The 15 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 $106

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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8.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Join EOS Yachts aboard a modern catamaran from Heraklion to Dia Island for 5.5 hours. Captain Thanasis and his English-speaking crew serve Cretan treats, chef-cooked seafood, wine, beer, and soft drinks, with time for swimming, snorkeling, SUP, canoeing, and fishing.

“Amazingly organized! Staff was incredibly thoughtful and attentive. Would recommend:)”

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9.Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys

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

Sail from Heraklion to Dia Island on a semi-private catamaran with a crew led by Jana and Wesley, a nutritionist-designed Cretan lunch, open-bar drinks, and water toys including a slide, sea scooter, kayak, and SUPs. Expect 5.5 to 7 hours on the water.

“Crew were awesome and the food was brilliant. A fantastic day out.”

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10.Dia Island Luxury Catamaran Cruise with Meal

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

Leave Heraklion’s Old Venetian Harbor aboard a Lagoon 450F catamaran with Sophia and an attentive crew. After passing Koules Fortress, you reach Dia Island for swimming, snorkeling, fishing, paddle boarding, drinks, and a Mediterranean meal. Choose a morning sailing or a sunset return.

“The best thing was that we could vary between snorkeling, swimming and being on the paddle board. It was so much fun doing everything and the crew was very attentive and friendly too. Would recommend it to everyone, who wants to enjoy the sun and the sea, as well as boat trips. The catamaran was very modern and clean. Also enjoyed the food and the drinks, everything was delicious and the crew was also very considerate of allergies or dislikes and very chill about everything. That made the experience even better but the most beautiful view was the sunset when we started to get back to the port.”

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11.Catamaran Cruise to Dia with Sunset, Meal & Bar

★★★★★★★★★★4.9 · 181 reviews · 5 - 6.5 hours · from $132

Spend 5 to 6.5 hours sailing from Heraklion to Dia Island aboard a semi-private DanEri Yachts catamaran. Swim, snorkel, kayak, paddleboard, ride the slide and sea scooter, then enjoy a nutritionist-designed Cretan meal, open bar, and sunset sail back.

“It was fantastic trip. Nice catamaran, friendly staff, very good food. We were very happy! Thanks again)”

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12.Dia Island Morning Sailing Trip with Snorkeling

★★★★★★★★★★4.9 · 100 reviews · 6 hours · from $82

Meet Cretan Yachts at Heraklion Old Port for a six-hour sailing trip to Dia Island. Captain Nickolas and crew members such as Dimitris and Alexandros have helped passengers steer, learn about sailing, snorkel, and relax with fruit, sandwiches, wine, and soft drinks.

“I liked captais and his saler. Tasty snacks, drinks snorkling goods was inthe boat, i like this trip”

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13.Sunrise Balloon Flight & Sunset Catamaran Cruise

★★★★★★★★★★5.0 · 45 reviews · 8 - 9 hours · from $353

Pair a sunrise balloon flight over the Lassithi Plateau with a semi-private sunset cruise from Heraklion or Hersonissos. You’ll help inflate the balloon, enjoy Greek breakfast, then swim, snorkel, fish, eat sushi, and watch sunset aboard a DanEri catamaran.

“The staff on board the margarita catamaran were fantastic , informative & made the trip a very relaxing and pleasant experience. The food that was made on board was delicious and exquisite with very nice wine & beer.”

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14.Semi-Private Full Day Sailing Trip with meal

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

Join Avanti Sailing for a six-hour trip from Heraklion to Dia Island, limited to 10 people. Swim, snorkel, paddleboard, fish, enjoy a homemade meal with local wine, and help with sailing when conditions allow.

“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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15.SUP Safari – Catamaran Cruise Dia Island & Gourmet Delights!

★★★★★★★★★★5.0 · 9 reviews · from $169

Sail from Heraklion to Dia Island aboard an EOS Yachts catamaran, then paddle and snorkel with Thanasis or another certified guide. You get quality equipment, 360° camera footage, Cretan treats, a gourmet platter, unlimited drinks, and five hours on the water.

“Very well organized, with a presentation that totally matched the description, full of friendliness, attention, and a focus on the client experience. The guide was highly experienced. A beautiful excursion in a stunning location. The catamaran was gorgeous. An experience worth repeating. Thank you for this wonderful day!”

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