Private Sailing Trip from Heraklion to Dia island

Thinking about exploring Crete from a different angle? A private sailing trip from Heraklion to Dia Island might just be the perfect way to enjoy the sea, soak up the sun, and see a side of Greece that’s less crowded and more relaxed. While I haven’t personally taken this exact tour, I’ve gotten a good sense of what it offers, and I think it’s worth sharing what you can expect if you decide to book.

What caught my eye are the luxury feel of the boat and the chance to enjoy premium local wine while cruising around gorgeous scenery. These little touches set it apart from more generic boat trips. Plus, the opportunity to actively participate in sailing procedures adds a bit of fun and authenticity. The one thing to think about is that this is a private group experience, which means it’s on the pricier side but also more intimate—ideal if you value comfort and personalized service.

That said, it’s not necessarily for everyone. If you’re looking for a high-energy, activity-packed day with lots of stops and excursions, this might feel a bit laid-back. But if your goal is to unwind, enjoy beautiful waters, and have a taste of what Crete’s coastline has to offer in style, this could be a great fit.

This trip is especially suited for couples, small groups of friends, or families who want a relaxing day on the water without the hustle of larger tours. And because it’s a private experience, it’s flexible enough to suit your pace and preferences.

Key Points

• Private and intimate: Perfect for small groups and those seeking personalized service.
• Luxury experience: Relax on a well-equipped boat with options to actively participate in sailing.
• Beautiful scenery: Expect scenic views of Heraklion and Dia Island’s crystal-clear waters.
• Includes premium amenities: Snacks, fresh fruit, local wine, soft drinks, and snorkeling gear.
• Flexible itinerary: Swimming, exploring ruins, and enjoying leisurely cruising.
• Cost reflects a high-quality, exclusive experience.

This tour offers a unique way to experience Crete’s coastline beyond the usual land-based activities. It’s a carefully curated experience that balances relaxation, exploration, and comfort. What really makes it shine is the luxury sailing boat and the attention to detail in service—from snacks and wine to the opportunity to help with sailing.

The duration of about 4.5 to 6 hours makes it a full, yet manageable day without feeling rushed. Plus, the inclusion of hotel pickup and drop-off (if you choose this option) simplifies logistics. You can just show up with your swimwear, sunscreen, and a hat, and leave the rest to the crew.

You can check availability for your dates here:

Starting Point: Cafe Marina in Heraklion

Your adventure kicks off at the left side of Marina Café, right at the Heraklion Venetian port. The captain is there 15 minutes early to greet you—something I always appreciate, as it sets the tone for a smooth start. The area is easy to find, with a large parking lot nearby, although there is a small fee.

First Stop: Dia Island (Scenic Cruise)

You’ll spend about an hour sailing north from Heraklion to Dia Island. The views along the way are a treat, especially if you love watching the coastline change as you go. The boat is spacious and comfortable, with plenty of room to relax or sunbathe on the deck.

The ride itself is smooth, but the highlight is the scenery—waves lapping against the boat, the gentle sea breeze, and distant views of Crete’s rugged coast. If you’re into photography, this stretch offers some excellent photo opportunities.

Second Stop: Exploring and Swimming at Dia

Once at Dia Island, you have roughly 2.5 hours to enjoy the island’s charms. The waters here are crystal clear, perfect for swimming and snorkeling. The crew provides snorkeling equipment, so you can get a closer look at marine life or simply float and cool off.

You can explore the ancient port ruins or take a walk on the island if you’re feeling up for it. Many reviews mention how peaceful and uncrowded this spot feels—ideal for a laid-back day. Plus, the boat provides snacks, fresh fruits, and a well-curated selection of local wine and soft drinks. The wine, in particular, gets praise—reviewers mention how good it is, and it really does elevate the experience.

Relaxing on Deck and Participating in Sailing

One of the nice touches is the chance to engage in sailing procedures. Whether you’re a seasoned sailor or new to it, the crew welcomes participation, making it interactive rather than just watching from the sidelines. For many, this adds a memorable touch to an otherwise tranquil day.

Return Journey: Scenic Cruise Back to Heraklion

As you cruise back, the views continue to impress. The boat glides smoothly for about an hour, and you can keep soaking in the scenery or just relax with a drink in hand. The trip concludes at the same spot where you started—Cafe Marina.

This tour covers a lot of bases. The experienced crew ensures safety and comfort, and you’ll enjoy drinking water, soft drinks, and premium wine. The meals or snacks are included—whether a light snack or a full meal depends on the option you choose—plus fresh seasonal fruit.

You’ll also find extras like stand-up paddleboards (SUP), snorkeling gear, and fishing equipment. These add extra fun if you’re feeling active or curious.

The hotel pickup and drop-off are optional but convenient, especially if you’re staying somewhere near Heraklion. Keep in mind, towels are not provided, so bring your own (around €25 if you decide to rent one locally).

At $700 for the entire group (up to 10 people), this experience leans toward the premium side. But considering the exclusivity, luxury, and all-inclusive amenities, it offers good value—especially if you’re traveling with a small group or family. The cost is essentially for private access, personalized service, and the chance to enjoy Crete’s waters in comfort.

If you’re after a peaceful, scenic, and luxury experience that combines gentle sailing with the opportunity to swim and relax, this trip fits the bill. It’s especially well-suited for couples, friends, or small families looking for a special day out in Crete without the crowds or busy schedules of larger tours.

That said, if you’re prone to motion sickness or prefer more active or structured excursions, you might find this slower pace less engaging. It’s also not suitable for wheelchair users, so keep mobility needs in mind.

This private sailing trip offers a well-rounded blend of luxury, scenic beauty, and relaxation. The highlight for many will be the quality wine and fresh fruits, paired with the beautiful setting of Dia Island’s waters. The opportunity to contribute to sailing the boat gives a personal touch that many travelers appreciate, making it more than just a cruise.

While the price might seem steep for some, the exclusivity and comfort make it a worthwhile splurge if you’re after a peaceful, high-quality day on the water. It’s perfect for those who want a slower, more intimate experience of Crete’s coast, away from the crowds but still immersed in natural beauty.

Is this tour suitable for children?
This tour is generally adult-focused, and participation in sailing procedures might be more suitable for older children or teens. It’s best suited for travelers comfortable with water and outdoor activities.

Do I need to bring anything?
Yes, bring a hat, swimwear, towel, sunscreen, beachwear, and your passport or ID. Towels are not provided, so consider renting or bringing your own.

Can I participate in sailing?
Yes, the crew encourages participation in sailing procedures, making it a fun and interactive experience.

Is food included?
Yes, snacks and a full meal are included, depending on the duration selected. Fresh fruits, soft drinks, and premium local wine are also provided.

What is the duration of the trip?
The trip lasts approximately 4.5 to 6 hours, including the cruising time, swimming, and exploring.

Where do I meet the crew?
The meeting point is at the left side of Marina Café at Heraklion Venetian port, 15 minutes before departure.

Is hotel pickup included?
It can be booked as an option. If you select this, your ride will be arranged to and from the port.

What if I need to cancel?
You can cancel up to 24 hours before the trip for a full refund. It’s flexible, so you can plan with confidence.

This private sailing trip from Heraklion to Dia Island offers an elegant way to enjoy Crete’s coastline. It combines comfort, scenic beauty, and a bit of adventure—perfect if you want a peaceful day on the water with a luxury touch.

You can check availability for your dates here: