Whether you have experienced sailing before or just want a unique Island Holiday in Greece, our Cyclades skippered Sailing Holidays offer an unequalled experience.
The Cyclades has been called one of the great ‘wonders of the world’. Visually, our holiday not only transports you to the epicenter of a geographically stunning paradise on earth, but also tours the origin of the whitewashed, blue-domed, narrow cobbled street beauty of the ‘Cycladic style’ of architecture that permeates & influences much of the world’s idea of Grecian eutopia. Added to that the local Culture, Climate, Cuisine and History, and you have a eutopia that is not just an idea but one that is realized during your voyage with us.
Book with confidence plus lots of extra options
With an Expert Skipper & all associated yacht costs included in the price, your experience is hassle-free with no hidden surprises. Furthermore, our Holiday is backed by Warmpenguin’s extensive range of land tours & partners throughout Greece as well as one of the largest Yacht brokerages in the Mediterranean which means that we can not only guarantee availability with a comprehensive infrastructure & a fleet of over 350 Yachts. but also offer a wealth of choices to make things even easier for you.
From simple airport transfers, to a full pre-sailing 7-night tour of the ‘Classical Greek’ Mainland Highlights with Hotels & Professional Archaeological Guides; Whilst during your sailing we have lots of options, from a chef-on-board, to organized Island Excursions. Just let us know what we can do to make your Holiday perfect & we will fully personalize your Holiday without extra cost.
Our Cyclades skippered sailing holiday combines some of the most beautiful sailing landscapes in the world with the sightseeing opportunities afforded by centuries of Ancient history, from ancient Temples to Byzantine, Venetian & Ottoman Castles, to the quintessential blue-white Cycladic Architecture which adorn a thousand postcards and Instagram shots.
Your choice of islands is large & we normally combine a mix of the most stunning & popular such as Santorini, with more undiscovered gems like Ios. Just scroll down for some info on the islands, suggested itineraries & further details. One caveat to bear in mind when considering the Cyclades for your Skippered Sailing Holiday is that Catamarans are less suitable in the month of August due to windy conditions.
We suggest a general itinerary involving visits to all the islands, but this is very flexible and will always be adapted to the preferences you indicate, be they more time for the beach, for exploring each new destination, or in finding the best restaurant, or deserted beach spot to spend the evening. Prior to departure, we will discuss with you the specific day to day itinerary, but each day your Skipper will also keep you fully informed about the days sailing including any transit times, what you can expect at each destination, and any options you may enjoy, from the best beaches, to recommendations on lots of other aspects from local beauty spots, to where the best fish tavernas are located, so you will be fully informed and can choose the ideal pattern to suit your group.
Our starting prices include all costs
Our prices include the Skipper and all related costs, and are inclusive of the often hidden extras such as fuel, mooring fees, end of port cleaning, insurance, extra bedding etc. so you only have food & drinks as extras. Yacht type is based on our lowest cost, entry-level, fully equipped luxury Yachts. Examples of which are specified in the respective booking category.
Easy Booking Process
You may either use the instant booking facility below, or send us an inquiry. After booking or deposit we confirm price & availability of specific Yachts, including any upgrade or newer models, within a few days. See our FAQ below for details of the booking process. Instant Booking options may also include a choice to select a catamaran Yacht. If you prefer a Luxury Motor Yacht, these are also normally available on request.
Pre-Booking Inquiries are welcome by email to firstname.lastname@example.org or from our contact form.
Examples of our most common Yacht range can be seen HERE.
Despite being closer to Athens, Kythnos remains a crowd free paradise.
Kythnos has drawn people from ancient times for its thermal baths & a modern spa center is in operation today in ‘Loutra’ with its natural spring waters reaching 52 degrees Celsius. Kythnos has 65 sandy beaches & its typical Cycladic rocky landscape is crisscrossed with low stone walls & dotted with around 350 white churches cobbled narrow streets, white houses, and windmills.
The most important local trade center of the C19th, its opulence is reflected in its beautiful neoclassic architecture.
As a former Venetian colony, its main town Ermopouli with narrow streets, traditional whitewashed houses, and many shops & eateries is great for a shore excursion. It retains a Medieval Quarter with a Catholic community that contributed much to the local architecture, such as the fortress-like St George’s Cathedral on St George hill and in general, there is a more eclectic cosmopolitan feel than some of its neighbors.
Regional Capital of the Cyclades, Syros has developed a number of Arts Festivals & has local dishes such as ‘Halva’, ‘loukoumi’, ‘loosa’ & the designated San Mihalis cheese. There are also many beautiful local villages to visit and wide variety of relaxed sandy beaches such as Vári, Foínikas, Yalissás and Kíni, with cafes & tavernas which provide perfect mooring spots.
A hidden-Gem, Tinos is unspoiled by tourism and one of the most important sites of local Pilgrimage in Greece.
Each year, Greeks travel to worship at the church of Panagia Megalochari which sits above the main town and port. Tinos has a long History & its capital has been open to trade & is nicely developed with the local cuisine, local arts & craft shops & cafes to enjoy.
There are around 40 villages on the island and a feature of these you will see when visiting are the ornate Pigeon lofts which were formally a sign of local status as well as food for the islanders. Most notable of the villages are Pyrgos with a marble working history, the picturesque Agapi, and its highest village of Arnados.
When Sailing around the south side of the island there are lots of secluded & organized beaches, with the best being Agios Ioannis, Porto beach, Agios Sostis beach, Agios Romanos.
Mykonos Island is known for its summer atmosphere & has almost surpassed Santorini in recent years as ‘the place to be’.
The capital town (Hóra) is one of the best examples of Cycladic architecture and a spellbinding attraction for visitors with narrow marble streets, whitewashed houses & with colorful doors and window frames, bougainvillea trees in purple bloom and hidden churches. For shopping, the most glamorous place is Matoyánni Street, lined with brand name stores, charming cafés and stylish restaurants & bars. Soak up the atmosphere along the lively waterfront and admire a fleet of fishing boats casting colorful reflections in the azure waters.
One of the most scenic corners of the island is Alefkántra or “Little Venice”, an 18th-century district, dominated by grand captains’ mansions with colorful balconies and stylish windows.
Naxos is the biggest and the greenest island in the Cyclades with lots to explore.
It has high mountains, fertile valleys, lush green gorges, stunning seascapes and traditional villages perched high on mountain tops, where the inhabitants still wear their traditional dress. Naxos is also home to beautiful old churches, monasteries and Venetian castles coexisting with the Cycladic architecture. Its simply one of the most beautiful islands you can visit.
Chora, the capital of Naxos, whose landmark is an imposing Venetian castle, is a unique blend of Cycladic and Medieval architecture, mansions with Venetian blazons still decorating their entrances, narrow arched alleys, catholic churches and fortifications.
There are lots of places to see like the Archaeological Museum, 10th-century Byzantine churches, impressive Caves, and traditional villages. Aperathos for example is a colorful mountainous village home to five museums, stone-built houses, beautiful squares, and narrow alleys paved with marble. Being the most fertile island of the Cyclades, Naxos also has a well developed local agricultural production & cuisine and has significant local festivals such as the Naxos Festival and local wine festival.
Stunningly beautiful Paros was the source of ‘Parian marble’ used for the most sought-after sculptures in Ancient Greece.
Today the island remains unspoiled by tourism & its natural beauty makes it one of the best islands of the Cyclades to visit.
Its capital ‘Parikia’ is full of whitewashed cubic houses and impressive neoclassical mansions with a well-preserved 13th-century Venetian hilltop castle standing in the village center offering an amazing view. The 6th-century church of Panayia Ekatontapyliani and the Archaeological Museum are worth visiting, as is the nearby Islet of Antiparos
Naoussa, & Lefkes are two of its most pretty traditional villages to see, and the beaches such as Chrissí Aktí, Santa Maria, and Poúnda have crystal clear water with impressive white rock formations on Kolymbithres beach, and red and green clay rock formations around Kalogeros beach. Both outstanding natural wonders. We also like to add Hiking & Horse-riding excursions which are available on the island.
Final home to the Poet Homer, Ios is one of the Cyclades most beautiful smaller Islands.
Its Harbour & Capital in Ormos are set in an amphitheater overlooked on the hilltop above by the ruins of a medieval castle. This traditional village is one of the finest examples of Cycladic architecture with twelve windmills, churches with arched belfries and light blue domes
It has many beautiful beaches to enjoy such as Mylopótas, Magganári, Psáthi, Yialós, Kálamos and Ayia Theodóti known worldwide with emerald waters, and many local dishes such as stuffed zucchini flowers, sun-dried picarel tsimétia (stuffed vegetable marrow flowers), ‘dolmadákia’ with fresh vine leaves from the numerous vineyards & cheeses like ‘skotíri’ (soft goat cheese with herbs).
Santorini is a group of islands, which are the rims of an ancient Volcano set around its central ‘Caldera’.
Firá is the picturesque capital of the island; perched high up on the edge of the Caldera, it looks like a marvelous painting. Firá, together with Oia, Imerovígli and Firostefáni located high above on a cliff, make up the so-called “Caldera’s eyebrow”, the balcony of Santorini, which offers an amazing view of the volcano. Other famous smaller villages are Akrotíri and Méssa Vounó, with their famous archaeological sites.
Santorini had developed as a luxury destination so there are plenty of high-end restaurants that take advantage of the local produce such as cherry tomatoes, white eggplants, fava, caper and “hloró tyrí”, all high in natural flavour grown in the volcanic soil. Similarly, there are wonderful local grape varieties like Assyrtiko, Aidani, and Mavrotragano producing distinct wines to enjoy.
With so many other islands with great sand beaches, and with sailing the Caldera one of the most beautiful experiences in Greece, Santorini is perhaps best enjoyed for its sailing, shore excursions & amazing views rather than for pure ‘beach time’. However, there are unique volcanic beaches with white, red or black sand or volcanic pebbles, spectacular rock formations and impressive lunar landscapes to uncover.
Named after the son of king Minos, Folégandros is a real off-the-beaten-path destination with untouched beaches & luminous blue waters
The Capital ‘Hora’ is partially built in a Venetian Castle with the balconies of its sugar-cube whitewashed houses full of bright colorful Bougainvillea’s, and sheer cliff drops convey the island’s ethereal, yet wild, beauty.
Ano Merá, a 19thC settlement is one of its many picturesque villages to see whilst only reachable from the sea you will find the natural cave of Chrysospiliá with impressive stalactites and stalagmites and inscribed with the names of ancient Greeks dating from the 4th Century BC.
Folégandros has many great beaches such as Hohlídia, Vitzétzo, Latináki, Pountáki and Livádi, a village with a sandy beach & turquoise waters. Kátergo is perhaps the most beautiful beach on the island, with thin pebbles and crystal-clear waters whilst Sheer cliff drops and azure waters embrace Agali beach to the west of the island.
For Sailing, Milos provides some of the most distinctive coastline with its rocky arches, caves, white cliffs & beaches.
The island’s villages are lovely too: from the stately capital, Pláka, the harbour of Adámantas, the beautiful Hivadolímni, the marvellous Emporiós with the little lagoon of Revary and the old iron mines.
For sightseeing there are early Christian catacombs, a prehistoric settlement in Fylakopi and the mining museum worth visiting and the Island offers some unique gastronomy. There are thermal springs and underwater paradise caves for diving enthusiasts.
With 80 amazing beaches, Milos is a great sailing experience with standouts being Sarakíniko and Kléftiko, and don’t miss, the open cave of Papáfragka.
The Islands cley soil & sun helped the ancient inhabitants of Sifnos develop as the pottery center of the Cyclades
Throughout the island there are many pottery workshops where you can buy ceramics for domestic use, utensils and decorative items
Apollonía, the capital town of Sífnos is built in the shape of an amphitheatre over three hills in the centre of the island and its narrow streets and whitewashed houses form a beautiful, traditional Cycladic settlement perfect for evening walks. Whilst a few kilometres away lies the traditional settlement of Artemónas, famous for its neoclassic mansions and its outstanding panoramic view of the island and where you will find some of the most famous restaurants and patisseries
The beaches in Sífnos offer azure waters and sun-drenched sandy beaches. Kamáres, the port of the island, is a sandy beach with trees and beach bars; Platís Yialós is the most cosmopolitan and buzzing beach in the island, whereas next to it lies Vathí, a sandy beach with shallow waters and many tavernas where you can enjoy fresh fish.
Serifos is a charming Island with a wild landscape embraced by the deep blue colours of the Aegean.
Traditional blue & white Cycladic Architecture dominates and the island offers a relaxed holiday with some nice local Festivals and well-developed outdoor activities such as hiking, climbing, mountain biking and diving!
Its elegant main town ‘Chora’ is built amphitheatrically on a rocky hill commanding the island from the top & is an ideal place for taking a stroll or making a stop by the nearby cafés, fish tavernas, and pastry shops. Located next to the seashore is the Serifos main Port, also known as Livadi. This area has a beautiful sandy beach but is also very close to Avlomonas and Livadakia beaches. Serifos also has a vibrant local cuisine with dishes like louzes, syglina (traditional cured pork) and sausages, as well as the island’s rich aromatic spices, marathotiganites (fennel pies baked or fried), as well as excellent local wines.
All our Cyclades skippered sailing holidays can be carried out with either Catamaran, Sailing Yacht or Motor Yacht. However, each vessel type has slightly different suitabilities. Catamarans are ideal for families. They are very stable and are perfect for the short hops around the Ionian Islands for example which have little or minimal wind even in August when the Cyclades can experience windy conditions. Sailing Yachts are suitable for all and are equipped with an engine to assist sail power so all the inter-island distances in each of our itineraries can be covered comfortably. Motor Yachts, without sail, offer the most speedy travel & are ideal for those who want to spend less of their time ‘hopping’ & more time sightseeing.
Options! Options! Options!
Why not combine your Cyclades skippered Sailing Holiday with a land-based itinerary or professionally guided activities. With our partners throughout Greece and years of experience, we are able to offer many additional exciting options to make your time together hassle-free, and designed to get the most out of your Greek experience. From multi-day Private Archaeological Site Tours of the mainland & other excursions to, a week’s Hiking & Biking tour in some of the most amazing landscapes in Greece, to simple airport transfers. Just ask for details & let us know your preferences.
FAQ / Cyclades Skippered Sailing
From single Guests to flotillas, we can cater for any number.
For our Cyclades skippered sailing holidays, Athens is the departure location. The exact Marina will be communicated after booking and transfers are also available if required.
Transfers / Airport Transfers.
Arranged from all locations in Greece on request.
Booking Process & Policy
3 Easy Steps
You may either use the instant booking facility or send us an inquiry. In 7-Days or less we then confirm price & availability of specific Yachts, including any upgrade or newer models you can also select. A deposit of 50% is required to confirm booking. Regards paperwork we need the name. Address, Nationality of the main Charterer. We will send you the charter contract for review.
Prior to 30 days before arrival you send us the Passport or ID number / Nationality, DOB & Address of all participants – required by law for search & rescue administration. The final payment for the Yacht is required.
On check-in you will sign the charter contract & pay the security deposit which is fully refundable.
