Heraklion: Dia Island Sunset Boat Tour with Dinner – A Hands-On Look

If you’re looking to add a splash of Mediterranean magic to your Crete trip, this Heraklion sunset sailing trip to Dia Island offers a compelling mix of scenic views, relaxing activities, and good food. The tour lasts around 6 hours and combines the thrill of sailing with the serenity of swimming in crystal-clear waters, topped with a Greek-style dinner. It’s a popular choice, with an impressive 4.9-star rating from 69 reviews, and once you read what people rave about, it’s easy to see why.
One thing I particularly like about this experience is how it balances adventure and relaxation. You’ll get time to snorkel in the azure waters, sunbathe with a drink in hand, or even try fishing—all in a small, intimate group. Also, the crew, including guides like George and Marcos, seem to make a real effort to make everyone feel welcome and comfortable —and that’s often what makes these trips memorable.
A potential consideration? The tour relies on good weather, especially for sunset views and sailing, so if you’re prone to seasickness or prefer more structured, land-based activities, this might not be your best fit. And, keep in mind, the alcohol served only when the boat is stationary—a small detail, but worth knowing if you’re eager for some bubbly during the sail back.
Key points / Takeaways

- Small groups (limited to 8 participants) create a more personal, engaging experience.
- Guides like George and Marcos are praised for their friendliness, professionalism, and local knowledge.
- The meal features Greek favorites with vegan and gluten-free options available, and unlimited drinks included.
- The crystal-clear waters of Dia are ideal for snorkeling, swimming, and paddleboarding.
- The sunset over Dia Island is a highlight, often described as mesmerizing and well-timed for photographs.
- The itinerary includes some sailing time in both directions, offering scenic views and dolphin sightings.
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The Experience: A Closer Look at the Itinerary

Starting Point and Pickup
You’ll meet at the “Old Anchor” near the Marina Cafe in Heraklion, where a representative from Set Sails greets you. The convenience of pickup depends on your chosen package—some include hotel transfers, which is excellent if you prefer to avoid the hassle of finding your way to the port. Parking is available nearby, so self-driving works too.
Heraklion Port: Safety Briefing & Departure
Once onboard, the crew provides a safety briefing, which is reassuring, especially for first-time sailors or those unsure about open water. The boat itself strikes a good balance—large enough for comfort, small enough to feel intimate. From here, your journey begins with roughly 80 minutes of sailing in the Aegean, offering spectacular views of the coast, and perhaps even dolphins if you’re lucky. Guests have mentioned guides like Georges making the trip educational and fun, sharing stories about Greek history and local lore.
Dia Island: The Main Event
Arriving at Dia’s Saint George Bay, you’ll find a peaceful spot perfect for a variety of activities. Expect to swim and snorkel in the famously clear waters, which reviews highlight as some of the best swimming experiences around Crete. There’s free snorkeling gear available, so don’t forget your swimsuit and towel. If you’re in the mood for a different view of the bay, you can try paddleboarding or fishing—equipment is provided, and many guests say the guides are happy to help.
Ready for more after-sunset magic? More evening tours we love in Heraklion
- From Heraklion: Private Sunset Trip With Our Hanse 470
- From Heraklion: Sunset Private Sailing Boat Trip
- Heraklion: Private Catamaran Dia, Sunset & Appetizers Cruise
- Heraklion: Sunset Private Sailing Trip to Dia Island
- Heraklion: Sunrise Balloon Flight & Sunset Catamaran Cruise
- Sunset – Sailing Cruise on Yacht Catamaran, Rethymno, Crete
The Meal and Sunset
As the sun begins to dip, you’ll gather for a Greek-inspired dinner on the boat—think fresh salad, pasta with shrimp, and seasonal fruits. Unlimited drinks are included, with guests noting that the hosts, like Pagnos and Eva, serve generous portions of wine, beer, soft drinks, and water. A handful of reviews emphasize the quality of the food and drinks, describing it as a good value considering the scenic setting and all-inclusive approach.
Returning to Heraklion
As night falls, the boat turns back in the direction of Heraklion, with another 80-minute sail. The sunset’s glow, combined with the gentle sea breeze and a final swim, leaves many feeling relaxed and happy. If you’ve booked a transfer, your driver will be waiting to bring you back to your accommodation.
Who Will Love This Tour?

