5. Milos – The island of lovers
One of Greece’s most magical spots for couples.
📍 Sunset in Plaka, white cliffs of Sarakiniko, and a romantic boat ride to hidden caves and beaches like Kleftiko and Tsigrado.
Want a romantic sailing trip just for two?
Leave your name and email, and we’ll help you plan the perfect route for your unforgettable escape: