Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

If you’re seeking a relaxing yet active way to explore Crete’s stunning waters, this sailboat cruise from Heraklion to Dia Island is a top choice. For around $90 per person, you’ll spend 4.5 to 6.5 hours aboard a luxury yacht, enjoying crystal-clear waters, scenic sailing, and a taste of local Greek hospitality. The experience combines adventure—swimming, snorkeling, maybe even fishing—with plenty of time to unwind and soak in the scenery.

What we really love about this trip are the attentive crew members who go out of their way to make the day special, and the chance to snorkel in vibrant marine life—a highlight according to many travelers. Plus, the onboard meal and unlimited drinks are a real bonus, especially considering the quality and variety. On the flip side, some might find the sea conditions variable or the duration a bit long for small children, so it’s best suited for those who enjoy boat trips or are comfortable on the water.

This tour suits adventurous travelers, families, couples, and anyone looking for a laid-back day on the water with some active options. If you like a mix of scenery, good food, and the chance to swim in beautiful surroundings, this cruise will suit you well.

This experience made our article of 15 Must-Try Tours In Crete.

Key Points

• Scenic Sailing: Enjoy the experience of navigating the Mediterranean aboard a comfortable luxury yacht with knowledgeable crew members.
• Dia Island Exploration: Discover Dia’s rugged coastline, clear waters, and historical sites, with plenty of free time for swimming, snorkeling, or walking.
• All-Inclusive Experience: Savor unlimited drinks, seasonal fruit, and a tasty onboard meal, with the option to customize for private trips.
• Flexible Options: Choose between shared or private cruises, with optional transfers from your hotel for added convenience.
• Family-Friendly: Suitable for travelers aged 4 and up, with life jackets provided and a relaxed, friendly atmosphere.
• Authentic & Personal: Customers praise the attentive guides, fun crew, and the intimate, non-crowded boat setting.

You can check availability for your dates here:

A Detailed Look at the Experience

The adventure kicks off at the meeting point in Heraklion’s marina, a short walk from central accommodations or easily reachable by taxi. The check-in process is straightforward, and if you book a transfer, your driver will pick you up from your hotel or apartment. Once aboard your luxury sailing yacht, you’ll feel immediately pampered—comfortable cushions on deck, plenty of space to relax, and a friendly crew ready to welcome you.

The Sailing and Transfer

The first leg is a one-hour sail from Heraklion into the Gulf of Saint George, giving you a chance to enjoy the sea breeze and watch the coastline slip by. Many reviews mention how smooth and enjoyable the ride is, even for those who might be wary of boats. The crew’s professionalism and friendliness shine through, and the small group size ensures a personal touch.

Exploring Dia Island

After anchoring near Dia, one of Greece’s more rugged and less touristy islands, you’ll have about 1.5 hours to explore. This is the moment to swim in the clear waters or snorkel among the fish with gear provided, as several reviews highlight how excellent the snorkeling spots are. Some guests mention the island’s fascinating history, including its ancient Minoan port—Jacques-Yves Cousteau famously explored these waters—adding a touch of intrigue to your visit.

Depending on your preference, you can explore Dia’s rocky coastlines on foot, take a leisurely walk, or just relax on the boat and enjoy the scenery. For those interested in fishing, the crew supplies gear and is happy to help you try your luck in the calm waters.

The Food and Drinks

Throughout the day, unlimited drinks flow freely—think water, soft drinks, and local wine, often praised for being well-chosen and refreshing. Several guests emphasize the quality of the meals onboard, particularly the Greek salads with fresh olive oil, and the main courses like chicken and rice, with vegetarian options available. The seasonal fruits are a sweet ending. The generous portions and tasty flavors make this meal feel more like a special treat than just a tour snack.

For private trips, there’s a chance to add on a special dinner or other extras—reviews mention how the meal’s quality enhances the overall experience, making it good value for the price.

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Return Journey and Final Relaxation

After your time on Dia, the boat sets sail back towards Heraklion. Many reviews comment on how peaceful and scenic the trip is, especially during the sunset hours. Lying on the deck, sunbathing, or simply listening to the waves makes for a memorable end to the day.

The Itinerary in Detail

• Start at the marina in Heraklion: Friendly check-in and onboard greeting.
• One-hour sail to Dia: Enjoy the breeze and the coastline views.
• Stop at Dia Island for 1.5 hours: Swim, snorkel, walk, or relax on the boat.
• Additional 30-minute stop: More swimming or soaking in the sun.
• Return sail of one hour: Scenic cruise back to Heraklion, often with beautiful sunset views.
• End at the starting point: Easy disembarkation and transportation options.

Authentic Experiences from Travelers

Customers repeatedly praise the knowledgeable crew members who make everyone feel comfortable and well-cared-for. Comments like “Captain Marco and Alexandra didn’t hesitate to ensure we had a great time” and “The staff were amazing and so polite” highlight how attentive the team is.

Snorkeling and swimming are frequently mentioned as standout features, with travelers enjoying the crystal-clear waters and marine life. Several reviews describe how the trip provided a perfect balance of activity and relaxation, with many noting it as the highlight of their Crete visit.

The meals also garner praise—not just for their flavor but for the generous portions and local ingredients, making the onboard dining feel authentic and satisfying. Many mention how the local wine complements the meal, adding to the festive atmosphere.

Practical Details and Tips

• Meeting point is at the Sailingtrips.gr location near Marina Cafe. Try to arrive 15 minutes early.
• Transfers from your hotel are available and recommended for convenience, especially if you’re staying outside central Heraklion.
• Book early to secure a spot, as the reviews suggest this is a popular experience.
• Bring essentials: sunhat, sunscreen, swimwear, towel, sunglasses, and a light jacket for the breeze.
• Age suitability: the minimum age is 4, making it family-friendly. Infants are welcome on private trips.
• Health & safety: life jackets are provided, and snorkeling gear is available—no worries if you’re not a confident swimmer.
• Cancellation policy is flexible, with free cancellation up to 24 hours in advance.

The Sum Up

This sailing trip from Heraklion to Dia Island offers a smart combination of adventure, relaxation, and authentic Greek hospitality. The small-group sailing ensures you won’t feel lost in a crowd, and the professional crew makes safety and comfort a priority. The stunning scenery, crystal waters, and good-quality food create a memorable experience that suits both active travelers and those just wanting to unwind.

If you enjoy being on the water, discovering new spots, and sampling local flavors, you’ll find this trip well worth the time and money. Its high rating and glowing reviews are evidence of a well-run experience that many visitors consider a highlight of their Crete holiday.

For families, couples, or solo travelers seeking a laid-back but engaging day in Crete’s natural beauty, this cruise hits the right notes. Just remember to bring your camera, sunscreen, and a sense of adventure.

FAQ

How long is the cruise?
The trip lasts between 4.5 and 6.5 hours, including sailing, swimming, and relaxing time on Dia Island.

Is transportation included?
Optional transfer services are available when booking. You can select this at checkout or arrange your own transport.

What should I bring?
Bring your passport or ID, sun protection (hat, sunscreen), swimwear, towel, sunglasses, and a jacket for the breeze.

Is it suitable for children?
Yes, the minimum age is 4 years old. Infants are welcome on private trips, and life jackets are provided.

Can I snorkel?
Absolutely. Snorkeling gear is provided, and many reviews mention how vibrant and enjoyable the underwater scenery is.

Are drinks included?
Yes, unlimited drinks are available, including water, soft drinks, and local wine.

What about the meal?
A full onboard meal is included in shared cruises, with vegetarian options available. Private trips can include custom meals as an add-on.

What’s the best time to go?
Check availability for your preferred dates. The experience is weather-dependent, but many reviews mention enjoying it during spring and summer.

Can I fish during the trip?
Yes, fishing gear is onboard and provided by the crew if you’d like to try catching fish in the calm waters.

This cruise offers a well-rounded day of sailing, swimming, and good food, making it a worthwhile addition to your Crete itinerary, especially if you love being on or near the water.

You can check availability for your dates here: