Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

This experience made our article of We Rank The 15 Best Boat Tours & Cruises In Heraklion.

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Imagine setting sail from Heraklion’s historic Venetian harbor, watching the ancient fortress fade into the distance as you head toward Dia Island, a jewel in Crete’s turquoise waters. For about $79 per person, you’ll spend between 4.5 to 7 hours exploring crystal-clear bays, trying your hand at snorkeling, paddleboarding, and fishing, all while enjoying drinks and a hearty Mediterranean meal onboard. This trip is a fantastic way to combine relaxation, adventure, and a taste of local mythology, making it perfect if you’re looking for an authentic Crete experience with a splash of fun.

What we really appreciate about this sailing cruise? First, the knowledgeable crew, who are not only experienced sailors but genuinely friendly guides sharing stories about the island’s legends. Second, the delicious onboard meal—a well-balanced mix of fresh salads, shrimp spaghetti, and refreshing drinks that keep spirits high. A minor consideration is that towels aren’t included, so bring your own if you plan to swim or paddleboard. This tour suits travelers who enjoy small-group atmospheres, scenic sailing, and active watersports, especially those eager to hear about local myths or just unwind on a boat with good company.

You can check availability for your dates here:

Key Points

• Balanced mix of relaxation and activity with snorkeling, paddleboarding, and swimming options.
• Authentic Crete experience through stories about Dia island’s legends and history.
• Excellent value considering the food, drinks, and personalized attention.
• Small group setting ensures a more intimate and engaging experience.
• Flexible options including hotel pickup or direct departure from the harbor.
• Great for all ages, though not suitable for wheelchair users or those with mobility challenges.

The Experience: What to Expect on Your Sailing Day

Starting Your Day with Convenience and Charm

You have the option to be picked up from your hotel in Heraklion, or you can meet directly in front of the Venetian harbor, where the vibe is lively, and the view of the historic fortress makes for a perfect pre-boarding photo. The crew will give you a brief safety chat—nothing too heavy, just enough to set your mind at ease—and then you’ll step aboard a cozy yacht.

If you’re like us, you’ll love the way the harbor’s old-world charm contrasts with the modern comforts of the boat. As the crew unfurls the sails, you might get a thrill feeling the wind catch them—most trips take advantage of the breeze, so be prepared for some refreshing spray.

Cruising to Dia: Sailing and Stories

The journey to Dia Island typically takes about an hour, depending on weather conditions. The crew often raises the sails if the wind cooperates, adding a traditional touch that’s both scenic and fun—nothing beats the feeling of a boat gliding through water powered by wind, rather than engines.

During the sail, you’ll enjoy the captivating stories about Dia’s legends and history, often shared by Nick and Olivia or other crew members. Multiple reviewers appreciated the informative guides who provided fun facts about Crete and Dia Island, making the journey both entertaining and educational. Keep your eyes peeled for dolphins—many travelers, including one reviewer, reported playful dolphin sightings during their cruise, adding an extra layer of magic to the trip.

More Great Tours Nearby

Arrival at Dia Island: Water Fun and Exploration

Once docked, you’ll have plenty of free time to explore. The island’s waters are famously clear, making snorkeling a highlight, especially with the provided gear. Many visitors enjoyed floating among colorful fish and observing the underwater scenery, which is a stark contrast to the land’s rugged beauty.

For the more active, paddleboarding and fishing gear are available—some reviews mentioned how Olivia or other crew members happily assisted with trying out paddleboards, even ferrying curious visitors to spots around the island. If walking is your thing, a scenic hike around the island offers stunning views, but be aware that some reviews suggest a degree of physical fitness is helpful for multiple water activities and hikes.

Lunch and Refreshments: A Mediterranean Feast

After working up an appetite, you’ll be treated to a generous Mediterranean meal, which often includes fresh salads, shrimp spaghetti, and a variety of snacks. The food is praised consistently for its quality—one reviewer even called the pasta with shrimp “very good.” Pair these dishes with local wine, soft drinks, or raki, and you’ve got a true taste of Crete’s culinary culture.

Many reviews praise the friendly, attentive crew who keep the drinks flowing and make sure everyone is well taken care of. On the return leg, some guests appreciated the opportunity to relax on deck with a drink, soaking in the sunset or just enjoying the gentle sway of the boat.

Swimming, Fruits, and the Return Journey

Post-lunch, you’re free to swim, snorkel, or just lounge and enjoy the scenery. Fresh fruit and raki are served, and many guests describe the experience of sailing back with the sunset illuminating the sky as magical. If you start the tour in the afternoon, this sunset return is often highlighted as one of the trip’s best moments—one reviewer even called it “incredible.”

