CYCLADES GREEK ISLANDS
SAILING TOUR

A guided sailing escape through Greece’s island gems — Big experiences, warm welcomes, and quintessential harbour towns.


6 to 20 June 2026
15 Days / 14 Nights

From A$5,995 per person
Group Size: 16 - 24 pax average

Start: Athens, Greece
Finish: Athens, Greece

FIND YOUR PERFECT SAILING HOLIDAY: FREE GUIDE

Sail the stunning Cyclades Greek Islands!


Discover the quieter side of the Greek Islands – whitewashed villages, seafood lunches by the water, and lazy afternoons under sail. You wake to the gentle rock of the yacht, a coffee in hand and a perfect blue bay at your feet. From the volcanic curves of Milos to the elegant charm of Sifnos and the untamed beauty of Kithnos, this is the Cyclades beyond the crowds — a string of Aegean gems waiting to be explored.

These are the classic Greek Islands you’ve seen in your daydreams — white buildings spilling down hillsides, fishing boats bobbing in tiny harbours, olive groves and sun-bleached stone. But here, in the western Cyclades, you’ll experience it all without the busyness of the more tourist-trodden islands further east.

Sail with a small group of like-minded travellers, guided by a professional skipper and host. Whether you're an experienced sailor keen to take the helm or a first-timer happy to relax and watch the coast drift by, this is a Greek island adventure that blends freedom with ease.

Itinerary Highlights
• Explore the dramatic coastline of Milos, including the sea caves and white cliffs of Kleftiko, only accessible by boat
• Wander the whitewashed laneways of Sifnos, then sip ouzo as the sun sets over the harbour
• Soak in the natural hot springs of Kithnos after a morning sail
• Drop anchor off the rugged coastline of Serifos, with time to hike, explore, or just unwind
• Swim in the turquoise bays off Poliegos — uninhabited and utterly peaceful

Explore Our Rates
Find the Perfect Option for You!

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

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

From AU$5,995 per person - double share
From AU$8,995 per person - solo traveller in a private cabin
Price includes private cabin with private bathroom on a Dufour 470 and a professional skipper also onboard.

BOOK NOW

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

From AU$4,995 based on 8 people sharing 47ft yacht

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 15-min 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?

Sailing Itinerary

Day 1 - Saturday
Welcome to Greece!
Arrive in Athens and make your own way to Alimos Marina. We’ll embark the yachts mid afternoon before sailing to a nearby bay where we will anchor for the evening and then enjoy welcome drinks onboard.

Day 2 - Sunday
This morning we'll sail to Kythnos, with a swim stop at Kolona Beach before heading ashore to explore the town of Merichas. Dinner is included tonight.

Day 3 - Monday
Spend a full day enjoying Kythnos. Kythnos is an unspoiled Greek Island mostly attracting Greek tourists. Locals are very friendly and life is slow. Explore this quiet island with its empty sand beaches and traditional villages.

Day 4 - Tuesday
Our destination for today is Platis Gialos, on the island of Sifnos.

Day 5 - Wednesday
Spend the morning relaxing or swimming at a nearby beach, before we take a local bus to the town of Apollonia for lunch. After lunch, we recommend a visit to the town of Kastro, which boasts the most photographed site on Sifnos, a small white church with blue dome. Lunch is included today.

Day 6 - Thursday
Today we will sail to Adamas, Milos. Dinner is included tonight.

Day 7 - Friday

Enjoy a full day exploring Milos. Spend the day swimming (Milos is famous for it's beaches!) or visit the main town Plaka for a magnificent view of the gulf of Milos.

Day 8 - Saturday
Spend the day circumnavigating Milos. A highlight of this sail will be a visit to Kleftiko cove. Tonight we will anchor in the beautiful bay of Pollonia.

Day 9 - Sunday
Set sail for Livadi, Serifos. Time and wind permitting we will stop at Kimolos or Poliegos islands for a swim and lunch stop. Dinner is included tonight.

Day 10 - Monday
Full day to explore Serifos.
Serifos is a quiet, traditional Greek Island with the main town perched high above the port. A visit to the main town (Chora) is highly recommended and easily reached by local bus.

Day 11 - Tuesday
Today we sail to Loutra, Kythnos. Spend the afternoon exploring Loutra, famous for its warm sulphurous spa-waters used since ancient times. Dinner is included tonight.

Day 12 - Wednesday
Visit the Archaeological Site of Karthaia, before sailing to Vourkari town, on the island of Kea, to discover a traditional slice of the Greek Islands.

Day 13 - Thursday
If you are feeling energetic this morning, we recommend climbing to the hilltop chora to experience daily life in the village. Return to the port via the old Roman road with great views to the sea as you descend.

After lunch, we'll sail to Cape Sounion and anchor beneath the stunning Temple of Poseidon, with time to explore the site before dinner.

Join us for a fun final dinner tonight to share your favourite stories from the trip. Dinner is included tonight.

Day 14 - Friday
Enjoy a leisurely morning relaxing or swimming, before we embark on our final sailing day and head back for our last night in Alimos marina.

Day 15 - Saturday
Disembark and continue onward with your adventures of Greece or beyond.

What's included?

• 14 nights’ overnight accommodation on yacht

• Welcome Drinks
• 1 lunch & 5 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 Kithnos, Sifnos, Milos, Serifos and Kea

• 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 AU$350 per day + food + cabin
• Personal travel insurance
• On board provisioning or meals ashore for meals not included
• 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
• 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
• Single supplement may apply for private cabins
• The prices are correct at the time of issue but subject to change without notice


Enquire now to book your tour or to learn more about sailing in
Greece in 2026