Private Luxury Sailing Trips to Dia Island

Introduction

This private sailing trip around Dia Island in Crete offers a blend of relaxation, adventure, and scenic beauty, all wrapped in a personalized, intimate setting. With a knowledgeable skipper at the helm, you’ll glide through St. Georges Bay — a calm, crystal-clear stretch of water perfect for swimming, snorkeling, and unwinding away from the crowds. The tour’s standout feature? Its exclusivity: only your group on a sleek, private vessel, making it ideal for couples, families, or small groups seeking a tailored experience.

One thing we really appreciate about this trip is the flexibility—you can choose to add lunch, champagne, or even a birthday cake, transforming an already beautiful day into a celebration. However, if you’re expecting a packed itinerary or a lively party atmosphere, this might lean more toward a serene escape. This sailing adventure is perfect for those wanting to combine comfort, privacy, and a taste of authentic Greek water life.

If you’re after a laid-back but memorable day on Crete’s waters, this tour suits travelers looking for a relaxing, all-inclusive experience with plenty of opportunities to snorkel, fish, and soak in the scenery.

Key Points

• Private, intimate experience with a knowledgeable skipper ensuring personalized attention
• Ideal for relaxation with swimming, snorkeling, and scenic sailing in a quiet bay
• Flexible add-ons such as lunch, champagne, and cake to upgrade your day
• All equipment provided — snorkeling gear, fishing rods, and refreshments included
• Free cancellation offers peace of mind in case of weather or schedule changes
• Suitable for most travelers, including families, couples, and small groups

What to Expect From the Sailing Trip

This six-hour adventure kicks off with a convenient pickup option, making your arrival seamless. Once aboard, you’ll set sail across St. Georges Bay, a tranquil spot perfect for unwinding and soaking up the sun. The journey begins with an hour of sailing, giving everyone a chance to enjoy the breeze and the panoramic views of Crete’s coast.

When you arrive at Dia Island’s bay, the boat anchors in water so clear and inviting that it practically tempts you into the sea. The highlight? A generous swimming stop where you can splash around, with snorkeling gear provided for those eager to explore underwater life. While the water isn’t known for abundant marine sightings, reviewers like Raymond G. appreciated the calm sailing and the opportunity to just relax in the beautiful, warm waters.

For those interested in fishing, the tour supplies fishing rods and raw bait, so you can try your hand at catching local fish—an activity that many found surprisingly enjoyable. From Betina K’s review, we learn that the staff is friendly and attentive, ensuring guests feel comfortable whether they’re snorkeling or just lounging.

The Island Stop: Dia Island

Dia Island itself is a small, uninhabited gem, offering a peaceful escape from busier tourist spots. The bay here is perfect for lazy floating, taking in the scenery, and snapping photos of the surrounding cliffs and clear waters. Because the island is mostly untouched, it offers a genuine feel of nature’s calmness rather than a commercialized environment.

Additional Luxuries

You can choose to enhance your experience with extras like a gourmet lunch, champagne, cake, or other treats. Many reviewers, including Jennifer W., highlight how the provided snacks, fresh fruit, and salads made the trip feel special, especially when paired with the friendly service of Captain Mario. The option to add a bottle of champagne or birthday cake can turn a simple day on the water into a celebration—perfect for anniversaries or special occasions.

Food & Drinks

Included in the base price are unlimited soft drinks, white wine, and bottled water, which are enough to keep everyone refreshed during the day. If you opt for lunch, there are choices such as chicken, vegetarian, or fish menus, with an extra fee. The boat’s crew, especially Captain Mario from reviews, is known for their excellent wine selection, adding a touch of luxury to your private cruise.

Practical Details & Comfort

The tour is designed for up to 8 people, making it a cozy but comfortable experience. The boat itself is modern and well-maintained, and the crew is praised for their friendly professionalism. The meeting point at Cretan Activities Cruise in Iraklio is easily accessible, and transportation options can be arranged for a small extra charge.

Travelers should remember to bring essentials like sun hats, sunscreen, and swimwear, as these aren’t included but are vital for comfort and protection during the day.

The Value of the Experience

At around $510 per group, this tour offers a level of privacy and customization that many other Crete excursions lack. Considering the inclusion of a knowledgeable skipper, snorkeling and fishing gear, unlimited refreshments, and the option to upgrade with food and drinks, the value is quite compelling—especially for groups wanting a VIP treatment on the water.

The private nature of this trip is a big plus; you won’t share the boat with strangers, and that means you set your own pace. The reviews consistently mention the friendly staff and the peaceful sailing, making it clear that the experience is as much about the vibe as it is about the scenery.

A Few Considerations

While most feedback is positive, some travelers might find the water around Dia Island not teeming with marine life—so if snorkeling or fishing are your main goals, it’s worth tempering expectations. Also, the extra costs for lunch or champagne can add up if you indulge in multiple treats. Still, many found the overall experience well worth the price, especially considering the personalized service and flexibility.

Who Is This Tour Best For?

This sailing experience is particularly suited for small groups or couples wanting privacy and a tailored itinerary. It’s ideal if you’re celebrating a special occasion or simply want a peaceful escape from the busy tourist spots. Families with children who enjoy swimming and snorkeling will also appreciate the calm waters and safe environment.

Active travelers interested in fishing or trying local seafood might enjoy the opportunity to catch their own fish, while those looking for a serene day of sunbathing and scenic views will find exactly what they need here.

The Sum Up

In the end, this private luxury sailing trip to Dia Island offers a combination of comfort, authentic water activities, and personalized service that few other Crete experiences can match. The friendly crew, flexible options, and tranquil setting make it a standout choice for travelers craving an upscale, relaxed day on the water.

While it does lean towards a more peaceful, less party-focused vibe, that’s exactly what many guests loved—a quiet, intimate escape to enjoy Crete’s beautiful waters with all the comforts of a private yacht. Whether celebrating a special occasion or simply seeking some downtime, this tour balances value and exclusivity beautifully.

If you’re after a stress-free, customizable, and scenic day with the option to indulge, this trip is a fantastic choice — especially if you value quality over quantity and authentic personal touches.

FAQs

Is transportation included in this tour?
No, transportation isn’t included, but transfer services can be arranged upon request for an extra fee.

What should I bring on the trip?
Bring sun hats, sunscreen, swimwear, and perhaps a towel. These aren’t included but will ensure you stay comfortable during swimming and sunbathing.

Can I add lunch or drinks to my booking?
Yes, you can choose to purchase lunch, champagne, or cake as extras. These options are available at an additional cost.

How many people can fit on the boat?
The tour is designed for groups of up to 8 people, making it a cozy, private experience.

What is the cancellation policy?
You can cancel free of charge up to 24 hours before the experience. Cancellations made less than 24 hours in advance are not refunded.

Is snorkeling equipment provided?
Yes, masks, fins, and snorkels are included, so you don’t need to bring your own.

This private sailing trip to Dia Island offers a fine balance of relaxation, scenery, and personalized service—perfect for those wanting a peaceful yet memorable water-based experience in Crete.