From Heraklion: Dia Island Private Sailing Trip

Imagine a day where you set out from the bustling port of Heraklion and find yourself aboard a comfortable sailing boat, gliding towards the rugged, lizard-shaped Dia Island. This private trip, costing around $678 per group of up to 10 people, lasts about 6 hours and offers a perfect blend of sailing, swimming, and natural beauty. The experience is led by a knowledgeable local captain, who will share insights and keep things lively.

What we appreciate most about this trip is the flexibility of a private group, allowing you to customize your day—whether you want to snorkel in crystal-clear waters or relax on the boat while soaking up scenic views. The second highlight for us is the opportunity to explore Dia’s quiet bays and cedar trees—a step away from crowded tourist spots. The only consideration might be that this experience doesn’t include transportation to the marina, so you’ll need to arrange your own transfer.

This tour is ideal for travelers who love personalized experiences, enjoy being on the water, and want a relaxed, immersive day in Crete’s coastline. If you’re seeking a tranquil escape with plenty of room to breathe and explore, this trip fits the bill.

Key Points

• Private and customizable: Perfect for small groups seeking personalized attention.
• Comprehensive experience: Combines sailing, snorkeling, walking, and scenic views.
• Expert guidance: Led by a knowledgeable local captain who shares insights about the area.
• All-in-one package: Includes snacks, unlimited refreshments, fruits, snorkeling gear, and music.
• Ideal for relaxers and adventure-seekers alike: Plenty of time for swimming, photos, and unwinding.
• No hotel transfer: You need to organize your own transportation to Heraklion Marina.

You can check availability for your dates here:

A Clear Overview: What to Expect

This 6-hour private sailing trip from Heraklion to Dia Island provides a well-rounded experience that balances scenic cruising with opportunities for swimming, snorkeling, and exploring. The trip kicks off at Heraklion Marina, where you’ll meet your captain and crew aboard the sailing yacht MARYLINE—a vessel praised for its excellent condition and performance.

The journey is divided into several key parts: a short walk and visit at Rocca a Mare Fortress, an invigorating sail to Dia, plenty of leisure time on the island, and a return cruise back to Heraklion. The private nature of the tour means you’ll have the flexibility to linger at spots or move at your own pace, whether you want to snorkel in the crystal-clear waters or just soak up the sun.

The Itinerary: A Closer Look

Start at Cafe Marina, your meeting point, where the crew will introduce the plan for the day. After a short 10-minute walk to Rocca a Mare Fortress, you’ll enjoy a quick sightseeing stop to snap some photos of this historic site and take in the scenic views en route. The fortress, while brief, offers a glimpse into Crete’s past and provides a good photo opportunity.

Next comes the main event—the cruise to Dia Island, which takes about 75 minutes. During this sail, expect stunning coastal vistas and the refreshing feel of the summer breeze. The crew will offer commentary on the coastline and the island’s features, making the journey both relaxing and educational.

Once on Dia, you’ll have around 3.5 hours to enjoy a mix of activities. This includes snorkeling in the clear waters, walking among the island’s cedar trees, or simply relaxing in the bay of Saint George—a small, tranquil cove with excellent views of Heraklion. The trip includes local snacks, fruits, and unlimited refreshments, so you can stay refreshed while enjoying the beautiful surroundings.

After your time on the island, you’ll cruise back via the Heraklion Yacht route, passing Rocca a Mare once more, and arriving back at the marina in the late afternoon.

What Makes This Trip Stand Out

One of the aspects travelers love, according to reviews, is the expertise of the captain. The guide’s friendliness and knowledge make the experience smoother—”a very friendly skipper” and “well catered for food and drink” are common praises. The boat itself is described as spacious and in excellent condition, making for a comfortable day on the water.

Another highlight is the scenic views—the boat’s vantage point offers a unique perspective over Heraklion and Dia Island, especially at sunset or under clear blue skies. The snorkeling gear allows you to explore the underwater world, which many find to be a highlight, as the waters are described as crystal clear.

Practical Considerations

While everything about the trip is geared toward comfort and enjoyment, there is one key element to plan for: transportation to the meeting point at Heraklion Marina. Since the tour does not include transfers, you must arrange your own way there, whether by taxi or public transport. The check-in process requires your full name, passport details, and other info a day before, due to coast guard regulations.

The price of $678 per group might seem steep at first glance, but considering the all-inclusive nature—snacks, drinks, snorkeling equipment, and private space—the value becomes clearer. For small groups or couples seeking a personalized, hassle-free day on the water, this is a compelling option.

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Authentic Experiences and Real Praise

Feedback from travelers echoes the high regard for this tour. One reviewer mentioned, “We had a fantastic day! A very friendly skipper, nice spacious boat, well catered for food and drink.” The fact that the boat is a recent addition to the fleet means you’re likely to enjoy modern amenities and comfort.

Another reviewer appreciated the opportunity to learn about the coastline while relaxing and swimming, making this not just a sightseeing tour but an educational, immersive experience. The scenic views and peaceful bays are a big draw, especially for those looking to escape the more crowded tourist spots.

Who This Tour Is Best For

This trip is perfect for families, couples, or small groups eager to enjoy a private, flexible day on the water. It suits travelers who value authentic experiences over cookie-cutter tours and who want a balance of adventure and relaxation. If you’re someone who enjoys snorkeling, scenic sailing, and discovering lesser-known spots, this tour ticks all the boxes.

However, if you prefer inclusive packages with transport, or are wheelchair users, this might not be the best fit. The tour’s focus on a personalized, relaxed day means it’s less about structured sightseeing and more about enjoying the natural beauty and peaceful ambiance of Dia Island.

In our view, the Dia Island private sailing trip offers excellent value for travelers seeking a high-quality, personalized experience. The combination of expert guidance, beautiful scenery, and leisurely activities makes for a memorable day. The crystal waters and quiet bays are perfect for swimming and relaxing, providing a genuine taste of Crete’s coastal charm away from the crowds.

The well-maintained boat and friendly crew ensure comfort and safety, while the flexible itinerary allows you to make the most of your time in Dia. For those wanting a luxurious yet authentic escape, this trip hits the sweet spot.

If you’re after a peaceful, scenic adventure that offers both cultural insight and natural beauty, then this private sailing trip to Dia Island is well worth considering.

How long is the cruise?
The entire trip lasts about 6 hours, including sailing, stops, and free time on Dia Island.

What is included in the price?
The package includes a private 6-hour cruise, snacks, unlimited refreshments, fruits, snorkeling equipment, sailing with a well-maintained yacht, and music.

Do I need to arrange transportation to the meeting point?
Yes, the tour does not include transfers, so you’ll need to organize your own way to Heraklion Marina.

Can I snorkel during the trip?
Absolutely. Snorkeling gear is provided, and travelers report that the waters are crystal clear, ideal for underwater exploration.

What should I bring?
Bring sunglasses, a hat, swimwear, a towel, sunscreen, and your passport or ID (a copy is acceptable).

Is this tour suitable for children or non-swimmers?
Kids over a certain age who can swim will enjoy the water activities. The tour is not designed for wheelchair users or those with mobility issues.

What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund, offering some flexibility if your plans change.

In all, this private sailing tour to Dia Island offers a memorable blend of scenic sailing, peaceful bays, and personalized service. It’s a great choice for travelers who value comfort, authenticity, and a chance to see Crete from a different angle. Whether you’re seeking adventure or quiet relaxation, this trip has what you need for a truly special day.

You can check availability for your dates here: