Greece: Western Cyclades Sailing Adventure

Departures: Greece

Western Cyclades Sailing Adventure

One of the most famous archipelagos in the world, the Cyclades have more to offer than pristine beaches, crystal clear waters and amazing sailing experiences. They are the cradle of over ten millennia of rich history, boast rich geographical diversity, abundant marine wildlife and feature the best of traditional Aegean architecture and Mediterranean cuisine. This sailing adventure goes beyond mere island hopping, giving you a chance to explore beyond each island’s marina, as well as immerse in local culture, savor the local flavors and learn about the history of this immensely beautiful part of the world.


We believe that to travel responsibly, a portion of our tour cost should benefit the communities we visit. For this trip, our donation will go to a non-profit organization we support that is having a very positive impact around the world: DOCTORS WITHOUT BORDERS—a humanitarian-aid organization that provides ongoing emergency medical aid around the world.


Starting at $1490*

For more information and to get started, contact us at How to Book.


May – October

8 Days, 7 Nights

Day 1

Athens – Kythnos

Your day starts in Athens with either a short stroll around the historic center or some last minute shopping, before boarding the sailboat that will be your home for the next week. As you depart the marina, enjoy views of the southern suburbs of Athens.

We head east, towards the Temple of Poseidon. Built high on a cliff over the dark blue waters at Cape Sounion, this is the place where the Aegean archipelagos gets its name from. Our destination for the night is the island of Kythnos, which boasts a lively main town, a world famous beach as well as postcard perfect views of the Aegean from the numerous chapels built high up in the cliffs.

Day 2

Kythnos – Serifos

Morning snorkel towards the sea urchin colonies in the cliffs on the southern side of Kolona beach. Then take a short, easy hike up to a white washed chapel, overlooking the Aegean. Late morning we leave Kythnos and sail south towards the island of Serifos. Well before the island’s marina, we stop for a swim in one of the tiny bays that dot the island’s eastern side.

Early evening we dock at the marina and head out to explore the island’s main town, up the mountain. With its tiny alleyways, numerous chapels and windmills, vibrant coffee culture and incredible views of the archipelago to the south, Serifos is iconic Greece.

Day 3

Serifos – Milos

After a quick swim, we head to the cosmopolitan island of Milos, a volcanic island boasting unique geological formations. Experience incredible sunset views without the crowds of Santorini. Add in lunar-like landscapes, a vibrant nightlife and incredible local food and you’ll understand why the island is by far our favorite destination.

On arrival, we’ll take you to the best place on the island to try lamb or goat stew. If you prefer seafood, the tiny fishing village of Apollonia is home to numerous family run tavernas serving fresh fish right on the water. In the evening we’ll take the local bus to the main town up in the cliffs and enjoy the boutique cafes, bistros, restaurants and shopping opportunities.

Day 4

Milos – Kleftiko Bay

This morning we sail to two beautiful swimming spots on the southern tip of the island. Crystal clear waters, sea caverns and rocks pointing towards the sky, all contribute to an amazing, unique landscape. Aboard the sailboat’s dinghy we’ll cruise through the caves, then snorkel and swim. With luck, we’ll spot some Mediterranean dolphins.

The evening is yours to continue exploring vibrant Milos. Our skipper will happily suggest things to do, places to visit and of course direct you to the most authentic restaurants on the island.

Day 5

Milos – Polyaigos – Sifnos

Today we head northeast. A short sail away is Polyaigos, a tiny, uninhabited island that is home to a small population of Mediterranean seals. The highlight of any visit to Polyaigos island is swimming. The island’s south side boasts some of Europe’s most terrific beaches, ideal for swimming and snorkeling.

In the evening we set sail north towards the island of Sifnos, where we’ll try to spend the night in the bay of Vathy on the southern part of the island. There’s a great sandy beach and two family run tavernas serving delicious, freshly prepared vegetables and salads straight from the garden, goat or beef stews, grilled lobster or mullets fresh from the sea for us to enjoy.

Day 6

Sifnos – Kythnos

After breakfast, we head back towards the eastern side of Kythnos. Our destination is the tiny fishing village of Loutra. Once there our suggestion is to unwind in the hot springs or opt for a relaxing spa treatment.

Early evening enjoy a guided tour of the island’s main town, a stunningly beautiful place, full of traditional whitewashed ancient houses, cobblestone streets and alleyways. After dark feel free to enjoy a bottle of cold, locally brewed beer right on the water, or put on a bathing suit and observe the Milky Way, while relaxing in the natural pools where the hot springs meet the sea.

Day 7

Kythnos – Temple of Poseidon

This morning, we st sails towards the mainland and Cape Sounion, home to the temple of Poseidon. We drop anchor in one of the numerous bays close to the cliffs and use the dinghy to get to shore. Once there, we’ll hike to the temple and visit one of the most important archaeological sites this side of the world.

Late afternoon we’ll head back towards the marina in Athens, stopping along the way for a swim. Once at the marina your guide will acompany you to the center of Athens for a proper farewell dinner in the historical center of Greece’s capital. Return to the boat for overnight.

Day 8

Athens – Home

After breakfast, we pack our bags and bid farewell to the sail boat that’s been our home for the past week as we disembark at the marina in Athens.


Extend your stay in Greece with time in Athens to explore.

For pricing and hotel information, contact us at How to Book. The specifics of this itinerary are subject to change based on local conditions at the discretion of Ponte Travels.

• Rates shown are per person, double occupancy, based on 6 people traveling. Airfare not included.