Private Sailing Trip from Heraklion to Dia island

Planning a day out on the water in Crete? This private sailing trip from Heraklion to Dia Island offers a blend of relaxation, adventure, and authentic Greek scenery that’s hard to beat. Whether you’re celebrating a special occasion or simply craving a memorable escape, this tour promises a taste of the sea with a luxurious touch.

What we love most about this experience is the personalized service on a private boat, making it feel like a bespoke adventure. The crystal-clear waters perfect for swimming and snorkeling are another highlight, alongside the chance to savor premium local wine and fresh fruits onboard. Plus, the opportunity to participate in sailing procedures adds a fun, hands-on element—if you’re into that.

One consideration, however, is that the trip runs for roughly 4.5 to 6 hours, which may be a long day for travelers with tight schedules or young children. Still, if you’re seeking a relaxed, intimate outing with time to truly unwind, this is an excellent choice. It’s ideal for those who want a more authentic, less crowded way to experience Crete’s stunning coast and nearby islands.

This tour suits travelers who love water-based activities, appreciate private and comfortable experiences, and enjoy good food and wine. It’s perfect for couples, small groups, or families looking for a special way to connect with Crete’s natural beauty.

Key Points

• Exclusive Private Experience: Travel in a private group of up to 10 on a luxury sailing boat.
• Flexible Itinerary: Swim, snorkel, and explore Dia Island at your own pace.
• Authentic Local Flavors: Enjoy premium local wine, fresh fruits, and tasty snacks onboard.
• Active Participation: Engage in sailing procedures and learn about the boat.
• Beautiful Scenery: Scenic views of Heraklion from the sea and a sunset spectacle over Dia.
• All-Inclusive Comfort: Drinks, meals, snorkeling gear, and paddleboards provided for a hassle-free day.

You can check availability for your dates here:

An In-Depth Look at the Experience

Starting Point and Logistics

Your adventure begins at the Venetian port of Heraklion, specifically on the left side of the “Marina Café – Restaurant.” The team from Avanti Sailing will be ready to greet you about 15 minutes before departure. If you opt for hotel pickup and drop-off, arrangements are included, which adds to the convenience, especially after a day in the sun.

The meeting spot has a nearby parking area, though expect a small charge, so plan accordingly. Make sure to have your passport or ID ready, as the port authority requires passenger information, including full name, nationality, date of birth, and passport number, provided at least a day before.

The Journey to Dia Island

Once onboard, the sailing adventure kicks off with relaxing views of Heraklion as you head northward. The boat is spacious, with a sundeck perfect for lounging and soaking up rays. If you’re feeling active, you can participate in sailing procedures—an engaging touch for those curious about boat handling.

The scenic cruise takes about an hour each way, giving you plenty of opportunities to admire the coastline and enjoy the sea breeze. Many reviews note the crew’s friendly professionalism, which makes the entire trip feel smooth and relaxed.

On Arrival at Dia Island

The island itself is a highlight. Known for its crystal-clear waters—perfect for swimming and snorkeling—the island’s tranquil atmosphere invites you to unwind. You might find the ruins of an ancient port, adding a touch of history to your visit. Most guests choose to take a leisurely walk around or simply lounge on deck, soaking up the sun.

The water here is praised for its clarity, making snorkeling a must. Equipment is provided, so you can explore marine life at your own pace. Several reviews mention how vibrant the underwater scenery is, with some spotting colorful fish or even small marine creatures.

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Dining and Refreshments

One of the most appreciated features is the onboard meal service. Depending on your chosen duration, you’ll enjoy snacks, a full meal, or both, all made with local ingredients. The included premium local wine is often mentioned as a standout—perfect for pairing with fresh fruits or relaxing after a swim.

Soft drinks and water are available throughout, keeping you refreshed under the sun. Guests frequently comment on the quality of the food, describing it as delicious, plentiful, and well-presented.

The Return Cruise and Sunset Views

After your time on Dia, you’ll set sail back toward Heraklion. The return trip offers more scenic views, golden hour lighting, and a chance to reflect on the day. Many travelers mention how the sunset creates a magical backdrop, transforming the sea into a canvas of changing colors.

The trip wraps up at the same port, leaving you relaxed and with plenty of photo memories. Some guests say it’s a perfect way to wind down after a busy day, feeling both invigorated and pampered.

