8 Dia Island Cruises, Compared

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 Dia Island aboard a yacht limited to 14 people. Swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. English-speaking crew members may include Mariana, Manos, Sofia, Giannis, or Captain Petros.

“Superb day out on the boat! The views are breathtaking A must do whilst in Crete and will do it again”

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2.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Sail from Heraklion to Dia Island on a shared or private yacht with an English-speaking crew. Swim and snorkel in Saint George Bay, try fishing, enjoy lunch, fruit, wine, soft drinks, and plenty of deck time. Crew members may include Marcos, Vasilis, Alexandra, or Dimitri.

“This activity was amazing, great communication from the get-go, staff were lovely and very knowledgeable, the transport shuttle was on time and quick, the boat and Dia Island were stunning and the food and drinks were great - especially if you like a sweeter white wine!”

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3.Sailing Cruise to Dia Island with Drinks and Meal

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

Spend six hours sailing from Heraklion to uninhabited Dia Island, with snorkeling, paddleboarding, fishing, swimming, and a Mediterranean meal included. The English and Greek-speaking crew, including captains such as Stelios or Nick, keeps the day relaxed and social. Hotel pickup is optional.

“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on board at the harbour and at the island had a chance to try snorkelling and SUP for the first time. Lunch was prepared while we swam and we had plenty of chance to sunbathe without feeling under pressure to do anything to a schedule. The whole experience was so relaxing, we felt like welcomed guests…”

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4.Dia Island Sailing Cruise with Snorkeling

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

Set sail from Heraklion with a small crew, usually 10 to 18 people, for Dia Island’s clear bays. Ernesto and George may guide your trip, sharing Crete stories while you swim, snorkel, paddleboard, and eat a simple Greek meal onboard.

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

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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 with Cretan Sailing Cruises for about 5.5 hours. You get a swim stop, snorkeling, SUP, fishing gear, shrimp linguini, Greek dishes, fruit, beer, wine, and soft drinks. Crews including Petros, Yannis, Katerina, and Christina may vary by departure.

“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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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 such as Ilias and Nikiforas. Swim in Saint George Bay, use the snorkeling, fishing, and paddleboard gear, and enjoy drinks and fruit. Add a Greek lunch, and hotel transfers are available for an extra fee.

“Although the wind was light we still had a fabulous day, our skipper was brilliant and the food was lovely. Swimming off the boat was great fun. Thank you, we’ll be back one day”

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7.Sailing Trip to Dia Island with Lunch & Swimming

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

Join Set Sails for a six-hour cruise from Heraklion to Dia Island, with crew such as George, Vaso, Spiros, and Marina depending on the boat. Swim in Saint George Bay, use the SUP and fishing gear, and enjoy shrimp pasta, Greek salad, fruit, and unlimited drinks.

“service was amazing. the whole process was streamlined and efficient. from the pick up to the drop off. our boat operators were attentive and informative and we had the most amazing day sailing.”

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8.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181Top rated

Set sail from Heraklion at 9:30 a.m. aboard a modern catamaran for a six-and-a-half-hour trip to Dia Island. Swim from the boat, snorkel, paddleboard, fish, and enjoy brunch, fresh Mediterranean lunch, dessert, and selected unlimited drinks. The English-speaking crew may include Spiro, George, Alexandria, or Sergey.

“We had a great day with George and Alexandra. This is basically a ride to Dia island off Heraklion where you anchor and pass the day swimming and sunbathing. Out at 10:00 back by 16:00. The food was ok. This trip is what you make it and depends on the other members of the group. If you want to walk on the island make sur to bring proper footware.”

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