Heraklion: Sunset Private Sailing Trip to Dia island

If you’re looking for a memorable way to enjoy Crete’s coastline, this private sunset sailing trip to Dia Island offers a blend of adventure, relaxation, and spectacular scenery. Departing from Heraklion’s Venetian port, you’ll spend about 4.5 hours exploring the crystal-clear waters, ancient ruins, and uninhabited Dia, all while enjoying the comfort and camaraderie of a small group – capped at 10 people for a personalized experience. The trip wraps up with a glorious sunset cruise, making it ideal for couples, families, or friends wanting to unwind and soak in Crete’s natural beauty.

What makes this trip stand out? First, the opportunity to sail in the Cretan sea and get involved in the sailing procedures if you’re feeling adventurous. Second, the delicious onboard snacks, local wine, and the chance to swim or snorkel in pristine waters are genuinely enjoyable touches. It’s a balanced mix of active and leisurely moments, perfect for those who want to experience Crete’s marine world without feeling overwhelmed.

One thing to keep in mind is that towels are not included, so bringing your own is recommended if you plan to swim or sunbathe. Also, this trip is most suitable for travelers who enjoy scenic boat rides, water activities, and relaxed evenings—it’s not a high-energy adventure, but rather a tranquil escape into nature and stunning coastal views.

This trip is an excellent choice if you value authentic sailing experiences, expert crew, and incredible sunsets. It’s especially suited for those who want to combine gentle adventure with the comfort of a private group.

Key Points

• Private and intimate experience with up to 10 guests
• Includes sailing procedures for the adventurous spirits
• Multiple activities: swimming, snorkeling, SUP boarding, fishing
• Delicious snacks and local wine enhance the experience
• Spectacular sunset views and scenic coastline
• Ideal for couples, families, and small groups seeking relaxation and adventure

You can check availability for your dates here:

A Closer Look at the Experience

This private sailing trip kicks off at the Venetian port of Heraklion, specifically from a designated meeting point near Marina Café. The boat, operated by Avanti Sailing, is well-equipped and run by an experienced crew, including a captain who is both knowledgeable and friendly—something travelers consistently praise, with reviews highlighting how “super friendly” and helpful the crew were.

The Journey to Dia Island

The first leg involves about an hour of sailing north from Heraklion. During this time, you can simply relax on the sundeck, breathe in the sea breeze, or engage in some of the sailing procedures if you’re curious or feel adventurous. The crew often encourages participation, which adds a layer of fun and educational value to the trip. We loved the way this creates a sense of connection to the sea rather than just being a passive observer.

Exploring Dia Island

Once you anchor near Dia, the real fun begins. The island itself is uninhabited and accessible only by boat, making it feel like a secret escape. You’ll have around 2.5 hours here to swim in the clear waters, snorkel amidst underwater remains, or try your balance on a SUP board. Snorkeling gear is provided, and we appreciated how safely the crew managed it—answering questions and ensuring everyone felt comfortable.

You can also explore ancient ruins that dot the island, adding a hint of history to your day. Several reviews mention the “lovely snorkeling and swimming,” which speaks to how inviting the waters are. We found that the opportunity to fish with gear provided adds a playful element, especially if you’re traveling with family or friends who enjoy trying their luck.

Scenic Return and Sunset

After enjoying Dia, the boat sets sail back towards Heraklion in the late afternoon. This return leg (about an hour) offers a different perspective: the changing colors of the skyline and the hinterland. Watching the sun dip below the horizon, painting the sky in shades of orange and pink, is described as “extraordinary” by travelers. The tranquil ambiance of the sea during this time enhances the sense of peacefulness, making it a perfect moment for photos or simply soaking it all in.

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Practical Details

The trip includes snacks, fresh fruits, premium local wine, water, and beverages—all thoughtfully provided by the crew. The boat is equipped with snorkeling gear, fishing equipment, and SUP boards, making it easy to switch between activities. If you want to swim or relax, remember to bring a towel (not included) and your ID or passport for safety.

Towels are the only notable omission, so pack accordingly if you plan to get wet. The activity ends back at the same meeting point, with the boat returning to Heraklion, completing a well-rounded journey.

Why Travelers Love This Experience

Based on reviews, the crew’s friendliness and helpfulness stand out, with many describing the team as “super friendly” and “very helpful.” The knowledgeable guides make the experience more engaging and ensure everyone feels safe and comfortable. The stunning vistas during sunset also receive high praise, with several reviewers remarking on how “extraordinary” the views are, turning a simple boat ride into a memorable visual spectacle.

Participants also enjoy the variety of water activities—snorkeling, swimming, SUP—which suit different interests and energy levels. The onboard snacks and wine are appreciated as well, adding a touch of indulgence to the relaxed evening.

Authentic and Intimate Experience

This trip’s small group size, capped at 10, ensures a personalized and intimate environment. We felt this made the experience more authentic and less touristic, allowing us to connect with the environment and fellow travelers.

Considerations for Travelers

While the experience is largely positive, it’s worth noting that towels are not provided, so bringing your own is advisable if you plan to swim. Also, the duration and timing are fixed, so if you’re more of a morning person or prefer longer excursions, you might want to explore other options.

This trip is best suited for those who enjoy scenic sailing, water activities, and sunset views. If you’re looking for a high-adrenaline adventure, this may feel a little calm. But if you appreciate a relaxed pace with opportunities for engagement and stunning visuals, it’s hard to beat.

The Sum Up

This private sunset sailing trip from Heraklion to Dia Island offers a fantastic way to experience Crete’s marine beauty without sacrificing comfort or authenticity. You’ll benefit from expert guidance, a variety of water activities, and breathtaking sunset views—all in a small, friendly group setting. It’s an excellent choice for couples seeking romance, families wanting a fun day out, or friends looking to unwind after busy days exploring the island.

The value here lies in the personalized attention, the chance to actively participate in sailing, and the chance to enjoy Crete’s natural beauty in a relaxed, memorable way. The combination of scenic views, good company, and quality local wine truly makes this a highlight for many travelers.

If you want a peaceful, engaging, and scenic experience that melds adventure with relaxation, this trip is certainly worth considering.

FAQ

How long is the sailing trip?
The total duration is approximately 4.5 hours, including sailing to Dia, time on the island, and the sunset cruise back to Heraklion.

What does the trip include?
Your experience includes the boat cruise, sailing, snorkeling equipment, fishing gear, SUP boards, snacks, fruits, local wine, water, beverages, fuel, and taxes.

Are there any additional costs?
Towels are not included, and you might find a small parking fee near the meeting point. Other than that, everything listed is covered.

Is hotel pickup available?
Yes, if you select the option, hotel pickup and drop-off are included in the package.

What should I bring?
Bring your passport or ID, a towel, and a jacket for the evening. Avoid high-heeled shoes for safety and comfort.

Can I participate in sailing procedures?
Yes, you’re encouraged to engage in sailing if you’re feeling adventurous. The crew is helpful and happy to teach.

What is the optimal time to book?
Check availability for 4.5-hour slots; consider booking in advance, especially during busy travel seasons, to secure your preferred time.

This detailed review should help you decide whether this sunset sailing trip fits your Crete adventure, balancing active participation with relaxing scenic moments and the chance to enjoy Greek hospitality at its best.

You can check availability for your dates here: