Heraklion: Private Full-Day Sailing Trip to Dia Island

This experience made our article of What Are The Best Cruises And Boat Tours In Crete? Our Top 14 Picks.

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Heraklion: Private Full-Day Sailing Trip to Dia Island

If you’re dreaming of a day filled with sun, sea, and relaxation in Crete, this private sailing trip to Dia Island promises an experience worth your time and money. While we haven’t personally been on this exact tour, the detailed reviews and itineraries paint a compelling picture of an adventure packed with gorgeous scenery, delicious food, and attentive guides.

What makes this tour stand out is the personalized nature—you can choose the boat size and tailor the day to your group’s pace. The stunning views of the Cretan coastline, the chance to snorkel in crystal-clear waters, and the option to indulge in local wine and fresh fruit give it a very tempting appeal.

A small consideration is that, as a full-day experience, it requires a decent chunk of your day, so it’s best suited for travelers who want to dedicate a good portion of their Crete trip to one memorable outing. If you love being on the water, prefer intimate, private experiences, and enjoy a mix of adventure and relaxation, this sailing trip is likely to suit you perfectly.

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Key Points

Private and customizable experience tailored to your group’s size and preferences
Multiple swimming and snorkeling stops with complimentary gear for marine exploration
Incredible views of the Cretan coast and Dia Island, including the Gulf of Saint George
All-inclusive drinks and fresh fruit, with optional onboard meals
Expert guides known for their friendliness and local knowledge
Perfect for those seeking a balanced mix of relaxation, adventure, and authentic scenery

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An Honest Look at the Full-Day Sailing Experience

This private trip from Heraklion is a well-rounded way to enjoy Crete’s marine beauty without the hustle of crowded tours. Spanning about 6.5 hours, the journey offers a mix of sailing, swimming, eating, and relaxing—an ideal combo for a full day on the water that’s both fun and leisurely.

The Itinerary Breakdown

The tour usually begins from one of two meeting points: Cafe Marina or a designated boat meeting spot**. After a quick safety briefing and an hour of sailing, your adventure officially kicks off with a scenic cruise toward Dia Island.

The first stop at the Gulf of Saint George is often highlighted as the trip’s gem. This bay, famously explored by Jacques Yves Cousteau, is one of the most vibrant and picturesque spots along the coast. Here, you’ll have 2.5 hours to swim, snorkel, or simply soak up the views. The complimentary snorkeling gear makes exploring easy, and reviewers like Andrew loved the fact that the boat’s captain, along with the first mate, was very friendly and helpful—especially with kids.

The second swimming stop gives you another chance for dips or snorkels, giving ample time to enjoy the water and the scenery. The crew often provides local white wine, bottled water, and soft drinks, so you can cool off while enjoying the landscape.

The Food and Drink

While the trip’s focus is on active relaxation, the onboard experience is far from bare-bones. A seasonal fruit platter is included, offering a refreshing snack in between water activities. For those wanting a culinary touch, an optional full onboard meal can be added during booking—think locally sourced ingredients, fresh seafood, or regional specialties. Many reviewers, like Paul, noted that “the food and drink were great,” adding to the trip’s value.

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The Crew and Service

A consistent highlight in reviews is the knowledgeable and friendly guides. Courtney mentioned her skippers were “very knowledgeable and friendly,” which made the entire experience feel personalized and caring. The crew, including guides like Kostas and Magda, are praised for their attentiveness, making sure everyone feels comfortable and engaged, whether they’re avid snorkelers or just sunbathers.

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The Boat and Comfort

With options for different group sizes, the boats are equipped with cushion mattresses and sun-protected areas. This setup ensures you can lounge comfortably between activities. The fueled, insured, and all marine fees are included, so there’s no hidden stress about extra costs or safety concerns.

Additional Options and Logistics

You can opt for hotel pick-up and drop-off, making this trip even more seamless. It’s worth considering if you prefer a stress-free start and finish to your day. Transfers are available at an extra cost, and the team is happy to coordinate this if you provide your hotel details.

Authenticity from Reviews

Real travelers like Andrew and Paul shared their positive impressions, emphasizing the fun sailing experience and delicious onboard lunch. Andrew noted that his crew was “very kind and helpful with our two kids,” highlighting the family-friendly side of the tour. Others, like Courtney, appreciated the overall knowledgeability of guides and the enjoyable, well-organized day.

The Whole Experience: What You Can Expect

The itinerary is designed to maximize your time on the water with two main swimming stops—one in the Gulf of Saint George, a bay once explored by Jacques Yves Cousteau—and another more relaxed session of swimming and snorkeling back near Dia Island. The scenic sailing between stops offers fantastic views of the coastline, with plenty of opportunities to snap photos or just soak in the scenery.

The timing of stops ensures you’re not rushing. The longer stop in the bay allows for a full immersion into the water, whether you prefer to snorkel, float, or enjoy a leisurely lunch on deck. The cruise back to Heraklion wraps up with about an hour of sailing, providing a peaceful conclusion to a busy day.

Value and Pricing: Is It Worth It?

At $666 for a group of up to six, the price may seem high at first glance. However, considering it’s a private, all-inclusive day with a dedicated crew, the boat, snacks, drinks, and optional onboard meals, it offers good value for those wanting exclusivity and a personalized experience. The flexibility in boat size and catering to your group makes it appealing for families, couples, or small groups of friends.

Many reviews highlight the quality of the guides and the boat, which can be a rare find in shared tours that often cut corners. The customizable itinerary and attention to detail—like the quality of snorkeling gear and the availability of local wine—add to the overall experience.

Who Will Love This Trip?

This tour is perfect for travelers who want a private and flexible day on the water. It’s ideal for families with children, thanks to the friendly crew and safe environment. It also suits couples and small groups looking for intimacy, personalized service, and a mix of adventure and relaxation.

If you enjoy sailing, snorkelling, and tasting regional wine and fruit in a scenic setting, this trip checks all the boxes. On the flip side, if you’re after a quick, budget-friendly activity or prefer larger groups with less customization, this might not be the best fit.

The Sum Up: Is This Tour Worth It?

For those seeking a private, scenic sailing adventure with plenty of swimming, snorkeling, and good food, this tour from Heraklion delivers on its promises. The knowledgeable guides, tailored experience, and stunning views make it a standout option for travelers who appreciate attention to detail and a personal touch.

It’s especially suitable for families, couples, or small groups craving a peaceful day on the water, away from crowded tours. Just keep in mind that it’s a full-day commitment, so plan accordingly if you prefer shorter excursions or strict budgets.

If you’re ready to enjoy Crete’s coastline with a mix of adventure, comfort, and authentic local flavors, this sailing trip could become one of your trip highlights.

FAQs

How many people can fit on this sailing trip?
The tour offers options for different boat sizes, accommodating groups of up to 6 people per booking, making it a very personalized experience.

What is included in the price?
The price covers the private yacht, a professional crew of two, unlimited drinks (water, soft drinks, wine), seasonal fruit, snorkeling gear, fishing equipment, and all marine fees and taxes.

Are meals included in the tour?
A seasonal fruit platter is included, with the option to add a full onboard meal during booking. Guests can also bring their own snacks if preferred.

Can I get transfers from my hotel?
Yes, private transfers can be arranged for an additional cost. You’ll need to provide your hotel details to coordinate this service.

What should I bring on the trip?
Bring a hat, swimwear, sunscreen, and your passport or ID. It’s also wise to wear comfortable clothing and bring a towel for swimming.

How long is the sailing journey?
The total experience lasts about 7 hours, including sailing, swimming, and relaxing stops.

Is this experience suitable for children?
Yes, the guides are known to be friendly and helpful with kids, making it a family-friendly option.

What is the best time of year to do this trip?
While the exact season isn’t specified, Crete’s warm Mediterranean climate makes spring through autumn ideal for sailing.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility for your plans.

In summary, this private sailing trip offers a well-balanced day of adventure and relaxation on Crete’s stunning waters. With excellent guides, scenic stops, and customizable options, it’s a fantastic choice for those seeking a memorable, intimate day on the sea—perfect for celebrating special occasions or simply indulging in a tranquil escape.