Private Sailing Trip from Heraklion to Dia with meal & SUP

Discover Crete’s Hidden Gem: A Private Sailing Trip from Heraklion to Dia with Meal & SUP

If you’re craving a peaceful escape from the lively streets of Heraklion, a private sailing trip to Dia offers a unique way to unwind and soak up authentic Aegean charm. While I haven’t taken this exact trip myself, reviews and detailed descriptions reveal a well-rounded adventure that balances scenic beauty, relaxation, and a touch of adventure.

What makes this experience stand out? First, the stunning views of Dia’s untouched landscape and crystal-clear waters are a highlight. Second, the chance to swim and snorkel in calm, turquoise waters provides genuine immersion in Crete’s natural beauty. Third, the personalized nature of a private boat means you can relax without the usual crowds.

However, a possible consideration is the timing of the day, especially if you’re looking for a sunset cruise—though the two-hour sunset sail sounds quite appealing, it might be shorter than some travelers expect for a full day of exploration.

This trip is perfect for those wanting a blend of tranquil scenery and light activity, especially couples, families, or small groups eager to enjoy Crete from a different perspective. If you enjoy being on the water and appreciate a personal touch, this experience should meet your expectations.

Good To Know

• Private experience: Personalized service with a dedicated skipper and assistant.
• Natural beauty: Unspoiled Dia island with stunning landscapes and turquoise waters.
• Activities included: Swimming, snorkeling, and stand-up paddleboarding for active travelers.
• Local flavors: Snacks and soft drinks served on board, perfect for a relaxed day.
• Duration: 5 hours, ideal for a half-day escape.
• Value: At $71 per person, the price includes a private boat, guide, and delicious snacks, offering good value for a tailored experience.

You can check if your dates are available here:

The Experience in Detail

Starting Point and Departure

The journey begins at the Marina Cafe in Heraklion, a convenient and lively spot close to the port. Travelers are asked to bring their passports for check-in, which makes the process smooth and straightforward. The meeting in the marina allows you to meet your crew—an experienced skipper and assistant—who will ensure your safety and comfort throughout.

Scenic Voyage to Dia

The first part of the trip involves about an hour of sailing from Heraklion’s port. During this time, you’ll enjoy the scenic views of the coast and possibly catch glimpses of the surrounding islands. The vessel itself is private, giving you space to relax, chat, or simply take in the sights while the crew handles the navigation.

A reviewer praised the “friendly crew” and the “beautiful scenery” along the way. Another mentioned feeling reassured by the skipper’s professionalism, which is crucial when you’re out on the water. This segment sets the tone for a peaceful, scenic journey, away from crowded tours.

Exploring Dia: The Uninhabited Paradise

Once you arrive at Dia, you’re greeted with calm, turquoise waters — perfect for swimming and snorkeling. The island’s untouched environment provides a private feel, ideal for photos and quiet contemplation. Guests reportedly love to take advantage of the snacks and drinks provided on board, which adds a relaxed, picnic-like vibe.

With about two hours on Dia, there’s ample time for multiple activities. Reviewers note that the snorkeling spots are calm and clear, making it easy for beginners and experienced snorkelers alike. The opportunity to stand-up paddleboard (SUP) also adds a fun, active element without requiring prior experience.

More Great Thing To Do Nearby

Sightseeing and Relaxation

Beyond swimming, travelers report that the views of Dia’s landscape are spectacular—steep cliffs meet lush greenery, offering photo opportunities. The island’s mythology and natural beauty make it an interesting sightstop, even if only from the boat.

Many describe their time on Dia as “peaceful and restorative,” emphasizing how the quiet, untouched surroundings helped them disconnect.

Sunset Sail and Return

As the day winds down, you’ll sail back to Heraklion, enjoying the scenic views of the sea at sunset. The sunset cruise, lasting around two hours, is often described as a perfect way to end the day, with warm hues reflecting off the water. This part of the trip is ideal for couples or anyone seeking a romantic, tranquil finale.

What’s Included and What to Consider

The tour includes a private sailboat with a skipper and assistant, plus snacks and soft drinks, which means you can focus on enjoying yourself without worrying about extra costs.

However, personal expenses and additional drinks are not included, so if you’re craving something special or alcoholic, it’s best to bring your own or purchase separately.

The total duration of five hours makes this a manageable half-day experience, perfect if you’re looking to combine it with other activities in Heraklion or Crete.

