Under sail · HERAKLION SAILING TRIPS

The 15 Best Heraklion Sailing Trips to Dia Island

26 sailings  ·  from $68 a head

Dia sits an hour off the Cretan north coast and is the reason Heraklion has a sailing fleet. The 15 below compare the morning trips, the sunset runs and the small-group boats on price and swim time.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why 14 passengers makes a difference
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - The one-hour crossing to Dia Island
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

2.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, a Mediterranean lunch, drinks, and a sunset return.

“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 recommend more! So so worth the money!”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - Arriving at quiet Dia Island
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Heraklion: Dia Island Sailing Cruise with Snorkeling

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Dia Island and the Quiet Cove
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

4.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to quiet Dia Island for snorkeling, paddleboarding, Greek food, swimming, and a sunset return cruise.

“A lovely experience, very relaxing. Just the right number of people to make it enjoyable. A nice dinner and snorkeling near Dia Island. Thanasis and Panagiotis were super nice and kind, also sharing curiosity and answering questions”

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Sailing Cruise to Dia Island with Meal and Water Activities - Three hours in Saint George Bay
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Sailing Cruise to Dia Island with Meal and Water Activities

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

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96

Review of the Dia Island sailing cruise from Heraklion, with swimming, snorkeling, paddleboarding, lunch, drinks, pickup, and practical tips.

“Amazing crew, so warm and welcoming. Food was all home made and delicious. Fishing, padel boarding and snorkelling was available plus jumping off the boat. So fun and so worth the money.”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - The crew gives the trip its character
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

6.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, fresh Cretan lunch, unlimited drinks, and warm small-group hospitality.

“It was overal a really nice experience. the pickup was well managed and the Boats were really clean. The crew did an amazing job to provide an amazing trip. thanks!”

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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar - Agios Georgios Sarantaris and Saint George Bay
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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

7.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★4.8 · 442 reviews · 3.5 - 4.5 hours · from $94

Review of Hersonissos’ sunset catamaran cruise, with sushi, open bar, swimming, SUP, snorkeling, and practical booking tips.

“We both really enjoy good time and fantastic see sunset plus lovely snack and drink also make new friends chat and laugh we enjoy best yacht trip fantastic”

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Dia Sailing Cruise With All-inclusive Meal And Drinks - Leaving From Heraklion’s Old Venetian Port
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Dia Sailing Cruise With All-inclusive Meal And Drinks

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

★★★★★★★★★★4.6 · 422 reviews · 5.5 hours · from $76

Review of Crete’s Dia Island sailing cruise, with swimming, SUP, snorkeling, sunset views, fresh food, wine, transfers, and practical tips.

“Loved it. Everyone made to feel very welcome. Food was simple but very tasty. 10 out of 10. I would highly recommend it. I would recommend offering the guests a drink while they wait to leave the marina as it’s really hot and some of us had to travel a bit to get there. If I ever return I would definitely take the trip with them again.”

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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu - A modern catamaran with room to spread out
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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

9.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

★★★★★★★★★★4.9 · 312 reviews · 5.5 hours · from $141

Review of EOS Yachts’ Heraklion catamaran cruise to Dia Island, with gourmet lunch, snorkeling, SUP, drinks, and practical booking tips.

“The yacht itself exceeded my expectations. It was very spacious with luxurious touches. The boat did not feel crowded. The crew were very attentive and welcoming. They were constantly offering us drinks or assistance. The meal was also delicious, gourmet quality. The sunset ride back was stunning. Highly recommend.”

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Heraklion: Small-Group Sailing Trip to Dia Island with Lunch - The one-hour crossing to Dia Island
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Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

10.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Review of Heraklion’s small-group sailing trip to Dia Island, with clear-water swimming, snorkeling, local lunch, transfers, and practical tips.

“Overall the experience is very well worth it indeed. The staff are absolutely great and so friendly. Loved having conversations with them. The coast at Dia island is beautiful and snorkelling is highly advised. Food is also reasonably good.”

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Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys - Sailing past Rocca a Mare Fortress
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Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys

11.Dia Island Catamaran Cruise with Lunch, Water Toys

★★★★★★★★★★5.0 · 229 reviews · 5.5 - 7 hours · from $132Top rated

Review of Crete’s Dia Island catamaran cruise, with lunch, open bar, water toys, snorkeling, paddleboards, and practical booking tips.

“Firstly, the crew were very friendly, helpful & knowledgeable (thank you Jana & Wesley) which made the experience feel personal. we were lucky to have guests who were also friendly and considerate. the food was delicious (thank you Chef Yarris) & the location by the bay was serene and peaceful. The only issue we faced was the delay coming back into harbour which was around 30 minutes but was not the crews fault, but that of the harbour police. Overall a wonderful experience.”

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Heraklion: Dia Island Luxury Catamaran Cruise with Meal - One hour across the Cretan Sea
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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar - Leaving Heraklion with coffee and a safety briefing
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Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar

Heraklion: Dia Island Catamaran Cruise with Water Toys - The Afternoon Stretch: Swimming Until 1:30 p.m.
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Heraklion: Dia Island Catamaran Cruise with Water Toys

14.Dia Island Catamaran Cruise with Water Toys

★★★★★★★★★★5.0 · 174 reviews · 5 hours (approx.) · from $151

Review of Heraklion’s Dia Island catamaran cruise, with swimming, water toys, healthy lunch, drinks, pricing, timing, and practical tips.

“Cruise was awesome! My wife and I were on the cruise with two other families who were great. We left the harbor and went across to the island, parked there, and swam around and snorkled. They fed us delicious food and we had a really great experience. I’d recommend this trip for sure. The boat itself is awesome and very nice. The crew is also really great. Someone had complained about the abandoned restaurant we parked by, but that was pretty silly. Directly across the bay is a beautiful white and blue church.”

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Heraklion: Dia Island Luxury Sailing Trip with Meal & Drinks - Choosing Between TREATON and JACKPOT
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Heraklion: Dia Island Luxury Sailing Trip with Meal & Drinks

15.Dia Island Luxury Sailing Trip with Meal & Drinks

★★★★★★★★★★4.7 · 107 reviews · from $68Best value

Review of Heraklion’s Dia Island sailing trip, with swimming, snorkeling, sunset views, a Mediterranean meal, drinks, and practical tips.

“It was a pleasure traveling onboard TREATON. The boat is very spacious, luxurious, and the owners keep it in excellent condition. Joseph and Thanos were great hosts and made the cruise an unforgetable experience. Would totaly recommend that to everyone.”

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