The 4 Best Private Sailing Charters in Heraklion

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

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

Sail from Heraklion’s Venetian port to Dia Island aboard a comfortable boat with a crew of up to 10 people. You can swim, snorkel, fish, use the SUP, explore the bay, and enjoy a meal with local wine and fruit. Dimitri is part of the crew, and the return trip includes more sailing and sea views.

“Très bonne journée passée avec nos deux capitaines sur l'ile. Beaucoup de poissons à observer en snorkeling. Très bon repas fait maison. En amélioration, faire un 2eme spot de baignade ailleurs serait sympa.”

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2.Private sailing to Dia Island with Lunch

★★★★★★★★★★4.8 · 16 reviews · 4.5 hours · from $471 per boat

Set sail from Heraklion’s Old Venetian port with a private group of up to eight. Your English, Greek, or Italian-speaking crew guides you to Dia Island for quiet-bay swimming, snorkeling, SUP time, local stories, and an optional fresh Cretan lunch. Vang and Aphro have earned praise for warm, attentive hosting.

“Six of us were in Crete last week and we we booked this boat trip which was an exclusive sailing boat with crew. The trip was faultless and perfect. I was with my 70+ parents and they were catered for from their mobility issues to vegetarian requirements for the gorgeous lunch prepared for us. There was swimming in the sea and just taking in the scenery: we could not have asked for more. We were picked and dropped off from our hotel and the crew were knowledgeable of the history and questions we had about Crete. I would highly recommend this as a must-do! 🌟🌟🌟🌟🌟”

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3.Private Sailing Cruise to Dia Island with Meal & Water Activities

★★★★★★★★★★4.5 · 10 reviews · 5 hours 30 minutes (approx.) · from $951 per boat

Sail privately from Heraklion to Dia Island for about five and a half hours with guides such as Harry, Christina, Captain George, and Martina. Expect a clean yacht, a swim stop, snorkeling, SUP, fishing gear, shrimp linguini, Greek salad, fruit, and drinks. Pickup covers much of Crete’s north coast, but wind and departure delays can affect the day.

“We had a fantastic time on this private sailing cruise. The staff were welcoming and attentive, making the whole journey enjoyable and relaxing. The food was delicious and plentiful, and the boat itself was in excellent condition—clean, comfortable, and well maintained. The mix of sailing, swimming, and water activities made it both fun and memorable. Highly recommend for anyone looking for a perfect day at sea.”

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4.Dia Island Private Sailing Cruise with Full Meal

★★★★★★★★★★5.0 · 6 reviews · 5.5 hours · from $931 per boatHighest rated

Set sail from Heraklion’s Venetian harbor on a private yacht for up to 10 people. Cruise past Koules Fortress, swim and snorkel in Dia’s clear bay, try fishing or paddleboarding, and enjoy shrimp linguini, Greek salad, fruit, and unlimited drinks. Crew members may include Amalia, Zoey, Spiros, Christos, or Giannis.

“Great crew, great experience, truly appreciated them calling to advise to switch booking for a different day for better weather, and the food was AMAZING”

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