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GUIDED SAILING TOURS
2026: Cyclades Greece Sailing Tour2026: Greek Islands Sailing Week2026: Sweden Sailing Tour2026: Corfu Greece Sailing Tour2027: Thailand Islands Sailing2027: Greece Ionian Sailing2027: Cyclades Greek Week Sailing2027: Amalfi Italy Sailing- Learn More About Our Tours- Searching for Somewhere Different?
YACHT CHARTERS
GULETS
ABOUT US
ReviewsFAQsSailing QualificationsMeet Your Fellow Travellers
CONTACT US
BOOK NOW

SAIL THE GREEK ISLANDS
THE CYCLADES

A guided sailing experience through the Cyclades Islands – ideal for those short on time, this one week tour offers the chance to explore quieter Greek islands, swim in clear waters, and wander through whitewashed villages.

19 to 26 June 2027
8 Days / 7 Nights

From A$3,495 per person
Group Size: 12 -18 pax

Start: Paros, Greece
Finish: Paros, Greece

FIND YOUR PERFECT SAILING HOLIDAY: FREE GUIDE

Sail the stunning Cyclades Greek Islands!


Discover a more relaxed side of the Cyclades – whitewashed villages, clear blue bays, and long lunches by the water, where each day blends sailing with time to explore. You wake to calm anchorages, coffee in hand, with another island just a short sail away.

From the volcanic coastline of Milos and its hidden sea caves, to the traditional charm of Sifnos, the laidback feel of Antiparos, and the lively harbours of Paros, this is the Cyclades at a gentler pace – away from the busiest island crowds.

You’ll sail with a small group of like-minded travellers, guided by a professional skipper and our Mariner Boating Tour Leader. No sailing experience needed – just come onboard, settle in, and enjoy island life by sea.

Itinerary Highlights
• Explore the dramatic coastline of Milos, including sea caves and hidden coves only accessible by boat
• Wander the whitewashed villages of Sifnos and enjoy a traditional waterfront meal in the evening
• Swim in the clear bays around Antiparos, with time to relax in its laidback island atmosphere
• Drop anchor in quiet bays along the way for swimming, snorkelling, and easy coastal sailing

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Explore Our Rates - Find the Perfect Option for You!

There are several ways for you to experience our amazing Cyclades Greek Islands sailing trip!

Travelling by yourself or with a friend/partner? Book a cabin!

Cabin for Two: AU$3,495 per person
Cabin for One: AU$4,995 - solo traveller in a private cabin

RESERVE CABIN NOW

Travelling with your friends or family in a group? Book a yacht!

Prices start from:
AU$3,395 per person based on 6 people sharing yacht
AU$4,295 per person based on 4 people sharing yacht

ENQUIRE NOW

Still unsure? Let’s talk.

Sarah, our trip director, has guided hundreds of people through this decision. She’s happy to answer questions, share stories, and help you figure out if this is right for you — no pressure.

BOOK A CALL WITH SARAH

🔍 Why Travel This Way?


• See Greece differently - We avoid the crowds, skip the bus tours, and sail straight into coastal towns and quiet coves.
• No sailing experience needed - Just a love for the sea and a sense of curiosity.
• Already a sailor? You’ll love the chance to crew, helm, or even charter a whole yacht with friends.
• Your hotel moves with you - No packing, no logistics, just fresh places and sea air each day.
• Local insight - Your guide handles the planning, bookings, and inside knowledge so you can focus on the experience.

WHAT MAKES OUR TRIPS UNIQUE?
IS THIS TRIP RIGHT FOR ME?

Cyclades Greece Sailing Itinerary

Day 1 - Saturday
Welcome to Greece!
Arrive in Athens and make your way to Alimos Marina for check-in. Settle aboard the yachts before a short sail to Antiparos, anchoring near town for your first night. Enjoy welcome drinks onboard as you ease into island life.

Day 2 - Sunday
Enjoy a relaxed morning sail to Sifnos, with swim stops along the way. Arrive at Platys Gialos and settle into this laidback coastal setting for the evening.

Day 3 - Monday
Sail to Milos, exploring the southern coastline and quiet bays along the way. Anchor overnight in a peaceful setting surrounded by dramatic volcanic scenery.

