Here’s the paradox of traveling to Greece. If you stay on a large island, like Mykonos, Santorini or Corfu, you’ll find lots to do — but also lots of tourists. If you sequester yourself on a tiny island, you can explore in peace — but after you’ve visited the few tavernas, historic sites and beaches, you may get a little restless.

That’s why sailing the Greek islands is so appealing. Each day you can explore a new place. Snorkel, swim or sunbathe; enjoy a leisurely lunch onboard or at a local restaurant; visit lovely villages and ancient ruins; then return to the boat and sail away.

Types of Greek Sailing Vacations

Maybe you’re an experienced sailor. Maybe you don’t know a clove hitch from a bowline. Either way, you can still enjoy sailing the Greek islands! Just make sure you know what you’re signing up for.

A bareboat charter means you rent just the boat and do all the work: serving as crew, provisioning, navigation and setting the itinerary. This only works if you’re traveling with a group of able sailors, and if at least one person on board has the skills necessary to serve as captain. If you’re considering a bareboat charter in the Greek islands, make sure your desired route matches your sailing ability. Sunsail offers a one-week bareboat charter from the island of Lefkas that stays close to the mainland, visiting coastal towns, the islets of Sivota, and Paxos.

A crewed yacht charter in Greece is a lot less work. You charter a private boat (monohull or catamaran) that comes with a captain and crew, so all you have to do is kick back and enjoy yourselves. A crewed charter isn’t cheap, however. Not only are you hiring the services of the crew and captain, you also must pay an advanced provisioning allowance for fuel and food (around 20-30 percent of the charter fee) and gratuity (around 10 percent of the charter fee).ⁱ

In Greece, flotilla sailing is a popular option for people who want to participate in sailing but prefer not to strike out on their own. You’ll be on your own sailboat in a small flotilla, following the lead yacht. Each day, the flotilla leader will meet with all the skippers to discuss the day’s weather, itinerary and anchorages. The leader can also help you solve any shipboard challenges.ⁱⁱ

If you’d rather just go along for the ride, consider sailing by the cabin in a flotilla or with a group charter. Some yacht charter companies offer this option, which is perfect for solo travelers or couples who love the social aspects of sailing. It’s much cheaper than chartering your own sailboat, although you may be responsible for cooking your own meals.

You can also book a cabin for a small ship sailing cruise — which is a bit of a misnomer, because these ships can be sizable. Windstar Cruises, for instance, sails the Greek islands in ships like the Wind Star, a 4-masted motorized sailing yacht that accommodates 148 guests. You get the romance of sailing with the amenities of a cruise ship: a pool, a casino, restaurants and spa. You can also sail aboard a tall ship, like Seafarer Cruises’ Star Flyer, a graceful craft with no fewer than 16 sails.

Read more: Planning a Private Cruise Adventure

Best Destinations for Sailing the Greek Islands

The appeal of a Greek sailing vacation is being able to reach the islands that large ships can’t. There, you’ll find picturesque villages and beaches untrampled by tourists. Some favorite destinations include:

Nisyros, an island between Kos and Tilos that’s home to an active volcano. “Along the crater, the brilliant white-and-blue houses and slumbering tabbys of the tiny village of Nikia serve as the postcard-perfect backdrop for sipping soumada, the traditional Greek almond soft drink served at one of the town's two tavernas,” Imogen Rowland writes for Conde Nast Traveler. ⁱⁱⁱ

Kythira is known for natural beauty: waterfalls, rocky gorges and beaches. It’s also the birthplace of Aphrodite, the goddess of love.^iv

The stunning Cyclades encircle the sacred island of Delos. Mykonos and Santorini are the best-known, but a sailing tour can visit less-visited islands like Kythnos (where you can soak in hot springs) and Sifnos (famous for its pottery workshops and excellent local cuisine).^v

Ikaria (or Nikaria) is a supremely relaxed island that’s one of the world’s five “Blue Zones” — places where people tend to be healthier and live longer than almost anyone else. Their secret? Strong red wine, herbal tea, a Mediterranean diet, lots of exercise, a strong sense of community, and afternoon naps.^vi Sounds perfect to us.

Travel Insurance for Greek Sailing Vacations

You absolutely must buy travel insurance if you’re planning to sail the Greek Islands. Because your trip costs are going to be substantial, you need a plan with trip cancellation and trip interruption benefits. Because you’ll be traveling overseas, where American health insurance plans are typically not accepted, you need a plan with emergency medical and dental benefits. And because you may be visiting remote islands, you need emergency medical transportation benefits to cover medical evacuation to the nearest appropriate medical facility, should you suffer a covered serious illness or injury at sea. Browse travel insurance plans and get a quote now! 

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