SAILING WORLDWIDE
The best days on the water.
The 15 most popular heraklion sailing trips. What each sail costs, how long you are on the water, and which crews run it well.
Small-group Dia Island sail from Heraklion with swimming, snorkeling, SUP, a Mediterranean meal, and unlimited drinks on board.
Most Popular“Amazing experience!! The food and staff were amazing, the location is stunning, we had the most beautiful day”
Heraklion to Dia Island by yacht for snorkeling, SUP, drinks, and a Mediterranean meal. Dolphins if lucky. 6 hours.
“The most magical and romantic experience to end our trip in Crete. Hosts were delightful, the snacks and drinks were excellent, the equipment and amenities provided for snorkelling, fishing and paddle boarding were amazing! The sights on the way and from the island were incredible - recommend the evening trip for the sunset. 100/10 couldn’t…”
Sail from Heraklion to uninhabited Dia Island for snorkeling and paddleboarding, plus drinks and Greek seafood meals on a small group yacht.
“The Sail Boat tour was extraordinary. We had such a beautiful sunny day. Both the Captains were very incredible. I booked for a Retreat I was hosting in Greece. We were 7 people and had the whole sailboat for ourselves. I booked the half day tour & honestly we loved it so much, that if…”
Heraklion to Dia Island at sunset: snorkel, paddleboard, and enjoy Greek food and drinks on a small catamaran.
“A pleasant sail with lovely hosts who are very skilled sailors.”
5.5-hour Dia Island sailing from Heraklion with swimming, snorkeling, SUP, and an on-board lunch plus drinks in a small group.
“We had the most incredible sailing excursion to Dia Island! Our captain (I’ll be posting a picture since I can’t remember his name) and the amazing deckhand Christina made the trip truly unforgettable. They were both so kind, welcoming, and skillful at navigating the wind, which made the whole experience smooth and enjoyable. Throughout the…”
Small-group sailing from Heraklion to Dia Island with lunch, unlimited drinks, snorkeling and SUP, plus dolphin-spotting at sea.
“We are a family of 5 and were lucky to share the yacht with just another family of 3 and our lovely guides George and Marcos. It was a very hot, still day so we couldn’t actually sail but this meant for beautiful calm waters and exceptional swimming and snorkelling when we got to Dia…”
5.5-hour Dia Island sailing from Heraklion with snorkeling and SUP, plus an all-inclusive Mediterranean meal and unlimited Greek wine.
“Wonderful day! The food was amazing, we had a lovely time!”
Sail from Heraklion to Dia Island for lunch plus snorkeling, SUP, and fishing. Unlimited drinks, dolphins, and time to swim.
“We took the sunset boat trip. It was really nice. The guides were friendly and professional. The food was tasty and in big portions. The water next to the island was clear and it was really beautiful. We highly recommend this trip. It was fun and relaxing experience.”
Luxury Dia Island catamaran from Heraklion with chef-cooked Mediterranean lunch, snorkeling gear, SUP, and sunset return for $141 pp.
“The staff were very friendly warm and welcoming. The journey was smooth and relaxing and the atmosphere was calm and relaxed. The food was fresh and delicious and a good serving including drinks non alcohol and alcohol. Also a good supply of fun activities, snorkelling, paddle boarding and just relaxing in the sun. I differently…”
Heraklion sunset catamaran to Dia Island with snorkeling, paddleboarding, and included food, drinks, wine, and raki.
“Me and my partner loved this boat trip. The boat itself was a good size, we were accompanied by 3 other couples and 2 crew members. Although there were 10 people on the boat, there was a comfortable amount of space. The bay at Dia island was amazing with its glassy clear blue water. We…”
Cruise from Heraklion to Dia Island on a modern catamaran with lunch, unlimited drinks, and serious water toys in clear Cretan water.
“Wow! What an amazing day! The crew was attentive, very professional, and extremely nice! The food and drinks were fresh and delicious!! The beautiful boat was very clean and the sailing was very comfortable. I highly recommend DanEri and their amazing team! Thank you for an unforgettable day!! We will be back!! 🫶 🥂⛵️”
Sail from Heraklion to Dia Island on a Lagoon 450F catamaran with unlimited drinks, snorkeling and fishing gear, and a Greek meal included.
“The best thing was that we could vary between snorkeling, swimming and being on the paddle board. It was so much fun doing everything and the crew was very attentive and friendly too. Would recommend it to everyone, who wants to enjoy the sun and the sea, as well as boat trips. The catamaran was…”
Sail from Heraklion to Dia Island on a luxury catamaran with open bar, water toys, a nutritionist-made Cretan meal, and sunset.
“If you are thinking about booking this, DO IT! Everything about this cruise was 100%, you won't regret it.”
Heraklion to Dia Island Bay catamaran with snorkel gear, SUP, sea scooter and slide, plus nutritionist lunch and open bar.
“Crew was very friendly and nice! Boat was clean and exactly what was expected. Thank you very much. It was fantastic.”
Catamaran cruise from Heraklion to Dia Island with open bar, lunch, and snorkeling plus SUP. Semi-private and family-friendly.
“Awesome and caring crew! Boat was super clean and enough seats were provided. You could chill on any place on the boat. Crew and captain Joana was superb!”
The sailing ports worth the trip, grouped by the sea they sit on.