Detailed Breakdown of the Itinerary

Stop 1: Heraklion Venetian Port

This is the starting point where you meet your crew. It’s a central location with easy access, and the friendly captain provides a quick briefing about the day ahead. The convenience of being near the city means you can combine this trip with a full day exploring Heraklion beforehand.

Stop 2: Sailing to Dia (1 hour)

The first leg of your journey offers breathtaking views of the coast and an introduction to sailing activities. Expect plenty of opportunities for photos, and if you’re lucky, the crew might share some stories about the area’s history.

Stop 3: Exploring Dia Island (approx 2.5 hours)

This is the main attraction. You’ll have time to swim in the pristine waters, snorkel to observe marine life, or simply relax on deck. The ruins of the old port provide a glimpse into the island’s past, though most guests focus on enjoying the calm beauty of the present.

Lunch/Dinner & Leisure Time

Depending on the trip length, you’ll be served a delicious onboard meal or snacks. Guests frequently mention the high quality of the food and the excellent wine selection, which elevates the experience. You might also indulge in some paddleboarding or fishing, provided equipment is included.

Return Journey (1 hour)

Cruising back, the ambiance is peaceful, with many guests noting how the sunset enhances the scenic beauty. The crew often keeps the mood lively with music or casual conversation.

End at Heraklion

The day concludes back at the port, with plenty of time to reflect on the experience or continue exploring the city.

What’s Included and What to Bring

Included:

• Experienced crew with local knowledge
• Refreshing drinks: water, soft drinks, and wine
• All necessary snorkeling and paddleboarding equipment
• Fruits and snacks or a full meal, depending on your booking
• Taxes and fuel
• Optional hotel pickup and drop-off (if selected)

What to Bring:

• Hat and sunscreen for sun protection
• Swimwear and towel for swimming
• Beachwear for comfort
• Passport or ID (or a copy)
• Towels are not provided, so bring your own

Not Allowed:

• High-heeled shoes (for safety and comfort on the boat)

Practical Details and Tips

• Duration: You can expect the trip to last between 4.5 and 6 hours, so plan your day accordingly.
• Cost: At $700 for the whole group—up to 10 people—this is an excellent value for a private, all-inclusive experience. It’s like having your own yacht at a fraction of the cost.
• Timing: Check availability for your preferred time slot; early mornings or late afternoons often offer the best light for photos.
• Group Size: Private trips mean fewer crowds, allowing for a more intimate and relaxed atmosphere.
• Accessibility: Not suitable for wheelchair users, as the boat and facilities are limited in accessibility.

FAQs

Is this trip suitable for children?
The tour is family-friendly, but keep in mind the duration and sun exposure. Children should be comfortable on a boat for several hours.

What should I wear?
Bring swimwear, a hat, sunscreen, and beachwear. Towel is not supplied, so pack your own.

Are the drinks included?
Yes, water, soft drinks, and local wine are included, along with snacks and fruits.

Can I participate in sailing procedures?
Absolutely. The crew encourages active participation, making it a fun and educational experience.

What kind of marine life can I expect to see?
While specific sightings aren’t guaranteed, guests often see colorful fish and enjoy the crystal-clear waters for snorkeling.

Is it possible to cancel?
Yes, with a full refund if you cancel at least 24 hours in advance.

Do I need to bring my own snorkeling equipment?
No, snorkeling gear is provided—just bring your enthusiasm and a sense of adventure.

Is hotel pickup included?
Yes, if you select that option, the crew will pick you up and drop you off at your hotel.

What if I want a longer or shorter trip?
The tour duration ranges from 4.5 to 6 hours, but check availability for your preferred timing. Custom options aren’t mentioned, so confirm with the provider.

If you’re after a personalized day on Crete’s waters with a touch of luxury, this private sailing trip to Dia Island ticks all the boxes. Its combination of scenic beauty, water activities, and high-quality food and wine makes it an excellent choice for those seeking a relaxing yet engaging escape. The private setting ensures you’ll avoid crowded tours, and the flexible itinerary allows you to savor the island at your own pace.

Ideal for couples, small groups, or families, this tour offers a wonderful balance of adventure, comfort, and authenticity—which is exactly what makes Crete so special. Whether you’re soaking up the sun, exploring marine life, or enjoying fine local wines, this trip promises a memorable and authentic slice of Greek island life.

This sailing trip is a fantastic way to see Dia Island in style. If you value privacy, personalized service, and scenic beauty, it’s worth every euro.

You can check availability for your dates here: