Greek Isles Gala: 15-Day Cyclades Sailing Extravaganza

Welcome to Greece! Start your adventure in the city of Athens surrounded by enchanting mythology and ancient architecture. Stroll the ruins of ancient marketplaces, magnificent temples, and crowded flea markets in the city center. You’ll have a chance to enjoy contemporary Greek cuisine and the city’s vibrant nightlife in the popular Pangrati neighborhood, amid live music of the Psyrri district, or in family-friendly Plaka.

Suggested activities: guided tour of the Parthenon, food tour of Athens, family mythology tour (suitable for children).

Start your tour of Cyclades islands on Kea. We anchor at a quiet bay with fewer boats. Spend the day relaxing on the beach, enjoy the watersports or explore the historical sites of Kea, leading with the stone-carved 20ft lion.  In the afternoon enjoy Ay Nikolaos, a city of tavernas. “There is no love sincerer than the love of food,” George Bernard Shaw said. Are you ready for fresh, delicious seafood for 2 weeks in a row? A dinner turns into after dinner drinks. A day well spent. Learn about the poet Simonides and physician Erasistratos – famous for his discovery that heart is not a center of sensation but just a pump. 

Start your tour of Cyclades on Tinos. Overshadowed by glamorous Mykonos, Tinos is often overlooked by tourists making it an ideal place to unwind. The island has fascinating history with winding streets, quaint villages, incredible hiking trails, and sandy beaches. In the afternoon swim at Agia Thalassa beach and enjoy your dinner in the fishing village of Panormos.

Suggested activities: visit famous Panagia Evangelistria, hiking to Exomvourgo mountain, cheese tasting at a local cooperative cheese shop.

Mykonos is the most popular island in the Cyclades chain and is known for its gourmet restaurants and vibrant nightlife. Explore the local boutiques, sandy beaches, or spend the day sampling local cuisine at one of the many waterfront restaurants. Remote Agios Sostis beach is a must-see for anyone seeking a quiet paradise, while Ftelia beach is ideal for watersports. If you’d prefer to immerse into local culture, opt for a cooking class to learn about Greek food, or sample it without the work in one of the gourmet restaurants.

Suggested activities: explore 18th century neighborhood Little Venice.

This island is a sacred place and a UNESCO world heritage site. At the center of the Cyclades during the Classical era, this island is known as the birthplace of twin deities Apollo and Artemis. Visit the Terrace of the Lions overlooking the sacred lake, where God Apollo was born under the palm tree.

This island is a sacred place and a UNESCO world heritage site. At the center of the Cyclades during the Classical era, this island is known as the birthplace of twin deities Apollo and Artemis. Visit the Terrace of the Lions overlooking the sacred lake, where God Apollo was born under the palm tree. 

You can choose to spend the day on the beach. If you’re interested in something more active, consider hiking some of the coastal trails or spend time strolling around the picturesque island villages. Have a leisurely al fresco lunch and enjoy dinner at sunset on the waterfront.

Naxos is next to Paros and offers more opportunities for relaxation. Spend the day at Agios Prokopios beach, named one of the best beaches in the world, or take an ancient hike. Hiking in Naxos is a five senses experience as you walk marble paths, surrounded by fragrant herbs and olive trees. Take in the hidden waterfalls tucked between quaint little villages like Apeiranthos, the crown jewel of Naxos. Another hiking option is he highest point in the Cyclades, the summit of Mount Zas, the mythological childhood home of Zeus, the ruler of the gods. Head inland to the town of Chalki, home to the island’s oldest market and find a spot in the shady square to while away the afternoon.

Suggested activities: the Temple of Demeter at Sangri, the Portara or entrance to the Temple of Apollo.

This island’s volcanic history has led to the formation of some of the more unique beaches in the Greek islands, along with the dramatic cliff views. Spend your day relaxing at the beach or exploring the village or Fira. If you love hiking, choose one of the many scenic walking routes, ranging from between two to eight miles each. At dinner, sample the island’s signature cherry tomatoes and white eggplants as guest stars in seafood dishes.

Spend the morning on the beach or shopping in Fira. In the afternoon you’ll take a guided tour that will show you a side of Santorini that most travelers don’t see. Visit Oia, the furthest town along the rim of the caldera packed with art and culture. Later, take a trip up to the highest peak on the island for sunset views, stopping in the medieval villages of Megalochori and Pyrgos along the way.

Enjoy a leisurely morning breakfast before taking some time to stroll and scope out small shops and boutiques in Fira, the capital of the island. Head back onboard and enjoy a cruise around the island which will include a stop at Red Beach. Swim and sunbathe before heading to a second stop at the White Beach. Along the way, take in Aspronisi, the Ancient Lighthouse, Indian Rock, the prehistoric city at Akrotiri, before relaxing in the hot springs at Nea Kameni at sunset.

Today we will start our journey up North and explore  the island of Ios.  First we will stop at  Manganari Beach for lunch then move to the harbor for overnight anchorage. Check out amazing Hora’s shops, restaurants and bars which all come alive in the evenings. Visit Panagia Gremiotissa (Church of the Virgin) to enjoy beautiful sunset views from a hilltop.

Considered one of the most exotic islands in the Aegean Sea, Milos is known for its extraordinary colors and landscapes. It is without doubt one of the most impressive islands in the Cyclades. Volcanic rocks paint the beaches red, pink and orange. Spend your day here exploring each of these colorful beaches.

You’ll spend the afternoon visiting island’s five main villages: Merichas, Chora (also known as Messaria), Dryopida, Loutra, and Kanala.

Relax in Loutra’s thermal springs, walk through Messaria’s labyrinthine streets, or visit the Katafiki Caves in Dryopida. Enjoy seafood dinner at the local tavern with a sea view.

Enjoy the last evening of your tour in Athens. Spend your evening in the Koukaki neighborhood where the off-the-beaten-path wine bars will introduce you to a wide selection of Greek wines amid friendly crowds. Be sure to make the most of your time in this magical city.

Disembark and say farewell to Greece!