Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Imagine setting sail from Heraklion with only a handful of fellow travelers, gliding across shimmering waters toward a pristine island. That’s exactly what this small-group sailing trip to Dia Island promises — a relaxed, intimate experience packed with opportunities for swimming, snorkeling, and indulging in a fresh Greek meal. From the friendly local crew to the scenic views and fun water activities, the experience aims to give you a true taste of Crete’s coast.

What we really love about this tour is how personalized it feels. With no more than 10 guests on board, it’s easy to relax, enjoy the company, and soak up the scenery without feeling crowded. Plus, the crew’s genuine hospitality — especially guides like Captain George and Vaso — creates a warm, friendly atmosphere that makes the day even more memorable.

One thing to keep in mind is that this trip is primarily about enjoying the sea and the natural beauty of Dia Island. If you’re after a more structured or luxury experience, this might feel a little simple. But for those craving authenticity, good company, and a true escape into Crete’s waters, this sailing adventure hits the spot.

This tour is perfect for solo travelers, couples, or small groups who want a day of sun, sea, and good food with a personal touch. If you’re looking for a laid-back yet engaging experience that combines scenic sailing with genuine local hospitality, this trip will suit you well.

Key Points

• Intimate Experience: Limited to 10 guests, creating a semi-private feeling.
• Authentic Hospitality: Friendly, knowledgeable local crew who treat guests like family.
• Activities & Relaxation: Swimming, snorkeling, paddleboarding, and sunbathing amid stunning scenery.
• Delicious Food & Drinks: Fresh Mediterranean lunch, unlimited local wine, beer, soft drinks, and water.
• Scenic & Wildlife: Expect breathtaking coastline views, possible dolphin sightings, and peaceful bays.
• Flexible & Convenient: Optional transfers from nearby towns, meeting at a central point, and all essentials included.

A Deep Dive into the Experience

Starting the Adventure

Your day begins at the “Old Anchor” monument near the Marina Cafe in Heraklion, where a Set Sails representative will meet you. This simple meeting point is convenient, with nearby parking, and sets the tone for a hassle-free start. If you’ve opted for the transfer service, a comfortable air-conditioned minivan will pick you up from select locations like Hersonissos, Malia, or Gouves — a real plus if you prefer not to organize your own transport.

Once on board, the atmosphere is relaxed. The crew, including Captain George (the seasoned sailor with a knack for storytelling) and Vaso (the young sailing champion), immediately make everyone feel at home. The small group size keeps conversations easy and the vibe friendly. Expect a quick safety briefing before setting sail into the Aegean Sea, where panoramic views of Crete’s coastline unfold.

The Sailing & Scenic Views

The boat departs from Heraklion Port and cruises for around 80 minutes before reaching Dia Island. During this trip, you’ll enjoy breath-taking scenery, with the coastline stretching in every direction, and the chance to spot dolphins playing in the wake — a highlight for many reviews. One guest even recounts that Captain George’s singing to the dolphins was a memorable and amusing part of the ride.

Discovering Dia Island

Once in Saint George Bay on Dia Island, the real fun begins. This secluded bay offers crystal-clear waters perfect for swimming and snorkeling. Expect to see vibrant marine life and underwater sights that make the activity worthwhile. Guests have praised how well the snorkel and paddleboard equipment is provided and how the shallow waters are ideal for both beginners and more experienced swimmers.

The island itself is peaceful, with plenty of space to sunbathe or explore. Reviewers like Katrin loved paddling a SUP in the clear water, while others just enjoyed soaking up the sun and the tranquillity. The calm, turquoise waters are often described as “breathtaking,” and the experience of floating in such pristine surroundings tends to be a highlight.

The Meal & Drinks

After some time in the water, your crew prepares a delicious Greek-inspired meal. You can choose between pasta with shrimp or a vegetarian pesto pasta, accompanied by a Greek salad and fresh fruit for dessert. Reviewers frequently mention how good the food is, especially considering it’s served on a boat — homemade, fresh, and satisfying.

Unlimited drinks are included, with a selection of white wine, beer, soft drinks, and water — a real value given the relaxed setting. The crew is careful to serve only what they would offer at their own table, ensuring quality and authenticity. Vegan and gluten-free options are available, a thoughtful touch for dietary restrictions.

The Return & Final Moments

As the boat sails back toward Heraklion, many guests find the experience peaceful and rejuvenating. Some reviews mention how the sunset views during the return trip add a magical touch to the day. The crew often keeps things lively with stories, music, or simply encouraging guests to relax and enjoy the moment.

Once back at the starting point, the pickup location, or your transfer drop-off, marks the end of a memorable day. Many guests comment on how the combination of scenic sailing, friendly guides, and the chance to unwind makes this trip feel like a true escape from the busy tourist spots.

Why the Reviews Speak Volumes

Guests consistently praise the knowledgeable guides like Georges and Vaso, who are not just sailing experts but also storytellers, making the trip informative and fun. The warm, friendly attitude of the crew creates a welcoming environment, whether they’re helping guests with water activities or sharing local stories.

The value for money is often highlighted, especially considering the included meal, unlimited drinks, and water sports equipment. Plus, the small group size ensures a personalized experience that many larger tours cannot offer. As one reviewer mentions, “this trip is highly recommended,” especially for those seeking a relaxed, authentic day at sea.

Some travelers note that the boat sailing back with “great wind and no engine power” added a special, traditional touch — a reminder of how sailing remains a genuine and eco-friendly way to explore.

Practical Details & Tips

• Duration & Timing: The tour lasts around 6 hours, with starting times varying. Check availability to plan accordingly.
• Transport: Optional transfers from major nearby towns simplify logistics; otherwise, meet at the designated point near the Marina Cafe.
• Group Size: Limited to 8-10 guests, enhancing intimacy.
• What to Bring: Passport or ID, swimwear, towel, comfortable shoes. High heels aren’t allowed.
• Food & Drinks: Freshly prepared lunch, unlimited drinks, gluten-free and vegan options.
• Accessibility: Not suitable for wheelchair users; inform the operator of any impairments for assistance.
• Cancellation & Payment: Full refund available if canceled 24 hours in advance; reserve now, pay later for flexibility.

Final Thoughts: Is It Worth It?

This sailing trip offers a genuine, laid-back taste of Crete’s coast — combining scenic sailing, water activities, and hearty local food. It’s best suited for travelers who value small-group intimacy, authentic experiences, and the chance to unwind in nature’s embrace. With knowledgeable guides and a friendly crew, you’re not just a passenger — you’re part of a small adventure.

The value is clear, especially considering the quality of the meal, drinks, and personalized service. If you’re after a memorable day that balances relaxation with fun, this trip delivers on all fronts.

Perfect for solo travelers, couples, or small groups eager to enjoy a peaceful day at sea, it’s a wonderful way to see a different side of Crete, away from the crowds. Expect stunning views, fun water sports, and the hospitality of true Cretan hosts who love sharing their island’s charm.

FAQ

Is there transportation included?
Yes, transfers from selected points in Crete are available if you choose the package with pickup. Otherwise, you’ll meet at the designated meeting point near the Marina Cafe.

What should I bring?
Bring passport or ID, swimwear, towel, and comfortable shoes. Avoid high heels as they aren’t allowed onboard.

How long is the trip?
The entire experience lasts around 6 hours, with approximately 80-minute sailings to and from Dia Island.

Can I participate in water activities?
Absolutely. Snorkeling, paddleboarding, and fishing equipment are provided. Guests mention that the shallow waters are perfect for beginners and experienced alike.

Are dietary requirements accommodated?
Yes, gluten-free and vegan options are available on board.

Is the lunch included?
Yes, a fresh Mediterranean meal is served, along with unlimited local drinks like wine, beer, and soft drinks.

What is the group size?
Limited to 8-10 guests for a more personal experience.

Can I cancel if my plans change?
Yes, full refunds are available if you cancel more than 24 hours in advance.

This sailing trip to Dia Island from Heraklion promises a day filled with beautiful scenery, authentic hospitality, and fun activities in a relaxed, small-group setting. It’s a wonderful way to see a different side of Crete’s coast and create memories that will last long after the boat has docked.