The 15 Best Dia Island Cruises from Heraklion

1.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Old Venetian Harbour to protected Dia Island aboard a small yacht for up to 14 people. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos may host your trip, with swimming, snorkeling, paddleboarding, a Mediterranean meal, unlimited drinks, and sunset options.

“Fantastic few hours in the Greek sea, lovely crew DELICIOUS food and gorgeous sunset! Love love love”

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2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.9 · 1,287 reviews · from $90

Join a small shared cruise or private sailing trip from Heraklion to Dia Island. Swim and snorkel in Saint George Bay, try fishing, enjoy lunch and unlimited drinks, and sail back with an attentive crew such as Marcos, Vasilis, Dimitris, or Alexandra.

“A beautiful and relaxed boat trip including a lovely little meal. I enjoyed it a lot. Thanks to captain and skipper and also the other travelers.”

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3.Sailing Cruise to Dia Island with Drinks and Meal

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

You’ll sail from Heraklion’s Old Venetian Harbor to Dia Island with a certified crew, often including Stelios, Celia, Captain Nick, Kristina, or Iorgu. Swim, snorkel, paddleboard, fish, hike, and enjoy shrimp spaghetti, salad, fruit, wine, soft drinks, and raki aboard a small-group yacht.

“Lovely chilled boat cruise with two swimming stops… the island is uninhabited just some goats but it’s all about boat life!! Lush food, beer and wine and soft drinks flowing all day and raki shots for the hard-core”

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4.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion with a professional crew, often including Ernesto and George, to uninhabited Dia Island. Swim in clear bays, snorkel, paddleboard, and enjoy Greek salad, tzatziki, seafood pasta, fruit, wine, and soft drinks. Choose a half-day or full-day trip, with small groups of up to 18.

“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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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 uninhabited Dia Island aboard a yacht or catamaran, with swimming, snorkeling, SUP, fishing, lunch, wine, beer, and soft drinks included. Expect about an hour at sea each way and three hours in a sheltered bay. Boats and crew may vary.

“We were collected from our hotel and taken to the port. Our first experience in a sail boat and really enjoyed it. Food and drinks were included. The water at Dia island was gorgeous to swim in. Then a journey back watching the sunset was the perfect ending.”

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6.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

Spend 4.5 hours on a private sailing boat from Heraklion to Dia Island, with a two-person crew, drinks, fruit, snorkeling gear, fishing equipment, and paddleboards. Anchor in Saint George Bay, the setting once explored by Jacques Yves Cousteau, and add a fresh onboard meal if you wish.

“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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7.Sailing Trip to Dia Island with Lunch & Swimming

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

Set Sails takes you from Heraklion to Dia Island on a small-group yacht cruise with swimming, snorkeling, fishing, SUP, and lunch. The crew may include George, Vaso, Spiros, or Marina. Choose port departure or selected transfers, then spend about three hours anchored at Saint George Bay.

“My partner and I loved this trip! Vaso & Spiros were fantastic guides. Snorkeling at Dia Island was super fun and the water was nice and warm. We enjoyed chatting with the others guests on the boat - had some wine together which was fun. Highly recommend this experience!”

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8.Sunset Cruise to Dia Island

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

Sail from Heraklion with a local captain and crew to Dia Island, where you have about 3.5 hours for swimming, snorkeling, snacks, and quiet time in Saint George Bay. Alex, Yannis, Kosta, and Niko have led recent trips, though the crew may vary.

“Everything was great and the crew was incredibly nice and entertaining.”

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9.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sail from Heraklion to uninhabited Dia Island with a small crew, swimming, snorkeling, paddleboarding, food, wine, and raki. Depending on the boat and departure, you may meet crew members such as Alex, Kostas, Emanuel, Constantine, Thanos, or Eleanor. Choose a shared or private catamaran and a half-day or full-day outing.

“This experience was the cherry on the cake for our trip here. For a cheap price a 4 hour boat-trip with food, amazing view on the sea and sunset, snorkling and swimming. The guides/captains were all very kind. 10/10 would recommend.”

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10.Dia Island Luxury Catamaran Cruise with Meal

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

From Heraklion’s Old Venetian Harbor, you sail to Dia Island aboard a Lagoon 450F catamaran with an English or Greek-speaking crew. Swim, snorkel, fish, or use the SUP board before a Mediterranean meal, unlimited drinks, and a relaxed return, with morning and sunset departures.

“The sunset on the boat, I truly recommend the evening trip.”

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

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72Top rated

You sail from Heraklion’s Old Venetian port to Dia Island with a certified crew, usually in a group of no more than 10. Expect a calm bay, swimming, SUP boards, snorkeling gear, an organic lunch, fruit, soft drinks, and wine. Pickup is free within 10 kilometers.

“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 were nowhere to be seen. After waiting 30 minutes we gave them a call and they had no record of our booking. Their explanation was that the tours for the previous day were cancelled because of the windy weather and moved to our day. This is understandable, but there is obviously an issue with them…”

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

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

Join DanEri Yachts for a five-hour catamaran cruise from Heraklion to Dia Island. Expect coffee, pies, a seafood and meat lunch, open bar, snorkeling, SUP boarding, fishing gear, Wi-Fi, and a friendly crew that may include Captain Giannis, Gianna, Konstantinos, or Joana.

“Everything was perfect, the boat is beautiful and very well equipped, the team members are very nice and friendly The food was very good, and the sunset on the way back to Heraklion is just stunning I had a great time thank you !”

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13.Dia Island Catamaran Cruise with Dinner and Wine

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

Join DanEri Yachts for a five-hour catamaran cruise from Heraklion to Dia Island. Expect coffee and Cretan snacks, swimming, snorkeling, SUP boards, fishing, unlimited drinks, and a fresh seafood and meat dinner. The afternoon departure brings cooler sailing and a sunset return.

“Fun adventure to Dia island. The three hosts were lovely and boat was modern and clean. The bay was gorgeous and there were plenty of snorkels/inflatables/paddle boards etc to explore with. The sunset views on the sail back were memorable! Would thoroughly recommend”

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14.Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

★★★★★★★★★★5.0 · 142 reviews · 4 hours 30 minutes (approx.) · from $36Best value

Sail from Heraklion to Dia Island aboard a 45-foot yacht with a small group of up to 10 people. Swim and snorkel in St. George’s Bay, enjoy a generous onboard meal with drinks, and choose a sunset return. Crew members such as Markos, Alexandra, Magda, and Georges provide warm, attentive service.

“This was a truly fantastic experience that my wife and I enjoyed thoroughly! First, we appreciated all the communication before the day of our trip, with all the practical information regarding the trip, which made the preparations and planning simple and easy. We felt the duration of 4.5 hours worked very well. The trip itself is awesome in all respects and definitely something one should do if they visit the area of Heraklio. The sailing experience is exciting, the water at Dia is marvelous, the meal is delicious, and the staff is amazing! Our captain and co-captain were Markos and Magda and each of them was the perfect combination of…”

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15.Private Full-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 140 reviews · 6.5 hours

Take a private sailing boat from Heraklion to Dia Island with a two-person crew, swimming stops, snorkeling gear, fishing equipment, paddleboards, fruit, drinks, and local white wine. Add hotel transfers or an onboard meal for a more polished day.

“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”

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