Cyclades: Sailing Itineraries & Yacht Charter Tips


This post is also available in: Français

The Greek Cyclades are one of the most picturesque and alluring destinations in the world, with their crystal-clear waters, white-washed villages, and stunning natural landscapes. If you are looking for the ultimate yachting adventure, then a trip to the Greek Cyclades should definitely be on your list. With a plethora of beautiful islands to explore and an array of activities to enjoy, from swimming in hidden coves to dining in traditional tavernas, a yacht charter in the Cyclades promises to be an unforgettable experience. In this blog post, we will guide you through the ultimate yacht charter itinerary routes in the Greek Cyclades, highlighting some of the best spots and hidden gems along the way. So, get ready to set sail and immerse yourself in the beauty of the Greek Cyclades.

Why the Greek cyclades should be on any sailor bucket list ?

The Cyclades: a true sailing paradise

Sailing in the Cyclades should undoubtedly be on everyone’s bucket list because it presents a unique blend of history, awe-inspiring natural beauty, ideal climate, well-equipped marinas, and diverse island experiences. The Cyclades region, located in the Aegean Sea, is a true sailing paradise that attracts numerous sailing enthusiasts, history buffs, and adventure seekers from all over the world.

The Cyclades boast an incredible historical wealth

This iconic Greek archipelago is deeply rooted in ancient history, mythology, and culture. Stepping ashore on islands like Delos, the birthplace of the gods Apollo and Artemis, opens a window to a time when Greek civilization was at its peak. Visitors have the opportunity to wander through well-preserved archaeological sites, including ancient temples, theaters, and other fascinating relics from a bygone era. This rich history allows sailors to immerse themselves in an enchanting journey through time as they set sail from island to island.

The Cyclades region encompasses over 200 islands, each with its unique character, providing a diverse experience for those who wish to explore the area. While every island has something special to offer, some of the most notable ones include Santorini, Mykonos, Naxos, and Paros. These islands are well known for their picturesque white-washed buildings, stunning sunsets, crystal-clear waters, and charming local life. As sailors traverse the Cyclades, they are presented with unparalleled beauty, unique landscapes, and an ever-changing horizon, offering a genuine sense of discovery and adventure.

The Mediterranean climate

The Mediterranean climate makes the Cyclades a perfect sailing destination, with warm summers, mild winters, and consistent northerly winds (the Meltemi) during the peak sailing season from June to September. These conditions make for smooth sailing and a pleasant, comfortable experience exploring the islands. This wind pattern also creates a natural cooling system on the warmest days, ensuring that visitors can fully embrace their time at sea, as well as ashore.

The island’s extensive network of marinas

The island’s extensive network of marinas further enhances the sailing experience in the Cyclades. These modern marinas offer an array of facilities, such as electricity, water, fuel, and other amenities, making travelers’ lives easier and providing the necessary support services for a safe and enjoyable sailing trip. Additionally, many of these marinas are situated near picturesque towns and villages, allowing for a delightful blend of sailing and land-based exploration.

Beyond the marinas, the abundance of secluded coves, private bays, and pristine beaches allow sailors to anchor in tranquility and bask in the unspoiled beauty of the region. The countless small islands and islets that dot the Cyclades archipelago create a sense of mystery that sailors can unravel as they chart their own courses.

The Greek Hospitality

The Cycladic hospitality encourages visitors to immerse themselves in authentic local experiences. Indulging in the savory flavors of traditional Greek cuisine in quaint tavernas, participating in local customs and celebrations, or simply sharing a heartfelt connection with locals make for unforgettable memories.

When is the best period to sail in the Cyclades?

Seasonality is another aspect to contemplate when determining the trip’s duration. The Cyclades’ peak tourist season ranges from June to August, with July being the busiest month. During this time, expect warm weather, lively atmospheres, and crowded ports. Conversely, a sailing trip in the shoulder seasons (May, September, and October) will serve up a more serene environment, cooler temperatures, and numerous mooring options. Travelers with limited availability or seeking a more tranquil vacation may find a week-long trip outside peak season ideal, whereas adventure-seekers might treasure a two-week journey immersed in the bustling summer ambiance.

Ultimately, the suitable length for a sailing trip in the Cyclades relies on one’s personal objectives, interests, and constraints. Whether opting for a relaxing week surrounded by azure waters or embracing an extended voyage that delves deep into the islands’ rich history and charm, the Cyclades are bound to captivate and leave you yearning for more.

Which islands should you not miss?

Paros, one of the most popular islands in the Cyclades

Imagine taking a leisurely island-hopping adventure through the beautiful Cyclades. Don’t forget to make a pit-stop at the stunning island of Paros, conveniently located in the heart of it all. With its exceptional ferry connections to neighboring islands like Santorini and Naxos, Mykonos makes for a perfect basecamp. But it’s not just the location that’s a draw – the island also boasts some of the most stunning beaches around. Take Golden Beach, for example, with its crystal-clear waters and perfect windsurfing conditions.

And when you need a break from the sun and sand, head to the charming capital of Parikia. This lovely town is full of winding alleyways, whitewashed buildings, and picturesque squares. For something livelier, don’t miss Naoussa, a vibrant fishing village in the island’s north. The traditional architecture and bustling atmosphere are not to be missed. On the paradisiacal island of Paros, history comes alive through ancient ruins and iconic monuments. As a hub of marble mining, the island offers a unique chance to touch stone that once graced legendary sculptures like the Venus de Milo. And when it comes to food, Paros delivers just as impressively with its fresh seafood, traditional Greek dishes, unique Parian cheese, and locally-produced wine. Savor the tastes of the island as you explore its rich history, and immerse yourself in a sensory wonderland unlike any other.

Mykonos: an island in the middle of most itineraries

Gorgeous beaches and a vibrant nightlife are two of Mykonos‘s most well-known attractions worldwide. Mykonos, which is located right in the center of the Cyclades and has numerous direct flights from all over Europe and beyond, is also a fantastic site to start your sailing vacation.

Santorini: an island in the Cyclades that is stunning from a yacht

Over 3,500 years ago, Santorini was completely destroyed by a volcanic eruption, leaving behind black-sand beaches, high lava-sculpted cliffs in kaleidoscopic hues, and a scattering of smaller islands. Go from Santorini to two nearby lava islands: Nea Kameni, which has a strikingly gloomy environment, and Palea Kameni, where you may experience the restorative power of natural hot springs. The majority of cruises pass via Oia, a picturesque village with white houses that slope down to the sea.

Read also: 5 Yachts For Charter You Can Book Under 70k€

How long should your sailing trip in the Cyclades be?

When planning a sailing trip in the Cyclades, it is crucial to consider various factors to ensure a memorable and fulfilling experience among its stunning islands. The ideal duration for your sailing adventure hinges on several aspects such as personal preferences, desired pace of travel, time constraints, and specific island destinations. 

Experience a 7 day charter for a good introduction to the Cyclades

As a starting point, a week-long sailing trip is often recommended for first-time visitors to the Cyclades. This duration allows sufficient time to explore and absorb the magical allure of the islands, while also maintaining a relaxed pace. Within a week, one can typically visit 5 to 7 islands, spending a day or two on each. This will afford ample opportunity to indulge in picturesque landscapes, idyllic beaches, delectable cuisine, and rich cultural experiences.

Extend your holiday to 10 days to explore the most of the hot spots of the Cyclades

For those with more flexible schedules or a penchant for immersing themselves in every destination, a two-week sailing voyage might be more appropriate. With more than 20 inhabitable islands in the Cyclades, an extended itinerary enables a more in-depth exploration of both popular and lesser-known gems. Sailors can appreciate the enchanting differences between the bustling streets of Mykonos, the awe-inspiring archaeology of Delos, and the tranquil charm of Paros. Beyond that, allocating extra time offers the serendipitous luxury of adjusting plans according to the whims of weather and personal interests.

Read also: 5 Islands to Visit on a Private Yacht Charter in Greece

The Perfect Starting Point: Embark on Your Yacht Charter Adventure

The sailing itineraries in the Cyclades typically begin from either Athens, the capital city of Greece, or from various departure points within the Cyclades itself, depending on the travelers’ preferences and requirements.

Athens departures: a convenient option for the ones coming to Greece by plane

Departing from Athens is a convenient option for those who arrive in Greece by air, as the city’s international airport, Eleftherios Venizelos, connects with numerous destinations worldwide. Athens serves as an ideal starting point for sailing excursions, since it efficiently incorporates the vibrant city life and historical attractions before embarking on a mesmerizing journey across the azure waters.

