Top Heraklion Sailing Tours

Sail to Dia Island: A Boutique Yacht Experience in Paradise Sun, blue waters, and good food—these are the things that define Greece, and Crete in particular. What if you could have them all at once? This all-inclusive, compact experience truly has it all. ✔ A true vacation-like islet with crystal-clear waters, sheltered bays, and the colors of the Mediterranean. ✔ The liberating feeling of real sailing as you glide across the Aegean. ✔ Fun on the water with snorkeling and even a spot for fishing for enthusiasts. ✔ A warm, freshly cooked dinner with a view, along with unlimited refreshments. Step aboard and be part of the journey. Come join us!

Join a small-group sailing adventure from Heraklion to the beautiful, unspoiled Dia Island. With a maximum of 10 guests on board, you’ll enjoy a relaxed, semi-private atmosphere as you cruise along Crete’s stunning northern coast. Swim in crystal-clear waters, snorkel, try paddleboarding, or simply relax and sunbathe on deck. Enjoy a freshly prepared Cretan lunch including seafood or vegetarian pasta, Greek salad, and fruit salad, paired with unlimited local white wine, beer, soft drinks, and water. The friendly local crew will make you feel at home, sharing stories, laughs, and even singing to dolphins if they appear! Choose to meet at Heraklion Port or add optional transfers from nearby areas like Malia, Hersonissos, Analipsi, Gouves, and more. Whether you're traveling solo, with a partner, or in a group, this is a truly authentic and unforgettable way to experience the sea, nature, and heart of Crete.

Feel the sun on your face and the breeze in your hair on this leisurely sailing catamaran cruise from Heraklion to the uninhabited island of Dia. Enjoy activities from snorkeling and stand-up paddle boarding (SUP) through to fishing and sunbathing in a group no larger than 20. As well as onboard Wi-Fi, your package includes a Mediterranean lunch with drinks: online booking means there’s no need to negotiate terms.

Join a unique catamaran adventure from Heraklion to the beautiful, unspoiled Dia Island. Sail in comfort and style aboard a spacious catamaran, enjoying a relaxed atmosphere as you cruise along Crete’s stunning northern coastline. Swim in crystal-clear waters, snorkel, try paddleboarding, or simply lounge on the wide deck or netting areas and soak in the sun. A freshly prepared Cretan lunch will be served on board, including seafood or vegetarian pasta, Greek salad, and fruit salad — all paired with unlimited local white wine, beer, soft drinks, and water. Our friendly local crew will make you feel right at home, sharing stories, laughter, myths about the Island of Dia. You can choose to meet us directly at Heraklion Port, or opt for convenient transfers from nearby areas like Malia, Hersonissos, Analipsi, Gouves, and more. Whether you're traveling solo, as a couple, or with friends, this catamaran trip is an unforgettable way to connect with the sea, nature, and soul of Crete.

Experience a Unique Sailing Adventure and savor our All-inclusive authentic Mediterranean menu, unlimited fragrant white wine, soft drinks and bottled water. The journey to the island lasts about an hour, offering tranquility, captivating sea views of the Cretan Sea, space for sunbathe on the comfortable and spacious deck and a chance to learn about eco-sailing and marine life. For those interested, our skilled skipper can guide you in sailing activities where you can take part in the sailing aspect of the journey. Upon arrival at Dia, we anchor at pristine wind protected coves with crystal- clear, turquoise waters, where you can enjoy swimming, use the diving equipment provided, or simply relax. Alternatively you can stay onboard and enjoy all the amenities that it has to offer. You can sunbathe on the deck, or socialize in the shaded cockpit, where you’ll find comfortable sofas with large, plush cushions.

With this full-day sailing trip, you can take your time and enjoy a full-day adventure on the water, without feeling rushed. Sit back, relax, and take in the spectacular views of Crete, with stops along the way so you can go snorkeling and visit remote beaches. Lunch, wine, and soft drinks are included, and hotel pickup is available for added convenience.

We invite you to step away from the everyday and join us for an unforgettable evening at sea aboard our luxury catamaran. As the sun begins to set, watch the sky turn gold and pink while you enjoy refreshing drinks from the open bar, paired with light snacks and freshly prepared sushi. Our luxury catamaran is elegant and designed for your ultimate comfort. Soft, cheerful music sets the tone for the day, filling the air with a joyful atmosphere as you enjoy your journey. You’ll savor a variety of delicious Cretan snacks and appetizers, along with a selection of sushi rolls — all included. Throughout the cruise, you can enjoy espresso, tea, water, soft drinks, and a choice of local Greek white wine and beer. For adventure lovers — try stand-up paddleboarding, snorkeling, or simply float on an inflatable noodle. And of course, our iconic pink flamingo float is ready for your next unforgettable photo moment.

Looking for an Escape? On a yacht, you have the opportunity to appreciate your downtime in an idyllic setting that offers relaxation, freedom, exhilaration, and plenty of fun, all in one experience at your own pace. Set yourself free and enjoy swimming into the refreshing crystal clear and azure waters of Agios Georgios Bay. The sun feels like happiness, sit back, swim, and snorkel at your leisure as the crew prepares the meals on board. You, your family, and your friends are our special guests on this island adventure! You can choose your departure and let's live together this amazing experience! Instant Energy!

Sail with us to the exotic Dia Island on our large and comfortable sailing yachts. Our journey begins at the Heraklion Old venetian port. After 1 hour of sailing, we arrive to Dia where we anchor in the bay of the island. There you can enjoy the crystal waters and water activities such as snorkeling, fishing and paddle boarding. (Please request the equipment from the Crew). The standup paddle boards are not available under rough wind conditions for safety reasons. About 1 hour later our delicious menu is served and includes Greek salad and several appetizers, while the main course is shrimp Linguini (we also offer vegetarian and gluten free versions of the menu upon request). You can also accompany your meal with the finest wine, beer, ice tea or soft drinks. Around 30 minutes later our fruit salad of tropical and local fruits is served. After you finish your meal you will have a few last moments of relaxation on the yacht or in the refreshing water before we sail back to Heraklion.

Skip crowded beaches and sail to uninhabited Dia Island or St. George Bay (dependent on tour option selected) on this intimate, small-group cruise, limited to just 10 guests. As you journey across Cretan waters, listen as your captain shares history and local secrets about the area. Upon arrival, enjoy free time to swim, snorkel, fish, sunbathe, or stroll to a charming church, before savoring a freshly prepared Cretan meal and included drinks. Choose between a 5-hour daytime trip with two island stops or a shorter 3-hour sunset cruise to St. George Bay.

Immerse yourself in the serene ambiance of island life aboard a luxurious yacht, surrounded by breathtaking views and attentive crew. Savor the delightful Mediterranean cuisine, and witness the captivating beauty of Dia Island or Agia Pelagia bay. As you moor in the secluded bay , indulge in the tranquility of its azure waters and lush, untouched landscape. This unforgettable experience promises relaxation and unparalleled joy from start to finish. Perfect From Beginning to End !

Just off the coast of Ierapetra, Europe’s southernmost town, lies one of Crete’s most stunning natural treasures: Chrissi Island. Known as the “Golden Island,” this protected Natura 2000 paradise is famous for its turquoise waters, rare ancient cedar forest, and beautiful golden beaches. Join us on a relaxing cruise across the crystal-clear Libyan Sea and enjoy spectacular views of Crete’s southern coastline. Once we arrive, you’ll have time to swim in the clear waters, unwind on the soft sands, and experience the untouched beauty of this unique island sanctuary. With years of sailing experience and thousands of happy guests, our crew ensures a smooth and enjoyable journey filled with sunshine, sea, delicious food, and unforgettable moments. Discover the magic of Chrissi Island and enjoy one of the most exotic day trips in Crete.

Relax and enjoy a peaceful day in our Semi-Private Cruise surrounded by natural beauty. Swim in emerald looking waters and enjoy a traditional meal by the sea. An ideal getaway for families & couples! Nine miles from Ierapetra, it has a unique cedar forest, pure white sand dunes, golden shallow sandy beaches and a sea with unbelievable tropical colors. The natural images and the rhythms of nature, immediately give the visitor a newfound sense of liberation. The sojourn on the island will be approximately 4 hours total , where we will visit 2 different beaches. The stay at each beach will be approximately 2hours . Relax on the beach, or take a long walk along the endless beach and marvel at the millions of colorful small shells. On board there is also lunch (Including Starters , Main-Dish(Vegetarian option available upon request) , and fruits or ice-cream) as well as unlimited drinks . Our friendly crew promises an unforgettable experience that will live on in your memories forever .

Looking for an Escape? Leave your comfort zone and embrace nature to the fullest. The best place to start your eco-quest is the island of Dia, so prepare for a biotope adventure that will inundate you with twists and turns, splashes and sparks. On a sailing yacht, you have the opportunity to appreciate your downtime in an idyllic setting that offers relaxation, freedom, exhilaration, and plenty of fun, all in one experience at your own pace. Do you dare to change your point of view? let's live together this amazing experience! Instant Energy!

Explore Dia Island and the gorgeous water of of St. George’s Bay with this private sailing charter. Your skipper will take care of the logistics, taking you through the bay and anchoring in crystal clear water. Snorkeling equipment is provided, so you don’t need to bring that yourself. Choose to add lunch, champagne, cake, and more for an additional charge.

What makes this experience stand apart is **the contrast — sharp, honest, and deliberate**. In one single day, you move from the stone logic of **Knossos Palace**, where Europe’s first civilization learned order and ritual, to the open Aegean, where order dissolves into wind, salt, and horizon. Most tours choose either land or sea. This one insists you understand both, the way Cretans always have: farm in the morning, sail in the afternoon, eat well in between. It is also **a rare pairing of living production and living nature**. The olive mill is not a staged stop; it is a working place, governed by seasons and patience, not schedules. Hours later, you are anchored off Dia, swimming and dining aboard a sailing yacht as the sun drops into the sea — not rushed, not over-scripted. One foot in history, one hand in the present, and the rest left to the day itself. That balance is not common, and it cannot be mass-produced.