Cyclades sailing charters are one of the most popular yachting options in all of Greece, the stunning archipelago, home to famous islands like Mykonos and Santorini, delivering that iconic Greek Island experience of everyone’s dreams. Although this maze of Aegean Sea islands is replete with an abundance of historical and archaeological sites, world-class marinas, quaint seaside villages and crystal-clear seas, the Cyclades offer a lot more than glitz and glamour. Sure, you can indulge in designer shopping, haute-cuisine and vibrant nighttime shenanigans on a few of the islands but you can also explore remote coves, discover uncrowded beaches and visit charming little villages that aren’t filled with souvenir shops. 

The sheer variety of Greek island ‘scenes’, short sailing distances, proximity to Athens and kaleidoscope of highlights, make Cyclades sailing charters not only ideal for first-time visitors but also perfectly suited to anyone, be they sailing with family or friends. 

Over 200 islands make up this archipelago which means a Cyclades sailing charter can be tailored to your desires. From the quaintest island to the most flamboyant; from the VIP-crowded gems to the almost completely deserted: the Cyclades offer you the best of Greece on a splendid turquoise-tinted platter.

Here are a few of the most popular stops you’ll want to include on your itinerary.

Paros & Ios

The largest islands in-between Mykonos and Santorini and among the most touristed, Paro and Ios are home to lovely marinas, beautiful beaches and a quite wicked nightlife, the latter attracting a young and vibrant crowd. For watersport and fishing aficionados, both islands are ideal, boasting windswept beaches, ideal for windsurfing. With their clusters of whitewashed villages adorned with blue-domed churches, Paros and Ios are the quintessential Cyclades sailing charter stopovers and although tourist crowds can be considerable in summer, finding quiet coves for relaxing days and evenings is surprisingly easy. Of the two, Paros is the quieter and lesser-visited of the two, so you can experience the best of the Cyclades and choose which side you’d love to spend more time in.

Mykonos

Often dubbed the Greek St Tropez, Mykonos is that one exhilarating island that made the Cyclades a household name. With its fashionable clubs attracting international celebrities, unparalleled nightlife, fabulous shopping and drop-dead-gorgeous beaches, Mykonos is a wonderful stop if you’d love to mingle with the crowds and soak up the party scene. Getting away from it all is not very difficult, however, a flurry of sensational remote coves always just ‘around the corner’. Yet this island is all about gourmet dining and shopping. For the ultimate Mykonos experience, enjoy a gourmet lunch in one of the many organic farms and a sundowner in Little Venice, shop for hand-made treasures along Matoyianni Street or take a traditional cooking class to learn the secrets behind the island’s culinary delights.

Santorini

Elegant, romantic, wild and distinctive: Santorini’s many faces are the island’s most alluring appeal and the main reason it’s as popular with honeymooning couples as it is with yachting families and groups of young friends. The sunsets of Santorini are as breathtaking as often described, with the island boasting a multitude of clifftop spots from where to enjoy them. The coastline is dramatic and rocky and the whole island, volcanic in origin, is a startling natural splendor. Santorini’s beaches are not sandy like its neighbor’s, which gives the island a most unique appeal. Villages here are traditional and vibrant, the array of trendy cafes, restaurants and bars, as well as vineyards and hiking trails, seducing visitors to shore. Your Cyclades private yacht’s array of toys will go to great use in the many calm bays around Santorini’s coastline and if you find an idyllic anchorage point facing on one of the seaside villages, you’ll have perhaps the most mesmerizing view of all. Santorini, from the sea, is absolutely resplendent.

Kythnos

Floating on the western edge of the Cyclades islands group, Kythnos is mostly renowned for its therapeutic hot springs, although the 70 or so miles of beautiful coastline and a total of 100 beaches are inarguably the biggest enticements for summer Cyclades sailing charter guests. Kythnos is more mountainous than its neighbors and offers a great many hiking options for active visitors who love nothing more than to explore traditional Greek islands on foot. With only two central villages, Kythnos is surprisingly quiet (given its accessibility) although August sees a healthy amount of holiday makers in Kythnos, most of them local. When Greeks go on vacation, they choose places like Kythnos precisely for their simplicity and authenticity. So don’t you miss out!

Folegandros

A smaller and quieter version of Santorini, one that’s swiftly becoming more and more coveted, Folegandros has some of the most picturesque villages in the archipelago, especially splendid Hora which sits on a hilltop affording sweeping views across the Aegean. One of the Cyclades’ smallest islands, Folegandros floats between Santorini, Sikinos and Mylos and covers merely 11 square miles.  Being surrounded by much bigger and more prominent islands has helped Folegandros retain an old-world charm and here you’ll find a little snippet of old Greece many don’t believe exists any more. Fabulous seafood and heart-pumping hiking are what Folegandros is all about.

Naxos

A wonderful hybrid of ancient history, gastronomic prowess and spectacular beaches, Naxos is a great Cyclades allrounder. The largest island and one home to a flurry of attractions and services, Naxos is considered a one-stop vacationing destination for many tourists. On a yacht charter in the Cyclades, however, she can just be your seductive bit on the side! Naxos town offers all the services you’ll ever need and a waterfront harbor many larger seaside cities would be envious to call their own. Not nearly as hilly as its neighbors, Naxos is a wonderful hiking and cycling destinations and one that’s particularly revered as a foodie’s dream. Some say the best restaurants in all of Greece are found right here.

Sifnos

The revered birthplace of some of Greece’s most prominent poets and chefs, Sifnos is an inspiring island to visit on Cyclades sailing charters. Laid-back, beautiful and traditional, this Cyclades splendor offers secluded sandy beaches, hilltop villages, seaside fishing towns, outstanding architecture and an abundance of historic sites dating back over 1,500 years. Some say Sifnos is where you’ll taste the best food in the Cyclades, the island’s interior peppered with olive and almond farms and hills drenched in wild aromatic herbs. Close enough o Athens to attract plenty of visitors yet still keeping the flow low-impact, Sifos is an exceptional inclusion to any sailing charter itinerary in these parts, with enough museums, archaeological sites, shopping, beach-hopping, nightlife and dining to satisfy everyone.

Delos

There probably isn’t a corner of Greece that doesn’t hide a treasure of antiquity (or 100) but if there’s one island in the Cyclades you shouldn’t miss if you’re a lover of ancient history, it would have to be Delos. Apollo’s mythological birthplace and an exquisite open-air museum if ever there was one, Delos is one of the least-known yet most unmissable stops on a Cyclades yacht charter itinerary. Venerated for over 5000 years (and UNESCO-inscribed in its entirety) Delos is considered the most important archaeological site in the Mediterranean, an island bursting at the seams with ancient sanctuaries, temples, mosaics, statues and homes. The views from the main ancient site are outstanding and the island’s relative anonymity means crowds tend to visit for just a few hours a day from nearby Mykonos, so if you visit in the early morning, you’ll have it all to yourself. Due to its historical importance, Delos is uninhabited bar for a few people who are employed, every summer, to oversee tourist crowds and guide visitors around. The contemplative peacefulness of Delos couldn’t be any more contrasting to the bustling scenes in Mykonos and Santorini, which only highlights the diversity of the glorious Cyclades.

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© Shutterstock