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Cyclades Island Hopping: The Ideal 3-Week Itinerary

Cyclades Cruise Itinerary


ith about 220 islands, the Cyclades make the ideal destination for island hopping lovers! Actually the best Cyclades cruise experience. It is not by chance that the Cyclades have been the preferred destination of people all around the world for years. Luxury, cosmopolitan essence, unspoilt nature, hidden gems, total peacefulness, whatever you long for can be certainly found on one of the islands that make up this diverse complex. And what’s a better way to discover them than a chartered yacht cruise? Follow this 3-week Cyclades itinerary and make the most out of your time in this stunning complex of Greek islands.

Week 1: Santorini, Ios, Sikinos, Folegandros  

As one of the most popular and beautiful islands in the world, Santorini is the best point to begin your yachting vacation in the Cyclades and is definitely worth 2-3 days of exploration. Wander around the bustling streets of Fira, lose yourself into the mesmerizing colors of Oia’s sunset and travel back in history with a visit to Ancient Thera. The island also features some beautiful beaches with red and black sand that are an absolute must!

Days 4-5 can be dedicated to Ios, another picturesque Cycladic island with whitewashed houses and a vigorous nightlife. Relax on its serene beaches, take a dive into archaeology at Skarkos and Homer’s Tomb, and party all night in Chora.

On day 6, you can get away from the buzzing crowds with a visit to Sikinos. Being one of the smallest Cycladic islands, Sikinos offers the perfect opportunity for a true connection with nature. Crystal-clear waters, untouched natural beauty and a mouthwatering local cuisine is all you need for an authentic Greek experience.

Folegandros provides the best ending to your first week in Cyclades. An alluring island with traditional villages, laid-back atmosphere and rugged landscapes that provide the perfect balance between Santorini’s vibrancy and Sikinos tranquility. With lots of secluded beaches to discover and hiking trails to explore, the island’s beauty will have you captivated.


I haven’t been everywhere, but it’s on my list. – Susan Sontag

Week 2: Sifnos, Antiparos, Paros, Naxos

From Folegandros, hop over to Sifnos for a great start of your second week in Cyclades. Have a swim at its beautiful beaches, visit its many monasteries and churches and get lost in the medieval narrow alleys of Artemonas for a well-spent day in Sifnos.

Then, move on to Antiparos, a charming Cycladic island that’s bound to steal your heart. From the magnificent Antiparos Cave to its pristine beaches, the exquisite beauty of this small island offers the perfect opportunity for exploration.

For days 3-5, venture to Paros, one of the most popular Cycladic islands. Spend a day discovering its golden beaches and enjoy the adrenaline rush of water sports, such as windsurfing. Get a taste of Greek tradition by visiting fishing villages, like Naoussa and Lefkes and experience the island’s eclectic nightlife.

This Cyclades itinerary could not be complete without Naxos. Week 2 ends with two days full of memorable experiences on the largest Cycladic island. Apart from a variety of stunning beaches, Naxos features a rich history with lots of archaeological sites, such as Apollo’s Temple and Portara. If you are into hiking, let your eyes feast on the panoramic views offered on the highest peak in Cyclades, Mount Zas.

Week 3: Mykonos, Delos, Rineia, Tinos, Syros

Your third week in Cyclades begins with a visit to the renowned island of Mykonos! If you are into cosmopolitan life and partying, you will certainly need 3-4 days to get the full Mykonian experience. Visit world-famous beaches, such as Super Paradise and Ornos, go clubbing among international celebrities, take incredible photos at the Windmills of Mykonos and enjoy magnificent sunset views at Little Venice.

While in Mykonos, grab the opportunity to sail to two nearby islets of great archaeological importance. Delos island was considered sacred in antiquity and it is now an open-air archaeological museum with significant showpieces, such as the Delos Theatre, the House of Dionysos and the Avenue of Lions.

Rineia, on the other hand, might not be as popular, but its archaeological ruins still bear importance. Largely uninhabited, this island also features a variety of virgin beaches for absolute relaxation.

Continuing the Cycladic exploration, the next two days are dedicated to Tinos, a multifaceted island that offers a diverse range of experiences. Visit its Venetian-style villages to admire the architecture and discover Tinos marble art at the Marble Crafts Museum. Unwind on the island’s exquisite beaches and, of course, do not skip a visit to Panagia Evangelistria Church, which has been a popular pilgrimage destination for decades.

Your cruise to Cyclades culminates in Syros, a charming island with a unique blend of history, cultural richness and lively atmosphere. Stroll through Ermoupolis scenic alleys, enjoy the breathtaking panorama of the island from Ano Syros and have the time of your life on its azure beaches.

A Cyclades Itinerary Tailored to Your Needs

Do not hesitate to adjust this 3-week Cyclades itinerary to your own needs! Planning a longer cruise? Spend some more days to explore some of your preferred Cycladic islands. Need to speed up your island hopping? You can skip some of the recommended islands to save time.

Whatever you choose to do, make sure to charter a yacht early enough. At Blu Cove Yachting you can browse a variety of yachts to find the one that will make your cruise totally unforgettable!

When you decide to visit greece, never miss the opportunity to experience a Cyclades cruise across the islands

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