Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal
Location: Crete, Greece
Price: $81 per person
Duration: Approximately 5.5 hours
Rating: 4.7 out of 5 from nearly 2,000 reviews
Supplier: Cretan Sailing Cruises

Imagine cruising across the sparkling waters of Crete, heading to the beautiful Dia Island aboard a spacious, comfortable sailboat. For around five and a half hours, you’ll enjoy a blend of sailing, swimming, delicious food, and plenty of drinks—whether you opt for the morning or afternoon cruise. The experience starts at Heraklion’s old Venetian port, passing by the iconic Koules fortress, and then out into the open sea, with knowledgeable guides sharing stories and legends along the way.

What we love about this trip is how smoothly it balances relaxation and activity. The boat is described as “beautifully maintained,” giving you space to lounge or participate in water-based fun, like snorkeling or paddleboarding. Plus, the meal — a generous serving of shrimp linguini, Greek salad, and fresh fruit — is both tasty and thoughtfully prepared, with vegetarian and gluten-free options available. The unlimited drinks, especially the wine and local beers, add that extra layer of enjoyment.

A possible consideration is the weather, as some water activities might be limited if the wind picks up, and paddleboarding isn’t advised under rough conditions. Also, since swimming and snorkeling are part of the experience, be prepared for a relaxed pace, not an adrenaline-fueled adventure.

This cruise suits travelers looking for a well-rounded day of sun, sea, good food, and charming scenery. It’s ideal for those who appreciate storytelling, authentic Greek cuisine, and the chance to unwind on the water with friends or family. If you’re after a memorable, value-packed day with beautiful vistas and an experienced crew, this trip is worth considering.

Key Points

• Authentic Crete Experience: Combines sailing, water activities, and local cuisine.
• Comfortable and Spacious Boat: Ensures plenty of room to relax or be active.
• Delicious Mediterranean Menu: Shrimp linguini, Greek salad, fruits, and unlimited drinks.
• Stunning Scenery: Views of Dia Island, the coastline, and sunset options.
• Expert Guides: Share stories about Dia’s history and legends.
• Good Value: For around $81, it offers a full day of fun, food, and scenic views.

You can check availability for your dates here:

A Deep Dive into the Heraklion Dia Island Sailboat Cruise

The Itinerary and What to Expect

Your day begins either in the morning or the afternoon, depending on your choice. The meeting point is at the “Cafe Marina” in Heraklion’s old Venetian port — a scenic starting point, with the fortress looming in the background. From there, you’ll board a large, modern sailboat that promises comfort and space. As you cast off, the crew will be quick to tell stories about Dia Island, adding a touch of local flair to the journey.

The first hour is spent sailing along the coast, offering scenic views of Crete’s coastline. You’ll pass by the historic Koules fortress, which adds a dash of history to the voyage and makes for a stunning photo backdrop. As you leave the harbor behind, your focus shifts to relaxation or water fun.

The Highlights of Dia Island and Water Activities

Once at Dia Bay, your boat drops anchor, and the real fun begins. The water is described as “crystal turquoise,” perfect for snorkeling and swimming — and many reviews mention how the water was an instant hit. The crew provides snorkeling gear, and you can try paddleboarding (though it isn’t available in rough winds). Some travelers even report dolphin sightings, adding a magical element to the day.

While anchored, you can explore the water at your own pace, with the crew offering equipment and unlimited drinks. Expect a friendly, laid-back atmosphere — reviews mention the crew as “very hospitable” and “helpful,” making sure everyone feels comfortable.

The Meal and Refreshments

One of the trip’s standout features is the Mediterranean menu. About an hour after arriving at Dia, the crew serves a generous lunch of shrimp linguini, Greek salad, tzatziki, olive paste, and fresh fruits. Reviewers rave about how delicious and fresh the food is, describing it as “tasty,” “beautifully served,” and “sensational.” Vegetarian and gluten-free options are available, ensuring everyone is catered to.