Day 4 - Tuesday
Spend the morning exploring the iconic sea caves of Kleftiko before continuing to Adamantas. Moor in town for the evening, with time to explore the harbourfront.

Day 5 - Wednesday
Spend the morning in Milos with a visit to Chora (Plaka), exploring its whitewashed lanes and island views before a short sail across to Kimolos. Arrive in the afternoon and enjoy this quieter Cycladic island.

Day 6 - Thursday
Sail back towards Antiparos, stopping in the Despotiko area for swimming in clear, calm waters. A relaxed day on the water with time to unwind and explore hidden bays.

Day 7 - Friday
Enjoy a leisurely morning of swimming and sailing before returning to Piso Livadi. Spend your final evening ashore in this traditional harbour village.

Day 8 - Saturday
Disembark after breakfast and continue your onward travels.

What's included?

• 7 nights’ accommodation on yacht

• Welcome Drinks
• 2 dinners ashore during the sailing itinerary

• Professional skipper onboard if booking a cabin
• 24/7 support from experienced guide
• 24/7 professional technical assistance for the yacht

Also included:
• Berthing/marina fees for first nights in Sifnos, Milos, Kimolos and Paros (Piso Livadi)
• Bed linen and bath towels
• Standard navigation equipment
• End of charter cleaning
•  Daily weather updates, regular newsletters with activity suggestions and local information

Additional costs
• All flights
• Pre & Post Accommodation or land arrangements e.g. transfers
• Local tourist taxes & National Park fees
• If you require a skipper the total cost is approx. AU$350 per day + food + cabin
• Personal travel insurance
• On board provisioning or meals ashore for meals not included
• Refundable security deposit for yacht (not applicable for cabin bookings)
• Fuel for the yacht and outboard motor (Estimate AU$300 total)
• Drinks during dinners or tours ashore are not included unless specified
• For cabin bookings, please allow approx.100 EUR for a local "kitty" to contribute to fuel plus skipper's meals and gratuities.

Travel Insurance
Travel insurance is strongly recommended by Mariner Boating Holidays. Travellers should ensure they have a valid policy at time of booking. Your travel insurance policy must provide cover against personal accident, death, medical expenses and emergency repatriation with a recommended minimum coverage of US$200,000 for each of the heads of cover. MBH also strongly recommend it covers cancellation, personal liability and loss of luggage and personal effects.

Please Note
• A deposit of AU$1,500 per person is required to confirm a booking
• Full terms & conditions for trip can be viewed here
• The designated skipper on board your yacht must possess suitable experience and qualifications
• Prices are subject to currency fluctuation until paid in full
• Credit card transactions are subject to merchant fees
• The prices are correct at the time of issue but subject to change without notice

⚓️ Cyclades Greece Guided Sailing FAQs

1. When is the best time to sail the Cyclades?

The June–September season offers reliable winds and clear skies. We sail in June, when conditions are warm and pleasant before the stronger Meltemi winds arrive.

2. How windy are the Cyclades compared to other Greek islands?

They’re generally breezier, but our experienced skippers plan routes and timing for comfort and safety — and sailing in June keeps conditions ideal.

3. What are the highlights of the Cyclades sailing route?

Expect the whitewashed villages of Sifnos, the beaches of Milos, and the traditional atmosphere of Antiparos, all linked by sparkling open-water passages.

4. Do I need sailing experience?

No at all, our team manages all the sailing. You can take part if you like or simply relax and enjoy the view.

5. Where do Cyclades sailing holidays start and finish?

Our Cyclades sailing tour departs from Paros and return there at the end of the trip. Along the way, you’ll visit a selection of beautiful islands including Sifnos, Milos, and Antiparos, exploring charming villages, stunning beaches, and crystal-clear waters.

6. Why doesn’t the Cyclades sailing trip include Santorini or Mykonos?

These islands are stunning but extremely crowded in summer. Streets can be shoulder to shoulder and harbours packed with day-trippers and cruise ships, which makes it hard to enjoy the relaxed island feel. Instead, we visit Antiparos, Milos, Sifnos and Kimolos — islands that offer the same whitewashed villages, turquoise bays and incredible food, but with space to explore and a more authentic Greek atmosphere.

Still have questions about our Cyclades Greece Sailing Trip?
Contact us — we love to chat travel.