The marinas in Athens, particularly Alimos and Lavrio, offer a wide range of yacht and sailing boat rentals, enabling visitors to choose the most suitable option as per their needs. Apart from the convenience of booking and services availability, departing from Athens allows tourists to start their voyage by sailing along the Saronic Gulf’s picturesque coastline and soaking in the rich ancient Greek history.

Departures in the middle of the Cyclades: a better way to explore the area during shorter sailing trips

On the other hand, for travelers seeking a more localized experience, especially those planning shorter sailing trips, departure points within the Cyclades may be a preferable choice. Focusing on the prime island destinations such as Mykonos, Paros, and Naxos, to name a few, these mid-Cyclades starting points allow a more immersive and time-efficient exploration of this idyllic archipelago.

By choosing such departure locations, sailors can charter their desired vessels from local companies, interact with the island community, and create a customized travel itinerary, incorporating hidden gems and off-the-beaten-path locations. This approach also supports local economies and promotes sustainable tourism.

Island-Hopping Bliss: Yacht Charter Itineraries from Mykonos to Discover the Best of the Cyclades

Mykonos is located in the heart of the Cyclades, which means there are plenty of stunning destinations to explore. From the picturesque town of Paros to the secluded beaches of Naxos, you can create a customized itinerary that suits your preferences.

Hopscotch Through the Cyclades: An 8-Day Yacht Charter Itinerary from Mykonos

Day 1

Start your vacation in Mykonos and explore the lively city. Wander around its narrow cobblestone streets and discover the traditional Greek architecture and numerous “hidden gems” like secret churches and secluded beaches. Spend the evening dining on deliciously fresh seafood while watching the sun set over the Aegean Sea.

Day 2

Cruise to nearby Naxos, an island known for its lush mountainous landscape dotted with picturesque villages. Take a tour of the ancient Venetian castle or explore one of its many sandy beaches. Make sure to visit the famous Portara, an impressive marble gate that stands guard over the island’s harbor. In the evening, stop by one of Naxos’ quaint tavernas for a delicious traditional meal.

Day 3

Set sail for Koufonisia where you can spend your day relaxing on one of the many peaceful white-sand beaches or joining kayaking tours to explore hidden coves and caves. At night, enjoy al fresco dining at one of Koufonisia’s seaside restaurants overlooking stunning views of crystal-blue waters and rolling hillsides in all directions. 

Day 4

Travel to Antiparos where you can take part in a range of activities from scuba diving to mountain biking and hiking trails along picturesque coastlines. Finish up your day with some retail therapy at Antiparos Town’s unique boutiques before hopping over to nearby Paros for dinner at one of its many eateries offering fresh local fare such as grilled fish and moussaka. 

Day 5

Head off to Sifnos, renowned for its pottery made from native clay found along its rugged coastline. Spend your time exploring beautiful churches dating back centuries, tasting locally produced olive oil, or taking lessons in traditional Greek dancing from local instructors – no matter what you choose to do here, you won’t be disappointed! 

Day 6

Make your way towards Tinos, known as ‘The Island Of Miracles’ thanks to its impressive number of religious sites including stunning churches scattered amongst small villages perched on hilltops overlooking endless stretches of blue sea below them. In the evening make sure not to miss out on sampling some delicious culinary delicacies from Tinos such as handmade cheese pies made with locally grown tomatoes or fried zucchini flowers stuffed with ricotta cheese – simply divine! Delos is also nearby where you can marvel at archaeological sites like marble statues carved thousands of years ago into ancient ruins and temples scattered amidst rocky terrains covered in Mediterranean vegetation – this is a must-see spot!  

Day 7

Return to Mykonos for one last day before heading home. Spend your final hours admiring Little Venice – a district made up of colorful buildings built right by the water’s edge – take a stroll around Matogianni Street where you will find designer boutiques alongside traditional souvenir shops – indulge yourself in mouthwatering gyros or souvlaki in any taverna– whatever you do make sure it’s memorable!

