Private Sailing Trip from Heraklion to Dia with meal & SUP

This experience made our article of 9 Must-Try Boat Tours & Cruises In Agia Pelagia.

Private Sailing Trip from Heraklion to Dia with Meal & SUP

Imagine gliding across the crystal-clear waters of the Aegean, your own private boat taking you away from the busy port of Heraklion, Greece, towards one of its most serene spots—Dia Island. For around $71 a person, this half-day adventure offers a blend of sailing, swimming, and relaxing in a setting that feels like your own secret hideaway. Led by knowledgeable skippers, this trip is perfect for those craving an authentic, quieter side of Crete.

What we really appreciate about this experience is how it balances professionalism with a relaxed vibe—the crew’s expertise guarantees safety and smooth sailing, while the opportunity to swim in turquoise waters or simply soak up the sun keeps the trip feeling personal and spontaneous. Plus, the inclusion of snacks and soft drinks offers a little extra comfort.

On the flip side, it’s worth considering that this is a private boat experience, so the price might seem steep if you’re traveling solo or on a tight budget. Also, because the trip is not suitable for wheelchair users, travelers with mobility issues should plan accordingly. This trip is best suited for those looking for a peaceful escape, whether you’re with a partner, family, or friends who enjoy a blend of adventure and downtime in a natural setting.

You can check availability for your dates here:

Key Points

• Personalized Experience: Private sailboat with skipper and assistant ensures a tailored journey.
• Natural Beauty: Swim and snorkel in calm, turquoise waters around Dia Island.
• Scenic Views: Enjoy breathtaking landscapes and sea vistas from the boat.
• Inclusive Snacks: Light snacks and soft drinks keep you refreshed during the trip.
• Flexible Booking: Reserve now, pay later, and cancel up to 24 hours in advance.
• Limited Accessibility: Not suitable for wheelchair users or those with mobility challenges.

A Deeper Look at the Sailing from Heraklion to Dia

This adventure begins at the Marina Cafe in Heraklion, where you’ll meet your crew and prepare for a private departure. The process is straightforward: bring your passport for check-in or send it early to avoid delays. The trip’s duration of approximately 4 hours includes sailing time, swimming stops, and time to relax on deck. The cost of $71 per person is quite reasonable when you consider the personal attention, private boat, and the exclusivity of the experience.

The Itinerary and Experience Breakdown

Starting Point: Marina Cafe
Your adventure kicks off here, where you’ll meet your skipper and assistant. This is your chance to ask questions, get familiar with the boat, and settle into the relaxed rhythm of the trip. The crew’s professionalism is often praised, with many reviews highlighting their friendly demeanor and knowledge. Having your passport ready helps speed up check-in, especially during busy times.

Sailing to Dia Island
Once on board, the boat gently sets sail, offering stunning sea views of Heraklion’s coast and the open blue horizon. As you leave the busy harbor behind, it’s easy to relax into the gentle sway of the boat—your crew navigates smoothly, making for a stress-free journey. The sailing itself is a highlight: watching the skyline recede as the breeze fills the sails gives a real sense of freedom.

Swimming and Snorkeling in Calm Waters
Your first stop is a secluded bay, famous for its crystal-clear waters and gentle currents. Travelers love to jump in for a swim or snorkel among the marine life. One guest remarked, “We loved the way the water was so calm, and the snorkeling was a highlight.” The natural environment here is unspoiled, making it ideal for those who want to escape the crowds and enjoy peaceful, unhurried swims.

Enjoying the Views of Dia’s Landscape
Dia Island itself is uninhabited, but its dramatic cliffs and lush greenery are visible from the boat. The sight of this untouched landscape is genuinely striking, especially with the Greek sun shining overhead. Many travelers comment on how the island’s quiet beauty contrasts with more tourist-heavy locations.

Snacks and Soft Drinks
Throughout the trip, you’ll be offered light snacks and cold beverages, a thoughtful touch that keeps you comfortable without overindulging. These are perfect for a quick refresh after swimming or simply enjoying as you soak up the scenery.

Sailing Back to Heraklion
As your time on Dia winds down, the boat begins its return journey, offering one last chance to sit back, take photos, and enjoy the breeze. Many reviews highlight the spectacular sunset views during the sail back, transforming the trip into a truly romantic experience.

What Makes This Trip Stand Out?

The personalized nature of the private sailing experience is a major plus. Unlike larger group tours, this allows for more flexibility—perhaps a longer swim, or a quick stop at a different spot if weather allows. The knowledgeable crew often share stories and insights about the local area, adding depth to your journey. Plus, the scenic views of Dia, coupled with the sensation of sailing in calm waters, make it a memorable escape.

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Possible Drawbacks and Considerations

While the experience is superb, it’s important to note that not everyone is suited for a boat trip. The experience requires a moderate level of mobility, and it’s not accessible for wheelchair users. Also, because it’s a private trip, the cost might be less appealing to solo travelers or those on a budget—but the price does reflect the exclusivity and tailored service.

Weather can also influence the trip. If winds are high or seas choppy, your skipper might adjust the itinerary or delay the start, so flexibility is key.

Who Will Appreciate This Tour?

This experience is ideal for couples wanting a romantic getaway, small families seeking a peaceful outdoor activity, or friends looking for a relaxed day on the water. If you’re eager to escape the crowds and enjoy natural beauty in a calm setting, this trip offers real value in both scenery and comfort.

Why It’s a Good Value

For just $71, you get a private sailing adventure, a knowledgeable skipper, and snacks and drinks—all in a setting of stunning natural beauty. The exclusivity means fewer people and more personalized service, which many consider worth the higher price compared to larger group tours. Plus, the flexible cancellation policy and the option to reserve now and pay later add peace of mind.

Final Thoughts

Choosing this private sailing trip from Heraklion to Dia provides a genuinely peaceful, scenic, and personalized experience. It’s perfect for those who appreciate authentic moments on the water and want to see a less-touristed side of Crete. The combination of snorkeling in turquoise waters, scenic views, and a relaxed sailing pace makes it a standout option for travelers seeking a restful yet engaging day.

If you’re after a calm, intimate escape, this trip hits the mark. Just remember to bring your swimsuit, sunglasses, and a sense of adventure—and prepare for a tranquil journey that leaves lasting memories of Greece’s natural beauty.

FAQ

How long does the trip last?
The experience lasts approximately 4 hours, including sailing, swimming, and relaxing time.

What is included in the price?
The price covers a private sailboat, a personal skipper and assistant, and light snacks and soft drinks.

Can I bring my own drinks or extra food?
Extra drinks or personal expenses are not included. You’re welcome to bring additional drinks or snacks at your own cost.

Is this trip suitable for children?
While not explicitly stated, families with children who are comfortable on boats and enjoy swimming would find this trip enjoyable. It’s best to check with the provider if you have specific needs.

What should I bring with me?
Bring your passport for check-in, swimwear, towel, sunscreen, and perhaps a hat or sunglasses for sun protection.

Is there any age restriction?
The information doesn’t specify age limits, but the trip isn’t suitable for wheelchair users or those with mobility issues.

Can I cancel or reschedule?
Yes, you can cancel up to 24 hours in advance for a full refund, and you can reserve without immediate payment, offering flexibility for your plans.

This private sailing trip from Heraklion to Dia offers a blend of adventure and tranquility, highlighting Greece’s stunning seascapes in an intimate setting. Whether you’re seeking a romantic escape or a quiet family outing, it’s a great way to connect with the natural beauty of Crete.

You can check availability for your dates here: