Sailing Holidays in Greece: The Ultimate Guide

Greece is a sailor’s paradise with over 6000 islands and islets scattered across sailors ‘ seas. Whether you’re an experienced captain or just looking to try a sailing vacation for the first time, chartering a boat allows you to cruise between snow-white villages and historic sites at a pace dictated by winds and whims alone. From idyllic routes in the Ionian Islands to island-hopping Cyclades favorites like Santorini and Mykonos, we cover everything you need to know to plan your perfect luxury sailing holidays in Greece below.

When is the Best Time to Visit Greece for Sailing?

With relatively mild weather much of the year, Greece offers ample wind for avid sailors nearly year-round. But the ideal conditions for leisurely cruising between islands are mid-May and early October.

During these sunny Mediterranean months, daily temperatures range comfortably between mid-20Cs and 30Cs. Meltemi winds regularly whip up to 35 knots across the Aegean Sea, allowing you to harness the breeze without unpredictable storm risks at the peak of summer.

If you prefer cooler weather, late September to early October brings average highs in the mid-20s Celsius and fewer crowds. It makes for exceptionally comfortable open water sailing between many Greek Islands with minimal waves.

No matter when you visit, you can always count on bright blue skies to unfurl your sails under during sailing holidays in Greece!


Top Sailing Destinations in Greece

From history-filled islands in the Saronic Gulf perfect for newbie sailors to vibrant hotspots in the Cyclades, deciding where to drop anchor along GGreece’s15,000km coastline can be challenging.

To help inspire the route for your sailing getaway, we cover favorite sailing playgrounds across the Greek waters below.

Ionian Islands

With sheltered bays and light winds, the Ionian is ideal for beginner and relaxed sailors. Base yourself out of sleepy Paxos to drift between olive grove-dotted islands like Antipaxos, Meganisi, and Kalamos, where quaint fishing villages offer front-row seats to fiery sunsets over the sea.

More experienced sailors can island-hop between Kefalonia, Ithaca, and Lefkada – backdrops to HHomer’sOdyssey dotted with dozens of secluded coves ideal for crossing between or staying put for a night.

Cyclades Islands

As the quintessential Greek island-hopping destination, the picture-perfect Cyclades attract partying yachties and solitude-seeking sailors alike. Start from vibrant Mykonos before heading to palm-fringed beaches on Paros and Antiparos, where tavernas beckon you ashore.

Continue south through the islands of Amorgos, Ios, Sikinos, and Folegandros, where whitewashed villages spill down cliffsides to the sea before ending at SSantorini’svolcanic caldera glowing red under the setting sun. With opportunities to drop anchor at a new stunning harbor every night, sailing the Cyclades tops bucket lists for good reason.

Dodecanese Islands

From the iconic windmills of Mykonos to the fairytale-like towns of Rhodes, the nearby Dodecanese Islands offer both must-see Greek highlights alongside off-the-radar spots waiting to be discovered by sailors. Linosa, Agathonisi, and Patmos bring opportunities for pulls into quiet coves and sleepy fishing hamlets between better-known islands like Kos, Kalymnos, and Nisyros, dotted with hot springs and lava flows.

With harbor towns and uninhabited islets to explore, sailors can easily craft two-week adventures hopping across these southern Greek jewels by boat.

Saronic Gulf

Just a quick sail from Athens, the Saronic Gulf brings newbies ideal conditions close to civilization. Base from lavish Porto Heli and drift between Hydra, Spetses, and Poros – islands studded with neoclassical mansions and trendy beach clubs frequented by Athenian weekenders. With short distances between landfalls, you can easily sail during the day before enjoying vibrant island nightlife after dusk.

More off-the-beaten-path gems like Agistri and Angistri also allow opportunities to find hidden swimming coves and experience village life untainted by mainstream tourism crowds. With a bit of everything to experience, the Saronic Gulf is one of the most convenient, varied places for Greek island sailing escapes.

Length of Sailing Holidays in Greece

Most bareboat and crewed catamaran charter companies offer short weekend jaunts between 4 to 7 nights and options for longer adventures spanning 7 to 14 days. It allows you to explore the Greek Islands at a pace that best suits your style and schedule.

