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Experience a luxury sailing trip from Heraklion to Dia Island with onboard lunch, snorkeling, and exploration — perfect for serene ocean lovers and curious travelers alike.
Imagine sailing away from the lively Heraklion harbor aboard a sleek, luxurious yacht, heading toward a peaceful, unspoiled island surrounded by crystal-clear waters. That’s exactly what this Dia Island sailing tour offers. It combines the thrill of being on the water with the chance to explore a protected, natural environment—and all complemented by a delicious onboard meal. Whether you’re craving a peaceful day on the sea, a taste of Greek hospitality, or a chance to snorkel in vibrant waters, this experience promises a well-rounded outing.
One thing we really love about this tour is how it balances luxury and authenticity. The yacht is described as a “luxury sailing yacht,” which hints at a comfortable, high-quality experience without the crowds or noise of larger cruise ships. Plus, the trip’s inclusion of fresh Greek food, local wine, and optional paddleboarding makes it feel both indulgent and relaxed. That said, it’s worth noting that the tour doesn’t include things like towels, so bringing your own swim gear is a smart move.
This experience is best suited for travelers who appreciate beautiful scenery, good food, and peace on the water. It suits those who want a smaller, private-group feel rather than a large, impersonal cruise. If you’re after a day of gentle sailing, a bit of exploration, and some time to unwind, this trip hits the spot.


Sailing fans have several other Heraklion options to choose from
Your adventure begins at the old Venetian harbor in Heraklion, a charming and historic spot filled with boats and local life. From here, the crew at AIOLOSCRUISES P.C. sets the tone for a smooth, relaxed trip. The boat itself is described as a luxury sailing yacht, which suggests plush seating and a stable platform for the journey ahead.
The sail to Dia Island takes approximately an hour, allowing you to settle into the rhythm of the sea. We loved the way the crew kept the atmosphere light and informative, making sure everyone was comfortable and aware of what to expect. The sailing is peaceful, with no engine noise to disturb the serenity—just the gentle sound of the wind in the sails.
Upon arrival at Dia, your first impression might be how untouched and tranquil this protected island appears. Part of the Natura 2000 program, Dia is a haven for birdwatchers, nature lovers, and anyone seeking calm.
You’ll have plenty of time to explore, whether by walking around the ruins of an ancient chapel and old structures or simply relaxing on the rocky shores. The island’s small size makes it easy to see everything on foot within a short span. Reviewers mention that the island’s history is palpable, with relics like ancient pottery resting quietly on the seabed, visible during snorkeling.
One of the trip’s highlights is snorkeling in the crystal-clear waters of the Gulf of Saint George. The reviewer from Germany was especially impressed, noting that “the crew read our wishes and helped us find the best spots to snorkel.” The visibility is reportedly excellent, revealing colorful fish, coral, and even some ancient pottery on the seabed.
Paddleboarding is another included activity, giving guests a more relaxed way to explore the calm waters. These options make the trip engaging beyond just lounging on deck, and the shallow, protected bay ensures safety for all skill levels.
The onboard meal is a significant part of the experience and is described as both delicious and generous. You’ll enjoy Greek salad, seafood pasta, fresh local fruit, and local white wine, all served as you float in this scenic setting. The meal is described as “fresh” and “well-prepared,” with vegan and gluten-free options available, which is a thoughtful touch.
The review from the German guest emphasized that “the crew literally read our every wish,” highlighting how attentive they were. This kind of personal service elevates the experience from a typical boat trip to a memorable occasion.
More ways to experience Heraklion from the water include these boat tours
As the tour winds down, you’ll sail back to Heraklion with the sails up, enjoying the quiet and beauty of the open water. The absence of engine noise and the sights of the coastline make the return journey just as peaceful as the outward leg. It’s a perfect time to reflect on the day, take photos, or simply soak in the sun and scenery.

When considering the $945 price tag for up to 10 people, this trip offers good value for a personalized, high-quality experience. The inclusion of food, drinks, snorkeling, paddleboarding, and the private group setting means you’re paying for an all-in day of relaxation, adventure, and cultural discovery. It’s especially attractive for those who prefer intimate, well-curated outings over crowded group tours.
The review mentions that the crew was highly attentive and accommodating, reading guests’ wishes carefully—an aspect that turns an ordinary boat trip into a tailored experience. The natural beauty, combined with the local cuisine and peaceful sailing, makes it clear why this tour has garnered a 5-star rating from travelers.

This sailing trip is ideal for travelers seeking a peaceful day on the water with a touch of luxury and cultural exploration. Perfect for couples, small groups, or families, especially those who appreciate good food, serene scenery, and personalized service. If you’re a snorkeler or paddleboarder, you’ll find plenty of opportunities to enjoy the waters around Dia.
It’s less suitable for travelers with mobility issues or those who prefer a more adrenaline-fueled or large-group experience. If you’re after a calm, scenic, and culturally immersive day in Crete, this tour checks all the boxes.
How long is the sailing trip?
The tour lasts approximately 5.5 hours, including sailing, exploration, and meal time, with the trip starting from Heraklion’s Venetian harbor.
What is included in the price?
The price covers the sailing trip, snorkeling gear, paddleboarding, a delicious meal with drinks (including local white wine, soft drinks, and water), and the private group experience.
Are vegan or gluten-free options available?
Yes, the onboard meal offers vegan and gluten-free options, so be sure to specify your preferences when booking.
Do I need to bring my own towel?
Yes, towels are not included, so packing one for swimming or sunbathing is recommended.
Is there any age restriction?
While not explicitly stated, the experience is suitable for those comfortable on a boat and able to enjoy water activities, but it is not recommended for wheelchair users.
What should I bring on the day?
Bring sun protection (hat, sunscreen), swimwear, towel, and any personal essentials. Comfortable shoes for walking on the island are also helpful.
This Heraklion to Dia Island sailing trip offers a memorable blend of scenic beauty, cultural discovery, and culinary delight. It’s a peaceful way to spend half a day, away from the hustle of Crete’s busier spots, with the added bonus of personalized service and authentic Greek flavors. The small group setting ensures a peaceful, intimate atmosphere that’s perfect for relaxing, socializing, and making the most of your Crete vacation.
If you love sailing, snorkeling, and good food—all wrapped up in a calm, scenic environment—this tour is likely to meet and even surpass your expectations. It’s well-suited for travelers who value comfort, authenticity, and a touch of the local charm that Crete offers.
Note: Always check the latest availability and confirm your preferred start times, as schedules can change due to weather or operational factors.