How To Make The Most Of Your Greek Island Sailing Holiday

A Greek Island sailing holiday is your chance to experience something unforgettable. At Sailing in Style, we combine insider knowledge, bespoke service and incredible destinations to create tailor-made adventures for every type of traveller. Whether you’re craving laid-back luxury, hands-on sailing or a trip filled with hidden gems, here’s how to make the most of your time on board.

5 Insider Tips For Effortless Greek Island Sailing

1. Plan The Perfect Route For You
With Sailing in Style, no two routes are the same because no two groups are the same. Our Greek Island sailing itineraries span calm, beginner-friendly waters to more adventurous crossings, and each one showcases a different flavour of Greece.

Want to get stuck into sailing? Great – our team will teach you the ropes and guide you every step of the way. Prefer to relax with a book and let us take the helm? Not a problem. This comes with the bonus of opening up every route we offer. Your sailing ability, interests and how hands-on you want to be will help us pick the perfect course, whether that’s the challenging waters of the Cyclades or the turquoise calm of the Ionian.

2. Book Restaurants Ahead (And Let Us Handle It)
Food is central to any Greek Island sailing getaway, but finding the best spots can be tricky if you don’t know the area. That’s where we come in. Tell us your food preferences and we’ll handle all restaurant and bar bookings in advance, securing your group tables at the best local tavernas, seafood hideouts and sunset-view spots. We’ll even throw in some of our dish recommendations.

For something extra special, we offer a private chef service on board, bringing restaurant-quality dining to the deck of your boat. You’ll enjoy fresh, locally-sourced meals while watching the sun dip below the horizon.

3. Experience The Unforgettable
A typical package holiday can only take you so far. With Sailing in Style, we go beyond the usual itineraries and unlock unique experiences.

• Swim at Atokos Pig Beach, a hidden Ionian gem.
• Explore the Papanikolis Sea Cave near Meganisi.
• Hike into the active volcanic crater on Nisyros.
• Visit the sacred Cave of Apocalypse in Patmos.
• Watch Kalymnos sponge divers in action.
• Private access to local artists’ studios or VIP entry to exclusive bars and clubs.

We’ll still take you to the classics, but at the right time to avoid the crowds. Your trip should feel like yours alone, not something lifted from a tourist brochure.

4. Try Something New
Balance is key on a Greek Island sailing holiday. We’re experts at helping you strike that perfect mix between recharging and adventuring.

On the water, we recommend:

• Paddleboarding to peacefully explore the coastline.
• Snorkelling right off the boat in uncrowded waters.
• Learning to sail, guided by our experienced crew.

On land, swap the usual sightseeing for:

• Hiking off-the-beaten-path trails.
• Quadbiking or moped tours through villages and hills.
• Horse riding along coastal paths.

5. Leave The Boring Stuff To Us
The easiest way to get the most out of your Greek Island sailing holiday is to let us take care of all the planning. From the moment you book an exploration call with Thomas, founder of Sailing in Style, we get to know everything that matters: your group dynamic, food likes and dislikes, preferred pace, activity level, island wishlist and sailing confidence.

Then we handle it all! Travel logistics, restaurant reservations, experiences, equipment and making sure every person in your group (no matter how diverse) has the trip of a lifetime. You’ll review the itinerary before setting sail and make tweaks as needed, but the heavy lifting? That’s on us.

How To Book Your Greek Island Sailing Holiday

Get started by filling in a short enquiry form on our website. You can also message us directly via Instagram or Facebook. Once we know what you’re looking for, we’ll take care of the rest.