16 to 30 September 2023

15 Days / 14 Nights

Group Size - 30 pax average

Start: Lavrion, Greece
Finish: Lavrion, Greece


We still have availability for our Ionian Greek Islands Sailing in July 2023!

Click here for more details!

A combination of sailing, food, and adventure, our Cyclades Greek Island Sailing trip offers travellers a unique way to experience the famous and spectacular Greek Islands. There is no level of experience required, just bring your sense of adventure!

This guided sailing holiday explores the western Cyclades from Lavrion, including the islands of Milos, Sifnos, Kithnos, Serifos, and Kea, all hidden gems of the Aegean Sea. So why not jump on board a self sail or skippered sailing yacht and spend two weeks sailing, relaxing and exploring.

Greece is where it all started for Mariner Boating, it’s a country that we hold dear to our hearts and we can’t wait to share it with you once more.

Pricing options


Why Mariner Boating Holidays?

Small group comfort
You’ll sail in comfort as part of a small group of yachts, sometimes called a Flotilla or Yacht Rally. Usually you'll be sailing with around 30 people across 4 to 5 yachts.

More time to explore
Our tours give you more time to immerse yourself and really get a feel for the destination. Our trips also include more leisure days where you can choose how to spend your day!

Flexible joining options
Our trips are designed so that everyone can sail with us - single travellers, couples or larger groups/families! For 1 or 2 people we offer the option of booking a cabin (max 6 guests plus a professional skipper on the yacht), whilst groups and families can book the whole yacht for themselves.

30+ years of experience
We've been doing this awhile and tend to know a secret spot or two. We know you want to visit the main sights (and why wouldn't you!), but we also love to share our favourite spots you might not find otherwise.

Your guides
A Mariner Boating guide and a local technician will travel with you to assist with the yachts, berthing, provide navigational support and have intimate local knowledge of things to see and do along the way.

Your travelling companions
Every group is different, but typically you’ll find your co-travellers will be aged between 40 and 65, enjoy keeping active, love the ocean, have a sense of adventure, love fine foods, an occasional glass of wine, and a good chat.

Is this trip right for me?

Do I need to know how to sail?
Absolutely not - the only "qualification" for joining our sailing tours is a desire to see yourself on the deck of a sailboat in one of the great travelling destinations of the world

That being said, if you wish to book a whole yacht you will need to either have International Certificate of Competence (ICC) or organise a professional skipper.

Will I have my own bathroom?

While vessel layouts will vary depending on which yacht you choose, most yachts generally have cabins with a private bathroom attached or just outside.

If you book a cabin we will always guarantee a private bathroom, but if travelling as a group on your own yacht you may need to share.

What's life on board like?
Our yachts are modern and comfortable with areas to relax both below and on deck. Most yachts have 4 double cabins and are usually less than 5 years old. Below deck you will find the kitchen (galley) where you can prepare meals with the option to dine at the adjacent table or on deck in the open air.

So throw down a cushion, curl up and read a book, or make use of the easy access to the water for a swim.

Will I get seasick?
Sea legs come naturally to some but unfortunately not so much for others. Your Mariner Boating guide will be able to suggest some options to help you with the effects of sea sickness if needed. The majority of this trip is on a yacht though so you will need to feel comfortable moving about the vessel, including using the stairs to get to cabins etc. below deck.

Sailing Itinerary

Day 1 - Saturday
Arrive Athens Airport and make your own way to Lavrion.
We’ll embark the yachts then enjoy welcome drinks and overnight on board the yachts at the marina.

Day 2 - Sunday
This morning we'll sail to Kythnos, for 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 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 today, 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.

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 Lavrion marina.

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

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

What's included?

• 14 nights’ overnight accommodation on yacht
• 1 lunch & 5 dinners ashore during the sailing itinerary

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

Also included:
• Berthing/marina fees for first nights in Lavrion, Kithnos, Sifnos, Milos, Serifos and Kea

• Bed linen and bath towels for two weeks
• 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$285 per day + food + cabin
• Personal travel insurance
• Reduced refundable yacht security deposit payable at the base
• 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

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 check availability or to learn more about exploring
the Cyclades in 2023