Cyclades Luxury Sailing: 8 Days Catamaran — Mykonos, Naxos, Paros & Santorini by Sea

Tour Overview

Sailing Route

Day 1: Mykonos — Embarkation

Board your luxury catamaran (Lagoon 450 or similar) in Mykonos new port. Welcome briefing from your skipper and hostess over sparkling wine. The catamaran is your home for the week — spacious cabins with en-suite bathrooms, a saloon with panoramic windows, and deck nets perfect for sunbathing. Afternoon: sail to a secluded cove on Mykonos’s south coast — your first Aegean swim in crystal-clear water. Evening: sunset dinner on board (your first taste of the hostess’s Greek cuisine). Overnight at anchor under the Cycladic stars — the Milky Way is spectacular away from city lights. Overnight on board near Mykonos.

Day 2: Mykonos to Naxos — The Largest Cyclades

Morning sail to Naxos (3-4 hours). Naxos is the largest and most fertile of the Cyclades, with mountains reaching 1,004m (Mount Zas, named for Zeus), fertile valleys growing potatoes, olives, and the island’s famous Kitron liqueur. Approach Naxos port — the Portara (Great Door) is the massive marble doorway of an unfinished Temple of Apollo (530 BC), standing alone on the islet of Palatia, framing every sunset photograph taken on Naxos. Afternoon: explore Naxos old town (Kastro) — a 13th-century Venetian castle district with narrow medieval streets and the Archaeological Museum in the former Jesuit School. Evening: dinner at a taverna in the old market, trying Naxos specialties like graviera cheese (PDO) and roast lamb with potatoes. Overnight on board in Naxos port.

Day 3: Naxos to Koufonisia — Hidden Paradise

Short sail to the Small Cyclades — Koufonisia, the archipelago’s best-kept secret. Ano Koufonisi has a population of 400 and some of the most beautiful beaches in all of Greece: Pori Beach (golden sand, turquoise water, a single taverna), Finikas, and Italida (accessible by footpath). The lack of mass tourism means these beaches remain pristine. Anchor in a sheltered bay and spend the afternoon swimming, snorkeling, and paddleboarding (equipment on board). The water clarity here is extraordinary — you can see the bottom at 15m depth. Evening: your hostess prepares a seafood feast on board — grilled catch of the day, Greek salad, and chilled Assyrtiko wine. Overnight at anchor in Koufonisia.

Day 4: Koufonisia to Amorgos — The Big Blue

Longer sail to Amorgos (4-5 hours). Amorgos is the easternmost of the Cyclades, famous since Luc Besson’s film The Big Blue (1988) was largely filmed here. The island is mountainous, austere, and deeply authentic. Anchor near Katapola and explore the Chora (400m elevation) — one of the most beautiful traditional villages in the Cyclades, with windmills on the ridge and views across the archipelago. The star attraction is the Monastery of Panagia Hozoviotissa, a Byzantine monastery built in 1088 literally into a vertical cliff face 300m above the sea. The monastery is 40m high, 5m wide, and accessed by 350 steps — the views are transcendent. The monks offer loukoumi (Turkish delight) and raki to visitors. Overnight at anchor in Amorgos.

Day 5: Amorgos to Ios — Beach & Party Island

Morning sail to Ios (4 hours), passing the uninhabited island of Ananes — a perfect mid-Aegean swim stop. Ios is known for two things: the tomb of Homer (the poet is said to have died here, and his mother was from Ios) and Mylopotas Beach (one of the finest beaches in the Cyclades). Afternoon: anchor off Mylopotas and swim ashore to the golden sand. Ios’s Chora is a classic Cycladic village of white cubes and blue domes — climb to the top for panoramic views. Evening: Ios has a famous nightlife scene (second only to Mykonos for partying), or you can find a quiet taverna in the Chora for a relaxed dinner. Overnight on board in Ios port.

Day 6: Ios to Santorini — Entering the Caldera

The most dramatic sail of the week. Depart Ios early and set course for Santorini (3-4 hours). The approach is unforgettable: the volcanic islands emerge from the sea, and you sail through the narrow entrance into the caldera — suddenly the sea floor drops to 400m depth, the cliffs rise 300m on all sides, and the white villages of Fira and Oia perch impossibly on the rim. Your catamaran is dwarfed by the scale of the caldera — it is one of the great natural harbors of the world, and entering it under sail is a lifetime memory. Anchor near the volcano island of Nea Kameni. Afternoon: tender ashore to hike the volcano crater, then swim at the hot springs where sulfurous water is warm year-round. Evening: dinner on board in the caldera — there is nothing else like eating dinner on a catamaran floating in the center of a volcanic crater, under the stars, with the lights of Fira twinkling on the cliffs above. Overnight at anchor in the Santorini caldera.

Day 7: Santorini — Caldera Exploration & Farewell

Morning: tender to Athinios port and ascend to Fira. Free time to explore Santorini’s cliff-top capital — the Archaeological Museum (frescoes from Akrotiri), boutiques, and the cable car. Not-to-miss: a donkey ride or cable car down the 588 steps of the old port path (the traditional way). Afternoon: sail along the caldera rim — pass beneath Oia, Thirasia, and the Red and White Beaches. Final swim stop in a secluded cove beneath the Red Beach. Farewell dinner on board — your hostess’s best meal: grilled lobster if the catch cooperated, lamb kleftiko, and Vinsanto (Santorini’s famous sweet wine) to toast the voyage. Overnight at anchor in the caldera.

Day 8: Santorini — Disembarkation

Final breakfast on board. Disembark in Santorini port. Transfer to Santorini Airport or your hotel for onward travel — thoroughly salt-crusted, sun-kissed, and with memories of sailing one of the world’s most beautiful archipelagos.

Included

• 7 nights on luxury catamaran (private double cabin with en-suite)
• Professional skipper & hostess/chef
• All meals on board (breakfast, lunch, dinner — Greek cuisine)
• Open bar: wine, beer, soft drinks, water
• Snorkeling & paddleboarding equipment
• All fuel, port fees, and marina charges
• Tender/shore excursions
• Santorini volcano hike (guide included)
• Linen, towels, beach towels
• Airport/port transfers on embarkation/disembarkation