The 15 Best Dia Island Sailing Trips

1.Dia Island Sailboat Cruise with Swimming and Meal

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

Small-group sailing from Heraklion to Dia Island for swimming, snorkeling, SUP, and a Mediterranean meal with unlimited drinks.

“It was amazing experience. Definitely a highlight of my vacation. Mariana and Manos was fun and helpful. Good food and beautiful views.”

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2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Sail from Heraklion to Dia Island on a yacht with snorkeling, SUP, unlimited drinks, and lunch on shared half-day trips.

“Excellent day! The water was perfect, our guide was great and the day was perfect. Sunset was beautiful.”

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3.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion to Dia Island for snorkeling, SUP, and a Greek meal with wine and raki, plus drinks on board.

“This was a fabulous trip. The staff were very friendly and committed to making sure everyone had a good time. They boat was fantastic and their were enough activities to keen everyone entertained during the cruise. Food was fantastic too. Highly recommend this tour to anyone in Heraklion for the day.”

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4.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, included snorkeling, and paddleboarding, with food and drinks onboard.

“The crew was super friendly. Even the weather condition was not the best, the travel went quite smooth. The bays are there just amazing. Only dis thing was, I was expecting to swim in more spots (we did 2), but the places we swam was fantastic 🥰 The food was not great but it tastes good since you became super hungry 😁”

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5.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sunset catamaran cruise from Heraklion to Dia Island for snorkeling, paddleboarding, and onboard food and drinks in small groups.

“This boat trip was amazing, we were picked up from out hotel and taken to the port. The drive was very quick and easy. We then met the captain of the boat and were amazed with how big and nice the boat was. We sat up the front of the boat having dia island in view the whole time. The boat crew made us a meal and always checked in to see if we needed anything. Great for all ages and people who love sunsets. Would highly recommend!”

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

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96.74

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, and a hearty lunch with drinks on board.

“Boat was overcrowded. Very little interaction with boat captains. They mostly stayed in the bottom as a couple. Find another excursion.”

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7.Sailing Trip to Dia Island with Lunch & Swimming

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

Sail from Heraklion to Dia Island for a small-group cruise with lunch, unlimited wine, snorkeling, SUP, and swimming in crystal water.

“It was a fun and entertaining experience, super friendly hosts, food was also very delicious. Definitely recommend. Ευχαριστώ”

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8.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459

Private 4.5-hour sailing to Dia Island from Heraklion. Snorkel, paddleboard, fish, swim, and eat on board with drinks included.

“Communication with the provider was excellent from point of booking to the day of the event. They answered my many questions and was helpful with facilitating a cake delivery for my daughters birthday. The round trip taxi service was fairly priced, the driver arrived in time & was very friendly and accommodating. The boat was lovely & the crew Ilias & Nikiforas were fantastic. Really friendly& welcoming guys. Dia Island was beautiful & the journey to and from the island was equally as enjoyable. All round a perfect excursion and well worth the money. Thank you”

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9.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Cruise from Heraklion to mythic Dia Island on EOS Yachts, with a chef-cooked gourmet menu, snorkeling gear, and calm-bay swimming.

“We were a group of five from Italy. The boat was spotless, very well maintained, and quite modern. The crew was helpful and super kind. We loved the whole experience from the beginning until the end. We would recommend it for sure to everyone.”

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

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

Sail from Heraklion to uninhabited Dia Island on a crewed yacht. Swim, snorkel, maybe spot dolphins, and enjoy local organic lunch.

“We had amazing time on this trip. Crew were very helpful and friendly. Amazing view from the sailing boat. We stopped in very beautiful shore, where we could swim in the sea and have relaxing time. Served food was also great. All in all 100 percent I would recommend this experience. Maybe I would suggest taking a day time trip, because it gets a bit chilly in the evening. But even in the cold weather I had a good time.”

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11.Sunset Cruise to Dia Island

★★★★★★★★★★4.8 · 259 reviews · 5.5 hours · from $82

Sail from Heraklion to Dia Island on a sunset cruise with snorkeling, snacks, and clear-water swimming around rugged Cretan coastline.

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

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12.Dia Island Catamaran Cruise with Lunch, Water Toys

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

Luxury catamaran cruise from Heraklion to Dia Island with water toys, snorkeling gear, and a chef-made Cretan lunch plus unlimited drinks.

“The cruise was amazing! The crew was super friendly and the food was just delicious!”

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13.Dia Island Luxury Catamaran Cruise with Meal

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

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

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

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14.Dia Island Catamaran Cruise with Water Toys

★★★★★★★★★★5.0 · 174 reviews · 5 hours (approx.) · from $151.23

Sail from Heraklion to Dia Island on a small catamaran with snorkeling, SUP, sea scooter toys, and a Mediterranean lunch plus open bar.

“Such a relaxing, fun day with great food and wonderful staff and amenities. Our family had so much fun swimming at our leisure, using the paddle boards and snorkelling.”

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

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72.59

Sail from Heraklion to Dia Island for snorkeling, SUP, and an organic lunch with drinks, plus wildlife spotting tips.

“Small group tour was amazing; our family of 3 and 2 friends we didn't know - perfect! George and Harry are super knowledgeable and great chefs, each always interacting with one of us. The island taken to was beautiful with the most crystal blue water and it was amazing to watch them direct the boat almost all the way to the beach around other boats anchored in the bay to get us the best spot. They even accommodated one of the girls birthday with a song, hats, and coordinated the surprise with the friend having the cake picked up and brought on board. Boat had plenty of shaded and sunny…”

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