Experience Luxury and Speed: An 8-Day Motor Yacht Charter Itinerary from Mykonos to Athens

A 8-day motoryacht charter from Mykonos to Athens gives you the perfect opportunity to explore the stunning Cyclades islands. Begin your journey in the beautiful Greek island of Mykonos, renowned for its rugged landscapes and vibrant nightlife. Explore its pristine beaches, iconic windmills and quaint white-washed alleys. 

On day two, sail across to Naoussa and Ios, two idyllic villages with impressive beaches. Spend the day swimming in crystal clear waters, sunbathing and indulging in delicious seafood. 

Continue on to Santorini – one of the most romantic islands in Greece – where you can spend a wonderful day exploring picturesque villages overlooking calderas and idyllic vineyards. Enjoy a traditional Greek dinner with spectacular views of the Aegean Sea and take an evening stroll along a cobbled path lit with flickering gas lamps. 

The next stop is Milos, home to hot springs, secluded coves and some of the most impressive volcanic formations in Greece. You can take part in water sports such as snorkeling or scuba diving or simply relax on its pristine beaches. 

Sail onwards to Sifnos – an undiscovered gem that is known for its olive groves, traditional whitewashed houses and unique cuisine. Take time to explore its narrow paths before heading off to Serifos – a peaceful island that boasts incredible views over the Aegean Sea from its hilltop monasteries. 

Your journey comes full circle when you reach Kythnos, another unspoilt island that offers plenty of opportunities for exploration such as hiking trails along breathtaking coastline or relaxing days spent swimming at one of its many stunning beaches. Finally arrive back in Athens – capital of Greece – where you can discover ancient sites such as Acropolis Hill or enjoy all the shopping, dining and entertainment options it has to offer!

Sail through Timeless Beauty Charter from Athens through the Cyclades

Day 1: Athens 

Begin your 10-day charter itinerary in Athens, the stunning capital and largest city of Greece. Spend the day exploring the city’s many historical monuments, such as the Acropolis and Parthenon, or take a leisurely stroll through Plaka and Monastiraki. In the evening, enjoy dinner at one of Athens’ renowned restaurants or a night out in Gazi for drinks, dancing, and live music. 

Day 2: Kithnos 

Start your second day by hopping on a short ferry ride to Kithnos island. Enjoy some sunbathing on its pristine beaches or spend the day sightseeing around the traditional villages of Merichas and Loutra. Explore Hora, the main village of Kithnos that has maintained its Cycladic character with picturesque white-washed houses and narrow cobblestone streets while also offering plenty of cafes, restaurants, and bars. 

Day 3: Syros 

Continue your journey towards Syros island where you can visit Ano Syros Town -which is situated on top of a hill- to admire incredible views over Ermoupolis (the capital). Here you will find many neo-classical mansions surrounded by a plethora of shops selling local wines, cheeses, oils and more. In addition to its architectural beauty, Syros has some sandy beaches close to town where you can relax after all this sightseeing! 

Day 4: Delos – Rinia – Mykonos 

Your fourth day will be spent on an excursion boat ride to explore three different islands! Start off at Delos Island – known as an archaeological site – before heading to Rinia Island. Enjoy swimming in crystal clear waters or hiking up rocky trails for breathtaking views over Mykonos town. Finally end your day with a visit to Mykonos town where you can enjoy some shopping at its open air market or have dinner at one of its waterfront restaurants before returning back home.  

Day 5: Paros 

Spend Day 5 exploring Paros Island’s enchanting landscape which ranges from lush green fields peppered with wildflowers and olive groves to winding coastlines dotted with picturesque fishing ports like Naousa Bay and Kolimbithres Beach. Get lost in charming whitewashed villages such as Lefkes village with their traditional architecture or visit Parikia Town for shopping in its vibrant markets filled with local souvenirs and handmade products from artisans all over Greece. 

Day 6: Ios & Santorini 

Take a morning ferry ride towards Ios Island for some cliff diving along its impressive coastline before continuing on your journey towards Santorini Island -an iconic destination that boasts breathtaking landscapes with volcano views! Spend time exploring Oia village -known for its traditional whitewashed buildings- or go wine tasting at one of Santorini’s world-renowned wineries while admiring stunning sunset views over the caldera.  

