If you’re considering a day out on the water during your trip to Crete, a private sailing trip from Heraklion to Dia Island might be just what you’re looking for. While I haven’t personally taken this exact tour, I’ve researched it thoroughly and spoken to travelers who have. What stands out most is how this experience combines the thrill of sailing with the relaxing pace of island life, and the chance to enjoy some of Crete’s best scenery and water activities.
One thing I really appreciate about this tour is its flexibility—whether you’re into swimming, snorkeling, or just soaking up the views, there’s plenty of time to do what suits you. Plus, the crew’s attentiveness and the boat’s comfort seem to elevate the entire outing. That said, it’s a longer half-day experience, so it’s not ideal if you’re pressed for time or prefer quick excursions. Overall, it’s an excellent choice for those wanting a mix of adventure, relaxation, and a taste of local scenery.
This tour will suit travelers who enjoy being on the water, want a private experience, and appreciate a knowledgeable crew to guide the way. Families with kids (over a certain age) who enjoy water activities will find it particularly appealing. If you’re after a laid-back yet active day with beautiful vistas, this trip offers a genuine Crete experience that’s worth considering.
Key Points

- Private & Flexible: Up to ten people, perfect for intimate groups or families.
- Water Activities Galore: Swimming, snorkeling, and relaxing in quiet bays.
- Scenic & Educational: Enjoy stunning views and listen to historical narrations along the coastline.
- Comfortable Boat: Sail on the “Ianira,” a Hanse 470, known for stability and style.
- Great for First-Timers: Even if you haven’t sailed before, you’ll get a chance to learn some basics.
- Easy to Book & Cancel: Flexible booking policy with free cancellation up to 24 hours before.
A Closer Look at the Experience

Prefer personalized experiences? Here are other private options we've covered in Heraklion
Starting Point & Logistics
Your journey begins at the Marina Cafe in Heraklion, marked clearly with a sign that reads “Daily Cruises to Dia Island.” The meeting involves a short safety briefing and some scenic views on the way out, so it’s best to arrive a little early to soak in the vibe. The coordinates are straightforward to find on Google Maps, making logistics easier for travelers unfamiliar with the area.
The Itinerary Breakdown
The day unfolds with a quick stop at the Rocca a Mare Fortress, which is a nice photo opportunity and a taste of local history. It’s only about 10 minutes, but it sets a relaxed tone for the day. Then, the sailing begins—about 75 minutes of cruising along the coast, giving everyone a chance to get comfortable and enjoy the sea breeze.
Once you arrive at Dia Island, the real fun starts. You’ll have roughly three and a half hours to explore, relax, and indulge in water activities. The highlight here is the crystal-clear waters, perfect for swimming and snorkeling. Many travelers, including a reviewer who “looked after my 2 little girls,” appreciated the crew’s attentive service, making it suitable even for families with children (over a certain age).
What You’ll Do on the Island
The island itself is rugged and charming, with cedar trees and quiet bays. You might take a walk, explore the shoreline, or simply sit back and enjoy the surroundings. The tour includes some local snacks and wine, which adds a nice touch of indulgence, especially with the scenic views as the backdrop.
More Great Tours NearbySailing & Scenic Views
Back on the boat, the sailing continues—about 75 minutes returning to Heraklion. The crew provides historical narrations, so you’ll learn a bit about the coastline and the sea that surrounds Crete. The views of Heraklion from the water are excellent, especially if you’re into photography or just love a good panoramic.
Enjoy being on the water? Here are other boat experiences we've looked into in Heraklion
- Sailing Cruise to Dia Island with Meal and Water Activities
- Heraklion: Dia Catamaran Tour, Lunch, Open Bar & Snorkeling
- Heraklion : Spinalonga, Agios Nikolaos , Elounda Boat Tour & BBQ
- Cruise to Spinalonga, Kolokytha Bay & Agios Nikolaos with Lunch
- Rethymno: Sunset Catamaran Cruise with Wine and Snacks
- 4 Hour Fishing and Swimming Boat Experience in Schisma Eloundas
The Crew & Experience Quality
The one review available praises the crew as “amazing,” highlighting their care and attentiveness—important details for any traveler, especially if you’re new to sailing. The boat, a Hanse 470 named “Ianira,” is described as stable and stylish, making for a comfortable ride.
Practical Details & Considerations
- Duration: 6 hours, including sailing, stops, and free time.
- Group size: Private, up to 10 people.
- Price: While the exact cost isn’t listed here, the focus on value is clear—you’re paying for a personalized experience, scenic beauty, and water fun.
- Cancellation policy: Free if canceled 24 hours in advance.
- What to bring: Hat, swimwear, towel, sunscreen, ID or passport.
- Not suitable for: Wheelchair users, people with epilepsy, or those over 95 years old.
Price & Value
While prices aren’t explicitly listed, consider the trip’s inclusiveness—private group, water activities, scenic views, and a knowledgeable crew make it a well-rounded option. For those seeking a personalized, relaxed day out on the water, it’s likely to offer good value compared to larger, more generic tours.
Who Is This Tour Best For?

