15 Best Heraklion Sailing Trips Worldwide

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

/ June 12, 2026

1.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Small-group Dia Island sail from Heraklion with swimming, snorkeling, SUP, a Mediterranean meal, and unlimited drinks on board.

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

/ June 12, 2026

2.Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Heraklion to Dia Island by yacht for snorkeling, SUP, drinks, and a Mediterranean meal. Dolphins if lucky. 6 hours.

★ 4.9

“Really nice sailing cruise to Dia island. Once you get out of the harbour, the fun really begins. We didn’t get into the water once at Dia, as it was a bit chilly. However, watching the sunset and admiring the rocky island was worth the price. The crew was competent and made us feel safe.…”

778 reviews6 hoursFrom $106by Sailing Grace

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Heraklion: Dia Island Sailing Cruise with Snorkeling

/ June 12, 2026

3.Heraklion: Dia Island Sailing Cruise with Snorkeling

Sail from Heraklion to uninhabited Dia Island for snorkeling and paddleboarding, plus drinks and Greek seafood meals on a small group yacht.

★ 4.7

“It was a beautiful experience and the guys were very polite and helpful towards us”

742 reviews4.5 - 7 hoursFrom $82by Sailing Crete

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Cruises & Boat Tours, Evening Experiences, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Sailing, Snorkel Sailing Trips, Snorkeling, Sunset Sails, Tour Reviews

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

/ July 26, 2026

4.Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Heraklion to Dia Island at sunset: snorkel, paddleboard, and enjoy Greek food and drinks on a small catamaran.

★ 4.7

“Andreas and Ianos (hope I am spelling it correctly) were great guides, answering a lot of questions about the island. The place is a pretty good place for snorkel activities but you have to venture a bit far out, especially by the old remains of a minoan port underwater. Food was really good, drinks at…”

529 reviews4.5 - 7 hoursFrom $82by Sailing Crete

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Sailing Cruise to Dia Island with Meal and Water Activities

/ July 26, 2026

5.Sailing Cruise to Dia Island with Meal and Water Activities

5.5-hour Dia Island sailing from Heraklion with swimming, snorkeling, SUP, and an on-board lunch plus drinks in a small group.

★ 4.5

“Guide’s voice was quiet. Not all of us could hear him. Lunch was good. Snorkeling was not the best. Very little fish to see.”

526 reviews5 hours 30 minutes (approx.)From $96.74by Cretan Sailing Cruises

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

/ July 26, 2026

6.Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Small-group sailing from Heraklion to Dia Island with lunch, unlimited drinks, snorkeling and SUP, plus dolphin-spotting at sea.

★ 4.8

“So amazing, the crew were so fun and so nice and they took us to aqua water coves. So beautiful !!”

517 reviews6 hoursFrom $100by Set Sails

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Dia Sailing Cruise With All-inclusive Meal And Drinks

/ July 31, 2026

7.Dia Sailing Cruise With All-inclusive Meal And Drinks

5.5-hour Dia Island sailing from Heraklion with snorkeling and SUP, plus an all-inclusive Mediterranean meal and unlimited Greek wine.

★ 4.6

“The trip was great, the food, which was freshly prepared, was very tasty... Island Dia is a special place and what can be more exciting than sailing? Alex and Costa took great care of everyone. Only the waiting time for the transfef back to the hotel could be a little shorter.”

422 reviews5.5 hoursFrom $76by Rocca a Mare sailing adventures

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

/ August 1, 2026

8.Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Sail from Heraklion to Dia Island for lunch plus snorkeling, SUP, and fishing. Unlimited drinks, dolphins, and time to swim.

★ 4.8

“The best day on Crete! Lovely crew, nice lunch, lots of time to go swimming,snorkelling, SUP and an unbelievable sailing experience. Got to see sunset as well,making it even more memorable. Highly recommend!!!”

414 reviewsFrom $67by Set Sails

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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

/ August 9, 2026

9.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

Luxury Dia Island catamaran from Heraklion with chef-cooked Mediterranean lunch, snorkeling gear, SUP, and sunset return for $141 pp.

★ 4.9

“There are plenty of companies out there, but if you’re looking for something truly luxurious, make sure to choose one that offers a catamaran experience with new boats. We’ve tried others before, and their boats were quite old - but this company really stands out. Professionals from step one of booking to the very end!…”

312 reviews5.5 hoursFrom $141by EOS Yachts

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Cruises & Boat Tours, Evening Experiences, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Sailing, Snorkel Sailing Trips, Snorkeling, Sunset Sails, Tour Reviews

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

/ August 16, 2026

10.Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Heraklion sunset catamaran to Dia Island with snorkeling, paddleboarding, and included food, drinks, wine, and raki.

★ 4.6

“The transfer went without any problems. The boat ‚Chill out‘ was great. The sea was quite rough, but it was fun and the captain and his assistant made sure that everyone was safe. On the way to Dia island, the captain told us about the mythical history of the island. Once we arrived we had…”

242 reviewsFrom $63by Sailing Crete

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Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys

/ August 18, 2026

11.Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys

Cruise from Heraklion to Dia Island on a modern catamaran with lunch, unlimited drinks, and serious water toys in clear Cretan water.

★ 5.0

“Crew were awesome and the food was brilliant. A fantastic day out.”

229 reviews5.5 - 7 hoursFrom $132by DanEri Yachts

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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

/ August 25, 2026

12.Heraklion: Dia Island Luxury Catamaran Cruise with Meal

Sail from Heraklion to Dia Island on a Lagoon 450F catamaran with unlimited drinks, snorkeling and fishing gear, and a Greek meal included.

★ 4.7

“This was by far one of the best experiences I’ve had on vacation. 9 of my closest friends joined me, and we had the time of our lives. Sophia, as well as the captain, were very knowledgeable, attentive to any needs we had, and they made an absolutely delicious lunch with the best Greek salad…”

194 reviews5.5 hoursFrom $127by Cretan Sailing Cruises

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Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar

/ August 27, 2026

13.Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar

Sail from Heraklion to Dia Island on a luxury catamaran with open bar, water toys, a nutritionist-made Cretan meal, and sunset.

★ 4.9

“Incredible day with the best crew ever! Food was tasty and catamaran in very good condition. 10/10”

181 reviews5 - 6.5 hoursFrom $132by DanEri Yachts

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Heraklion: Dia Island Catamaran Cruise with Water Toys

/ August 29, 2026

14.Heraklion: Dia Island Catamaran Cruise with Water Toys

Heraklion to Dia Island Bay catamaran with snorkel gear, SUP, sea scooter and slide, plus nutritionist lunch and open bar.

★ 5.0

“Great boating trip, great staff, highly recommend if you are visiting Crete. Delicious food and plenty of space.”

174 reviews5 hours (approx.)From $151.23by DanEri Yachts - Luxury Catamaran Cruises on Crete & Milos, Greece

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Heraklion: Dia Catamaran Tour – Lunch, Open Bar & Snorkeling

/ September 2, 2026

15.Heraklion: Dia Catamaran Tour – Lunch, Open Bar & Snorkeling

Catamaran cruise from Heraklion to Dia Island with open bar, lunch, and snorkeling plus SUP. Semi-private and family-friendly.

★ 4.9

“I had the pleasure of experiencing a catamaran cruise to Dia Island, and it was spectacular. This trip provided a perfect blend of relaxation, adventure, and breathtaking scenery. The catamaran itself was modern, spacious, and well-maintained. The seafood was just perfect. Big bravo to the chef Konstantinos. The boat had plenty of sea toys like…”

161 reviewsFrom $141by DanEri Yachts

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