Discover the Cyclades Islands: Including Mykonos or Santorini

Discover the Cyclades Islands: The Ultimate Greek Yacht Charter Itinerary

Temple of Poseidon yacht charter vacation cape sounio

The Cyclades Islands are among the most iconic and breathtaking destinations in Greece. Known for their whitewashed villages, crystal-clear waters, golden beaches, and ancient history, the Cyclades are a sailor’s dream. Chartering a yacht from Athens to the Cyclades offers the perfect blend of luxury, adventure, and cultural immersion. Whether you’re a seasoned sailor or a first-time guest on a crewed yacht, this 7-day itinerary through the Cyclades Islands provides the ideal route for a Greek island-hopping adventure.

In this guide, we’ll explore a detailed Cyclades yacht charter itinerary from Athens to Athens, covering must-see islands like Kea, Syros, Mykonos, Paros, Naxos, and Kythnos. We’ll also highlight travel tips, local cuisine, historic sites, and the best anchorages for overnight stays.

Why Choose a Cyclades Yacht Charter?

Chartering a private yacht in Greece offers a unique opportunity to explore the Greek islands in style and comfort. The Cyclades archipelago consists of over 200 islands, but this curated 7-day itinerary focuses on the most stunning and accessible highlights. The region offers:

Consistent Meltemi winds (ideal for sailing during summer, but can be problematic as well. Read about Meltemi Winds here.)
Beautiful anchorages and marinas
A mix of popular and off-the-beaten-path islands
Easy access from Athens marinas (Lavrion or Alimos)

Whether you’re on a bareboat charter or a fully crewed luxury catamaran, the Cyclades Islands are a top-tier destination for sailing vacations in the Mediterranean.

7-Day Cyclades Yacht Charter Itinerary – Athens to Athens

Day 1: Embarkation in Lavrion / Sail to Kea (15 NM)

Your Cyclades adventure begins in Lavrion, just 40 minutes from Athens International Airport. After a welcome aboard your yacht and safety briefing from your crew, set sail to Kea, your first island stop.

Kea is peaceful and green, with charming villages like Korissia and Ioulis perched in the hills. Enjoy a relaxing swim at Koundouros Bay, followed by a sunset dinner ashore at a taverna. Don’t miss the famous Lion of Kea, carved from stone and dating back to 600 BC.

Highlights:

Easy first sail
Traditional Cycladic architecture
Secluded bays and authentic village charm

Day 2: Kea to Syros (37 NM)

kea island greece yacht charter vacation

Syros is the capital of the Cyclades, and a lesser-known gem. The port of Ermoupoli is one of the most elegant in Greece, filled with neoclassical buildings, marble streets, and a cosmopolitan feel. Visit the Apollo Theater, modeled after La Scala in Milan, or stroll through Ano Syros, the island’s medieval quarter.

Syros offers great dockside dining options and boutique shopping, making it a fantastic blend of culture and comfort.

Highlights:

Sophisticated harbor town
Historical landmarks and architecture
Less crowded than neighboring islands

Day 3: Syros to Mykonos (19 NM)

crewed yacht charter to mykonos in the greek islands

Your next stop is the world-famous Mykonos. Known for its chic vibe, lively nightlife, and stunning beaches, Mykonos is a must-see destination. Dock at Tourlos Marina and head into Mykonos Town to explore the iconic windmills, the maze-like streets of Little Venice, and designer shops.

By day, relax at beaches like Psarou, Paraga, or Agios Sostis. At night, enjoy a gourmet dinner or dance under the stars at one of Mykonos’ legendary clubs.

Highlights:

Iconic Cycladic scenery
Upscale dining and nightlife
Beautiful beaches and stylish boutiques

Day 4: Mykonos to Paros (26 NM)

Coast of Paros island in Greece view from above in the sunset out of focus in a summer

Sail to Paros, an island that beautifully balances vibrant culture and relaxed Greek charm. Drop anchor in Naoussa, a picturesque harbor village buzzing with waterfront cafes and bars.

Spend the day exploring Kolymbithres Beach, with its unique rock formations, or take a short trip to the inland village of Lefkes. Paros is also known for kiteboarding and windsurfing, if you’re feeling adventurous.

