If you’re planning a trip to Crete, chances are you’re after experiences that combine scenic beauty, good food, and a touch of adventure. The Dia Sailing Cruise offered by Rocca a Mare Sailing Adventures promises just that—a day on the water exploring Dia Island, with the added perks of unlimited drinks and a tasty Mediterranean meal. But is it worth your time and money? That’s what we’re here to help you decide.
What we really like about this trip is how it balances relaxation with activity. The cruise’s all-inclusive menu and unlimited drinks make sure you’re well-fed and refreshed, no matter whether you’re lounging on deck or snorkeling in the clear waters. Plus, the chance to see dolphins and witness a spectacular sunset makes it a memorable outing. On the flip side, some might find the duration (5.5 hours) a bit long, especially if you’re not used to boat trips or if your schedule is tight.
This cruise is particularly suited for travelers who love being on the water, appreciate good food, and want a relaxed yet engaging experience. It’s not a party boat or a high-energy tour, but rather a laid-back adventure that offers plenty of opportunities to soak up the natural beauty of Crete’s coast. If you’re after a genuine, all-around enjoyable boat day, this might just be your pick.
Key Points

- Stunning scenery and water activities: Snorkeling, paddleboarding, and marine life watching make this a fun day out.
- All-inclusive food and drinks: Mediterranean dishes, unlimited Greek wine, and soft drinks add to the experience.
- Flexible options: Choose between a daytime cruise or a sunset cruise for different moods.
- Comfort and safety: Well-equipped with life jackets, safety instructions, and certified staff.
- Eco-conscious voyage: Dia Island is part of Natura 2000, so it’s a protected area full of biodiversity.
- Transportation included: Hotel pickup and drop-off make it easier to relax from start to finish.
Setting the Scene: What You Can Expect on This Cruise

The Dia Sailing Cruise kicks off from the Old Venetian Port of Heraklion, a historic and lively starting point. If you opt for the hotel pickup, your day begins with a comfortable transfer—no stress about navigating to the port yourself. Once on board, the highly skilled captains and crew set a friendly, welcoming tone that makes even first-time sailors feel at ease.
You’ll be sailing out on a comfortable yacht, the journey lasting about an hour over calm waters, heading towards Dia Island. We loved the way the boat was spacious enough to move around, with music adding a laid-back vibe. As the boat cruises through the sea, you get to enjoy impressive sea views, with plenty of space to relax on the large front deck or in shaded areas.
Enjoy being on the water? Here are other boat experiences we've looked into in Heraklion
The Journey to Dia Island
The trip to Dia is not just about the destination but also about the journey. During this hour of sailing, you’re treated to panoramic views of the coast, and the chance to learn about eco-sailing and marine life from your crew. Keep your eyes peeled—you might even spot dolphins, as several reviews mention.
This island is uninhabited and protected by Natura 2000, meaning it’s a haven for biodiversity and local myths. Once you arrive, the boat anchors at pristine, wind-protected coves, perfect for a variety of water-based activities. Whether you want to snorkel, paddleboard, or just relax on deck, there’s plenty of space and equipment provided.
Water Activities and Free Time at Dia
Aquatic fun is a key highlight—snorkeling gear, paddleboards, and opportunities to watch marine life make this part of the trip engaging. You’ll also find that some of the reviews praise the generous free time for snorkeling and relaxing. If you’re not into water activities, you can stay onboard, soaking up the sun or enjoying a glass of white Greek wine.
The All-Inclusive Mediterranean Meal
One of the best features? The meal served onboard. It’s a simple yet delicious Mediterranean menu, with linguine with shrimp and tomato sauce (vegetarian options available), Greek salad, and seasonal fruits. Reviewers have raved about the quality of the food, with one even calling it “phenomenal.” The drinks flow freely—unlimited Greek white wine, soft drinks, and water—so you can toast the day as you watch the scenery.
More Great Tours NearbySunset Cruise Magic
If you opt for the sunset cruise, you’ll enjoy the same route but with the added bonus of witnessing a breathtaking sunset on your way back. The sky turns vibrant shades of orange and pink, creating a perfect backdrop for photos or just soaking in the peaceful moment. Many reviews recommend this for a romantic or special occasion, as the atmosphere is truly magical.
Drawn to sailing? We've examined these other wind-powered adventures in Heraklion
- Rethymno: Sunset Catamaran Cruise with Wine and Snacks
- Heraklion: Nature Reserve Full day sailing to Dia Island & Lunch
- Heraklion: Dia Island Private Sailing Cruise with Full Meal
- Heraklion: Dia Island Morning Sailing Trip with Snorkeling
- Heraklion: Private Catamaran Cruise to Dia with Meal&Drinks
- Heraklion: Sunset Private Sailing Trip to Dia island
The Itinerary: How the Day Unfolds

Start Point: The cruise departs from the Marina Cafe at the Old Port of Heraklion. You’ll find a large sign indicating the cruise, with easy directions via Google Maps.
Journey to Dia Island: After about an hour of sailing, you arrive at the island. This part of the trip is smooth and scenic, offering a good chance to learn about the area’s mythology and environment.
Time at Dia: You’ll have around four hours on the island, which might seem long, but it’s enough to snorkel, relax, explore, or enjoy regional food and wine. The crew is friendly and knowledgeable, and many guests mention how they appreciated the guides’ insights into the local myths and marine life.
Return Trip: The boat then heads back, either in the daytime or at sunset, depending on your choice. The return journey is often highlighted as a serene, picturesque experience, especially during the sunset cruise.
Drop-off: The trip concludes with stops at multiple locations including Heraklion, Kokkini Hani, and Hersonissos, which makes it flexible for your transportation needs.
What’s Included and What To Keep in Mind

