Dia Island: Semi-Private Full Day Sailing Trip with meal

A full-day sailing adventure to Dia Island from Heraklion offers a taste of Greek maritime life with the chance to swim, indulge in local wine, and enjoy beautiful scenery. This experience, run by Avanti Sailing, combines comfort, authentic moments, and a touch of luxury — all in a small group setting that often feels like sailing with friends. The trip lasts about six hours and features a mix of relaxing cruising, water activities, and a generous onboard meal.

What I appreciate most about this tour is how it balances seaside relaxation with interactive sailing—you get to feel the sea breeze on the deck, and if you’re interested, you can actively participate in steering the boat. Plus, the inclusion of a delicious meal with fresh fruits and premium local wine makes it a surprisingly good value for just under $100 per person.

However, potential travelers should note that hotel pickup and towels are not included, and the activity requires you to provide specific personal details. It’s a small detail, but worth remembering if you want to pack light. Also, this tour isn’t suitable for those with mobility issues, as it involves boat boarding and movement on deck.

This trip is a delightful choice for those seeking an authentic sailing experience — especially if you love good company, scenic views, and a relaxed pace. The crew’s friendly attitude and the beauty of Dia Island itself make it a memorable day on the water.

Key points / Takeaways

• Small Group Feel: Limited to 10 participants, ensuring a more personal, relaxed atmosphere.
• Interactive Sailing: Opportunities to help with sailing procedures, making it more than just a boat ride.
• Authentic Greek Hospitality: Friendly crew, knowledgeable guides, and a family-run vibe.
• Scenic and Water Activities: Swimming, snorkeling, paddleboarding, and marine life viewing.
• Excellent Value: All-inclusive price covers meals, drinks, water sports gear, and fuel.
• Comfort and Convenience: Elegant boat with plenty of space to relax, sunbathe, or socialize.

You can check availability for your dates here:

Entering the World of Crete’s Sea and Islands

This full-day sailing trip out of Heraklion offers a genuine escape into the waters of Crete, with Dia Island as the star attraction. The journey begins at the picturesque Venetian port, where you meet at the café Marina, just beside a large parking lot. The crew from Avanti Sailing, who are known for their friendly, accommodating approach, will welcome you 15 minutes before departure.

The boat itself is an elegant vessel, offering enough space to comfortably relax or engage in water activities. From the outset, I appreciated how the boat felt more like a shared adventure than a generic tour. The small group size allows for more interaction, and the crew’s knowledge about the area adds a layer of authenticity that larger, impersonal tours often lack.

The Itinerary: A Day of Relaxation and Discovery

Starting from Heraklion’s Venetian Port

The first leg of the trip is a scenic hour-long cruise northward from Heraklion to Dia Island. During this part, you’ll enjoy the gentle sway of the boat, the sea breeze, and panoramic views of the coast. You can lounge on the deck, sunbathe, or simply take in the scenery. The crew encourages participation, so you might find yourself helping to steer or set the sails, which adds a fun, hands-on element.

Many reviews highlight how friendly and helpful the crew is, with Nicole describing her experience: “Had a wonderful trip… the captain was very friendly and told us about the island.” That personal touch truly makes a difference.

Stop 1: Explore Dia Island for Four Hours

Once on the island, the fun really begins. You’re free to swim in the crystal-clear waters, snorkel to see marine life, or walk around the historic ruins of an ancient port. The water temperature in summer is perfect for swimming, and the soft sandy beaches invite lazy lounging.

The crew serves a delicious onboard meal—think fresh, seasonal fruits, generous portions, and local wine that’s notably well-received. Farsaraki noted the importance of safety, appreciating that “everyone was very kind, but the most important thing was the safety I felt.” That reassuring attitude makes it easier to relax and enjoy the surroundings.

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Scenic Return Cruises

After the island exploration, the boat gently cruises back to Heraklion, offering more scenic views and chances to unwind. During the return, you can continue to swim, paddleboard with the included SUP, or simply soak up the sun. The boat’s gentle motion combined with the fresh air leaves many feeling refreshed and sun-kissed.

Authentic Water and Land Experiences

Swimming and snorkeling are major highlights, with the water’s clarity often praised. Nicole loved the chance to see fish and urchins snorkeling just off the boat. The inclusion of snorkeling equipment and stand-up paddleboards means you can easily extend your water fun beyond just swimming.

The scenery on the way to and from Dia Island offers a continuous feast of views — rugged coastlines, distant hills, and the shimmering Aegean. The boat’s route is designed to maximize scenic beauty, making every moment on deck a photo opportunity.

The Meal and Drinks

The onboard meal is more than just a snack; it’s a well-prepared, flavorful lunch with fresh fruits and a selection of premium local wines and soft drinks. Many reviews, including Nicole’s, mention how good the food was, and Farsaraki appreciated the “kind” family-run crew, emphasizing the care put into the experience.

Logistics and Practical Tips

The tour lasts approximately 6 hours, with flexibility in start times depending on availability — check ahead. The meeting point at the Venetian port is straightforward, next to the Marina Café. Arriving 15 minutes early is advisable to settle in and meet your crew.

Cost-wise, at $96 per person, this experience provides excellent value considering the inclusions — meals, drinks, water sports gear, and fuel. You won’t find many similar full-day trips that include such a comprehensive package at this price point.

Remember:
– Bring your hat, swimwear, towel, sunscreen, and beachwear.
– Towels are not included, so pack accordingly.
– Bring your passport or ID, as personal info is required at booking.
– Tow high-heeled shoes are not allowed on the boat for safety reasons.
– Hotel pickup is extra, so plan accordingly.

Who Will Love This?

This trip is ideal if you’re after a more intimate, authentic sailing experience rather than a crowded tour. It suits travelers who appreciate friendly guides, beautiful scenery, and good food and drink. If you’re interested in actively participating in sailing or water sports, you’ll find plenty of opportunities here.

It’s perfect for couples, small groups, or solo travelers eager for a relaxed day on the water with like-minded adventurers. Those with mobility issues or very young children might find the boat boarding and onboard activities challenging.

Final Thoughts: Is It Worth It?

For under $100, you get a mix of scenic cruising, water activities, authentic Greek hospitality, and a delicious onboard meal—that’s a pretty good deal. The friendly crew and small-group atmosphere make the day feel special, not just a commercial operation. Plus, the chance to swim in crystal-clear waters, combined with a scenic sail and local wine, makes it a well-rounded experience.

This tour offers a genuine slice of Crete’s maritime charm, with a good balance of relaxation and activity. It’s best suited for travelers who value authenticity, comfort, and a touch of adventure. If you’re after a memorable day on the Aegean that combines scenic beauty with friendly service, this sailing trip to Dia Island could very well be the highlight of your trip.

FAQ

Is hotel pickup included?
No, hotel pickup is not included. You’ll need to meet at the Venetian port next to Marina Café.

How long is the sailing trip?
The total experience lasts about 6 hours, including cruising, swimming, and the island stop.

Are water sports equipment provided?
Yes, snorkeling gear, stand-up paddleboards, and fishing equipment are included.

What should I bring?
Bring a hat, swimwear, towel, sunscreen, beachwear, and your ID or passport.

Is this tour suitable for children or those with mobility issues?
It’s not suitable for wheelchair users, and boarding might be challenging for some with mobility issues.

What is the price and what does it include?
At $96 per person, the price covers the boat crew, all water sports gear, meals, soft drinks, wine, and fuel.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours before for a full refund, providing flexible planning options.

To sum it up, if you’re seeking a laid-back yet engaging way to explore Dia Island with good company, delicious food, and stunning views, this sailing trip from Heraklion ticks all the boxes. It offers genuine value, a memorable experience, and a taste of Crete’s maritime charm — perfect for those who love authentic adventures on Greece’s waters.

You can check availability for your dates here: More Great Tours Nearby