Heraklion: Private Full-Day Sailing Trip to Dia Island

Trying to picture a day on the water surrounded by the stunning scenery of Crete’s coast? This private sailing trip from Heraklion to Dia Island promises just that, with a blend of relaxation, adventure, and local charm. While I haven’t personally set sail on this boat, the glowing reviews, detailed itinerary, and thoughtful offerings make it clear this experience hits the sweet spot for many travelers.

What I love about this trip? It’s private, so you get a tailored experience; the crew is praised for their knowledge and friendliness; and the itinerary offers plenty of stops for swimming, snorkeling, and unwinding. One thing to keep in mind is the price — at $666 for up to six people — it’s an investment, but considering everything included, it’s a fair value for a full day on Crete’s waters.

This trip suits couples, families, or groups looking for a personalized, laid-back day away from the crowds. If you’re someone who appreciates authentic experiences, good food, and a touch of adventure, this could be your ideal getaway.

Good To Know

• Private experience: Tailored to your group, with options for a fully customized day.
• All-inclusive details: Unlimited drinks, fresh fruit, snorkeling gear, and fishing equipment included.
• Dedicated crew: Knowledgeable guides like Kostas and Magda earn praise for their friendliness and helpfulness.
• Multiple swim stops: Enjoy two planned swimming and snorkeling breaks at stunning locations like the Gulf of Saint George.
• Flexible options: Add onboard meals or private transfers for extra convenience.
• Valuable for relaxation and adventure: Perfect for those who want a mix of sunbathing, swimming, and light activity on the water.

You can check if your dates are available here:

What to Expect on the Day

This private full-day sailing adventure offers a well-structured itinerary designed to maximize your time on the water and at the sights. The day begins with a choice of two meeting points—either the Cafe Marina or a designated meeting spot—making it easy to start your journey from Heraklion. Once on board, a safety briefing kicks things off, followed by about an hour of sailing to Dia Island.

The Journey Begins: Sailing from Heraklion

Sailing out from Heraklion, you’ll appreciate the ease of a private yacht tailored to your group size and needs. The crew, typically led by friendly guides like Kostas and Magda, ensure everyone feels comfortable and informed. As your boat cuts through the waves, you’ll enjoy panoramic views of the coast, often accompanied by insightful commentary about the local sights. Several reviewers, such as Andrew, pointed out how well the crew accommodated specific interests, like focusing on sailing rather than just sightseeing.

First Swim Spot: Gulf of Saint George

The first major highlight is the Gulf of Saint George, a bay famously explored by Jacques Cousteau, and one of the most beautiful spots on the island. It’s a favorite for snorkelers and swimmers alike—clear waters, vibrant marine life, and stunning surroundings make it an ideal spot to jump into the water. Guests find that the complimentary snorkeling gear makes the experience accessible even for beginners. Some reviews mention how the guides are helpful with snorkel instruction and actively assist guests in getting comfortable.

Relaxation and Snorkeling at Dia

After the initial splash, you’ll spend about two and a half hours exploring Dia’s pristine waters and scenic views. Here, the crew often serve refreshing drinks and seasonal fruits to keep everyone energized. This is the perfect time to unwind, sunbathe on the deck’s cushion mattresses, or snorkel around the rocky coastline. Many reviewers, including Courtney, appreciated how the guides’ friendliness and knowledge added to the enjoyment.

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Second Swim & Free Time

Following the first swim, you’ll have another two hours for more swimming, snorkeling, or simply relaxing. The freedom to do what suits your mood — whether it’s floating on your back and soaking up the sun or trying your luck with fishing using the provided equipment — is what makes this trip stand out. Guests like Hoang appreciated the crew’s kindness and the fun vibe onboard, which kept everyone entertained.

Return Sailing & Final Views

The return journey to Heraklion lasts about an hour, giving everyone a chance to reflect on the day, snap photos, or simply enjoy the peaceful motion of the boat. The sunset views from the water can be especially scenic, adding a dreamy ending to your day.

The Value of This Experience

When considering the cost of $666 per group, the value hinges on what’s included. The price covers not just the boat and crew but also all the amenities — unlimited soft drinks, wine, fresh fruit, snorkeling gear, and fishing equipment. For those looking for a personalized day on the water, this all-inclusive setup means fewer worries about additional costs and a more relaxed experience.

The optional onboard lunch, available at checkout, is a nice addition for those wanting a proper meal without leaving the boat. Based on reviews, the crew takes pride in offering locally sourced, fresh ingredients, making the meal a highlight for many guests. If you prefer to bring your own snacks, that’s also welcome, and dietary restrictions can generally be accommodated with prior notice.

While the price might seem steep compared to group tours, it’s competitive given the private nature and high level of service. Many guests, like Paul, highlighted the professionalism of the crew and the quality of the yacht, which adds to the perceived value.

The Experience in Detail: What Sets It Apart

The Private Yacht and Crew

You’ll be aboard a vessel suited to your group size, whether a cozy boat or a more spacious yacht. The crew behind the scenes — often Kostas and Magda — receive glowing reviews for their friendliness and local knowledge. They’re praised for their helpfulness with snorkeling equipment, ensuring everyone feels comfortable, and their ability to adapt the day based on guest preferences.

The Scenic Stops

The two main swimming spots are carefully chosen for their clarity and beauty. The Gulf of Saint George is particularly notable for its legendary exploration by Jacques Yves Cousteau and its vibrant waters. The second stop on Dia Island offers a chance to unwind in quiet coves, explore the rocky coastline, or simply soak up the sun.

Food and Drinks

Unlimited drinks, including local white wine and soft drinks, along with fresh seasonal fruit, keep everyone refreshed. The optional onboard meal, if added, delivers a taste of local flavors, often described as delicious and made from fresh ingredients.

The Overall Atmosphere

Guests consistently mention how the guides’ friendliness and attentiveness elevate the experience. Courtney’s comment about the “knowledgeable and friendly” skippers perfectly encapsulates the vibe — relaxed, fun, and informative.

Who Will Love This Tour?

This trip is perfect for couples seeking a romantic day, families with kids, or small groups of friends wanting a private, customized experience. If you value good food, flexible activities, and expert guides, this sailing adventure delivers. It’s especially appealing to those who want a mix of lounging, swimming, and light exploration without the hassle of large tour groups or overcrowded spots.

Practical Tips & Considerations

• Book early: With limited availability and high demand, securing your spot in advance is recommended.
• Bring essentials: Hat, sunscreen, swimwear, and your ID or passport for port regulations.
• Optional transfers: Available for an extra fee, making logistics smoother if you prefer not to self-arrange transportation.
• Meals: Consider adding the onboard meal if you want a hearty lunch; otherwise, seasonal fruit keeps you energized.
• Group size: Unlimited up to 6 guests, so the experience remains intimate and personalized.
• Timing: Check availability for your preferred start time; the tour lasts about 7 hours including sailing, swimming, and relaxing.

Frequently Asked Questions

• What is included in the tour price?

All the essentials: private yacht, professional crew, unlimited drinks, seasonal fruit, snorkeling gear, and fishing equipment. Optional onboard meals are extra.

• Are transfers available?

Yes, private transfers across Crete can be arranged for an additional cost, which you can set up after booking.

• How long is the sailing portion?

The sailing time is approximately 2 hours, split into outbound and return legs.

• Can I bring my own food?

Yes, guests are welcome to bring snacks onboard, and special dietary needs can usually be accommodated with prior notice.

• Is snorkeling gear provided?

Yes, complimentary snorkeling equipment is included in the package.

• What should I bring?

Bring a hat, swimwear, sunscreen, and your ID or passport for port checks.

• Is there a meal option?

An onboard meal can be added at checkout, featuring fresh, locally sourced ingredients. If not, a seasonal fruit platter will be provided.

• What is the group size?

The experience is private, with a maximum of 6 guests per booking.

• Can I cancel if I change my mind?

Yes, free cancellation is available up to 24 hours in advance for a full refund.

This private sailing trip from Heraklion to Dia Island offers a well-rounded day of relaxation, adventure, and authentic Cretan charm. With expert guides, stunning scenery, and a focus on personalized service, it’s an experience that appeals to those who want a special day on the water without the crowds.

While the price might seem high, the all-inclusive nature, private setting, and quality of the crew justify it for travelers seeking something more intimate and tailored. Whether you’re celebrating a special occasion or simply want to enjoy Crete’s coastline with a touch of luxury, this trip delivers a memorable escape.

Ideal for small groups, families, or couples, this sailing adventure combines the best of Crete’s natural beauty with the comfort of a private boat, making it a standout choice for a day of pure relaxation and fun.

Ready to set sail? Booking ahead ensures your spot on this highly-rated, authentic Crete experience.

You can check if your dates are available here: