Small Greek Island Holidays With Sailing In Style

Visiting the lesser-known Greek islands offers a unique and special experience. Small Greek Island holidays provide an authentic glimpse into traditional Greek life, where charming whitewashed villages remain unspoiled by mass tourism and locals welcome visitors with genuine warmth. The beaches are often quieter, with crystal-clear waters and stunning landscapes offering a sense of seclusion that’s hard to find in bustling tourist hubs. Here, you can savour fresh seafood at family-run tavernas, explore ancient ruins without the crowds, and immerse yourself in a slower way of life.

Why Choose Sailing In Style?

We’ve spent years uncovering the most breathtaking hidden gems across the Greek islands, and now, we’re ready to share them with you. Our custom-made trips are designed around your tastes, be that history, water sports, cuisine or relaxing beach days. With our exclusive access to private parties, boutique shops, renowned artists’ workshops, and the best family-run tavernas, you’ll experience Greece in a way that few others ever do. We handle everything, from planning activities and securing festival tickets to arranging restaurant reservations, so all you have to do is relax and soak it all in.

Rather than booking a predictable package holiday, small Greek Island holidays allow you to feel like a local, especially with our knowledgeable crew introducing you to secret swimming spots and family-run vineyards! Moreover, you’ll have the chance to learn the art of sailing, adding another unique slant to an already extraordinary holiday. Under the guidance of our experienced crew, you can take the helm, gaining hands-on experience while exploring some of the most beautiful waters in the world.

Including Festivals In Small Greek Island Holidays

When you hear the word ‘festival’, you might think of huge, raucous music events, but on the Greek Islands, festivals take on a different, more meaningful character. Here, they are deeply rooted in tradition, celebrating moments of history, religious significance or the local produce that sustains island life. For example, on the island of Spetses, the Armata Festival reenacts a historic naval battle, complete with fireworks and cultural performances. Over on Kalymnos, the Sponge Festival honours the island’s deep-sea diving heritage with fresh seafood feasts and traditional music. In celebration of the patron saints of the island, Ithaca comes alive in August with feasts, music and dancing into the early hours. Sailing in Style can weave these quirky festivals into bespoke small Greek Island holidays, ensuring you and your group experience these unique traditions.

How Do We Plan Small Greek Island Holidays?

We travel to over 30 islands, but the exact route of our small Greek Island holidays depends on your starting point. If you set sail from Athens or Lavrio, we’ll explore the Aegean Sea, visiting a mix of vibrant harbours and secluded anchorages like Aegina, Spetses or Hydra. Departing from Corfu or Lefkas, we’ll chart a course through the Ionian Sea, taking in lush green islands, tranquil bays and charming coastal villages. We design every trip to match your interests, balancing iconic destinations with hidden gems that few travellers ever reach.

A Selection Of Islands We Travel To…
From Athens: Aegina, Poros, Ermione, Spetses, Nafplio, Kilada, Hydra, Dokos, Agistri.
From Lavrio: Kythnos, Syros, Mykonos, Paros, Antiparos, Serifos, Kea, Andros, Tinos, Delos, Serifos, Milos, Poliegos.
From Corfu: Parga, Syvota, Paxos, Antipaxos, Corfu (North & Town).
From Lefkas: Meganisi, Kefalonia, Ithaca, Atokos, Kastos, Kalamos, Zante.

Book An Exploration Call

Set sail on a journey designed just for you! Our expertly planned small Greek island holidays are tailored to your interests, whether you’re dreaming of exploring historic towns, savouring authentic cuisine or uncovering secluded beaches. Book an exploration call today to make your 2025 island escape a reality!