This trip suits travelers seeking a laid-back, scenic, and social experience. It’s perfect if you enjoy small-group adventures where guides like Georges or Marcos can share local insights and make the experience feel personal. The balance of sailing, swimming, and dining makes it appealing for couples, friends, or solo travelers who want to enjoy Greek hospitality on the water.
It’s especially well-suited for those who appreciate unlimited drinks, good Greek food, and stunning sunset views. If you’re keen on snorkeling and paddleboarding, you’ll find plenty of opportunities, and the short sailing legs keep the trip manageable for most.
However, keep in mind that seasickness can be an issue, and the tour isn’t designed for wheelchair users. If you’re looking for more structured or land-based activities, this might not be your best fit. Also, if you’re expecting a party vibe, this is more about relaxed enjoyment than loud entertainment.
Price & Value Analysis

Considering the all-inclusive drinks, meal, and activities, many reviews suggest this tour is good value. The small group size, knowledgeable guides, and beautiful setting add to the experience’s worth. While it’s not the cheapest option available, the personalized feel and quality of the guides, like George, make it stand out. If you love the idea of sailing into the sunset, snorkeling in pristine waters, and dining on Greek delicacies in a relaxed atmosphere, this trip offers a lot for its price.
Final Thoughts: Is It Worth It?

If you’re after a peaceful, scenic evening that combines the beauty of Crete’s coastline with the fun of being on the water, this cruise hits the mark. It’s a chance to slow down, enjoy the sunset, and indulge in excellent food and drinks—all in a friendly, intimate setting.
Perfect for couples, small groups, or solo travelers wanting an authentic Mediterranean experience, it offers a good balance of adventure and relaxation. The knowledgeable guides help elevate the trip, making it both entertaining and informative.
Just remember: good weather is key, and if seasickness is a concern, prepare accordingly. This tour is a delightful way to see Dia Island and enjoy Crete’s famed hospitality from a unique vantage point.
FAQ

How do I find the meeting point?
You’ll meet at the “Old Anchor” monument near the Marina Cafe in Heraklion. A Set Sails representative will be waiting to lead you onto the boat.
Is hotel pickup included?
It depends on your booking choice. Some options include hotel pickup and drop-off, making it easy to start and end the day comfortably.
What should I bring?
Bring comfortable shoes, a sun hat, towel, sunscreen, and your passport or ID. Avoid high heels and bringing your own drinks, as the tour provides all-inclusive beverages once anchored.
Can I snorkel and paddleboard?
Yes. Snorkeling equipment and a SUP board are included, giving you the chance to explore Dia’s waters at your leisure.
How long is the sailing segment?
Each leg of sailing lasts about 80 minutes, giving you ample time to enjoy the views and perhaps spot some dolphins.
Are gluten-free and vegan options available?
Absolutely. The onboard meal accommodates dietary preferences, including vegan and gluten-free choices.
Is this tour suitable for people prone to seasickness?
It might be challenging, as the trip involves open water sailing. If seasickness is a concern, consider taking precautions or choosing a land-based activity.
This Heraklion: Dia Island Sunset Boat Tour with Dinner blends scenic sailing, water-based activities, and Greek hospitality into a well-rounded experience that appeals to travelers craving a relaxed, authentic evening by the sea. Whether you’re celebrating a special occasion or simply want a memorable night, this trip offers a special taste of Crete’s maritime charm.
More Boat Tours & Cruises in Heraklion
- From Heraklion: Sunset Cruise to Dia Island
- Spinalonga with Guide, Kolokitha Bay Cruise, Swimming & BBQ
- Heraklion: Dia Island Ultimate Catamaran Cruise with Meal
- Heraklion: Dia Island Morning Sailing Trip with Snorkeling
- Heraklion: Private Sunset Catamaran Cruise to Dia with Wine
- Heraklion Half-Day Tour, Cruise Friendly, Knossos+Top Sights
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