Newcomers to sailing holidays often opt for one-week charters, offering adequate time to relax into life at sea while island hopping between 2 to 4 destinations at a comfortable pace. It allows stops at a few highlight islands to swim offshore, sample authentic Greek cuisine dockside, and perhaps enjoy on-land activities like wine tours or hiking without rushed itineraries.

More experienced sailors often extend to 10-14 day trips to link top bucket list islands into figure 8 routes ending at your original starting point harbor. On 2 week sailing holidays in Greece, you can easily island-hop through main Cyclades hot spots and smaller Dodecanese Islands or circle Sicily-sized Crete, stopping at a new stunning village or beach every night.

Splitting longer charters across crew mates with on-off options also makes completing the ultimate island hopping adventures over 2 weeks more affordable by yachting.

No matter the length you choose for your sailing holidays in Greece, finding a route to satisfy every interest and seafaring skill level is easily achievable with endless anchors to drop across aquamarine bays!

Booking Your Sailing Holiday: Choosing a Charter Company & Boat

From sleek sailboats to expansive catamarans equipped with all the comforts of a luxury villa, selecting the ideal boat for your Greece sailing adventure tops the preparation list. Carefully compare offerings across charter companies when booking to get the features and space best suited for your group, budget, and style.

Most vessels accommodate between 4 and 12 passengers across convertible saloon sofas and cabin berths equipped with private ensuite heads and showers. Larger catamarans often feature multiple alfresco lounge spaces, shaded dining nooks, and even water toys from stand-up paddleboards to inflatable unicorns to take your island hopping up a notch!

When selecting your charter operator, look for professional Hellenic Yacht Charter Association members who exceed stringent requirements for quality, safety, and transparency. Before booking, please don’t be shy about asking questions about the age and upgrades of their vessels and inspecting onboard amenities to have smooth sailing all week.

Established sailing specialists like Niriides Yacht Charter receive rave reviews for their exceptional personalized service and armadas of modern yachts vetted to excel across the Ionian, Saronic Gulf, and Cyclades. They also offer route planning assistance and provisioning coordination so you can fully relax into the captain’s role once aboard.

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Luxury outfitters like Black Tomato also curate exceptional bespoke catamaran escapes around the Greek Islands, with private chefs, watersports instruction, and guided land excursions. This lets anyone ease into sailing holidays in Greece without prior on-water experience but with ultimate comfort across your custom odyssey.

Provisioning Tips for Sailing Holidays in Greece

While sampling authentic Greek specialties ashore definitely ranks as a top highlight of sailing holidays in Greece, providing boats with supplies to whip up casual onboard fare is also part of the fun!

Most charter companies offer add-on provisioning packages or put clients directly in touch with Greece-based providers like Easy Yacht Provisioning. They expertly stock boats based on detailed order forms you fill out beforehand covering preferences across categories like:

Breakfast essentials: Greek yogurt, nuts, honey, whole grain breads, eggs

Lunch snacks: Hummus, pita bread, sandwiches, salads, cheese, cured meats

Cocktail hour: Ouzo, wine, beer, juices, olives, chips

Dinners: Chicken, lamb, beef, and seafood proteins along with vegetables, rice, pasta

Fruit: Melons, strawberries, cherries, oranges

Whether you prefer catered meals or casual bites aboard, the azure waters surrounding Greece make the perfect picturesque backdrop for dining al fresco on sailing holidays!

Top 5 Routes for 10-Day Sailing Holidays in Greece

Ready to start mapping out an iconic island-hopping route for your sailing getaway? To inspire your trip planning, we cover dream-worthy 10-day ways awash in top bucket list sights and glittering hidden gems below. We don’t think you should blame us for this when these itineraries have you daydreaming of the Greek seas for months to come!

1. Athens to Ionian Islands Loop

Explore hotspots near Athens before sailing to the idyllic Ionian Sea on this 10-night route. After kicking off your sailing holidays from Greece’s vibrant capital, continue to the island quintet of Poros, Hydra, Spetses, Agistri, and the ancient ruins on Aegina in the Saronic Gulf. Next, set sail for the olive grove-dotted Ionian Islands like Paxos, Antipaxos, Meganisi, and finally Kefalonia – backdrops for an OOdysseus’adventures and home to dozens of pristine swimming coves. Wrap up by island hopping up the mainland on your return to Athens.

2. Cyclades 10-Day Highlights Hop

No sailing holidays in Greece would be complete without weaving together critical pearls of the Cyclades like Mykonos, Paros, and Santorini. This relaxed route through the heart of the Aegean allows you to tick off top bucket list islands while leaving time for open-water relaxation, swimming stops, and absorbing endless island sunsets. 

Start by exploring Mykonos and nearby Delos before heading to the palm-lined beaches of Paros and Antiparos. Continue south through volcanic Naxos, making the iconic shot of the windmills a must before wrapping up with an ending worthy of the Greek gods soaking in SSantorini’scrimson sunsets over the sea from your private catamaran.

3. Crete and Surrounding Islands Loop

For ancient sites and culture immersion, sail clockwise around Crete – the most significant island dotted with palm-lined beaches, vineyards, and Minoan and Venetian rule relics. After picking up your catamaran in Heraklion, stop to explore the ruins of the Palace of Knossos before drifting south to the white sand of Elafonissi and Preveli Beaches tucked at the ends of crevices slicing inland. 

Sail east along CCrete’s southern coast for rocky coves and rustic harbors before ferrying to exotic Chrisi – an uninhabited red sand bar offshore. Stop for a soak in the natural hot springs of Santorini and Nisyros after crossing the Sea of Crete back north or overnight under the glow of the sleeping volcano on Kos. With must-see landmarks and off-radar spots, Crete makes the ultimate island for your modern Odyssey by private yacht charter.

4. Dodecanese Islands Hopping Adventure

Sail between the iconic windmills of Mykonos and the fairy tale-esque towns of Rhodes on a cruise through the Dodecanese Islands. Start by exploring hidden caves and monasteries on Patmos in northeast Greece. Next, please go south through Kalymnos and its sponge-diving villages, followed by the volcanic thermal springs on Kos. 

Continue west to Nisyros to glimpse smoking craters before angling back north through islands like Leros, Agathonisi, and Lipsi, dotted with fishing hamlets rarely seen by other travelers. Wrap up by exploring medieval walls and cobblestone laneways of Rhodes town – where the Colossus, an original Wonder of the Ancient World, once straddled its harbor in mythic times.

5. The Ionian Sea to the Cyclades

Begin your adventures sailing the sheltered bays of Kefalonia – rumored to be Odysseus kingdom in Homeric times – ringed by pastel villages and olive groves. Wind your way south through Ithaca, Meganisi, and finally, Lefkada, where white cliffs plunge into the shallow aquamarine offshore. Then, sail onward to explore the uninhabited beauties of Skorpios Island, once owned by Onassis.

Continue past Paxos and Antipaxos onto Corfu, soaking up Venetian influences in mansion-lined harbors before crossing towards Parianos. From here, thread between Paros and Antiparos to marvel at iconic Cycladic windmills and sugar cube architecture. Cap off your adventures by reveling in the MMykonos’ all-night party atmosphere to celebrate completing your modern epic, crossing the best of the Ionian Sea to the Aegean Sea by private yacht charter!

Wrapping Up Your Sailing Holidays in Greece

We hope this sailing guide has inspired you to set sail on your own Odyssey, exploring azure coves and snow-white villages scattered across the Greek seas. From one-week to two-week adventures, crossing these mythic waters by private catamaran or sailboat allows you to immerse yourself in island life at an unrushed pace dictated by winds alone.

With countless routes, Cruising shoulders with celebrities in the Saronic Gulf, dancing under the stars in Mykonos, or finding your hidden Ionian cove feels like a dream. But the most challenging part is deciding your ideal adventure to make those sailing holiday dreams a reality. Exploring famous and off-the-radar hidden gems and compiling the ultimate island-hopping route is half the fun of planning sailing holidays in Greece!

We just don’t think you should blame us for this when you get bitten by the sailing bug, and this fantastic European sailing destination will stay on your wander list for repeat adventures among glittering Greek Islands for years to come. We promise that gazing out over earthy olive groves backed by whitewashed villages fading into the distant sea never gets old from the captain’s seat of your private yacht!

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