Top 14 Sailing Trips in Heraklion

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion to Dia Island in a small group for swimming, snorkeling, SUP, a Mediterranean meal, and sunset views with unlimited drinks.

“Here’s a smoother, more natural version of your text: This was the last day of our trip through Crete, and we ended it in the best way possible. The cruise was incredible, the weather was perfect, and the crew and food were fantastic. It was everything I wanted and more. We were having so much fun that we didn’t even have enough time to try all the activities - which is actually a good thing!”

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2.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion to Dia Island on a cozy yacht with snorkeling, SUP, and a full onboard meal plus drinks and raki.

“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. The snacks were really tasty. The captain also put some music, made the trip back really enjoyable.”

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3.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island for snorkeling, paddleboarding, and a Greek meal, with small-group sailing and drinks.

“The team,the activities snd spots with clear water”

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4.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sunset sail from Heraklion to Dia Island for snorkel, paddleboard, Cretan food, drinks, and a classic Crete sea-to-sunset experience.

“The sailboat had the perfect atmosphere—spacious and comfortable with just the right number of people. Great music set the mood, and the skippers were not only professional but also genuinely pleasant, making the whole experience even better.”

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

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

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, and a full lunch with wine and beer on a small group cruise.

“Amazing experience, a very relaxed activity, the vive , the staff, everything was great. A day to remember.”

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6.Sailing Trip to Dia Island with Lunch & Swimming

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

6-hour small-group sail from Heraklion to Dia Island with lunch, snorkeling, SUP, and unlimited wine, beer, and swim time.

“The crew were all so lovely and such sweet people! We sailed out to Dia island and did some snorkelling but mainly relaxed on the catamaran with some drinks. It was such a relaxing day chilling on beanbags and enjoying the water. Would love to do this again- such a cool experience!”

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

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

Sail to Dia Island from Heraklion for a 5.5-hour cruise with all-inclusive Mediterranean lunch, unlimited white wine, snorkeling, SUP, and sunset.

“I truly enjoyed the entire experience. The crew made it fun for all on board, the meal was delicious. Nikos and Kostas were extremely welcoming and made the trip memorable! Great day sailing!!”

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8.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Luxury catamaran cruise from Heraklion to Dia Island with chef-cooked Mediterranean seafood lunch, snorkeling, SUP, drinks, and raki.

“What can we say - what an absolutely outstanding experience! My partner and I had an amazing time, everything was exceptional. The staff were so friendly and welcoming and really looked after us. You have time to have a dip and use paddle boards after reaching Dia island, which was so much fun! Shoutout to the chef too, for the super tasty food! It was also my birthday so was surprised with a cake! Very sweet of them going the extra mile. Sailing back into the sunset is an unforgettable experience. 10/10 highly recommended!!!”

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9.Dia Island Catamaran Cruise with Lunch, Water Toys

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

Sail from Heraklion to Dia Island on a modern catamaran with snorkeling gear, water toys, and a Cretan lunch plus unlimited drinks.

“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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10.Dia Island Luxury Catamaran Cruise with Meal

★★★★★★★★★★4.7 · 194 reviews · 5.5 hours · from $127

Luxury catamaran cruise from Heraklion to Dia Island with a Mediterranean meal, snorkeling, fishing, and unlimited drinks.

“Amazing! Couldn’t fault a thing. 100% recommend. We had a great day”

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11.Catamaran Cruise to Dia with Sunset, Meal & Bar

★★★★★★★★★★4.9 · 181 reviews · 5 - 6.5 hours · from $132

Heraklion to Dia Island sunset catamaran with open bar, nutritionist lunch, and sea scooter, slide, kayak, SUP, plus snorkeling.

“A must do experience, great boat and crew, plenty of food and wine 😉 and lovely mix of guests, swimming was great as well.”

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12.Dia Island Morning Sailing Trip with Snorkeling

★★★★★★★★★★4.9 · 100 reviews · 6 hours · from $82

A 6-hour morning sail from Heraklion to Dia Island for snorkeling, swimming, and scenic coastal views on a well-run boat by Cretan Yachts.

“Wonderful experience from start to finish! Crew were fun and informative, food was delicious, water was our favourite place to swim in Europe. All round, great experience that we would recommend and do again. Relaxing day on the water and snorkeling. Crew even if helped me out and let me steer the yacht when I was feeling seasick.”

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13.Sunrise Balloon Flight & Sunset Catamaran Cruise

★★★★★★★★★★5.0 · 45 reviews · 8 - 9 hours · from $353

Sunrise hot-air balloon over Crete’s Lassithi Plateau, then an all-inclusive sunset catamaran from Heraklion with swimming, snorkeling, and open bar.

“Amazing to see Crete by sea and by sky. Went with my young children who had an amazing time with both activities. All crews professional. The hot air balloon ride was so special! Easy to work with the company, no issues finding meeting place. Very recommended.”

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14.Dia Island: Semi-Private Full Day Sailing Trip with meal

★★★★★★★★★★4.7 · 19 reviews · 6 hours · from $100

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, and a meal with local wine, on a small semi-private boat.

“A Perfect Day on the Water – Unforgettable Trip to Dia Island! ⭐⭐⭐⭐⭐ Our boat trip to Dia Island was absolutely incredible – the highlight of our holiday! From the moment we stepped on board, everything was perfectly organized and relaxed. The crew was warm, professional and made us feel completely at ease. The boat itself was spotless, spacious and comfortable, with plenty of shaded areas and sunbathing spots. The journey to Dia Island offered stunning views of the Cretan coastline, and once we arrived the crystal-clear turquoise waters were just breathtaking. We anchored in a bay where we had time to swim, snorkel , fish and paddleboard – all…”

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