Greek Sailing Adventure

Western Cyclades Sailing Adventure Sample Itinerary

Please note that this itinerary is a sample and all aspects of this tour can be customized to suit your preferences and goals. Whether you want an easier, family-friendly vacation or one full of epic adventures, this is the trip for you.

Day 1 Athens – Cape Sounion – Kythnos

Depending on your arrival time to Athens, you may have time to explore this historic city or shop for supplies for your sailing adventure. Head to the marina in the afternoon and get settled in on the sailboat that you will call home for this week. After a short orientation, set sail from the marina and head east, with views of some of the suburbs south of Athens. Continue past the Temple of Poseidon, one of the most impressive and iconic landmarks in Greece since ancient times. It sits high on a cliff at Cape Sounion. When you reach the island of Kythnos, spend the night at anchor in Kolona Beach. Here, a natural strip of sand creates a beautiful double bay. Kythnos is considered the gateway to the archipelago, and the island has amazing beaches, a lively town, and many chapels built in the cliffs which boast incredible views of the Aegean Sea.
Overnight Location: Aboard the sailboat
Meals: None

Day 2 Kythnos – Serifos

Start your morning with breakfast and a refreshing swim, then spend the morning exploring Kythnos. On the southern side of Kolona beach, there are sea urchin colonies in the cliffs. Snorkel from the boat over to this amazing area. Then take a short, simple hike to a whitewashed chapel that overlooks the Aegean Sea. Bring your camera to take pictures of the view, and of the wild goats who have made themselves at home in the chapel’s courtyard.

Return to the boat and sail to Serifos, stopping for a swim on the eastern side of the island. Dock at a marina for the night and leave the boat to explore the main town on the island. The town of Serifos is everything you picture in an iconic Greek town: narrow alleys, abundant chapels, windmills, plenty of great coffee, and stunning archipelago views. If you enjoy eating fresh, delicious seafood on the beach, here is a great place to do so. Return to the marina and spend the night on the boat.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 3 Serifos – Milos

Once again, begin your day with a leisurely breakfast and swim as the boat is prepared for a new day of sailing adventures around the Greek islands. Today, set sail for the island of Milos. This volcanic island is very cosmopolitan, but also boasts fascinating and unique geological formations. Milos offers all the attractions of Santorini without the crowds. Take in the traditional architecture, cafes, restaurants and bistros, and plenty of shopping opportunities. Breathtaking sunsets are guaranteed, and the moon-like landscape of Milos gives your visit a very exotic feel. There is also a vibrant nightlight. Your guide will help you find a restaurant to suit your tastes, whether it’s the best lamb or goat stew on the island or a family-run taverna right on the water that serves incredible fresh fish. End the day on a balcony overlooking the sea, sipping a cocktail.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 4 Milos – Kleftiko Bay

Continue exploring Milos today. You’ll often be reminded that this is a volcanic island, due to the unusual geological formations that can be seen all around the island. After breakfast, sail to two different swimming areas, including the incredible Kleftiko beach on the far southern point of the island. The amazing landscape and sparkling clear waters will enchant you. Discover why Kleftiko cove was previously used by pirates as you take a dinghy tour through the sea caverns and caves. Swim, snorkel, and watch for dolphins, which are often attracted to the sound of music so come prepared! Return by boat to the marina in the evening for more opportunities to explore the things you missed the night before, or repeat your favorites. Your skipper can help you find something fun to do or a great restaurant for dinner.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 5 Milos – Polyaigos – Sifnos

Leaving Milos today, you’ll sail to the northeast past the Strait of Kimolos. Visit the small, uninhabited island of Polyaigos where you can see Mediterranean seals as they hunt for fish. Spend the day swimming and snorkelling on some of Europe’s most amazing beaches on the southern side of the island. You can also choose to go for a hike, where you’re almost certain to find a herd of wild goats grazing. Leave Polyaigos in the evening and sail to Sifnos. On the southern side of this island is the Bay of Vathy, where you’ll find yet another fantastic beach and two family-run tavernas. Many guests consider this meal to be their favorite in Greece, full of fresh, local ingredients.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 6 Sifnos – Kythnos

After breakfast, leave the island of Sifnos and return to Kythnos. This time, visit the eastern side of the island, stopping along the way in a remote southern bay for a midday swim. Today’s destination is Loutra, a small fishing village where you’ll have the opportunity to soak in the hot springs or relax with an inexpensive spa treatment. Early in the evening, follow your guide for a tour of the main town on Kythnos, which is full of the traditional Greek-island atmosphere. The ancient buildings are whitewashed, the narrow streets and alleys are cobblestone, and they offer some of the best meat in the Cyclades. It is everything you ever imagined the Greek islands to be, and you’ll feel as though time truly moves more slowly here. Continue relaxing long into the evening, sitting under the stars with a bottle of cold local beer by the water or relaxing in a natural pool where water from the hot springs meets the sea. Feel your cares washed away into the Aegean Sea and sleep well on the gently rocking boat.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 7 Kythnos – Temple of Poseidon – Athens

Start the day today with a traditional cup of coffee in the village of Loutra, then sail toward the mainland. Your first stop will be the Temple of Poseidon at Cape Sounion. The sailboat will sit at anchor as we take the dinghy to shore and hike up to the temple. The Temple of Poseidon archaeological site is considered to be one of the most important in the world and you’ll be able to experience it up close. Later in the afternoon it will be time to set sail back to Athens, but not without one more swimming stop on the way. From the marina in Athens, your guide will escort you to historic central Athens where you’ll enjoy a farewell dinner. Return to the boat for one last night onboard.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 8 Departure

Sadly, your Western Cyclades sailing adventure has come to an end. Pack your bags after breakfast and say farewell to your boat and skipper. Pleasant travels home or on continued adventures!
Overnight Location: Aboard the sailboat
Meals: Breakfast