Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Key Points

• Small-group experience with a maximum of 10 guests for a personalized feel
• Includes a delicious Mediterranean lunch with seafood or vegetarian options and unlimited local drinks
• Activities such as snorkeling, paddleboarding, and swimming in crystal-clear waters
• Expert guides and crew who are friendly, attentive, and passionate about sharing Crete’s waters and stories
• Convenient pickup options from Heraklion and nearby areas, with a known meeting point at the “Old Anchor” monument
• Highly rated with a 4.8/5 star score based on 430 reviews, emphasizing the trip’s relaxing, friendly atmosphere

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Discover Crete’s Coastline and Dia Island on a Small-Group Sailing Trip

This 6-hour sailing adventure from Heraklion offers a relaxed way to see some of Crete’s most beautiful waters and islands. Limited to 10 guests, the trip feels more like a private cruise, with plenty of time for swimming, snorkeling, and enjoying local food and drinks. The journey starts at the Old Anchor monument near the marina in Heraklion, with options for pickup from nearby towns like Malia, Hersonissos, and Gouves.

A friendly local crew welcomes guests aboard, making everyone feel at home. The guides are known for their warmth, storytelling, and attentiveness, which shines through in the many positive reviews. The trip’s highlight is reaching Dia Island, just 6 nautical miles north of Heraklion, famous for its clear waters and peaceful bays.

From Heraklion to the Unspoiled Dia Island

The departure from Heraklion Port involves a scenic 80-minute sail across the Aegean Sea, during which guests enjoy stunning views of Crete’s coastline. The trip is often marked by sightings of dolphins, especially when the captain sings to them, adding a touch of magic to the voyage.

Once in the Saint George Bay on Dia Island, guests have several options. They can swim in the transparent waters, snorkel to explore marine life, or try paddleboarding for a bit of fun and exploration. The calm, peaceful environment makes it ideal for unwinding and soaking up the sun in nature’s tranquility.

A Scrumptious Cretan Meal with Unlimited Local Drinks

While relaxing on deck or in the water, the crew prepares a fresh Mediterranean meal using local ingredients. The lunch menu includes pasta with shrimp or vegetarian pesto pasta, accompanied by a traditional Greek salad and a fruit salad for dessert. All ingredients are fresh and served as if at a home table.

Guests can enjoy unlimited drinks, including white wine, beer, soft drinks, and water. Gluten-free and vegan options are available, ensuring everyone’s dietary needs are met without any extra charge. The crew’s commitment to offering only what they would serve at their own table adds an authentic touch to the experience.

Meet the Passionate Crete-Local Crew

The guides and crew are a big part of what makes this trip special. Captain George, called the Fisherman, knows every corner of Dias waters and often shares lively stories about sea life and island lore. Panos, always dancing and singing, brings a joyful energy, while Vaso, a national sailing champion, impresses with her sailing skills and friendly attitude.

The crew’s friendliness, storytelling, and genuine passion shine through in reviews. Many mention how the guides go above and beyond to make sure everyone feels comfortable, whether helping with water activities or sharing local tales. This personal touch makes each trip feel like visiting friends on the water.

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Activities at Saint George Bay: Snorkeling, Swimming, and Paddleboarding

Once docked at Dia Island’s Saint George Bay, the focus shifts to enjoying the water. Guests can swim in the crystal-clear waters or snorkel to observe underwater marine life. The paddleboard is available for exploration or just relaxing on the water.

The deep waters are safe, with pool noodles and life jackets provided for extra security, especially for less experienced swimmers. The overall environment is calm and quiet, making it a wonderful escape from crowded beaches, with plenty of time allotted for water activities.

The Delight of a Day with No Engine Power and Sunset Views

An especially praised feature of this trip is sailing back with wind power, with no engine noise, creating a serene atmosphere. Many highlight the sailing experience as peaceful and authentic, emphasizing the connection to traditional sailing.

As the trip concludes, the return sail offers spectacular views of the sunset, with lights flickering on the island and stars beginning to emerge. This twilight sail adds a romantic and tranquil end to the day, making it a favorite detail among reviews.

Practical Details: Meeting Points, Transfers, and Group Size

The meeting point is at the Old Anchor monument near the marina, with a Set Sails representative ready to greet guests. Parking is available nearby, simplifying arrivals. Optional transfers from Hersonissos, Malia, and other nearby towns make it easy to join without hassle.

The tour is limited to 8 to 10 participants, ensuring personalized service and a relaxed atmosphere. Pickup from designated locations is available, with air-conditioned minivans providing a comfortable start to the day.

Value for Money and Overall Experience

At 6 hours long, the trip offers great value for the inclusive price, which covers transfers, a yacht cruise, lunch, drinks, water activities, and insurance. The reviews consistently praise the friendly guides, good food, and relaxing pace as key strengths.

While the food and drinks are top-quality and unlimited, some may find the seafood pasta or vegetarian options as the main meal to be simple but satisfying. The trip’s focus on authentic, local hospitality and sea-life encounters makes it worthwhile for those seeking a relaxed, enjoyable day on Crete’s waters.

Crete’s Best Kept Secret: A Calm Day at Sea with a Friendly Crew

This small-group sailing trip from Heraklion to Dia Island stands out for its personalized atmosphere, excellent guides, and quality water activities. The emphasis on local hospitality and authentic sailing makes it a memorable choice for travelers who appreciate intimate experiences in beautiful surroundings.

Most guests leave with a sense of having shared a special day, thanks to the warm crew, delicious meal, and peaceful waters. The sunset sail on the way back adds that extra touch of magic, making this trip more than just a boat ride—it becomes a heartfelt experience.

Frequently Asked Questions

Is the tour suitable for children or less experienced swimmers?
Yes, the water activities like paddleboarding and snorkeling are supervised, and life jackets are provided for safety. However, very young children or those uncomfortable in the water may need supervision.

Are there vegan or gluten-free meal options?
Absolutely. Vegan and gluten-free options are always available on board, matching the crew’s commitment to accommodating dietary needs.

What should I bring for the trip?
Guests should bring a passport or ID, comfortable shoes, swimwear, and a towel. High-heeled shoes are not allowed onboard.

Can I join the trip if I don’t have my own transportation?
Yes, transfer options are available from various locations in Crete, including Heraklion, Malia, and Hersonissos, for added convenience.

How long is the sailing part of the trip?
The sailing from Heraklion to Dia and back involves two 80-minute scenic cruises, with plenty of time at the island for water activities.

What is the maximum group size?
The trip is limited to 8 or 10 guests, ensuring a relaxed, intimate experience.

Is the trip suitable for people with mobility issues?
Since the tour is not suitable for wheelchair users, mobility limitations should be considered before booking.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours in advance, providing flexibility for your plans.

This sailing trip to Dia Island offers a balanced mix of adventure, relaxation, and authentic hospitality—a true highlight for anyone wanting to explore Crete’s waters with a friendly crew.

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