Included in your ticket are professional captains, unlimited soft drinks, water, and wine, and a well-prepared Mediterranean meal. The crew provides safety equipment like life jackets and safety instructions, so you can relax knowing you’re in good hands.
Extras to note: Towels are not included, so bring your own if you plan to swim or sunbathe. Also, if you want a seamless experience, consider requesting transportation when booking—though it’s not included, the pickup service is available at an extra cost.
Weather considerations: The cruise is weather-dependent and may be canceled or postponed if conditions aren’t suitable. In such cases, you’ll get a full refund.
Pricing and Value
At around 5.5 hours, this cruise offers a comprehensive experience, combining scenic sailing, water activities, and a full meal and drinks. While the price might seem steep at first glance, reviews indicate that the value is solid—especially considering the all-inclusive drinks and delicious food. Plus, the added comfort of hotel pickup (when arranged) makes it easier to relax and focus on enjoying the day.
Real Opinions from Travelers

Customer feedback backs up the high ratings. Sarah called it “a once-in-a-lifetime opportunity” and praised the phenomenal food and breathtaking sights. Ksenija appreciated the crew, saying, “Manuel and Billy are the best,” and many mention the friendly, accommodating hosts. Leanne loved the boat’s comfort, the gorgeous sunset, and how much fun everyone had snorkeling and relaxing onboard.
Final Thoughts: Who Should Consider This Tour?

This cruise is ideal if you want a combination of scenic sailing, water fun, and great food in Crete. It suits travelers who appreciate a relaxed pace, enjoy good company, and want to experience Dia Island’s natural beauty without too much hassle. It’s not suited for those with mobility issues or pregnant women, mainly because of the boating nature of the trip, and towels aren’t provided, so pack your essentials.
In essence, if you’re after a well-organized, enjoyable day on the water with delicious food and stunning views, this cruise ticks all those boxes. It’s a wonderful way to see a less crowded, protected part of Crete, with the added bonus of local mythology and marine life encounters.
Dia Sailing Cruise With All-inclusive Meal And Drinks
“This was a once and a lifetime opportunity. It was such an amazing experience. The food by Alex was phenomenal, the sights are breathtaking and def…”
FAQs

How long is the cruise?
The entire experience lasts approximately 5.5 hours, with departures either in the morning or afternoon, depending on your choice.
Is transportation to the port included?
Not automatically, but you can request pickup when booking. It’s a convenient option, especially if you prefer not to navigate to the port yourself.
What should I bring?
Bring essentials like a passport or ID, sunglasses, hat, swimsuit, towel, sunscreen, and a jacket for cooler moments. Towels are not provided.
Can I snorkel and paddleboard?
Yes, all necessary gear is provided, and you’re free to enjoy snorkel, paddleboarding, and marine viewing during your time at Dia.
Is the menu suitable for vegetarians or vegans?
Yes, vegan and gluten-free options are available upon request, and the main dish is pasta with shrimp (or vegetarian alternative).
What happens if the weather is bad?
The cruise is weather-dependent; if conditions are unfavorable, the trip might be postponed or canceled with a full refund.
If you’re looking for a relaxed, scenic day with good food, friendly crew, and a chance to unwind by the sea, the Dia Sailing Cruise is a solid choice. It offers more than just a boat ride—it’s an authentic taste of Crete’s beauty, mythology, and hospitality.
You can check availability for your dates here:More Sailing Experiences in Heraklion
- From Heraklion: Dia Island Private Sailing Trip
- From Heraklion: Private Sailing Trip with our Hanse 470
- Heraklion: 1-Hour Sailing Tour with Drinks
- Heraklion: Dia Island Sailing Cruise with Snorkeling
- Dia Island: Semi-Private Full Day Sailing Trip with meal
- Heraklion: Sunrise Balloon Flight & Sunset Catamaran Cruise
More Boat Tours & Cruises in Heraklion
- From Heraklion: Dia Island Private Sailing Trip
- Heraklion Half-Day Tour, Cruise Friendly, Knossos+Top Sights
- From Heraklion: Private Sailing Trip with our Hanse 470
- Heraklion: 1-Hour Sailing Tour with Drinks
- Heraklion: Dia Island Sailing Cruise with Snorkeling
- Dia Island: Semi-Private Full Day Sailing Trip with meal
More Tour Reviews in Heraklion
- Semi Private Food & City Tour in Heraklion with Pastry Mesum
- Knossos Palace guided tour – Heraklion City tour + market
- Tour to Sitia, Toplou Monastery and Vai Palm Beach from Ierapetra
- From Heraklion: Dia Island Private Sailing Trip
- Olive Oil Festival in Cretan Farm with Traditional Dinner
- Aquaplus Admission Ticket
More Heraklion experiences we've covered
- Knossos Palace guided tour – Heraklion City tour + market
- Dia Sailing Cruise With All-inclusive Meal And Drinks
- Tour to Sitia, Toplou Monastery and Vai Palm Beach from Ierapetra
- From Heraklion: Dia Island Private Sailing Trip
- Olive Oil Festival in Cretan Farm with Traditional Dinner
- Aquaplus Admission Ticket
- Family Excursion: From Sea Wonders to Mythical Realms Adventure
- Crete : Cooking Lessons In Lasithi Plateau
- Buggy Safari Tours In Crete Heraklion
- Heraklion Half-Day Tour, Cruise Friendly, Knossos+Top Sights
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