The 7 Best Heraklion Sailing Trips

1.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Venetian Harbour to protected Dia Island aboard a comfortable yacht with a maximum of 14 people. Swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. Afternoon departures can include a beautiful sunset sail back.

“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.Sailing Cruise to Dia Island with Drinks and Meal

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

Spend six hours sailing from Heraklion to uninhabited Dia Island with a certified crew, snorkeling and SUP gear, fishing equipment, drinks, and a Greek meal. You can join the sailing, swim in clear water, hike, or simply relax on deck. Hotel pickup is available.

“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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3.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion’s Venetian harbor to uninhabited Dia Island with a small crew, usually including Ernesto or George. Swim in clear bays, snorkel, paddleboard, and enjoy wine, soft drinks, and either seafood pasta or a lighter half-day meal.

“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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4.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sail from Heraklion to uninhabited Dia Island with a small crew of up to 18 people. Swim, snorkel, paddleboard, eat Greek food, and watch the sunset on the return journey. The crew, including guides such as Andreas and Ianos on some departures, adjusts the plan to wind and sea conditions.

“This was one of the best experiences I’ve ever had!! Stella and Elena are two wonderful hosts who did everything to make the trip amazing! Thank you to them! We had a delicious dinner with pasta, salad, and fruit, the chance to enjoy the beauty of the sea, and saw an incredible sunset! I highly recommend it to everyone!”

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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, about an hour offshore, then anchor near Saint George Bay for swimming, snorkeling, SUP, fishing, and lunch. The crew, including captains such as Petros and Yannis, provides equipment, drinks, and a shrimp-linguine meal for up to 14 people.

“Very pleasant cruise out to Dia Island. The crew was wonderful and provided excellent service. We did have to wait to dock, but it was pleasant to chat with other passengers while waiting. Would definitely recommend this trip.”

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6.Sailing Trip to Dia Island with Lunch & Swimming

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

Sail six nautical miles from Heraklion to Dia Island with Captain George, George the Fisherman, Panos, or Vaso. Swim in Saint George Bay, use the SUP and snorkel gear, and enjoy shrimp or vegetarian pasta, Greek salad, fruit, and unlimited drinks aboard a small yacht.

“We had a lovely experience and enjoyed every moment! The food was amazing and we had some lovely couples with us on the boat. The water was crystal clear and we did some snorkelling. A truly lovely day.”

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7.Dia Sailing Cruise With All-inclusive Meal And Drinks

★★★★★★★★★★4.6 · 422 reviews · 5.5 hours · from $76Best value

Sail from Heraklion’s Old Venetian Port to protected Dia Island for swimming, snorkeling, and paddleboarding. The crew, including guides such as Alex, Nikolas, Fabio, and Manuel, serves shrimp linguine, Greek salad, fruit, wine, soft drinks, and water. Choose a daytime or sunset sailing.

“the trip was amazing with excellent and experience guides. The food was more than perfect with variety of drinks,snacks and fruits . The stuff was very kind and helped as a lot with everything. We as well did surfing and some other activities on the dias island. I 100% recommend it to anyone thats visiting crete it was the highlight of the holiday for sure and value of money.”

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