“Chose this trip for the day of my birthday and it certainly delivered! We absolutely loved every second, the accommodating and friendly crew, the bouncy ride, swimming in crystal clear waters, the incredible scenery, skimming stones on the private island beach, a delicious lunch and a heavenly trip back sunbathing on the deck with my…”

1,287 reviewsFrom $90by SAILINGTRIPS.GR

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

May 17, 2026 by

3Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Sail from Heraklion to Dia Island for snorkeling, SUP, dolphins stories, and a full onboard Mediterranean meal with drinks.

★ 4.9

“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on…”

778 reviews6 hoursFrom $106by Sailing Grace

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Heraklion: Dia Island Sailing Cruise with Snorkeling

May 17, 2026 by

4Heraklion: Dia Island Sailing Cruise with Snorkeling

Sail from Heraklion to uninhabited Dia Island for snorkeling, paddleboarding, drinks, and Greek food on a small yacht.

★ 4.7

“A really enjoyable and relaxing day. The group was small and everyone chatted with eachother and also with the two crew who were great. It was my first time on a sailing boat which I really enjoyed as well. Would highly recommend!”

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

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Sailing Cruise to Dia Island with Meal and Water Activities

May 17, 2026 by

5Sailing Cruise to Dia Island with Meal and Water Activities

Sail to Dia Island from Heraklion for snorkeling, SUP, swimming, and a full lunch with drinks, plus time on board to relax.

★ 4.5

“Our excursion to Dia Island from the port in Heraklion was very enjoyable. About an hour from port, the captain anchored the boat in a small bay off the island. There were two small beaches there. Once arriving, we had 3-4 hours of free time for all sorts of water activities (snorkeling, paddle boarding, swimming…”

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

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Heraklion: Private Half-Day Sailing Trip to Dia Island

May 18, 2026 by

6Heraklion: Private Half-Day Sailing Trip to Dia Island

Sail privately from Heraklion to Dia Island for 4.5 hours. Snorkel, fish, paddleboard, swim, with drinks and fruit.

★ 4.9

“Fantastic trip on our own little boat to Dia Island. The hosts were super friendly and really attentive, we felt very well looked after. The boat was wonderful and really clean. We had a lovely smooth sail there, plenty of time for a swim and snorkel and then lunch on board. We went for the…”

466 reviews4.5 hoursFrom $459by SAILINGTRIPS.GR

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

May 19, 2026 by

7Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Sail from Heraklion to Dia Island for snorkeling, SUP, fishing and a Greek lunch with unlimited drinks in a small group.

★ 4.8

“Very nice experience, and friendly host on the boat.”

414 reviewsFrom $67by Set Sails

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From Heraklion: Sunset Cruise to Dia Island

May 19, 2026 by

8From Heraklion: Sunset Cruise to Dia Island

Sail from Heraklion to Dia Island on a small yacht for snorkeling, cedar-tree walks, and time in a quiet Saint George bay.

★ 4.8

“Brilliant experience - stunning scenery, lovely food and the guides were friendly and helpful. Definitely recommend!”

259 reviews5.5 hoursFrom $82by Cretan Yachts

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

May 19, 2026 by

9Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Heraklion to Dia island catamaran at sunset with snorkeling, paddleboarding, Greek food and drinks, plus a small group feel.

★ 4.6

“This experience was the cherry on the cake for our trip here. For a cheap price a 4 hour boat-trip with food, amazing view on the sea and sunset, snorkling and swimming. The guides/captains were all very kind. 10/10 would recommend.”

242 reviewsFrom $63by Sailing Crete

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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

May 19, 2026 by

10Heraklion: Dia Island Luxury Catamaran Cruise with Meal

Heraklion to Dia Island on a Lagoon catamaran: snorkeling, SUP and swim time plus a Mediterranean meal and unlimited drinks.

★ 4.7

“Excellent activity! Really nice boat (around 26 persons per boat) and the waters in dia island are amazing. A really special activity and great crew.”

194 reviews5.5 hoursFrom $127by Cretan Sailing Cruises

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Heraklion: Dia Island Catamaran Cruise with Water Toys

May 19, 2026 by

11Heraklion: Dia Island Catamaran Cruise with Water Toys

Half-day catamaran cruise from Heraklion to Dia Island with tons of water toys, nutritionist-made lunch, and unlimited drinks in a small group.

★ 5.0

“Amazing day trip - fabulous boat, crew, food, location. Really recommend it. We travelled with my three year old and he loved it so much too - crew were great with him and even had activities on board. The best day of our holiday for sure!”

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

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Dia island : Small Group Sailing Trip to Dia Island with Lunch

May 19, 2026 by

12Dia island : Small Group Sailing Trip to Dia Island with Lunch

Small-group sailing to Dia Island from Heraklion with snorkeling or SUP, organic lunch, drinks, and a protected wildlife stop.

★ 5.0

“Absolutely fantastic excursion! We ended up having the entire boat to ourselves and the team really accommodated us and ensured we really had an amazing time. Lunch/wine onboard was delicious and they were fantastic photographers making sure we got ample amount of photos”

162 reviews4 hours 30 minutes (approx.)From $72.59by Altersail

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Heraklion: Dia Island Catamaran Cruise with Dinner and Wine

May 19, 2026 by

13Heraklion: Dia Island Catamaran Cruise with Dinner and Wine

Cruise from Heraklion to Dia Island on a luxury catamaran with dinner, Cretan wine, swimming, snorkeling, SUP, and sunset views.

★ 4.8

“We had the best time on this sunset cruise, the crew were amazing and very attentive to ensure you were having the best time! The spot at Dia Island was beautiful with crystal clear waters and plenty of water activities. Hats off to the chef also as the food was fantastic. The sunset on the…”

147 reviewsFrom $120by DanEri Yachts

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Heraklion: Private Full-Day Sailing Trip to Dia Island

May 19, 2026 by

14Heraklion: Private Full-Day Sailing Trip to Dia Island

Private 6.5-hour sailing from Heraklion to Dia Island for up to 8. Snorkel, fish, swim stops, crew drinks, optional meal.

★ 4.9

“Magnifique journée avec un guide très sympathique et professionnel, on a adoré.”

140 reviews6.5 hoursFrom $695by SAILINGTRIPS.GR

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

May 19, 2026 by

15Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

Small-group catamaran from Heraklion to Dia Island with open bar, Wi-Fi, snorkeling and SUP, plus a fresh Mediterranean lunch.

★ 5.0

“A 5* day all around. There was a small group of us on board (9 people) so the boat did not feel crowded. The chef and the captain were great and gave clear directions we should adhere to throughout the day. The food and snacks provided throughout the day were top tier and freshly prepared.…”

126 reviews6 hours 30 minutes (approx.)From $181.41by DanEri Yachts - Luxury Catamaran Cruises on Crete & Milos, Greece

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