Complement your meal with local wine, beer, soft drinks, or iced tea — endless drinks that keep the mood lively. After the meal, a tropical and local fruit salad is served, perfect for a light, refreshing finish.

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The Return Journey and Sunset Views

Post-lunch, you can relax or enjoy some last swims in the inviting waters. Then, it’s time to set sail back to Heraklion. The return route often offers a different perspective, especially if you choose the sunset option — many reviewers mention how breathtaking the sunset views are during the sail back. The gentle rocking of the boat, combined with the fiery sky, makes for a picture-perfect end to your day.

The Overall Experience — What Makes It Stand Out

What truly makes this cruise appealing is the combination of authentic Greek hospitality, scenic sailing, and good value. The guides and crew are described as “friendly,” “professional,” and “attentive,” making the journey feel personal and relaxed. The boat itself is well-maintained, spacious, and equipped for water activities.

Plus, the reviews consistently highlight the quality of the food and drinks — many say it’s “good value for money,” with some even mentioning it as “the best thing they did in Crete.” Others appreciated the informative storytelling, adding a cultural layer to the experience.

Who Will Love This Tour?

This trip suits travelers who want a laid-back, day-long escape from the hustle of Heraklion’s city life. It’s perfect for those who enjoy sailing, snorkeling, and good food in a scenic setting. It’s also great for families, couples, or groups of friends, especially if you appreciate excellent service, a friendly crew, and stunning sunset views.

However, if you’re very sensitive to wind or seasickness, be aware that the water activities depend on weather conditions, and paddleboarding might be unavailable in rougher winds. Also, since swimming and snorkeling are part of the plan, it’s best suited for those comfortable in open water.

The Sum Up

The Heraklion to Dia Island sailboat cruise offers a balanced mix of scenic sailing, water fun, and delicious Mediterranean cuisine, all set against the backdrop of Crete’s stunning coastline. It’s a well-organized trip that provides authentic hospitality, with multiple reviews praising the friendly crew, excellent food, and breathtaking views — especially at sunset.

For travelers who love being on the water, enjoy storytelling and local flavors, and want a full, yet relaxed day out, this cruise delivers great value. The experience’s focus on comfort and variety makes it particularly suitable for families, couples, or anyone looking to add a memorable maritime adventure to their Crete holiday.

If you’re seeking a scenic day with some active water moments, good food, and friendly hosts, this tour is a solid choice — and one you’ll likely talk about long after you return home.

FAQ

Is transportation included?
Yes, if you select the pickup option, the tour provides hotel pickup and drop-off from various locations around Heraklion.

How long is the cruise?
The entire experience lasts about 5.5 hours, with roughly an hour sailing to Dia, three and a half hours at the island, and an hour back.

What water activities are available?
Snorkeling, fishing, and paddleboarding equipment are provided. However, paddleboarding may not be available in rough wind conditions for safety.

Can I join if I don’t swim?
Yes, but keep in mind that swimming and snorkeling are optional water activities. You can also relax on the boat or enjoy the scenery from the deck.

Are vegetarian or gluten-free options available?
Yes, the main meal can be tailored to vegetarian and gluten-free diets if requested, making it inclusive for different dietary needs.

What should I bring?
Bring your passport or ID, a towel, and possibly sun protection — sunscreen, hat, and sunglasses — for a comfortable day in the sun.

Is there a dress code?
Casual, comfortable clothing suitable for being on a boat and in the water is best. Swimsuits, cover-ups, and perhaps a light jacket for the breeze are advisable.

Can I upgrade my experience?
The tour offers private or small groups, so check if there are options for a more exclusive trip if you prefer.

This sailboat cruise combines scenic beauty, cultural insights, and good old-fashioned fun on the water. It’s a value-packed way to experience Crete’s coast and islands, perfect for those who want to savor the sea without the fuss.

You can check availability for your dates here: