Top 13 Sailing & Catamaran Cruises in Heraklion

1.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a fresh Greek meal, drinks, and sunset views.

“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 so clear we could see schools of small fish in it. There’s even a small beach which we had time to sunbathe on before going back to the boat (we chose the half day). Before we set off back towards Heraklion, we had some delicious Greek salad, fruits, cheese and bread. Our Captain also took…”

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2.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion to uninhabited Dia Island for swimming, snorkeling, paddleboarding, Greek food, wine, and relaxed small-group sailing.

“The Sail Boat tour was extraordinary. We had such a beautiful sunny day. Both the Captains were very incredible. I booked for a Retreat I was hosting in Greece. We were 7 people and had the whole sailboat for ourselves. I booked the half day tour & honestly we loved it so much, that if I was doing it again, I would book the whole day! Highly recommend this experience! So worth it. 🤍 A big Thank you!!!!!! 🇬🇷 Best ever. Oh & the food was simple, but great! & we had lovely music for the whole tour, good ambiance!!!! +++5 stars ✨”

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3.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, paddleboarding, a Cretan lunch, drinks, and a sunset return.

“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.”

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4.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 414 reviews · from $67

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, fishing, a Greek lunch, unlimited drinks, and sunset views.

“Ilis and Vaso were our guides and we were really pleased with their hospitality. They were very welcoming, ensured we were looked after and had the best possible experience. Food was really lovely and great variety of drinks available on board. They had a paddling board and snorkelling masks available for everyone for when we stopped off to swim. Would recommend, 10/10 experience.”

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5.Sunset Catamaran Cruise with Snacks and Drinks

★★★★★★★★★★4.8 · 328 reviews · from $90

Review of Hersonissos sunset catamaran cruise with swimming, snorkeling, SUP boards, snacks, drinks, and golden-hour views of Crete.

“Great experience, i think the hosts need to mention the islands as we pass or enter so we are aware”

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

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

Sail from Heraklion to protected Dia Island for clear-water swimming, snorkeling, a local lunch, and a relaxed small-group day at sea.

“Everthing was very Nice :) Maybe the Trips should be a Bit longer.”

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7.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.6 · 242 reviews · from $63Best value

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

“Absolutely amazing experience ! I recommend and for sure we would repeat it in the future when we visit Greece again . It was the best value for money !”

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8.Dia Island Luxury Catamaran Cruise with Meal

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

Cruise from Heraklion to Dia Island on a spacious catamaran with swimming, snorkeling, paddle boarding, a Cretan meal, and drinks.

“We were very happy and glad during and after the trip, the staff was friendly, smiling and helpful. I especially want to note the attitude towards passengers from the crew, we felt comfortable and safe. Just simply had a great time 👌. I can confidently recommend others to also enjoy spending time on board with this company and their crew 🫶”

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9.Dia Island Catamaran Cruise with Water Toys

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

Review of Heraklion’s five-hour Dia Island catamaran cruise, with lunch, open-bar drinks, snorkeling, paddleboards, and water toys.

“The crew were excellent. The food and drinks were very good. It was a smaller catamaran so there was not too many people.”

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10.Dia Catamaran Tour – Lunch, Open Bar & Snorkeling

★★★★★★★★★★4.9 · 161 reviews · from $141

Sail from Heraklion to Dia Island on a five-hour catamaran cruise with lunch, open bar, snorkeling, SUP and family-friendly fun.

“I couldn’t fault anything on this trip. The entire crew from the Captain and his first mate, the chef, and our tour leaders were great. The boat was a good size, comfortable and clean, meals were tasty and varied. The length of the trip was just right and the spot to Dia island was just a jewel with crystal clear waters and amazing scenery. The whole concept of the excursion was outstanding. Would definitely recommend this trip to anyone.”

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11.Dia Island Catamaran Cruise with Dinner and Wine

★★★★★★★★★★4.8 · 147 reviews · from $120

Sail from Heraklion to Dia Island for swimming, SUP, seafood dinner, unlimited drinks, and an Aegean sunset on a luxury catamaran.

“A truly fabulous experience enjoyed by us adults and our teenagers, made even better by the wonderful crew. Swimming in the turquoise cove at the island, playing on the SUP boards and snorkels and being served a lovely meal before watching the spectacular sunset on the sail home. Wonderful! Highly recommend!”

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12.Dia Island Luxury Sailing Trip with Meal & Drinks

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

Sail from Heraklion to protected Dia Island for swimming, SUP, snorkeling, a Mediterranean meal, drinks, and sunset views.

“It was a totally amazing adventure! The guides were super friendly and helpful. We were a small group on the boat and had a nice time. The meeting point was easy to find.”

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13.Dia Island Morning Sailing Trip with Snorkeling

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

Sail from Heraklion to Dia Island for snorkeling, swimming, snacks, and scenic Cretan coast views on a friendly six-hour yacht trip.

“Absolutely fantastic. They were such great guides & we had a wonderful day. One of my families favorite moments of the trip 💗”

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