Private Sailing Trip from Heraklion to Dia with meal & SUP

Thinking about adding a splash of adventure to your Crete trip? This private sailing tour from Heraklion to Dia promises a relaxed day on the water, with plenty of chances to unwind, explore, and enjoy the views. If you’re after a personalized experience away from the crowds, this trip could be just what you’re looking for.

What we really appreciate about this experience is how it combines authentic sailing with stunning scenery. Plus, the flexibility it offers—swimming in crystal-clear waters, trying out stand-up paddleboarding, and munching on local snacks—makes it feel like a genuine escape. However, a potential consideration is that the tour is around five hours, so it’s best suited for those comfortable with a full day on the water, especially if you’re not keen on long boat trips.

This experience tends to appeal most to travelers craving a peaceful, scenic outing with a touch of adventure. Whether you’re a couple seeking romance, a group of friends, or a family (depending on your children’s age and comfort with boat trips), it offers a tailored way to see Dia beyond the usual crowded tours.

Key Points

• Private, personalized experience for a more intimate day on the sea
• Includes swimming, snorkeling, and stand-up paddleboarding in calm waters
• Enjoy scenic views of Dia’s landscape and the tranquil Aegean Sea
• Snacks and drinks provided, perfect for a relaxed day
• Ideal for travelers who appreciate comfort and stunning scenery without overly crowded tours
• Duration of 5 hours makes it a full but manageable trip

You can check availability for your dates here:

An Inside Look at the Experience

When considering this tour, what truly stands out is how it offers a more intimate way to explore Crete’s coast. Instead of joining a large group, you’re on a private sailboat with your own skipper and assistant. This means more flexibility, a tailored pace, and the chance to enjoy the journey at your own speed.

The journey kicks off in Heraklion’s marina, where you’ll meet your team at the Marina Cafe. Bringing your passport for check-in makes the process smooth—just a small detail that shows how organized the operation is. Once aboard, you’ll set sail with a safety briefing and then enjoy about an hour of scenic cruising along the coast.

The boat glides past iconic sea views, giving an authentic sailing feeling that’s often missing from bigger, more commercial excursions. We loved the way the boat’s gentle movement creates a calming backdrop, perfect for relaxing and soaking in the scenery.

The Day at Dia: What to Expect

Arrival at Dia

Once you arrive at Dia, the uninhabited island just off Crete’s coast, the real fun begins. With two hours allocated here, you’ll have ample time to explore, relax, and indulge in various activities.

Exploring Dia

Dia’s untouched natural beauty makes it a highlight. The island’s landscape, with its rugged cliffs and clear waters, creates a picture-perfect setting for photos. One traveler noted, “The views of Dia’s landscape are breathtaking and worth every minute of the trip.” It’s a great spot to snap some pictures or just take a quiet moment away from the busy mainland.

More Great Tours Nearby

Swimming & Snorkeling

The calm, turquoise waters around Dia are ideal for swimming and snorkeling. We loved the way the water feels warm and inviting—perfect for cooling off after some sunbathing. The snorkeling, even for beginners, offers the chance to see marine life in its natural habitat, although specific marine sightings aren’t guaranteed.

Stand-Up Paddleboarding

If you’re into something more active, stand-up paddleboarding (SUP) is included. It’s a fun way to take in the scenery from a different perspective and a novelty for many. Most reviews mention that it’s beginner-friendly, with the calm waters making it easy to balance and enjoy.

Food & Snacks

Local snacks and soft drinks are included, making the experience feel relaxed and fuss-free. The snacks are simple but effective, giving you enough to keep you energized for the day. Some reviews mention that the soft drinks and light snacks are a nice touch, especially since you’ll be outdoors for a few hours.

Sunset & Sailing Back

As the day winds down, you’ll set sail back to Heraklion just in time for the sunset. The views during this part of the trip are often described as stunning. Expect to be seated comfortably, enjoying the gentle breeze and watching the sky change colors—a peaceful way to end the day.

The Overall Value

For $71 per person, this tour offers a lot if you’re looking for a private, scenic day on the water. The inclusion of a private boat, a skipper, snacks, and activities like snorkeling and SUP makes it a good value, especially compared to larger group excursions that might be less personalized. The flexibility and comfort tend to appeal more than the hurried pace of bigger tours.

One thing to keep in mind is that, while the experience is largely praised, it’s not a luxurious cruise with gourmet meals or extensive amenities. Think of it as a well-organized, authentic sailing adventure with all the essentials.

Who Would Love This Tour?

This trip is best suited for travelers who appreciate quiet, scenic experiences and want to avoid the crowds. It’s perfect if you enjoy water activities like swimming and paddleboarding but prefer a calm, guided environment. It’s also suited for those who value personalized service and a flexible itinerary.

It might also appeal to couples celebrating something special, friends looking for a memorable day, or families with older children comfortable on a boat trip. Since it’s a private experience, it can be tailored slightly to your pace and interests.

Practical Details & Tips

• Duration: 5 hours, so plan your day accordingly.
• Meeting Point: Marina Cafe in Heraklion, with check-in requiring your passport.
• Price: $71 per person, which covers the boat, skipper, assistant, snacks, and soft drinks.
• Not Included: Personal expenses, extra drinks, or anything not mentioned.
• Group Size: Private or small groups available—great for a more intimate experience.
• Language: Guides speak English and Greek.
• Not suitable for: Wheelchair users (as per the info provided).
• Cancellation policy: Free cancellation up to 24 hours in advance—perfect for flexibility.

FAQ

Is this tour suitable for children?
While not explicitly stated, the relaxed, scenic nature suggests it could work for older children comfortable on boats. Check with the provider if you have young kids or specific needs.

What should I bring?
Bring your passport for check-in, swimwear, sunscreen, and a towel. You might also want water shoes or sandals for walking on the island.

Is food included?
Snacks and soft drinks are included, but not a full meal. If you want more extensive food, you might need to bring extra or arrange something separately.

How long is the sailing part?
About an hour of scenic sailing to Dia, with additional sailing back during sunset.

Can I do this trip if I don’t swim?
While swimming and snorkeling are optional, you can relax on the boat if you prefer not to swim.

Is this tour private?
Yes, it’s designed as a private or small group experience, offering more personalization.

Are there any restrictions?
Alcohol and drugs are not allowed onboard. It’s not suitable for wheelchair users.

What’s the best time of day for this trip?
Most trips include a sunset sail back, which is highly recommended for the views.

Is the boat comfortable?
The boat is a private sailboat with a skipper and assistant, designed for comfort and safety.

What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund, making it flexible if your plans change.

This private sailing trip from Heraklion to Dia offers a well-rounded blend of scenic beauty, water activities, and relaxed comfort. It’s a good pick for travelers wanting a more intimate experience, away from crowded tours, with plenty of opportunities to swim, snorkel, or simply soak up the views. While it doesn’t include gourmet dining or luxury amenities, the value lies in its flexibility, personal touch, and stunning scenery.

If you’re someone who values peace, natural beauty, and a bit of adventure on the water, this trip will check those boxes. It’s particularly suited for those who want to experience Crete from a different perspective—calm, scenic, and personalized.

Remember:

Book early, bring your essentials, and get ready for a memorable day on the Aegean Sea. Whether it’s a romantic escape or a fun day with friends, this tour offers a genuine taste of Crete’s nautical charm.

You can check availability for your dates here: