Skippered Sailing Holidays in Greece
All-Inclusive Yacht Charters in the Greek Islands

Skippered Sailing Holidays in Greece

The Ultimate Skippered Sailing Holidays: Relaxation & Adventure Combined

Discover the magic of Greece at your own pace with our skippered sailing holidays aboard our sailboat JOJO. Imagine exploring enchanting islands, sailing with the wind, swimming in unspoiled coves, and experiencing the charm of beautiful port towns & traditional villages, discover historical landmarks, and the Greek cuisine—all while surrounded by family and friends aboard your very own floating hotel.

All-Inclusive, Hassle-Free Packages

We’ve created a unique package to ensure a stress-free experience at a transparent price. Our comprehensive offer includes everything you need for unforgettable skippered sailing holidays:

Experienced Crew: Sit back and relax while we handle all the navigation and logistics.
Homemade Lunches: Every day enjoy freshly prepared meals on board.
Essential Extras: From fresh drinking water, diesel, and mooring fees to linen towels, yacht insurance, and cleaning, we’ve got it all covered.
Amenities: Complimentary Wi-Fi and full access to onboard equipment, including paddleboards, snorkeling gear, and more.

Unparalleled Flexibility

Flexible Start Dates: No rigid schedules here! Start your sailing vacations any day of the week to match your travel plans.
Custom Departure Points: Choose embarkation points like Athens, Aegina, Poros, Epidaurus, or Lavrio, ideal for exploring the Cyclades (weather permitting).
One-Way Trips: Maximize your adventure by sailing one-way, free of charge, across the Argosaronic islands.

Tailor-Made Itineraries for Your Skippered Sailing Holidays

Get inspired by our suggested itineraries for a sailing vacation or create your own personalized adventure. Whether you have specific destinations in mind or unique activities you want to include, we’re here to help. Simply send us an email with your preferences, and within 24 hours, you’ll receive a tailored response with ideas and recommendations to make your trip truly special.

Set sail with us and experience the best skippered sailing holidays in Greece—one island at a time!

Duration
From 1 week | Prefer a shorter trip? See our 2-5 days sailing trips
Location
Argosaronic Gulf & Cyclades & Peloponnese

Pax
Up to 8 Persons
Price for the All-Inclusive Yacht Charter (Not per person)
From 3910 €

Sailing Regions

During a week-long skippered sailing holiday, set sail to one of two breathtaking island groups: the serene Argosaronic Islands or the more adventurous Cyclades, perfect for those ready for longer travel legs. If you have more time, you can combine both regions or venture further to the tranquil and less-traveled east coast of the Peloponnese peninsula.

Having extensively traveled through these regions, we are well-equipped to provide you with all the necessary information to craft the ideal skippered sailing holiday itinerary tailored to your personal preferences. Whether you seek relaxation, adventure, or a mix of both, our sailing vacations ensure a seamless and unforgettable journey through Greece’s most stunning destinations.

The Argosaronic Islands

This island group enchants visitors with its divers landscapes, blending turquoise waters, lush vegetation, picturesque port towns and world-famous archaeological sites. Their close proximity, coupled with steady breezes and protection from strong prevailing winds—especially in summer—makes them an ideal destination for skippered sailing holidays for beginners and families alike.

The Cyclades in the Aegean Sea

The striking blue of the sky and sea, along with the whites of the sandy beaches, mirrored in the typical architecture of the traditional villages with their blue-domed churches and whitewashed houses. Secluded beaches, rugged landscapes and hidden gems make sailing here a special experience. However, it’s important to note that sailing conditions can be challenging, as the area is often exposed to strong prevailing winds.

The East Cost of Peloponnese

The ideal destination for those with a bit more time to spare, seeking to escape the crowds and explore off the beaten paths. Sail along the stunning, mountainous coast, moor in tranquil villages, and drop anchor in secluded coves with pristine beaches accessible solely by boat. And don’t miss the chance to explore a medieval town that serves as a testament to the great Greek civilizations that once thrived in this region.

The Itinerary

A New Island Every Day

Whichever route you choose, you can explore up to six stunning islands and destinations in just one week. With our in-depth knowledge of the Greek islands, we’ll help craft the perfect itinerary tailored to your preferences and the weather.