Why This Tour Offers Great Value

For $71 per person, you’re paying for a tailored sailing experience that includes a private boat, a knowledgeable guide, and refreshments. Compared to larger group tours, the intimacy and flexibility of a private trip are a big plus. Plus, the choice to swim, snorkel, or paddleboard makes it more than just a boat ride—it’s an active, engaging way to connect with the sea.

The reviews mention that the crew is professional and friendly, with guides who know the area well. This adds a layer of reassurance, especially for travelers new to sailing or snorkeling. The experience produces a sense of exclusivity and personal attention, which is often hard to find at this price point.

The Itinerary Breakdown

Heraklion to Dia (1 hour)

The voyage begins at the marina, with a brief safety briefing and some basic instructions from your crew. You’ll then sail across calm waters, with panoramic views that make every moment picture-worthy. Expect the crew to point out interesting sights along the coast, sharing snippets of local lore or geography.

Dia Exploration (2 hours)

Once in Dia, you’ll have plenty of time for swimming and snorkeling. The waters are described as calm and turquoise, ideal for leisurely floats and underwater exploration. Reviewers appreciate how accessible the snorkeling spots are, even for those new to the activity.

You might also enjoy the stand-up paddleboarding, which many travelers find surprisingly relaxing. Light snacks and soft drinks serve as a perfect refreshment midway through your dip into this serene environment.

Return Journey & Sunset Views (1 hour)

The cruise back offers a chance to relax on deck, watch Crete’s coastline drift past, and enjoy the sunset. The gentle sea breeze and warm hues of sunset make this a memorable, photo-worthy moment. Some reviewers mention that the sailing back is smooth, with the crew providing commentary or just allowing guests to soak in the views quietly.

Additional Details and Practical Tips

• Meeting point: Marina Cafe, where you check-in and meet your crew.
• Duration: 5 hours, with the main activities scheduled during the middle.
• Included: Private sailboat, skipper, assistant, snacks, soft drinks.
• Not included: Personal expenses, extra drinks, and anything not listed.
• Group size: Private or small groups are available, ensuring a personalized experience.
• Language: Tours are conducted in English and Greek, making communication easy for most travelers.
• Cancellation policy: Free cancellation up to 24 hours in advance, giving flexibility if plans change.

While not suitable for wheelchair users, the tour is perfect for those who enjoy water-based activities and scenic boat rides. It’s a relaxed experience, aimed at travelers wanting a quieter, more personal day on the water.

Who Should Consider This Tour?

This sailing trip suits travelers looking for a peaceful escape rather than a high-energy adventure. It’s ideal for couples wanting a romantic outing, families seeking a manageable yet fun experience, or small groups eager to explore Crete from the sea. The private aspect adds a layer of intimacy, perfect for special occasions or just a quiet day away.

If you enjoy spectacular sea views, snorkeling, and relaxing on a boat, this would be a great fit. Just keep in mind that it’s less focused on sightseeing and more about tranquility and personal connection with nature.

Frequently Asked Questions

Is this trip suitable for children?
While the tour is designed for small groups and families, children should be comfortable with water activities and boat trips. Always check with the provider about age restrictions.

Do I need previous sailing or snorkeling experience?
Not at all. The experience is suitable for beginners, and the crew is there to assist with activities like paddleboarding and snorkeling.

What should I bring with me?
Bring a swimsuit, towel, sunscreen, hat, and sunglasses. If you want to snorkel or paddleboard, consider bringing your own gear, or use what’s provided.

Can I purchase additional drinks or food?
Snacks and soft drinks are included in the price. For other beverages, you might need to bring your own or buy at the marina beforehand.

Is it possible to do this trip at sunset?
Yes, a sunset cruise is offered, lasting about two hours and providing beautiful views as the sun dips into the sea.

What if the weather is bad on the day of my trip?
The provider offers free cancellation up to 24 hours in advance. In case of poor weather, the trip can be rescheduled or refunded.

To sum it up, this private sailing trip from Heraklion to Dia combines stunning scenery, gentle water activities, and personalized service, all at a reasonable price. It’s an excellent choice for anyone wanting to experience Crete’s waters in a calm, intimate setting, with plenty of opportunities for relaxation and fun. Perfect for small groups or couples, it offers a genuine taste of the Aegean’s natural beauty—without the crowds or rush.

You can check if your dates are available here: