Under sail · HERAKLION SAILING TOURS

Sailing in Heraklion: the 8 Best Trips

8 sailing trips  ·  seats from $76 each

The coast of Heraklion from the water: 8 sailing trips with their prices, how long each is out and what is served on deck.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Dia Island from a protected bay
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Top of the fleet

Sail from Heraklion’s Venetian Harbour to protected Dia Island aboard a yacht limited to 14 people. You’ll 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, with morning and sunset departures available.

“This was a top notch experience: I strongly recommend this sunset boat trip!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - The one-hour crossing to Dia Island
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

2.Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

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

Join Sailing Grace for a six-hour cruise from Heraklion to Dia Island. You’ll sail with an English or Greek-speaking crew, hear island legends, swim, snorkel, fish, paddleboard, and eat a Mediterranean meal onboard. Hotel pickup is available, and afternoon departures can include a sunset return.

“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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Heraklion: Dia Island Sailing Cruise with Snorkeling - Arriving at Dia’s clear-water bays
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Heraklion: Dia Island Sailing Cruise with Snorkeling

3.Heraklion: Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion’s old Venetian harbor to uninhabited Dia Island with a small crew of up to 18 people. Ernesto and George are among the crew members you may meet. Swim in clear bays, use the included snorkeling and paddleboard gear, and enjoy drinks plus either seafood pasta or a lighter half-day meal.

“Despite the 40 min delay by transit authority that required us to divvy out passengers into several boats, they added 30 min on the end. The boat ride was refreshing and had a nice ship on the catamaran prepared by the skipper, wonderful views, about 30 min of swimming, snorkeling. The snorkeling equipment wasnt great and not much underwater sealife , so dont plan on itlooking like the Caribbean. The captain, Station was fun and full of stories”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - What makes Dia Island different
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

4.Heraklion: 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 10 to 18 people. You can snorkel, paddleboard, swim, eat Greek food, and watch the sunset from a catamaran. Half-day and full-day options are available, with hotel pickup offered from selected areas.

“We had a wonderful time! There were a lot of people on the boat but it didn’t feel crowded. The cove where we anchored was lovely — our only complaint was that a party boat anchored nearby and played loud (bad) house music the whole time. It made the experience slightly less idyllic, but we tuned it out eventually, food was delicious, guides were friendly and cooked a delicious dinner, and the sunset was dreamy. A perfect way to spend our afternoon/evening in Heraklion!”

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Sailing Cruise to Dia Island with Meal and Water Activities - Saint George Bay and Dia’s unusual character
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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 aboard a yacht or catamaran with a maximum of 14 people. Swim in a protected cove, snorkel, paddleboard, fish, and enjoy shrimp linguine, Greek salad, fruit, beer, wine, and soft drinks. Pickup is available across much of Crete.

“Wonderful experience. The crew was great and the food was so fresh and delicious. Perfect day trip !”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Three hours in Saint George Bay
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

6.Heraklion: 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 a maximum of 10 people. Captains George, Panos, and Vaso bring local stories and easygoing Cretan hospitality, while you swim, snorkel, paddleboard, fish, and eat shrimp or vegetarian pasta with 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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Dia Sailing Cruise With All-inclusive Meal And Drinks - The one-hour trip to Dia Island
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Dia Sailing Cruise With All-inclusive Meal And Drinks

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

★★★★★★★★★★4.6 · 422 reviews · 5.5 hours · from $76Lowest fare aboard

Sail from Heraklion’s Old Venetian Port to uninhabited Dia Island on a 5.5-hour cruise led by an English-speaking crew. Swim, snorkel, paddleboard, and enjoy pasta with shrimp, Greek salad, fruit, wine, soft drinks, and water. Day and sunset departures are available, with hotel transfers by prior arrangement.

“You know those nights that just feel… perfect? This was one of them. We set sail for Dia Island, hoping for one of those crazy-colorful sunsets. The sun was a little shy, but honestly? It didn’t even matter. The crew was amazing, making us feel so at home, and the food and wine were delicious. It was just one of those magical, simple moments that you never want to end.”

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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu - Meeting the crew at Heraklion Port
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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

8.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Join Captain Thanasis and the EOS Yachts crew for a 5.5-hour semi-private catamaran cruise from Heraklion to Dia Island. You’ll swim in a quiet cove, use snorkeling and SUP gear, enjoy seafood cooked onboard by Chef Charis, and return with Cretan dessert, drinks, and wide Aegean views.

“If you’re unsure which cruise to book, THIS is the one. The crew is professional, speaks perfect English, and truly cares about every guest. The catamaran is pure luxury-spacious, spotless, and incredibly comfortable, with plenty of room to relax and enjoy the view. And the food… wow. Fresh, flavorful, and far beyond what you’d expect on a boat. From start to finish, the company goes above and beyond. Don’t waste time comparing, Book this one, You won’t regret it ⭐️⭐️⭐️”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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