Small Group Sailing Cruise from Heraklion to Dia Island

Planning a day on the water while exploring one of Crete’s lesser-known gems? This small group sailing cruise from Heraklion to Dia Island offers a more intimate, laid-back alternative to the often crowded boat tours, and it’s got plenty to recommend it. Whether you’re a seasoned sailor or just someone looking for a relaxing day in beautiful surroundings, this trip could be a perfect fit.

We love the combination of crystal-clear waters, a relaxed atmosphere, and the chance to see authentic local wildlife—not to mention the delicious onboard meal and premium local wine. Plus, the chance to explore ancient ruins and enjoy the sun makes it a well-rounded experience. The only thing to keep in mind is this is a small group tour limited to 10 travelers, so it’s best to book in advance if you want a spot.

This cruise is ideal for travelers craving a more personal, relaxed sailing experience with plenty of opportunities for swimming, snorkeling, and socializing. It’s particularly suited for those who appreciate good food and wine after a day on the water, and for anyone eager to see Dia’s quiet bays and unspoiled nature.

Good To Know

• Intimate Experience: Limited to 10 travelers for a more personal feel
• Beautiful Setting: Crystal waters, quiet bays, and ancient ruins await
• Delicious Food & Drink: Onboard meal paired with premium local wine
• Flexible Activities: Swim, snorkel, walk on the island, or relax on deck
• Expert Crew: Friendly team that ensures safety and enjoyment
• Excellent Reviews: Consistently high ratings and glowing feedback

Why You’ll Love This Sailing Cruise

Imagine setting sail from the historic Venetian port of Heraklion, feeling the breeze on your face and the salty air in your lungs. This cruise manages to strike a lovely balance between relaxation and adventure, offering both a scenic voyage and plenty of chances to get active.

The luxury sailing boat is comfortable and well-maintained, with a sundeck perfect for sunbathing or simply gazing at the horizon. The crew, referred to as “the excellent team” in reviews, are friendly and attentive, making everyone feel at ease. From snorkeling to walking on Dia’s ancient port ruins, there’s enough variety to keep everyone engaged.

At its core, this trip is about enjoying Greece in a genuine way—away from the crowds, with authentic local touches like premium wine and seasonal fruits. Reviewers mention the delight of crossing paths with dolphins and sea turtles, which adds a magical element many travelers cherish. The sunset tour option offers a relaxed schedule without early mornings, perfect for travelers wanting a more leisurely day.

The Itinerary in Detail

Departure from Heraklion

The adventure begins at the Venetian port of Heraklion, a lively and historic hub. The meeting point is conveniently located at Epimenidou 19, ensuring easy access via public transportation or taxi. Once onboard, you’ll quickly feel the difference from larger, bustling tours—this is a small, cozy group that encourages interaction.

Sailing to Dia Island

As you set sail, you’ll notice the gentle motion of the boat and the inviting sea breeze. The crew will often involve guests in sailing procedures, adding a sense of participation. This isn’t just a sightseeing trip; it’s a shared experience, which many guests find more rewarding.

Exploring Dia Island

Arriving in Dia, you’ll see why this uninhabited island is such a special spot. Surrounded by rocky inlets, the island has four quiet bays, including the Gulf of Agios Georgios, where boats moor, and the Bay of Panagia, perfect for a relaxed swim.

Snorkeling and swimming are major highlights, with crystal-clear waters revealing colorful fish, and even the chance to spot sea turtles, as one guest did during their sunset cruise. The island’s ruins of an ancient port provide a touch of history, and a leisurely walk offers views that are truly worth the effort.

Onboard Dining and Wine Tasting

Midway through the trip, you’ll be served a delicious onboard meal. The food is described as tasty, with fresh seasonal fruits and well-selected premium local wine—a real treat for wine lovers. Reviewers note that the excellent wine selection was a highlight, making the experience feel extra special.

Cruising Back to Heraklion

As the cruise winds down, you’ll enjoy a gentle cruise back, with soft drinks available and plenty of time to relax on deck. The scenery and gentle rocking of the boat create a soothing atmosphere to reflect on the day.

Transportation, Timing, and Group Size

This tour begins at the Heraklion port and is designed for small groups, with a maximum of 10 travelers, creating an intimate setting. The total duration is around 6 hours, with roughly 4 hours and 30 minutes of sailing and activities on Dia.

Most travelers book about a month in advance, which indicates high demand for this popular experience. The price point of around $101, considering the included meal, wine, and personalized service, offers great value for those seeking a high-quality, authentic experience.

What Reviewers Say

Feedback consistently praises the friendly crew and the excellent value. One reviewer highlighted their excitement about seeing sea turtles and different fish while snorkeling, describing it as a wonderful time. Others appreciated the no early start aspect of the sunset tour, making it an ideal option for those who prefer a more relaxed schedule.

The wine selection was specifically mentioned as a highlight, with guests enjoying the premium local wines served alongside the onboard meal. The sense of camaraderie, along with the stunning scenery and the chance to see dolphins, enhances the overall experience.

Who This Tour Is Best For

This sailing cruise is perfect for adventurous travelers eager to combine relaxation with some active fun like swimming and exploring ruins. It’s also well-suited for those who value small group intimacy and personal attention from the crew. If you’re someone who enjoys good food and wine with scenic views, this tour ticks all those boxes.

While it’s accessible for most travelers, those with mobility issues or who prefer very structured guided tours might find the freeform nature less ideal. But for anyone wanting a beautiful day out on the water, away from crowds and with authentic local touches, this cruise offers remarkable value and memorable moments.

FAQs

How long is the tour?
The entire experience lasts about 6 hours, including sailing, exploring Dia, and returning to Heraklion.

What’s included in the price?
You get the sailing experience, a delicious onboard meal, premium local wine, soft drinks, and seasonal fruits.

How many people are on the tour?
The tour is limited to a maximum of 10 travelers, making it a more personal and intimate experience.

Can I snorkel during the trip?
Yes, snorkeling is available, and guests have noted seeing fish and even sea turtles while in the water.

Is there a specific departure time?
The tour can be booked as a sunset cruise or a daytime trip; the sunset option allows for a later, more relaxed start.

What should I bring?
Bring swimwear, a towel, sun protection, and your ID (as mentioned in reviews to avoid issues). A hat and sunglasses are also recommended.

Is the tour suitable for children?
While not explicitly stated, the relaxed, scenic nature suggests it’s suitable for older children and families, especially those comfortable on boats.

Final Thoughts

This small group sailing cruise from Heraklion to Dia Island offers a well-rounded day of relaxation, adventure, and authentic Greek charm. You’ll enjoy outstanding scenery, the chance to snorkel with sea turtles, and a delicious onboard meal paired with premium local wine—all in an intimate setting that fosters camaraderie.

It’s an excellent choice for travelers who want to experience the less touristy side of Crete in style and comfort, without sacrificing quality or personal service. Whether you’re pausing to marvel at ancient ruins, swim in crystal waters, or simply soak up the sun, this tour provides a genuine taste of Crete’s natural beauty and warm hospitality.

For those seeking a balanced mix of relaxation, adventure, and authentic local flavors, this cruise is likely to leave you with wonderful memories—and perhaps a new appreciation for Heraklion’s coastal treasures.