If you’re looking for a memorable day on the water near Heraklion, the Dia Island luxury sailing trip from Crete might just be what you need. This excursion offers a blend of comfort, scenic beauty, and genuine activity — whether you love swimming, snorkeling, or simply soaking up the sun. With options for private or group sailings aboard some of Heraklion’s largest and most comfortable sailboats, this adventure is designed to cater to travelers seeking both relaxation and a touch of adventure.
What we find especially appealing about this trip is the luxurious setting combined with the chance to actively participate in sailing or just kick back on spacious decks. Plus, the included Mediterranean meal paired with drinks makes this a solid value, especially when you compare it to land-based tours. One thing to consider is the group size, which can influence how intimate the experience feels — smaller groups tend to foster a more personal vibe.
This tour would suit adventurous travelers, families, or anyone wanting to combine a maritime escape with great food and stunning views. If you enjoy being on the water, appreciate well-maintained vessels, and value authentic experiences over cookie-cutter excursions, this trip ticks a lot of boxes.
Key Points
- Luxurious sailboats up to 22 guests, offering a spacious, comfortable environment for everyone.
- Multiple options including private, shared, morning, sunset, and full-day trips.
- Activities like swimming, snorkeling, paddleboarding, and fishing in crystal-clear waters.
- Delicious Mediterranean cuisine with vegetarian and gluten-free options available.
- Beautiful sunset views on the return trip, perfect for romantic or reflective moments.
- All-inclusive drinks including seasonal fruit, beer, wine, and soft drinks, adding to the relaxed vibe.
An In-Depth Look at the Experience
You can also read our reviews of more tours and experiences in Heraklion Regional Unit.
The Boats and Setting
You’ll be cruising on one of Heraklion’s largest sailboats: either the 53-foot TREATON or the 49-foot JACKPOT. Both are air-conditioned, which is a relief in Crete’s summer heat, and come equipped with modern amenities like electric toilets and showers, ensuring comfort after a swim or snorkel. Their spacious decks, including oversized mattresses on the front and generous stern platforms, are where you’ll likely spend most of your relaxing hours.
Many reviews emphasize how well-maintained and luxurious these boats are, with one reviewer noting that the boat’s condition and staff care made for a top-tier experience. The space onboard allows for both socializing and solitude, depending on your mood — perfect for families, couples, or small groups of friends.
The Itinerary and Timing
The cruise begins at Heraklion’s Venetian Port, with pickup options from various nearby areas like Karteros, Kokkini Hani, or Malia. The exact timing varies depending on whether you opt for a morning or sunset trip, but all options run around 5.5 hours, with some full-day trips extending to 8.5 hours.
The journey includes a scenic sail to Dia Island, an uninhabited, protected Natura 2000 site. On the way, you’ll enjoy photo stops and views of Heraklion’s coast, which many travelers find charming. Once on Dia, you’ll have approximately 3.5 hours to swim, snorkel, paddleboard, or just lounge onboard. The water’s reputation for being crystal clear and turquoise makes it ideal for underwater activities.
Activities on Dia Island
The highlight for most visitors is the chance to dive into the inviting waters. Snorkeling equipment, paddleboards, and fishing gear are provided, enabling guests to explore or just float around in the tranquil environment. Multiple reviews mention how crystal-clear waters and plenty of fish make snorkeling extra enjoyable.
Swimmers and sunbathers alike find plenty of space on the boat’s stern platforms and front decks, which are set up with high-quality mattresses for lounging. One guest noted that there are ample spots to relax while enjoying the sun or the cool breeze.
More Great Tours NearbyThe Meal and Drinks
A key part of this experience is the Mediterranean meal served onboard. It includes pasta with shrimp in tomato sauce, a Greek salad, seasonal fruit, and a variety of soft drinks. Beer and white wine are unlimited, offering a nice way to unwind after swimming. Vegetarian and gluten-free options can be requested, which adds to the inclusive nature of the trip.
Guests raved about the quality of the food — many reviewers called it “delicious” and “fresh,” with some saying they’d happily do the trip again just for the meal. The inclusion of fruits and drinks ensures guests stay refreshed, especially in the summer heat.
Sunset Views and the Return Journey
For those who choose a sunset option, the return trip is a highlight. Watching the sun dip below the horizon while sailing back over calm waters creates a perfect, romantic backdrop. Several reviews describe the stunning sunset and the peaceful twilight, which provides a calming end to the busy day.
