Shared Sailing trip to Dia Island, Meal+Drinks, Heraklion, Crete

If you’re dreaming of a day spent sailing around Crete’s stunning waters, this shared cruise to Dia Island might catch your eye. While we haven’t personally taken this exact trip, the detailed info paints a picture of what to expect: a relaxing, scenic voyage on a roomy, well-equipped sailboat, with plenty of time to swim, snorkel, or just soak up the views. It’s perfect for travelers looking for a laid-back day on the water without the hassle of a private charter.

What really draws us in about this tour are the combination of comfort and activity options—from snorkeling and paddleboarding to fishing gear and water toys—plus the inclusion of a delicious meal and drinks. On the flip side, it’s only about 5.5 hours, so if you’re after a full-day adventure, this might feel a bit short. But if you want a good balance of sailing, swimming, and relaxing, this tour could be just right, especially for those who enjoy small-group experiences and genuine hospitality.

This trip feels suited for anyone who values a comfortable, well-organized boat, and loves the idea of exploring an uninhabited island with some water-based fun. It’s not specifically tailored for families with very young children or those with mobility issues, but most travelers seeking a scenic, leisurely day on the water will probably find it a great fit.

Key Points

• Comfortable, luxurious sailboats renovated in 2024 offer plenty of space to relax.
• Water activities like snorkeling, paddleboarding, and fishing gear are included for flexible fun.
• Meal and drinks—including pasta with shrimp, Greek salad, fresh fruit, white wine, beer, and water—are part of the package.
• Flexible schedule options include daytime or sunset cruises, fitting different plans.
• Small group size (up to 4 travelers) means a more personalized experience.
• No disembarkation on Dia for environmental reasons, but swimming or paddleboarding are options.

A Closer Look at the Experience

Sailing from Heraklion’s Old Venetian Harbour, this trip combines the allure of traditional Greek sailing with modern comforts. The boats—Treaton or Jackpot—are among the largest and safest in the port, renovated recently in 2024 to ensure a smooth and safe ride. The spacious front decks, equipped with plush mattresses, invite you to lounge as you cruise through the waters, with ample cockpit tables and massive swimming platforms that make cooling off or socializing easy.

The itinerary is straightforward but well thought out. You start with about an hour and ten minutes of sailing in the Cretan and Aegean Seas, giving you a chance to get a feel for the boat and enjoy the views of Heraklion. The captain welcomes participation, so if you’re into sailing, you can learn some basics, or if you prefer, simply sit back and take in the scenery.

The highlight is undoubtedly the stop at Dia Island, an uninhabited, protected spot renowned for crystalline waters and wild scenery. The two-hour cruise to the island is a perfect break, allowing plenty of time to swim, snorkel, or paddleboard around the coves. The waters here are said to be crystal clear, making for wonderful underwater exploration. One reviewer mentioned, “Two hours of sailing total and we were anchored near the island for about 4 hours; as soon as we arrived you can swim and use SUP or snorkeling,” which captures the relaxed, unhurried vibe.

The island itself is legendary for its natural beauty and windswept landscapes—perfect for a quick escape into nature. Since disembarkation isn’t permitted for environmental reasons, your main access points are swimming and paddleboarding, which, based on reviews, are enjoyable and well-managed.

On the return journey, you have a chance to relax and admire the views as the boat heads back toward Heraklion. For sunset cruises, the opportunity to watch the sun set over the Aegean adds an extra touch of magic, although the standard daytime trip offers equally stunning vistas.

The onboard amenities make this trip stand out. The inclusion of snorkeling gear, stand-up paddleboards, and fishing gear means you can tailor your water time. The meal is hearty and authentic—pasta with shrimp, Greek salad, and fresh fruit—paired with white wine, beer, or water, making it a true indulgence after some time in the water.

Customer reviews echo the overall positive impression. One reviewer called the experience “accurate, punctual, nice, and very friendly,” mentioning that they appreciated the crew’s professionalism. They also noted the opportunity to swim and use water toys shortly after arriving at Dia Island, which highlights the relaxed pace of the trip.

The Value of This Trip

At around $84 per person, this cruise offers a good value, especially considering the included meal, drinks, and water activities. The modern, spacious boats and small group size mean you’ll get personalized attention and comfort, which is often hard to find on larger group excursions. The flexibility of choosing a daytime or sunset cruise lets you tailor the experience to your preferred timing.

While the trip doesn’t include disembarkation on Dia for environmental reasons, the ability to swim or paddleboard around the island helps make up for it. The only notable downside might be the limited duration—if you’re looking for a full-day adventure, you might find this somewhat short. Also, beach towels and hotel transfers are not included, so plan accordingly.

This experience suits travelers who want a relaxed sailing day with some water-based fun, excellent views, and good food. It’s especially well-suited for those who appreciate small-group settings, comfort, and a touch of luxury.

Who Would Love This Tour?

This trip is perfect for those who enjoy scenic sailing but prefer a laid-back, intimate setting over large, busier tours. If you’re into snorkeling, paddleboarding, or simply lounging on a boat with a glass of wine and stunning views, you’ll find plenty to enjoy here. It’s also a good pick for couples or small groups seeking a personal experience, and nature lovers who want to spend time in a protected, wild environment like Dia Island.

However, if you’re traveling with very young children or have mobility challenges, you’d want to check the specific restrictions, as the tour is not suitable for kids under 4 or those with severe mobility impairments. Also, if a full-day adventure is your goal, you might want to look for longer options or different tours.

FAQ

How long is the cruise?
The total experience lasts about 5 hours 30 minutes, including sailing, time at Dia Island, and returning to Heraklion.

What is included in the price?
The price covers the use of a luxury sailboat, snorkeling gear, paddleboards, fishing gear (on request), and a full meal with drinks including white wine, beer, water, and soft drinks.

Can I disembark on Dia Island?
No, disembarkation is prohibited for environmental reasons. But you can swim or paddleboard around the island.

What should I bring?
Bring swimwear, a towel (not included), sun protection, and perhaps a light jacket for the boat if it’s breezy.

Is this tour suitable for kids?
It’s not suitable for children under 4 or those with serious mobility issues. The experience is more adult-focused, centered on relaxation and water activities.

Are the boats comfortable?
Yes, the boats are among the largest and most comfortable in Heraklion port, renovated in 2024, with spacious front decks and ample entertainment areas.

What’s the cancellation policy?
You can cancel up to 24 hours in advance for a full refund. The tour is weather-dependent; if canceled due to poor weather, you’ll be offered a different date or a full refund.

Final Thoughts

This shared sailing trip to Dia Island offers a balanced mix of comfort, natural beauty, and water fun. It’s ideal for travelers who want a relaxed, well-organized day out on a luxury sailboat, with plenty of time to swim, snorkel, or simply enjoy the scenery. The inclusion of quality food and drinks elevates the experience, making it more than just a boat ride.

While it’s not a full-day adventure, the trip’s intimacy and relaxed pace make it a worthwhile option for those looking to unwind and connect with Crete’s stunning waters. For anyone who appreciates a small-group vibe, excellent views, and a chance to enjoy Crete’s coastal nature, this cruise could be just the ticket.

Happy sailing and exploring Crete’s beautiful waters!