Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Imagine a day spent on the water, bobbing gently under the Crete sun, surrounded by crystal-clear waters and scenic ocean views — that’s exactly what this sailing trip to Dia Island promises. While I haven’t personally taken this cruise, we’ve gathered plenty of insights and reviews to help you decide if it’s the perfect addition to your Crete itinerary.

What I love about this experience is its small-group vibe — with a maximum of 10 guests, it’s a chance to enjoy a more intimate, less crowded adventure. The crew, made up of local Cretans like Captain George and Vaso, are not just guides but genuinely friendly faces who treat guests like family. Plus, the fresh Mediterranean meal served onboard, along with unlimited local drinks, makes it feel more like a floating feast than a typical tour. The chance to see dolphins playing in the wake is another highlight that keeps travelers coming back.

One thing to keep in mind is the limited duration — at around 6 hours, it’s a full day but might feel rushed if you’re looking for a longer, more leisurely sea experience. However, the balance of activities like swimming, snorkeling, and paddleboarding ensures you get plenty of water fun without feeling overwhelmed. This tour suits those who love a relaxed, scenic day out with good company and authentic touches, especially if you enjoy a mix of adventure, culture, and delicious food.

Good To Know

• Intimate Group Size: Limited to 8-10 guests for a relaxed, personalized experience
• Authentic Local Crew: Friendly, knowledgeable guides who share stories and sea life insights
• All-Inclusive Comfort: Fresh food, unlimited drinks, and water activities included
• Activities Galore: Snorkeling, paddleboarding, swimming, and dolphin spotting on a scenic route
• Beautiful Scenery: Stunning views of Crete’s coastline and Dia Island’s peaceful bay
• Value for Money: Well-rounded experience combining adventure, culture, and cuisine in one day

You can check if your dates are available here:

The Journey Begins: From Heraklion to Dia Island

The adventure kicks off at Heraklion Port, where you’ll meet your crew, possibly near the iconic Old Anchor monument. The process is smooth, with options for pickup from various nearby locations, including Malia, Hersonissos, or Gouves, making it accessible no matter where you’re staying. The transfer is in an air-conditioned minivan, which is a relief after a warm morning wandering Crete’s streets.

Once onboard, the small group feels more like a gathering of friends rather than a tour bus. The crew, which includes Captain George — a seasoned sailor with a calm, humorous manner — immediately makes you feel at home. His stories and the singing to dolphins during the cruise are often mentioned as memorable highlights by past travelers.

Sailing out into the Aegean Sea, the boat glides past the stunning coastline, with the wind filling the sails and creating a gentle, peaceful rhythm. The views are spectacular, and many reviews note how relaxing the ride is, especially when the boat turns off its engine to sail back with just the wind. If you’re lucky, dolphins might join the show, playing near the boat — a magical moment that keeps guests smiling long after.

Exploring Dia Island: Swimming, Snorkeling, and Relaxation

The main anchor point is Saint George Bay on Dia Island, a quiet, unspoiled haven perfect for water lovers. Expect around three hours here, which many reviewers find ample for swimming, snorkeling, and soaking up the sun.

The waters are a highlight — crystal-clear, inviting, and perfect for discovering underwater life. The crew provides snorkeling gear, and one guest shared that they enjoyed snorkeling in the warm water, seeing fish and underwater sights they won’t forget. Paddleboarding is also available, with guests often praising the fun of exploring the calm bay on a board. The shallow areas are safe for beginners, and life jackets are provided for confidence.

When hunger strikes, the onboard meal is a highlight. The chef serves a Mediterranean feast featuring pasta with shrimp or vegetarian pesto pasta, complemented by a Greek salad and a fresh fruit salad for dessert. Many reviews mention the high quality of the meal, with one guest noting, “George’s prawn pasta was fantastic.” The meal is prepared fresh with local ingredients, and the crew pride themselves on serving only what they would serve at their own table — that means wholesome, tasty, and satisfying.

Unlimited drinks, including white wine, beer, soft drinks, and water, flow freely throughout the day. Dietary options like vegan and gluten-free are available, ensuring everyone feels cared for. Reviewers often mention the drinks as a highlight, especially enjoying the local wine as they relax on deck.

Sailing Back: Enjoying the Voyage and Sunset Views

After the island stop, the boat heads back into the Aegean Sea for the return journey. This part of the trip offers a chance to unwind, reflect on the day, or simply enjoy the scenery. Many travelers rave about the sailing experience — with some trips returning with the sails up, no engine noise, and just the sound of the wind.

The cruise back often coincides with sunset, turning the sky into a canvas of colors. One reviewer described the scene as “unforgettable,” with the lights coming on and stars appearing as the boat gently rocks. It’s perfect for those looking for a peaceful end to a lively day.

Who Will Love This Experience?

This sailing trip is ideal for travelers seeking a mix of adventure, relaxation, and cultural authenticity. The small-group setting means it’s perfect for couples, solo travelers, or small groups wanting a personal touch. The inclusion of water activities and delicious food makes it suitable for families or anyone who loves a hands-on experience.

While the trip is not suitable for wheelchair users, it offers a good balance of fun and comfort for most able-bodied guests. The emphasis on local storytelling, dolphins, and good company creates a genuine connection to Crete — much beyond a typical tour.

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Pricing and Value

At around six hours, this cruise offers a full day of activity, food, and scenery at a price that many reviewers find reasonable given the quality. The all-inclusive approach — with lunch, drinks, and water activities — means you won’t need to worry about extra costs, making it good value.

Some may consider the trip’s duration and limited time at the island as a drawback, but many guests say the balance of water time, land exploration, and a hearty meal makes it worth every euro.

Final Thoughts

This Heraklion sailing trip to Dia Island delivers a well-rounded experience — combining scenic sailing, water fun, authentic local hospitality, and excellent food. The knowledgeable guides like George and Vaso ensure you feel looked after, and the small group size creates a friendly, laid-back atmosphere.

If you’re after a day of genuine Crete charm, stunning views, and engaging water activities, this cruise is a fantastic pick. It’s especially suited for those who appreciate a mix of relaxation and adventure, with the bonus of sailing with a crew that feels more like friends.

FAQs

How do I meet the boat?
You’ll start at the “Old Anchor” monument near the Marina Cafe. A representative from Set Sails will be waiting to guide you to your vessel.

Is transportation included?
Transportation from selected pickup points in Crete, like Hersonissos or Malia, is offered depending on your booking option. The transfer is in an air-conditioned minivan.

What should I bring?
Bring your passport or ID, comfortable shoes, swimwear, and a towel. High-heeled shoes are not allowed onboard.

Can I request special dietary options?
Yes, gluten-free and vegan options are always available, and the crew is happy to accommodate dietary needs.

What if I want to cancel?
You can cancel up to 24 hours in advance for a full refund, offering flexibility in case your plans change.

Are there any age restrictions?
While not explicitly stated, the tour is geared towards able-bodied guests, and activities like swimming and paddleboarding are at your discretion.

The Sum Up

This Heraklion to Dia Island sailing adventure is a wonderful way to experience Crete’s stunning coastline and unspoiled waters. It offers a cozy, intimate atmosphere with a crew that genuinely cares about your experience, making it feel more like visiting friends than just a tour. The combination of water activities, delicious locally prepared food, and beautiful scenery makes it a great choice for those seeking a relaxed yet engaging day on the sea.

Perfect for small groups, couples, or solo travelers craving authentic hospitality and memorable moments, this trip balances fun, relaxation, and cultural flavor. Whether you’re after dolphin sightings, snorkeling in clear waters, or simply soaking up the sun, this sailing trip promises a day full of genuine Crete charm.

You can check if your dates are available here: