Discover The Best Greek Islands With Sailing In Style

Sailing through the sparkling waters of the Greek Islands makes for an unforgettable holiday. At Sailing in Style, we offer a bespoke experience that takes you beyond the typical tourist routes, showing you the best Greek Islands and hidden gems that few visitors ever see. We’re well-versed in adventurous trips for friends, special family holidays and romantic breaks for groups of couples, tailoring the perfect Greek Island getaway for everyone who steps aboard.

Why Choose A Sailing Holiday With Us?

We’ve spent years exploring the best Greek Islands and know them like the back of our hands. With Sailing in Style, you won’t just visit the popular spots, you’ll discover secret coves, dine at family-run tavernas and enjoy an authentic Greek experience that’s far from the standard package holiday. From planning your travel arrangements to booking restaurant reservations and activities, we take the hassle out of holiday planning so you can focus on enjoying yourself.
Let us know what interests your group – exploring ancient ruins, indulging in gourmet meals, or finding secluded beaches – and we’ll create a bespoke itinerary to match. Our expert team is passionate about sharing the best that Greece has to offer, ensuring that every moment of your sailing holiday is memorable and stress-free.

Visit The Best Greek Islands

With over 30 incredible islands in our itinerary, it’s hard to choose just a few to highlight! While we’ve selected a handful of the best Greek Islands to share in this blog, there’s so much more to explore. Get in touch with us to learn more about the wide range of experiences we offer.

Kythnos

Kythnos is a peaceful island known for its laid-back charm and authentic Greek hospitality. It’s the perfect place to relax and unwind, with stunning beaches like Kolona, where the sand stretches out in a double-sided strip into the sea. Kythnos also boasts natural hot springs, offering a little extra indulgence for those looking to soothe the body and mind. With its quiet villages and friendly locals, Kythnos is a slice of Greece that feels like a home away from home.

Kefalonia

Kefalonia is one of the best Greek Islands in the Ionian Sea and is renowned for its dramatic landscapes, including the stunning Myrtos Beach, towering cliffs and lush green hills. History lovers will appreciate the island’s rich cultural heritage, with ancient ruins and Venetian castles to explore. If your group enjoys a bit of adventure, Kefalonia offers fantastic opportunities for hiking, diving and exploring caves like the famous Melissani Cave.

Syros

Syros is the beating heart of the Cyclades with a sophisticated, cosmopolitan feel. Its capital, Ermoupoli, is full of neoclassical architecture, chic cafés and an impressive arts scene. From local art studios to boutique shopping, Syros offers a one-of-a-kind experience. It’s one of the best Greek Islands to soak up history and culture all while enjoying the slower pace of island life.

Antiparos

If you’re seeking a more off-the-beaten-path experience, Antiparos is a true hidden gem. With its whitewashed villages, crystal-clear waters and tranquil beaches, this island is perfect for escaping crowds of tourists. The nearby caves are an adventurous highlight and it’s also one of the best Greek Islands for kitesurfing and windsurfing.

Naxos

Naxos is the largest of the Cyclades islands and offers a little bit of everything. From the buzzing atmosphere of Naxos Town to its traditional mountain villages, it’s a great option for groups with diverse interests. History buffs can explore the ancient Temple of Apollo, while foodies will love tasting the island’s famous cheeses and locally produced olive oil. Naxos is ideal for a mix of adventure, culture, and relaxation.

Hydra

Hydra is one of the best Greek Islands if you want to experience a truly unique setting. With no cars allowed, the island maintains a peaceful, old-world feel that’s far removed from busy modern life. The cobbled streets are lined with art galleries, elegant mansions and quaint cafés, making it a haven for creatives and those looking for a sophisticated escape.

The Perfect Vessel For Your Group

At Sailing in Style, we offer a range of vessels to suit your needs, whether you’re looking for a luxurious, relaxing catamaran cruise or a more hands-on sailing adventure. Our catamarans range from 42-54 feet and can comfortably accommodate up to 10 people, making them ideal for families or larger groups looking for a spacious and relaxing experience. If you’d prefer a more traditional sailing experience or want to learn the ropes, we offer monohulls between 45-57 feet. These vessels are perfect for groups of up to eight and are ideal for those who want to experience the thrill of learning to sail as part of their holiday.

Plan Your Dream Trip To The Best Greek Islands

At Sailing in Style, we’ll plan every detail of your island tour. We’re already getting booked up for 2025, so get in touch to reserve your preferred dates. Book an exploration call via our website or connect with us via Instagram. We look forward to hearing from you!