Greece · HERAKLION SAILING TRIPS

Heraklion Boat Trips: the 15 Best Days to Dia and Beyond

25 sailing trips  ·  from $68 a seat

Dia sits seven miles off the harbour with three bays on its south side and nothing else on it. The 15 below compare the sailboats and catamarans that go there on price, on how long they stay and on what lunch looks like.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - The One-Hour Sail to Dia Island
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Number one

Spend 5.5 hours sailing from Heraklion’s Old Venetian Harbour to protected Dia Island. With no more than 14 people aboard, you’ll swim, snorkel, paddleboard, eat shrimp linguini and Greek salad, and enjoy unlimited drinks. Crew members may include Mariana, Manos, Sofia, Giannis, or Captain Petros.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Dia Island gives you room to choose your own pace
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

2.Sailing Cruise to Dia Island with Drinks and Meal

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

Spend about six hours sailing from Heraklion’s Old Venetian Harbor to Dia Island with an experienced crew, often including Stelios, Celia, or Captain Nick. Swim, snorkel, paddleboard, fish, hike, and eat a Greek meal aboard. Hotel pickup is optional, and afternoon departures can finish with a sunset sail.

“Literally so nice, personable and professional. We made friends with others on the tip facilitated by the captain. Not been cheesy but we will be lifelong friends.”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - Reaching quiet Dia Island
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Heraklion: Dia Island Sailing Cruise with Snorkeling

3.Dia Island Sailing Cruise with Snorkeling

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

Join Ernesto, George, and the Sailing Crete crew for a small-group cruise from Heraklion’s Venetian harbor to Dia Island. Sail for about an hour, then swim, snorkel, paddleboard, and eat onboard in a quiet bay. Choose a half-day or full-day trip, with hotel transfers available outside central Heraklion.

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

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - What makes Dia Island worth the crossing
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

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 professional crew such as Andreas, Manos, or George. Swim and snorkel in a quiet bay, use the paddleboard, eat Greek food onboard, and sail home at sunset. Shared and private options are available, with hotel pickup offered from selected areas.

“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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Sailing Cruise to Dia Island with Meal and Water Activities - Why Dia Island feels different from a beach outing
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Sailing Cruise to Dia Island with Meal and Water Activities

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 on a yacht or catamaran with a maximum of 14 people. You get about three hours in a sheltered cove for swimming, snorkeling, paddleboarding, and fishing, plus shrimp linguine, Greek salad, Cretan appetizers, fruit, beer, wine, and soft drinks. Captains such as Petros, Yannis, and Pedro adjust the route when wind or waves change.

“This was one of the best tours we booked! Amalia was amazing! We had a blast swimming, snorkeling and paddle boarding in the beautiful area of Dia Island!”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Leaving Heraklion Port
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

6.Sailing Trip to Dia Island with Lunch & Swimming

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

Join a small group of up to 10 people for a six-hour sail from Heraklion to Dia Island. Captains George, Panos, and Vaso bring local stories and good humor, while you swim, snorkel, paddleboard, fish, and enjoy shrimp or vegetarian pasta with Greek salad, fruit, and unlimited drinks.

“George and Marco were friendly and informative and made the trip very enjoyable. We spent a good amount of time snorkelling using the equipment they provided and enjoyed a nice lunch of pasta, salad and fruit. It’s a small group of 10 so the boat isn’t overcrowded and you get to know the people well. Highly recommend”

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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar - From Hersonissos Port to the open sea
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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

7.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★4.8 · 442 reviews · 3.5 - 4.5 hours · from $94

Set sail from Hersonissos on a modern catamaran for 3.5 to 4.5 hours of swimming, snorkeling, paddleboarding, sushi, local wine, beer, and sunset views at Saint George Bay. The English-speaking crew serves welcome Prosecco, fruit, snacks, and soft drinks. Groups are limited to 20, with optional pickup from selected areas.

“Great trip and the Catamaran…the crew were superb and very accommodating Highly recommended”

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Dia Sailing Cruise With All-inclusive Meal And Drinks - Four hours around Dia Island
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Dia Sailing Cruise With All-inclusive Meal And Drinks

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

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

Sail from Heraklion’s Old Venetian Port to Dia Island aboard a comfortable yacht with captains such as Alex, Nikolas, Fabio, and Mel. Spend four hours swimming, snorkeling, paddleboarding, eating fresh pasta and Greek salad, and sipping unlimited wine and soft drinks. Choose a daytime or sunset departure, with hotel pickup available by arrangement.

“This was the highlight of our vacation!! The drive was funny and relaxing and the food amazing!! They got all the things for snorkeling and to SUP around and it felt more like a friend outing than a payed tour, since they made you feel so comfortable. I would highly recommend to anyone who‘s thinking about it!!!”

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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu - What makes the catamaran feel luxurious
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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

9.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Sail from Heraklion to Dia Island aboard EOS Yachts’ modern catamaran, with Captain Thanasis and a professional English-speaking crew. You’ll get welcome treats, a chef-prepared seafood lunch, wine and beer, snorkeling, SUPs, canoeing, fishing, and time to swim in a quiet bay. The semi-private cruise carries up to 22 people.

“The staff were very friendly warm and welcoming. The journey was smooth and relaxing and the atmosphere was calm and relaxed. The food was fresh and delicious and a good serving including drinks non alcohol and alcohol. Also a good supply of fun activities, snorkelling, paddle boarding and just relaxing in the sun. I differently recommend the Heraklion Luxury Dia Isla cruise. Thanasis And his crew were amazing, Thank you for the amazing experience.”

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Heraklion: Small-Group Sailing Trip to Dia Island with Lunch - What makes Dia Island different
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Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

10.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Join a crewed sailing yacht from Heraklion’s Old Venetian port and sail about an hour to Dia Island. With up to 10 people aboard, you’ll swim, snorkel, use a SUP, and enjoy a fresh local lunch with drinks and wine. The crew, including guides such as Stratos, Stefanos, and Aphrodite, also shares island myths and marine-life facts.

“We stayed in malia which was more than 10km away from Heraklion. Cost for transportation is 20e. We took the bus which was cheaper. The crew was very friendly they explained everything we wanted to know. We arrived to the island in 1 hour stayed there for 2.5 hours and left. The food was absolutley amazing. Souflaki very good and thr salad very fresh. Wine was very good. We did snorkeling and saw tons of fish. Very nice experience overall. Absolutely worth the money.”

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Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys - What makes the catamaran comfortable
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Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys

11.Dia Island Catamaran Cruise with Lunch, Water Toys

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

Join DanEri Yachts for a 5.5 to 7-hour cruise from Heraklion to Dia Island, limited to 20 people. The English-speaking crew, including Jana and Wesley, serves espresso, healthy snacks, a nutritionist-designed lunch, and open-bar drinks. Swim, snorkel, kayak, paddleboard, ride the slide, or relax on deck.

“Wonderful day on a luxury boat . Team was great and beautiful island.”

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Heraklion: Dia Island Luxury Catamaran Cruise with Meal - Three hours and 45 minutes in Dia’s sheltered bay
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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

12.Dia Island Luxury Catamaran Cruise with Meal

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

Sail from Heraklion’s Old Venetian Harbor to Dia Island aboard a Lagoon 450F catamaran with an English- or Greek-speaking crew. Swim, snorkel, fish, and try paddle boarding in a sheltered bay, then enjoy Greek salad, local appetizers, pasta, fruit, and unlimited drinks. Choose a morning cruise or a sunset return.

“⭐⭐⭐⭐⭐ The catamaran was beautiful, the staff was absolutely amazing and so friendly — they made everyone feel welcome and taken care of from start to finish. The cruise itself was unforgettable: the water around Dia Island was crystal clear and perfect for swimming, and watching the sun slowly set over the sea was just magical. The meal served onboard was delicious and added such a nice touch to the whole experience. If you’re visiting Heraklion, don’t miss this tour — it’s the perfect mix of relaxation, stunning views, and great vibes.”

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Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar - Boarding at Marina Café in Heraklion
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Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar

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

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

Spend a relaxed afternoon sailing from Heraklion to protected Dia Island aboard a semi-private catamaran for up to 20 people. You’ll get espresso, healthy Cretan food, unlimited water, soft drinks, beer, and white wine, plus swimming, snorkeling, kayaking, SUPs, a sea scooter, and a slide before sailing home at sunset.

“Seamless organisation, spotless boat and the team were amazing. Highly recommend!”

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Heraklion: Dia Island Catamaran Cruise with Water Toys - Dia Island’s bay and the main water session
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Heraklion: Dia Island Catamaran Cruise with Water Toys

14.Dia Island Catamaran Cruise with Water Toys

★★★★★★★★★★5.0 · 174 reviews · 5 hours (approx.) · from $151

Join an English-speaking crew aboard a Lagoon 450 catamaran for a five-hour morning trip from Heraklion to Dia Island. Swim in a sheltered bay, use the slide, sea scooter, kayaks, SUPs, snorkeling gear, and fishing equipment, then enjoy a nutritionist-designed Cretan lunch with drinks. Captain Giannis, Wesley, and chef Giulia have all been part of the friendly onboard team.

“I literally could not recommend this trip highly enough! The captain and the entire staff were extremely friendly, accommodating, and pleasurable. The food and drinks were phenomenal and truly added to the experience. We had plenty of time to swim in the sea and get plenty of sunshine.”

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Heraklion: Dia Island Luxury Sailing Trip with Meal & Drinks - TREATON and JACKPOT: choosing the right sailing
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Heraklion: Dia Island Luxury Sailing Trip with Meal & Drinks

15.Dia Island Luxury Sailing Trip with Meal & Drinks

★★★★★★★★★★4.7 · 107 reviews · from $68Cheapest deck

Sail from Heraklion’s Venetian port to Natura 2000 protected Dia Island aboard TREATON or JACKPOT. You’ll have about 3.5 hours for swimming, snorkeling, fishing, paddleboarding, and lunch with beer, wine, fruit, and soft drinks. Choose a shared, private, sunset, morning, or full-day sailing, with crews including Cosmos, Joseph, Thanos, and Nikos on different departures.

“We had a wonderful day onboard TREATON. Everything was great, the sailboat, the trip, the island. The food was absolutely delicious. The crew was amazingly kind, helpful and passionate. Thanks again for this spectacular experience. I would do it again and again if I could. I definitely recommend the cruise to everyone going to Crete !!”

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Just added in Heraklion Sailing Trips

★ 4.5Private Sailing Cruise to Dia Island with Meal & Water ActivitiesFrom $951 per boat10 reviews
★ 5.0Dia Island Private Sailing Cruise with Full MealFrom $931 per boat6 reviews
★ 4.8Private sailing to Dia Island with LunchFrom $471 per boat16 reviews
★ 4.7Dia Island: Semi-Private Full Day Sailing Trip with mealFrom $10019 reviews

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