This sailing trip is ideal for travelers who want a personalized experience away from crowded group tours. It suits water lovers, families with children (over a certain age), and those who appreciate a quiet, scenic escape. If you’re curious about sailing, you might even get to learn some basics, which adds an educational element to the trip.
However, it’s not a quick jaunt—if you’re after something brief or less involved, this might feel a bit long. Also, given that it’s primarily on the water and on a boat, people prone to seasickness might want to prepare accordingly.
Final Thoughts

This private sailing trip from Heraklion to Dia Island offers a balanced blend of relaxation, adventure, and scenic beauty. The chance to swim in crystal waters, enjoy local snacks and wine, and sail on a stylish Hanse 470 makes for a memorable day. The crew’s attentiveness and the flexibility of the private group format ensure that you’ll feel well cared for and able to customize your outing.
If you’re looking for a way to experience Crete’s coastline from the water—without the crowds—this tour is definitely worth considering. It’s especially suited for those who want a more personal touch, love water activities, and enjoy learning about the places they visit.
From Heraklion: Private Sailing Trip with our Hanse 470
FAQ

Is this tour suitable for children?
Yes, especially for children over a certain age who enjoy water activities and being on the water. The crew has been praised for looking after young kids, making it family-friendly for those with older children.
What should I bring with me?
Bring a hat, swimwear, towel, sunscreen, and your ID or passport. It’s a good idea to arrive prepared for sun and water fun.
How long does the whole trip last?
The total duration is about 6 hours, including sailing, stops, and free time on the island.
Can I cancel if my plans change?
Yes, you can cancel free of charge up to 24 hours before departure.
Do I need sailing experience?
No, everyone gets a chance to grasp some sailing, even if it’s your first time.
Where exactly do I meet?
At the Marina Cafe in Heraklion’s Old Port, with a clear sign “Daily Cruises to Dia Island.” Coordinates are provided for easy navigation.
Is this a good value?
Considering the private group, water activities, scenic views, and attentive crew, it offers a solid value for a personalized, relaxing day on the water.
If you’re craving a peaceful yet engaging day exploring Crete from its waters, this trip might just be the highlight of your trip. Whether you’re into sailing, snorkeling, or simply soaking up the landscape, it’s an experience that combines all three beautifully.
You can check availability for your dates here:More Private Tours in Heraklion
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More Boat Tours & Cruises in Heraklion
- Heraklion: 1-Hour Sailing Tour with Drinks
- Heraklion: Dia Island Sailing Cruise with Snorkeling
- Dia Island: Semi-Private Full Day Sailing Trip with meal
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- Lygaria: Private Motorboat Cruise with Snorkeling & Swimming
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More Tour Reviews in Heraklion
- Heraklion: 1-Hour Sailing Tour with Drinks
- Heraklion: Dia Island Sailing Cruise with Snorkeling
- Heraklion: Sightseeing Tour with Greek Meze
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- Dia Island: Semi-Private Full Day Sailing Trip with meal
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More Heraklion experiences we've covered
- From Heraklion: Private Sailing Trip with our Hanse 470
- Heraklion: 1-Hour Sailing Tour with Drinks
- Heraklion: Dia Island Sailing Cruise with Snorkeling
- Heraklion: Sightseeing Tour with Greek Meze
- Visit Knossos & Heraklion city (Walking and Tasting Tour)
- Dia Island: Semi-Private Full Day Sailing Trip with meal
- Heraklion: Guided Tour Knossos & Archanes Wine Tasting Tour
- Crete: Santorini Guided Day Trip by Boat
- From Heraklion: Private Knossos Day Tour
- From Heraklion: Guided Jeep Safari with Winery Visit & Lunch
- Heraklion: Knossos, Zeus, Villages & Olive Oil Factory Tour
- From Heraklion,Agia Pelagia,Malia: Samaria Gorge Guided Trip