The trip also includes stops at dramatic viewpoints like Rocca a Mare Fortress and scenic coastal spots, perfect for photos or simply soaking in the views. The entire cruise is designed to combine relaxation with some sightseeing, making it suitable for travelers who want both.
Practical Details and Considerations
Group Size and Atmosphere
Shared cruises typically host up to 16 guests, which strikes a good balance between social and private. Smaller groups tend to feel more intimate, allowing for better interaction with crew and more space to relax. Some travelers appreciated having fewer companions onboard, noting it made the experience feel more exclusive.
Price and Value
At $68 per person, the trip offers excellent value. For what’s included — a spacious, modern sailboat, professional crew, a full meal, drinks, and activities — it stacks up well against land-based tours or smaller boat rides. The all-inclusive drinks, especially wine and beer, are a nice touch, reducing the need to carry extra cash or worry about ordering at a bar.
Accessibility and Logistics
The tour doesn’t accommodate wheelchair users, and travelers are advised to bring essentials like hats, swimwear, towels, and sunscreen. Due to regulations, oversized luggage isn’t allowed onboard. The meeting point is at Cafe Marina in Heraklion’s Venetian port, with pickup offered from various nearby locations, making it convenient if you’re staying in the area.
Seasickness and Safety
Seasickness could be a concern for some, especially on open water. The tour recommends taking anti-seasickness pills 30 minutes before departure, and again before returning from Dia. The boats are designed for safety, with professional skippers and crew onboard, and reviews consistently mention how safe and well-managed the trips are.
Authentic Experiences and What Travelers Say
Many reviews highlight how knowledgeable and friendly the crew is, often going beyond just safety to share insights about the island and the sea. Several comments mention the delicious food and the friendly atmosphere, which help make the trip feel both luxurious and authentic.
One guest praised the small group size for allowing more personal interactions and better access to the crew’s knowledge. Others loved the crystal water and the chance to see sea urchins during snorkeling adventures. The sunset cruise is repeatedly described as romantic and breathtaking, perfect for couples or travelers looking for a peaceful end to their day.
This sailing trip is ideal for anyone wanting a luxurious, relaxing day on the water in Crete. It’s well-suited for travelers who appreciate comfort, good food, and authentic maritime experiences. Families with children who enjoy swimming and water activities will find plenty to do, while couples might adore the quiet sunset views and romantic setting.
Though it’s a bit more upscale and spacious than some other tours, the value for money is quite good given the amenities, food, and scenery. If you’re looking for a day that combines gentle adventure with comfort and fine company, this trip is a practical, enjoyable choice.
However, if you’re sensitive to seasickness, plan ahead with medication, and keep in mind the limited accessibility for wheelchair users.
Is transportation provided?
Yes, if you select the optional pickup, you’ll be transferred from specified areas like Karteros, Gournes, or Malia to the port.
What is included in the price?
The price covers the yacht cruise, a professional skipper and steward, onboard amenities like air conditioning and showers, the Mediterranean meal, seasonal fruit, and unlimited drinks including soft drinks, water, beer, and wine.
Can I bring my own drinks or food?
No, all drinks and food are included and provided by the crew. Outside food or drinks are not permitted onboard.
What activities are available during the trip?
You can swim, snorkel, paddleboard, and fish in Dia’s clear waters. Equipment for these activities is provided onboard.
How long is the cruise?
The trip lasts approximately 5.5 hours for shared and private options, with full-day trips extending to about 8.5 hours.
Are vegetarian or gluten-free meals available?
Yes, vegetarian and gluten-free options can be requested in advance.
What should I bring?
Bring a hat, swimwear, towel, sunscreen, a jacket for the evening, and a passport or ID. Oversized luggage isn’t allowed.
Is this tour suitable for children?
Yes, especially children who enjoy swimming and water activities. However, the tour is not suitable for wheelchair users.
What are the group sizes?
Shared cruises typically host up to 16 guests, while private options are for your group only.
What’s the best time of day to book?
Both morning and sunset trips are popular. Sunset cruises create especially beautiful scenery, but it depends on your schedule and preference.
In essence, the Dia Island luxury sailing trip offers a well-balanced mix of comfort, activity, and scenery — perfect for travelers wanting to enjoy Crete from a different perspective.
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