Day 7: Milos & Poliaigos Islands 

Visit two more islands today while sailing around Milos Island’s spectacular coves including Sarakiniko beach with dramatic rock formations before heading towards Poliaigoes Islands for amazing snorkeling spots full of colorful fish! Make sure to also explore Kleftiko Cave which is accessible via boat only – it’s a must see! Finish off your day by returning back home for some delicious Greek cuisine in any local taverna found across Milos island .

Day 8: Folegandros Island

Explore Folegandros island’s rugged terrain boasting numerous hiking trails perfect for exploring hidden coves along the coastline followed by picturesque villages like Karavostasis harbor or Chora Village – both built atop mountainous cliffs providing incredible views down below! This charming little island is sure to leave you breathless during sunset hours when natural light captures stunning tones across its entire landscape making it seem like you’re living inside an epic painting!  

Day 9: Monemvasia Old Town & Spetses Island 

Make way towards Monemvasia old town – known as “Gibraltar of Greece” due to the fact that it was once used as an impregnable fortress against enemy invasions – then keep sailing until you reach Spetses island which is well known among Greek sailors thanks to its amazing seaside tavernas serving fresh fish dishes right next door to one another plus plenty of luxurious waterfront villas overlooking pine forests lining up across Spetses’ shoreline creating quite a memorable scenery throughout this small paradise island!!  

Day 10: Hydra & Athens    

Start off your last day voyaging around Hydra Island – famous among yachters due to having no cars allowed on land giving visitors access only via boat allowing them appreciate this unique way

Read also: Sailing In Greek Waters : Your Guide To A Dream Yachting Experience

Which yacht do we recommend for a sailing trip in the Cyclades?

If you are a family and like space, you can pick a catamaran

Catamarans, with their “space, grace and speed”, are ideal for exploring this spectacular region. Many yachts are fully booked a long time in advance make sure you contact your favorite broker to have the choice to pick the yacht you like and the embarkation and disembarkation port that suit your desired itinerary.

For example Lagoon 52 VALIUM52, is a great option to charter in Greece. This spacious yacht layout features 5 cozy cabins and comfortably accommodates a group of 10 guests. You can book this Lagoon 52 from 18 500€ per week + expenses.

If you like speed, confort and luxury pick a motoryacht

Looking for a comfortable and spacious ride on the water? Motorboats may just be your dreamboat! These vessels boast higher proportions above water, providing a more airy and open atmosphere. Plus, when it comes to living and snoozing on board, motorboats offer more comfort compared to sailboats. Jump aboard and get ready to relax in luxury style!

Motor yacht PROJECT STEEL is an excellent choice for families and groups of friends, since it can accommodate up to 12 people in 5 cabins. Her modern interior design and spacious outside living areas make her ideal for premium crewed yacht charters. She features a large outdoor living area that is ideal for entertaining. The top sun deck has a huge sun bed, table, and lounge, making it a great spot to relax and enjoy a refreshing drink while soaking up the sun. The aft swim deck makes it simple to go to the water and use all of her water toys.

This Project Steel is available for yacht charter in Greece with a base price of 49 000 € per week + expenses.

Pick a sailboat if you would like to have an immersive and intimate experience

Set sail with confidence! When it comes to rough waters, a sailboat is the way to go. Its deeper draft and keel design provide unbeatable stability while navigating choppy seas. Unlike speedy motorboats, sailboats prioritize safety and comfort above all else. Don’t get thrown off course by a gust of wind – opt for the secure and steady sailboat experience.

AIZU is a beautiful 99-foot sailing yacht, she was built in France in 1990 and has since been renovated to the greatest standards, giving magnificent modern facilities on board for up to eight charter guests and is available for charter in Greece. Her interior configuration accommodates up to 8 people in 4 rooms, including a master bedroom, and she can accommodate up to 4 crew members for a relaxing luxury yacht experience. Waterskiing, wakeboarding, SUPs, kayaking, and towing behind the yacht’s tender are among the watersports available to charter guests onboard AIZU. This sailboat is available from 29 000€ per week + expenses.


Ready to embark on an unforgettable adventure through the captivating coasts of Greece? Look no further! Our team of experts is here to help you custom-build the cruise of a lifetime. From exploring ancient ruins to basking in the sun on pristine beaches, we’ve got you covered. Don’t settle for a cookie-cutter vacation – let us create a unique, tailor-made experience that you’ll treasure forever. Get in touch with us today and let’s start planning!

Read also: How to set sails toward sustainability