Returning to Heraklion

As the cruise winds down, the crew will escort you back to your transfer or the original meeting point. The small group size and attentive crew contribute to a feeling of personalized care, making the whole day feel special rather than just another tourist outing.

Why This Tour Works for Many Travelers

Reading through countless reviews, it’s clear that this sailing cruise’s charm lies in its friendly guides, beautiful scenery, and well-organized itinerary. The trip’s flexible timing and small-group vibe make it suitable for couples, families, or friends seeking a mix of adventure and relaxation.

Some travelers appreciated the informative stories, especially about Dia’s legends, which added depth to their experience. Others raved about the quality and variety of the food and drinks, making the price feel like excellent value. The ocean activities—snorkeling, paddleboarding, and fishing—bring a hands-on element that many find memorable.

Potential drawbacks? Not much—except for the fact that the towels aren’t provided, so packing one is recommended if you plan to swim or paddleboard. Also, the trips are not suitable for wheelchair users or those with mobility challenges, so plan accordingly.

The Itinerary in Detail

Start Point and Pickup

Depending on your choice, you can be picked up from your hotel or meet directly at the historic Venetian harbor. The harbor’s lively atmosphere and views of the old fortress set a perfect scene to begin your adventure.

Heraklion Port and Safety Briefing

After a brief safety introduction, you’ll board the yacht, where the crew’s friendly attitude immediately puts you at ease. Expect a short walk along the promenade to reach the boat, which is described as cozy yet spacious enough for a small group.

Sailing and Scenic Views on the Way

Most trips feature a scenic cruise with the sails up if conditions permit. The guides often share stories about Crete and Dia Island, which many reviewers find both amusing and informative. The chance to spot dolphins along the way adds a touch of wildlife wonder, making the journey as exciting as the destination.

Arrival at Dia and Water Activities

On arrival, the crystal-clear water quickly draws everyone in. Snorkeling gear is provided, and the water’s visibility impresses many guests. Paddleboarding is equally popular, with guides assisting newcomers or those nervous about water. Fishing is also available, and if you’re lucky, you might catch a small fish or two.

Lunch, Relaxation, and Return

Post-water activities, the onboard Mediterranean meal is a highlight—fresh, flavorful, and generously served. Many reviews mention the delicious pasta with shrimp and the refillable drinks that keep spirits high. After lunch, guests have time to swim, relax, or explore the island further before the boat heads back to Heraklion, often during sunset, providing a stunning end to the day.

Final Thoughts: Who Will Love This Tour?

This sailing cruise offers a wonderful blend of scenic sailing, water-based fun, and authentic local flavor. It’s best suited for travelers who enjoy small-group experiences, want to learn about Crete’s legends, and appreciate good food and drinks. The opportunity to snorkel, paddleboard, and relax on deck makes it appealing for families, couples, and groups of friends alike.

If you’re after a leisurely yet active day on the water, with the chance to see dolphins and enjoy a delicious meal in a beautiful setting, this tour will not disappoint. Just be prepared for some physical activity if you want to maximize water fun, and remember to bring a towel!

FAQ

Is hotel pickup included? Yes, if you select the option, your transfer from your hotel in Heraklion will be arranged.

How long is the cruise? The trip lasts between 4.5 to 7 hours, depending on the schedule and weather conditions.

What activities are available? Snorkeling, paddleboarding, fishing, and swimming are all included with provided equipment.

Is food and drinks included? Yes, the full-day trips include a Mediterranean meal, fresh fruit, and drinks such as wine, soft drinks, and raki.

Can I join without having previous sailing experience? Absolutely. The crew is friendly and helpful, and many reviews mention how they assist beginners.

Is there a dress code? Comfortable clothes, swimwear, sun hat, sunscreen, and shoes suitable for boarding are recommended.

Are towels provided? No, towels are not included, so bring your own if you plan to swim or paddleboard.

Is this tour suitable for children? Generally yes, but consider mobility limitations since it’s not wheelchair accessible.

What should I bring? Sun protection, swimwear, towel, comfortable shoes, and a sense of adventure.

Final Words

This Heraklion sailing trip to Dia Island offers a well-rounded day of scenic sailing, active water fun, and authentic Mediterranean cuisine. The friendly guides, beautiful scenery, and the chance to spot dolphins or enjoy a lively sunset make it stand out among Crete’s many excursions. It’s an excellent choice for those seeking a memorable, value-packed adventure that combines the best of land, sea, and local culture.

Whether you’re looking to relax under the sun, learn a bit about local legends, or just enjoy the thrill of sailing, this tour hits most of the right notes. For those who want a small, friendly setting with plenty of opportunities for water-based activities, this cruise provides a genuine and enjoyable Crete experience.

You can check availability for your dates here: