MYKONOS TO SANTORINI

Base: Marina of Tourlos, Mykonos

This Cyclades itinerary is designed for experienced sailors seeking a demanding and rewarding sailing adventure, combining iconic destinations with longer passages and frequently challenging weather conditions. Departing from Mykonos and crossing open Aegean waters, travelers should expect strong Meltemi winds, choppy seas, and extended daily sailing hours, often ranging from 5 to 7 hours on board, depending on conditions. The route offers fewer sheltered passages and requires confident boat handling, good planning, and flexibility in decision-making. The best period to attempt this itinerary is late May to June and September, when the Meltemi is generally less intense, while July and August are recommended only for highly skilled crews. Despite its demanding nature, the experience is exceptionally rewarding, offering dramatic caldera approaches in Santorini, long blue-water sails between islands, and a powerful sense of achievement.

Day 1

Mykonos
Check in at 17:00

Your sailing week begins in Mykonos, one of the most iconic islands of the Cyclades. After embarkation, take time to settle on board and enjoy your first swim in a nearby bay with crystal-clear waters. Spend the afternoon exploring Mykonos Town, wandering through its whitewashed alleys, visiting the famous windmills and browsing stylish boutiques. As evening approaches, enjoy dinner by the sea and a relaxed walk through Little Venice, where the sunset reflects beautifully on the water, setting the perfect tone for the days ahead.

Day 2

Mykonos to Rhenia and Naxos (Port)
28 NM 4h
Depart Mykonos and head to the nearby island of Rhenia, a quiet and unspoiled paradise with crystal-clear waters, perfect for swimming and snorkeling in complete tranquility. After a leisurely swim, continue towards Naxos. Arrive in the late afternoon and dock near the main port or anchor nearby. In the evening, explore Naxos Town, visit the Portara at sunset, and enjoy a traditional Cycladic dinner at a local taverna.

Day 3

Νaxos to Ios
29 NM 4h
Sailing south, you reach Ios, an island known for its stunning beaches and authentic Cycladic charm. Drop anchor at the impressive Manganari Beach, a vast natural bay with calm, shallow waters ideal for swimming and relaxing. Spend the day enjoying the sea and the peaceful surroundings before heading ashore in the evening. Visit Ios Chora, perched on the hill, where you can explore charming alleys, enjoy panoramic views, and dine at a traditional restaurant overlooking the Aegean.

Day 4

Ios to Santorini
21 NM 3h
Today’s sail brings you to the spectacular island of Santorini. Approaching the caldera is an unforgettable experience, with dramatic cliffs rising from the sea and white villages perched above. Anchor or dock and spend the day exploring the island, visiting Fira or Oia, discovering volcanic beaches, or enjoying a wine tasting at a local winery. In the evening, experience one of the world’s most famous sunsets, followed by dinner with breathtaking caldera views.

Day 5

Santorini to Sikinos

24 NM 4h

Leaving the dramatic scenery of Santorini behind, sail towards Sikinos, one of the most authentic and untouched islands of the Cyclades. Anchor near a quiet bay or dock at Alopronia and enjoy swimming in deep-blue, crystal-clear waters. Sikinos offers a peaceful atmosphere, ideal for slowing down after the intensity of Santorini. In the evening, stroll through the small port or visit Chora and enjoy a traditional meal at a family-run taverna, experiencing genuine Cycladic hospitality.

Day 6
Sikinos to Paros

28 NM 4h

After a morning swim, sail back to Paros and head to Naoussa, one of the island’s most charming and lively villages. Wander through its picturesque harbor, explore boutique shops, and enjoy a long lunch or dinner at one of the renowned seaside restaurants. Naoussa offers a perfect mix of traditional Cycladic character and vibrant nightlife, making it an ideal final stop before returning to base.

Day 7

Naousa of Paros and back to the base

29 NM 5h

On the final day, enjoy a relaxed morning sail back to the base. Take one last swim along the way, reflect on the highlights of your Cycladic adventure, and enjoy a smooth return, bringing an unforgettable week of island hopping to a perfect close.