Important Note: Weather and Itinerary Flexibility

Sailing routes are subject to wind and weather conditions, which may require adjustments to the program. While we strive to follow a planned itinerary, flexibility is key, as routes can change at any time. A approximate itinerary will be finalized on the day of embarkation, prioritizing your comfort and safety and factoring in prevailing weather conditions. In favorable weather, we can stay within your preferred sailing area.

For inspiration, explore our fully customizable sample itineraries:

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Skippered Sailing Holidays in the Argosaronic Gulf

Aegina – Poros – Spetses – Ermioni – Dokos – Hydra – Methana

Discover Aegina, where you can wander through its charming port town, or admire the well-preserved Aphaia Temple, and swim in the turquoise waters of unspoiled coves and uninhabited islets. Later in the evening, take a stroll through the picturesque streets of Poros, enjoy hilltop views before savor local cuisine at a cozy taverna.

As your journey continues south, you will arrive the next days at the elegant island of Spetses and the mainland town of Ermioni. Here, you can swim in serene coves, paddle on SUPs, and indulge in freshly prepared lunches in secluded bays. Furthermore, a true highlight of your trip may be anchoring overnight at Dokos Island, and sleep under a dazzling starlit sky.

Afterward, set sail for Hydra, one of Greece’s most iconic destinations. While exploring this artist’s haven, take in its creative charm and vibrant atmosphere. You anchor in a nearby bay, with easy town access via water taxi.

For the final stop of your adventure, choose between Methana, where you can hike up to an ancient volcano, or Perdika, a quaint fishing village renowned for its fresh seafood.

Skippered Sailing Holidays in the Saronic Gulf (not only) for Families

Korfos – Epidaurus – Vathi – Perdika – Poros – Agistri

The Saronic Gulf offers a smooth sailing experience, perfect for beginners and families, even in windier conditions. To keep children entertained, we plan shorter distances with frequent swim breaks in calm, turquoise bays.

Your adventure starts in Aegina, where you’ll swim at a secluded islet before heading to Korfos for the night. Next, explore Old Epidaurus—snorkel over a sunken city or visit the renowned ancient theater just a short taxi ride away.

Continuing to Methana, unwind in Vathi’s charming harbor or hike its ancient volcano. Then, sail to Perdika, a quaint fishing village, before reaching Poros, famous for its winding streets, cozy tavernas, and delicious gelato.

Finally, the journey ends in Agistri, a lush green island with stunning coves—perfect for a peaceful swim before heading back.

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Skippered Sailing Holidays in the Western Cyclades

Kea – Kithnos – Serifos – Sifnos -Syros – Milos/Kimolos

Weather permitting, a week-long skippered sailing holiday in the Western Cyclades offers adventure, culture, and natural beauty, with two longer sails of about eight hours each.

First, we head to Kithnos, where we can stay at Merikas port or anchor in the stunning Kolona Bay. Next, we sail to Sifnos, famous for its delicious cuisine, before choosing between Milos, known for its breathtaking beaches, or Kimolos, a charming island with a quaint village near its tiny port. Nearby, the uninhabited Poliegos awaits with Caribbean-like waters.

Continuing, we reach Serifos, where the hilltop Chora offers spectacular views. Then, we visit Syros, home to a Venetian-influenced capital and an ancient bay with rock carvings from early sailors.

Finally, we stop at Kea, where you can explore the ancient city of Karthea and its newly uncovered theater, accessible only by boat—a true hidden gem.

Route options for Skippered Sailing Holidays 1 week +

Explore the Wild East Coast of the Peloponnese Peninsula

If you’re looking to escape the crowds, consider sailing to hidden gems like Kiparissi and Leonidio, where pristine beaches meet dramatic mountains.. Next, discover Gerakas, a picturesque fjord village, before continuing to the medieval town of Monemvassia, where ancient walls transport you back in time. Meanwhile, along your route, you’ll have plenty of opportunities to enjoy refreshing swims in stunning, secluded bays accessible only by boat.

Combine the Saronic Islands & Cyclades

For a truly unique experience, why not blend the charm of the Saronic Islands with the allure of the Cyclades? This way, you can enjoy the best of both worlds, experiencing the distinct character of each region.

Venture Further Afield into the Cyclades

Extend your journey by visiting the lively islands of Paros and Naxos, then continue to the tranquil Small Cyclades, including Koufonissi, where you’ll find unspoiled beauty. Alternatively, for a more cosmopolitan escape, set sail for vibrant Mykonos. the stunning islands of Folegandros, or world-famous Santorini.