SECURITY DEPOSIT (compulsory) Upon Embarkation paid ONLY by CREDIT CARD. Sailing yachts ≤ 40’ 2.000 Euro, Sailing yachts ≥ 41’ & catamarans 3.000 Euro
ADDITIONAL TOURS & SERVICES. We would also love to hear about any preferences you may have, or the need for any other services you may need such as excursions or transfers so we can include everything in your itinerary.
Cancellation Policy – Cyclades Skippered Sailing
30 days before charter: 100% of total charter price 30 – 60 days before charter: 50% of total charter price 60 days or more before charter: 30% of total charter price
Skippers. Will they fit with my group?
Foremost, your skippers job is to navigate you through your various destinations with safety as an absolute primary priority.
Secondly, our skippers are all highly qualified professionals who are very experienced with hosting all types of groups with the utmost consideration for the privacy and needs you will have along your voyage.
A key part of their role with you will be in laying out each day’s itinerary in terms of what you can expect, transit times, and any details you would like to know, from recommending the best places to eat, to discussing any & all options for visiting the local beauty spots & moorings at each new location. Your skipper’s aim is to provide you with the best experience possible so you will find him/her to be flexible & helpful throughout.
Chef or Host/ess
Ideal for larger groups of flotillas, adding a Chef or Host/ess will give you much more hands-free time & is also a very economical option when sharing the cost between group members. Daily total costs (not per person) are from 150 Euro for a chef and 130 Euro for a Host/ess.
Groceries. Where can we shop for food?
Each location has a range of Markets / Mini-Markets & shops where you will be able to buy what you need. At most destinations each day it is also possible to order provisions for delivery to the boat, and order takeaway food also. Your skipper will always be happy to coordinate this for you and communicate anything on your behalf whenever necessary.
Accommodation. What is included?
Each Yacht has everything you will need for a week including bedding with changes, and a well-equipped kitchen with a gas stove & oven. Just think of the things you may expect in a hotel room with a catering facility.
What should we pack?
Just think of that Cyclades beach holiday with a mix of swimming, exploring, relaxing & sightseeing. Light clothes are best with a hat, sunscreen & rubber-soled shoes. Even in the summer months, the evenings can sometimes be cool so a light sweater or weatherproof jacket, & if visiting at other times of the year one or two more layers.
Don’t forget your swimwear, beach towels & flip flops! Not a lot else is necessary.
Snorkel gear is normally included but if you need any over or undersize masks just let us know. Additional gear such as paddleboards may be added on request.
What is the best time of year for Sailing in Greece?
The sailing season in Greece starts around mid-April and ends in late early November. For our Cyclades Skippered Sailing Holidays, you can expect almost perfect sunny hot weather between June to September with warm water temperatures often extending into November.
Do temperatures & conditions vary in the Cyclades?
The Cycladic Islands have strong seasonal winds ‘meltemi’ during July and August which start blowing moderately around mid-June. September is the best time to visit for less experienced sailors when the winds calm down and the weather is perfect. Rain is rare in the Summer months & temperatures are similar to those of the Ionian Islands, but the air is slightly cooler & dryer. Inter-Island distances are longer in these islands which can mean longer sailing times. In general, Catamarans are less recommended for the months with the wind, and these Island Itineraries are perhaps best suited to Motor Yachts which will cover distances more easily.
Can you arrange Hotels & extra land Tours for us?
Of course! We have years of experience & partner with Hotels & Activity Partners throughout Greece as an essential part of what we do. We specialize in personalized itineraries so we can accommodate most additional needs.
an I talk to a real person about cyclades skippered sailing?
If you want to ask us anything about our Cyclades skippered sailing holidays you can message us via the WhatsApp or messenger channel on our site (bottom corners of the screen), email us at email@example.com or use the Contact Form. You can also just call us directly on (0030) 6955297050, request a Skype call, or set up a zoom meeting HERE. We would love to hear from you!
Can I Tailor a different itinerary with shorter or longer duration?
Yes. Just contact us & let us know what you prefer.