Greek island hopping on a sailboat

You will enjoy a vacation to remember forever, aboard a sailboat. You will arrive sailing to cities and towns that you will fall in love with at first sight. In several days you can visit several islands and meet new people.

The Greek Islands are composed of several archipelagos, each with its own charms. The advantage of sailing on a sailboat is that you will not have to make large displacements to travel several of these islands.

Depending on the route we choose, you can visit more or fewer islands.

Mykonos is one of the islands that we can highlight, its capital Chora, an authentic maze of white buildings and narrow alleyways. A true paradise both from far and near.

One of the most photographed places is Santorini, an island formed on the caldera of an ancient volcano, hence its impressive cliffs. When you are in Fira (Thira) on the sailboat you can take some amazing photos where you will see the blue vaults of the church and the white buildings. Fira is a more touristy population while Oia is a quieter and more evocative place.

Rhodes, an island near Turkey has a totally different landscape than the previous islands. This flirtatious "medieval" city has abundant vegetation and mountainous orography.

Crete is the largest island in Greece, stands out for its mountainous orography. An island of idyllic beaches, lost corners, dream villages and nature worthy of admiration; An island of contrasts full of color and joy.

Corfu has a bright beauty, with immense beaches and coves. We can find of all kinds some more cosmopolitan, other deserted, where to enjoy the nature of Greece.

The price range varies mainly depending on the duration of the holidays, the type of boat, the places to be visited.

The Saronic Golfo is one of the prettiest destinations to visit while sailing. Given its meteorological conditions, for its beautiful mountainous landscapes, completely flat beaches, beautiful blue waters to sail around Greece by sailboat ...

The distances between islands from a sailboat are very short, where you can make many stops on the most wonderful beaches you can imagine. You will also visit its picturesque villages that have a lot of charm.

Are you going to miss going on a sailboat cruise in Greece?

A sailing trip in Greece is often cheaper than a classic hotel holiday when you combine transport and accommodation.

• Weekly price: Expect to pay between €650 and €1,300 per person, depending on the season.
• Onboard expenses: In Greece, mooring fees are significantly lower than in Croatia (often only €10-30 per night). Therefore, the onboard expenses for food and fuel are usually a moderate €150 to €250 per week. Many Sailwiz skippers offer package prices that include final cleaning – check the details in the respective offer description.

• Sailing yacht (monohull): The choice for the “real” sailing experience. More affordable and more maneuverable in small Greek harbors.
• Catamaran: Offers significantly more living space and stability. Thanks to its shallow draft, our skippers can anchor much closer to the beach in the Cyclades. Especially popular with families and groups who value a large saloon and a flat deck for sunbathing.

• May & June: Perfect for nature lovers. The islands are green, the temperatures are a pleasant 25°C and the marinas are empty.
• July & August: High season. Consistent winds (Meltemi) in the Cyclades provide cooling at 30°C+, ideal for experienced sailors.
• September & October: The water is warmest at 24 °C. Wind speeds decrease, allowing for relaxed sailing in the Dodecanese or Ionian Sea.

Our skippers recommend places away from the hotspots:

• Hydra: A port without cars and mopeds – transport is purely by donkey.
• Milos: Famous for Sarakiniko, a lunar landscape of white volcanic rock that only reveals its full splendor from the water.
• Kastellorizo: A hidden gem in the far east for absolute peace and quiet.
• Epidaurus: Combine your trip with a visit to the ancient theater, which is just a short walk from the port.

What guests appreciated:

• "We were initially hesitant because we hadn't found any sailing experience. But our skipper Kostas was not only a professional, but also the best guide. He knew bays on Milos that we would never have discovered on our own." – Elena S., holiday in the Saronic Gulf.
• Community on cabin charter: "As a solo traveler, I was initially worried, but the group on the boat became a small family within a week. Sitting together in the tavernas in the evenings was the highlight." – Markus T., Cyclades trip.
• The flexibility: "No fixed schedule like on a cruise ship. If we liked a bay, we simply stayed longer to snorkel." – Müller family, Ionian Sea.

Insights from our skippers:

• Insider tip: "I love taking my guests to Polyaigos. The water there is so blue that they initially think it's a filter – until they jump in." – Captain Yannis.
• Safety & Comfort: "In Greece the weather is usually stable, but I always make sure to plan the route so that we have the wind at our backs. For me, comfort means that my guests feel safe." – Skipper Maria.

To find the perfect offer on Sailwiz, you should compare these points:

1. The port of departure (logistics)

• Athens (Alimos/Lavrio): Ideal for the Saronic Gulf or the Cyclades. Excellent flight connections.
• Lefkada/Corfu: Perfect if you want to explore the Ionian Sea (green islands, calm waters).
• Rhodes/Kos: The best starting point for the Dodecanese (near Turkey, very sunny).

2. The boat's equipment

• Cabins & Bathrooms: Pay attention to how many people share a bathroom. Catamarans often offer more privacy in this regard.
• Extras for fun: Check the description for "Extras": Is there a stand-up paddleboard (SUP), snorkeling equipment, or a dinghy with an outboard motor for shore excursions?
• Power & WiFi: If you need to charge devices, check if there is an inverter (220V) on board.

3. What is included in the price?

• Transparency regarding the onboard expenses: Check whether fuel, final cleaning and port fees are paid separately or are already included in the price.
• Meals: Is shopping and cooking done together, or is breakfast already included?

4. The skipper profile & reviews

• Read reviews: At Sailwiz, you can see star ratings from previous guests for a specific skipper. An experienced skipper is not only a seaman but also a host.
• Languages: Does the skipper speak English, German, or Spanish? This is important for communication on board.

5. The group size
Would you like a private yacht for 6-8 friends, or is a berth in a double cabin sufficient for meeting new people? The maximum capacity is clearly stated in each offer.

The best experience depends more on your preferences than simply choosing the most popular island. Before booking, you can consider a few things:

• If you are traveling alone: look for experiences by berth where you can share the boat with other travelers.
• If you're traveling as a couple: a cabin can give you more privacy without having to rent a whole boat.
• If you are traveling with friends or family: compare the full boats and the capacity of each vessel to find a suitable option for your group.
• If you want to visit several islands: pay special attention to the itinerary and the number of sailing days.
• If you're looking to relax: you might be interested in a route with short stages, more anchorage time, and services included on board.
• If you want to sail: look for experiences where sailing plays an important role and ask the skipper about the type of route planned.

And above all, check the specific conditions of each activity. Two week-long trips to Greece can be completely different depending on the boat, the route, the number of travelers, and how the experience is organized.

Each boat trip in Greece has its own particularities and the skipper is the best person to explain what the experience will be like.

Before booking, you can contact the skipper to ask about the planned route, the type of sailing, the boat, the cabins, the level of experience required, or how each day is organized.

Furthermore, the route can be adapted to weather conditions. In some Sailwiz experiences, for example, the planned itinerary changes depending on the wind to maintain the best possible sailing conditions.

Tell them what you're looking for: whether you want to explore many islands, spend more time at anchor, sail for longer periods, travel as a couple, share a boat with other travelers, or enjoy a private trip with friends. Their experience can help you choose the perfect sailing holiday in Greece.