CRETE · DESTINATION

Best Dia Island Sailing In Crete

Crete’s best days out.

The 15 most popular dia island sailing on Crete — what each day actually involves, what it costs, and the operator running it.

15 Best Dia Island Sailing In Crete

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Meeting at Cafe Marina and getting on the yacht without stress

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Meeting up near Marina Cafe: small timing details that matter

2Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion to Dia Island sailing with snorkeling gear, unlimited drinks and local wine, and a filling onboard lunch on a small yacht.

4.9

“Had the most wonderful experience with Vasilis and Polina! My family of 5 set out to Dia on a beautiful sailboat and Vasilis explained everything to us and made us feel comfortable especially because my 3 kids had never been on one. The day was gorgeous and we were able to snorkel and swim and…”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - The Onboard Meal and Drinks: What a Mediterranean Lunch Feels Like at Sea

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

“Our Captain came to our hotel in Agia Pelagia to pick us up in the morning and he was lovely from the get-go. The boat ride to Dia Island was fun, and the island itself was amazing. We got to hike up the island and have a look around. The water was so blue and…”

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Heraklion: Dia Island Sailing Cruise with Snorkeling

Heraklion: Dia Island Sailing Cruise with Snorkeling - Dia Island: the swimming, snorkeling, wine, and photo stop package

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!”

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Sailing Cruise to Dia Island with Meal and Water Activities

Sailing Cruise to Dia Island with Meal and Water Activities - Getting on board: pickup, meeting point, and what to expect

Heraklion: Private Half-Day Sailing Trip to Dia Island

Heraklion: Private Half-Day Sailing Trip to Dia Island - The private yacht setup: comfort, shade, and real “vacation mode”

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

“We were looking for a day away from the crowds in a cruise ship port and this was perfect! Picked us up and drove us back to the port. Very attentive to time we needed to be back on board. The sail boat was beautiful and we enjoyed the day. Sailing the Aegean Sea is…”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Getting on board: Old Anchor meeting point and optional transfers

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

“The boat trip was very enjoyable, the guides were friendly and very accommodating and the views were stunning. There is plenty of time to stop and swim, nap, relax, listen to music and lunch is served with fruit and there are unlimited drinks and fruit. Not to mention the breathtaking sunset. Definitely recommend!”

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From Heraklion: Sunset Cruise to Dia Island

From Heraklion: Sunset Cruise to Dia Island - From Cafe Marina to Rocca a Mare: the quick start that helps the day feel easy

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Half-Day vs Full-Day: Choosing the Right Amount of Sea Time

Heraklion: Dia Island Luxury Catamaran Cruise with Meal

Heraklion: Dia Island Luxury Catamaran Cruise with Meal - From Cafe Marina to the Catamaran: Getting There Without Panic

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

“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…”

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Heraklion: Dia Island Catamaran Cruise with Water Toys

Heraklion: Dia Island Catamaran Cruise with Water Toys - Price and value: why $151.23 can make sense

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 trip would recommend for anyone of all ages. The food was delicious with pasta and feta salad also mussels with all allergies taken into consideration. Swimming was great with bonus of using the paddle board and snorkel equipment as well as inflatable pink flamingo!! Fabulous time had by our family.”

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

Dia island : Small Group Sailing Trip to Dia Island with Lunch - The protected cove stop: snorkeling, SUP, and wildlife chances

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

“We booked this tour in the afternoon the day before the booking and was recommended it by Viator when we called them. And after booking Viator said the tour was confirmed in our confirmation. We arrived at the port (after a 1.5 hour drive) the next morning, at the meeting point but the Aftersails team…”

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Heraklion: Dia Island Catamaran Cruise with Dinner and Wine

Heraklion: Dia Island Catamaran Cruise with Dinner and Wine - Boarding at Marina Café: Getting There Without Stress

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

“Excellent from start to finish, pucked the afternoon sail so could see the sunset on way home and it didn’t disappoint. Crew were exceptional, very professional and helpful. Food was lovely, fresh fish, greek salad, panicotta and fresh fruit. Lots to drink and fun in the water on paddle boards etc in a beautiful setting.…”

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Heraklion: Private Full-Day Sailing Trip to Dia Island

Heraklion: Private Full-Day Sailing Trip to Dia Island - Boat, Crew, and the Comfort Details You’re Actually Paying For

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

Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Comfort on Deck: Wi‑Fi, Restrooms, Showers, and Space

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

“The staff was wonderful and very accommodating. The food was made fresh on the boat with flowing drinks. It was relaxing on the deck but also fun to play in the majestic water with all the water toys. We met some cool people too which was enjoyable”

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More Dia Island Sailing In Crete