Private Sailing Trip from Heraklion to Dia island

If you’re looking to combine the thrill of sailing with the chance to explore one of Crete’s most captivating spots, a private trip to Dia Island might be just what you need. Offered by Avanti Sailing, this experience takes you on a tailored journey from Heraklion’s Venetian port to the serene, unspoiled waters of Dia Island. It’s a chance to enjoy the sea in comfort, with plenty of opportunities to swim, unwind, and indulge in local delicacies.

One standout feature of this experience is its private setting — up to 10 guests can enjoy a personalized adventure on a luxury sailing boat. The chance to participate in sailing procedures adds a fun, hands-on element that appeals to those wanting a more active role. Plus, the inclusion of premium local wine and fresh fruits makes it feel truly special.

However, a key consideration is that this tour is not suitable for wheelchair users, and towels are not included, so packing accordingly is important. Nonetheless, if you’re after a flexible, intimate, and authentic Crete adventure, this trip offers an excellent balance of relaxation and activity.

Who would this suit best? It’s perfect for couples, small groups of friends, or families seeking a private escape, especially those interested in sailing, scenic waters, and enjoying local flavors in a comfortable environment.

Key Points

• Private, customizable experience for up to 10 guests, ensuring personalized attention and flexibility.
• All-inclusive amenities include drinks, snacks, fruits, and the option to participate in sailing activities.
• Excellent value considering the duration, private setting, and premium offerings.
• Ideal for those craving relaxation, scenery, and a touch of adventure without the crowds.
• Not suitable for wheelchair users and requires travelers to bring their own towels.
• Multiple stops with time for swimming, exploring, and enjoying local cuisine make for a well-rounded day.

An In-Depth Look at the Private Sailing Experience

Navigating the waters of Crete with a private sailing trip offers a unique way to see the island from a different perspective. From the moment you arrive at the Heraklion Venetian port, you’re greeted by the experienced crew of Avanti Sailing, who set a welcoming tone and take care of all the details. The boat itself is described as luxurious and comfortable, making the journey smooth and enjoyable, whether you prefer lounging on the sun deck or actively taking part in sailing.

Starting Point: Heraklion Venetian Port

The experience begins at Cafe Marina, located on the left side of the port. The captain arrives 15 minutes before departure to greet guests, check IDs, and ensure everyone’s ready to go. The meeting point is straightforward, close to parking with a small fee, making logistics manageable even if you’re arriving by car or taxi.

The Voyage to Dia Island

The journey to Dia takes roughly an hour, sailing northward across Crete’s waters. During this time, you’ll have opportunities to relax or try your hand at sailing procedures — a feature that adds a delightful touch of participation. The boat’s spacious deck is perfect for sunbathing or simply enjoying the panoramic views of Heraklion slipping away behind you.

Arrival at Dia Island: A Tranquil Haven

Once at Dia, the real fun begins. The island’s crystal-clear waters invite you to take a refreshing dip, with snorkeling gear provided for marine life viewing. You might explore the ancient port ruins or take a leisurely walk along the shoreline, soaking in the unspoiled beauty. The island’s tranquility makes it an ideal spot for unwinding, with plenty of space to stretch out and enjoy the sun.

Lunch and Leisure

A highlight of this tour is the onboard meal, which is included regardless of the trip duration. Depending on the package chosen, you’ll enjoy snacks or a full meal, paired with local wine—something guests frequently praise as a standout aspect. As one reviewer noted, “The wine was top-notch and perfectly complemented the meal.” Fresh fruits are served to refresh and energize you for the afternoon.

The Return Journey

After hours of swimming, exploring, and relaxing, the boat gently sets sail back to Heraklion. The return leg offers scenic views and a chance to reflect on the day’s adventures. Many guests mention how the boat’s crew effortlessly maintained a balance between laid-back relaxation and engaging activity.

What Makes This Tour Stand Out

The private setting is a major advantage, allowing you to tailor the experience to your group’s preferences. Whether you want to spend more time swimming, enjoying a meal, or simply soaking up the sun, the crew is accommodating. Plus, the inclusion of premium local wine, soft drinks, and fresh fruits elevates the experience beyond typical boat tours.

The scenic cruise along the coast, with views of Heraklion from the sea, adds an extra layer of beauty. The boat’s sailing capability also offers an element of adventure for those interested in participating in the sailing process, which many reviews describe as genuinely fun and engaging.

Why the value is compelling: For around $700, you get a nearly half-day private experience for up to 10 people, including all amenities, transfers (if selected), and the opportunity for unique, Instagram-worthy moments. Compared to group tours or public cruises, the exclusivity and personalized service offer a sense of luxury at a reasonable price.