Highlights:

Lively harbor towns
Water sports and beach time
Traditional villages and laid-back charm

Day 5: Paros to Naxos (15 NM)

A short sail brings you to Naxos, the largest island in the Cyclades. With its lush interior, ancient ruins, and long sandy beaches, Naxos is often a guest favorite.

Walk through the iconic Portara, the marble gate of an unfinished temple to Apollo, especially at sunset. Explore the Old Town (Chora), or visit traditional mountain villages like Halki for local olive oil and citrus liqueur tastings.

Highlights:

Fertile landscapes and charming mountain villages
Historical ruins and the Portara gate
Excellent cuisine and traditional products

Day 6: Naxos to Kythnos (50 NM)

Kythnos Greece-Stephanie-Top-hill-sailing-yachts- FYLY- FX Yachting

Begin your return leg with a longer sail to Kythnos, known for its relaxing thermal springs and authentic atmosphere. Anchor in Loutra, a quiet harbor with a warm, local feel.

Kythnos is a great place to unwind — enjoy a soak in the thermal spa, hike the surrounding hills, or simply relax on Kolona Beach, a double-sided sandbar that’s one of the most unique in Greece.

Highlights:

Thermal hot springs
Quiet, non-touristy vibe
Ideal final night anchorage

Day 7: Return to Lavrion (26 NM)

On your final day, enjoy a leisurely breakfast and a swim before your return sail to Lavrion. If time allows, stop for lunch and a final dip in Sounion Bay, beneath the famous Temple of Poseidon.

Disembarkation typically occurs by 9:00 AM the next morning.

Tips for a Smooth Cyclades Sailing Vacation

When to Go: The best time to sail the Cyclades is between May and October. The Meltemi winds are strongest in July and August — great for experienced sailors, but may require itinerary flexibility.
Crewed vs Bareboat: Crewed charters are ideal for luxury and stress-free travel, while bareboat charters offer independence for licensed sailors.
Packing List: Bring lightweight clothing, reef-safe sunscreen, deck shoes, and a light jacket for breezy nights.
Provisions: On a crewed yacht, meals are often tailored to your preferences. Bareboat charters may require provisioning in Athens or island ports.

Important Itinerary Note – Plan Accordingly

While the idea of exploring iconic destinations like Mykonos and Santorini on a yacht charter from Athens sounds dreamy, it’s important to plan with realistic expectations.

Distance Matters:
Both islands are located on the far side of the Cyclades, meaning long sailing legs—especially if you’re traveling on a sailing catamaran or monohull (not a motor yacht).

Time Constraints:
A round-trip Athens itinerary including both Mykonos and Santorini typically requires more than 7 days to do comfortably and safely. If you’re limited to a week, expect long sailing days, fewer stops, and the possibility of weather delays due to the Meltemi winds.

Our Tip:
If Mykonos and Santorini are must-sees, consider either:

Starting or ending your charter closer to those islands (e.g., Paros, Naxos, or Santorini itself), or
Extending your trip to 10–14 days for a more relaxed and enjoyable pace.

Still unsure? Reach out — we’ll help you customize the perfect route based on your priorities and timeframe.

Why Book with Songs In The Sails Yacht Charters?

At Songs In The Sails, we specialize in tailor-made yacht charter vacations across Greece. Our deep local knowledge, access to the best fleets, and focus on guest experience make us the go-to choice for families, couples, and groups seeking an unforgettable sailing journey.

We help with everything — from choosing the right boat and crew to creating custom itineraries, provisioning, and even booking special experiences like winery tours, scuba diving, or cultural excursions.

Luxury crewed yacht charters
Catamarans, monohulls, and power yachts
Local support and expert planning
Transparent pricing and white-glove service

Book Your Cyclades Yacht Charter Today

Ready to experience the magic of the Greek islands by private yacht? There’s no better way to explore the Cyclades than by sea — with endless views, vibrant culture, and the freedom to follow the wind.

Call us today: 706-901-7525
Email: yachtcharters@songsinthesails.com
Website: www.songsinthesails.com