The Itinerary: A Well-Structured Day

Stop 1: Meeting at Cafe Marina
A convenient starting point, with easy parking and close to Heraklion’s city center. The crew’s prompt arrival ensures the day begins on time.

Stop 2: Sailing to Dia (1 hour)
This leg offers scenic views and a chance to relax or participate in sailing activities. Guests often comment on how peaceful and scenic this part of the journey is.

Stop 3: Exploring Dia (2.5 hours)
The island’s crystal waters are perfect for swimming and snorkeling. Visitors can explore old port ruins, take leisurely walks, or just lounge on deck soaking up the sun. The onboard meal, accompanied by premium wine, makes this a true highlight. One guest mentioned, “The food and wine were excellent, making the experience feel very exclusive.”

Stop 4: Returning to Heraklion (1 hour)
The cruise back features more scenic views and opportunities to enjoy the sea breeze. Many guests find this part calming and a fitting end to a relaxing day.

Stop 5: Return to Cafe Marina
An easy return, with plenty of time to reflect on the day’s highlights.

Included and Not Included

The all-inclusive package covers the crew, drinks (water, soft drinks, and wine), snacks or meals, fresh fruits, and equipment such as snorkeling gear, stand-up paddleboards, and fishing gear. The only notable extra cost is towels, which are not provided, so bringing your own is recommended.

Hotels or accommodations can be arranged for pickup and drop-off if you opt for that, making logistics simpler. Taxes and fuel are also included, ensuring no hidden costs.

Practical Tips for Your Trip

What to bring: Pack a hat, swimwear, towel, sunscreen, and beachwear. Since towels are not provided, bringing your own is a must. A passport or ID is required, as the port authority needs this information in advance. High-heeled shoes are not allowed on the boat, so opt for comfortable, flat footwear.

Timing: The duration varies from 4.5 to 6 hours, so check the available departure times to fit your schedule. The experience is ideal for daytime, with plenty of time for swimming and relaxing.

Accessibility: Not suitable for wheelchair users, so consider this if mobility is an issue.

The Experience Provider: Avanti Sailing

With a reputation for creating memorable private trips, Avanti Sailing emphasizes safety, comfort, and authentic enjoyment. Their crew, typically English-speaking, is praised for professionalism and friendly service, ensuring guests feel well cared for throughout the journey.

Final Thoughts: Who Is This Tour Best For?

This private sailing trip to Dia Island offers a blend of luxury, adventure, and relaxation in a personalized setting. It’s perfect for those who want a tailored experience away from crowded group tours, especially if you enjoy sailing, scenic waters, and quality local food and wine. The flexibility and all-inclusive nature mean you can focus on unwinding rather than logistical worries.

While not suitable for everyone—particularly those with mobility challenges or needing special accommodations—it’s an excellent choice for couples, small groups, or families seeking a memorable day on Crete’s waters. The combination of scenic beauty, engaging sailing, and premium amenities makes it a worthwhile experience for travelers looking for comfort and authenticity.

FAQ

Do I need to bring anything specific?
Yes, bring a hat, swimwear, towel, sunscreen, and beachwear. Towels are not included, so packing your own is essential. Also, remember to bring your passport or ID for the port.

Is this tour suitable for children?
It’s generally suitable for families with children, provided kids are comfortable on boats and can swim. However, the tour is not specified as kid-focused and may involve some sailing participation.

How long does the trip last?
The trip duration is between 4.5 and 6 hours, depending on the selected option and itinerary. Check availability for specific departure times.

What is included in the price?
All meals or snacks, drinks (water, soft drinks, and wine), fresh fruits, snorkeling equipment, paddleboards, fishing gear, taxes, and fuel are included. Hotel pickup and drop-off are available if selected.

Can I participate in sailing procedures?
Yes, guests often enjoy actively participating in sailing activities, which adds a fun, interactive element to the trip.

Is it possible to customize the experience?
Since it’s a private tour, the itinerary and activities can be tailored to your preferences, making for a personalized day on the water.

Are there any restrictions?
The tour is not suitable for wheelchair users. High-heeled shoes are not allowed onboard. Also, towels are not provided, so be sure to pack your own.

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

How do I book this experience?
Reservations can be made online, with the option to reserve now and pay later, ensuring flexibility in planning your Crete adventure.

This private sailing trip from Heraklion to Dia Island offers a superb balance of comfort, adventure, and authenticity—ideal for travelers wanting to experience Crete’s coastal charm in a personalized way. Whether you’re after a relaxing day in pristine waters, a scenic sailing adventure, or a memorable meal paired with local wine, this journey delivers with style.