Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Dia Island turns a day trip into a real escape. On this small-group yacht cruise from Heraklion, I like that you get proper sailing time plus real water activities in one go—then you top it off with lunch onboard while the crew keeps the vibe easy, often with guides like George and Vaso doing the hosting.

The best part, from your perspective, is the mix: dolphins spotted on the way, then anchor time at Dia Island for swimming, snorkeling, SUP, and even fishing gear. One thing to consider: you’re out on the water, so plan for cooler water temps at times and expect the lunch to be good and practical rather than a fancy meal.

Key things worth knowing before you go

• Small group (max 8) so you actually get time at the water stops without feeling rushed
• Dia Island stop in Saint George Bay with swimming, snorkeling, SUP, and sun time
• Included fishing gear gives you a shot at catching something big
• Unlimited drinks onboard (wine, beer, soft drinks, water) that keep the day comfortable
• Lunch served family-style onboard with Greek salad, shrimp pasta, and fruit
• Optional transfers from several Cretan areas like Hersonissos, Malia, and Gouves

Entering the day: meeting at Old Anchor and getting set up

Your day starts at the Old Anchor monument near the Marina Cafe. A Set Sails representative will be waiting at the meeting point to guide you to the boat. If you’re driving, there’s parking near the spot, which is a nice bonus in Heraklion—getting the first step right matters, especially on a half-day-ish day tour.

Once you’re aboard, you’ll get a quick walkthrough and safety briefing before you set off. This part sounds basic, but it’s the difference between feeling calm in open water and feeling like you’re winging it. The crew tends to keep things friendly and straightforward (and yes, English support is included), so you won’t spend the first 20 minutes guessing what happens next.

A quick practical note: the port authorities require full names, passport numbers, and countries of origin for everyone. It’s not a “nice-to-have” detail. If your booking asks for it, do it quickly so you don’t slow down the group that’s boarding.

Sailing out of Heraklion: dolphins, wind, and a smooth pace

After you leave Heraklion Port, you’ll spend about 80 minutes sailing across the Aegean Sea toward Dia. This is not a long grind. It’s paced so you can enjoy the coastline views from the water while still having enough energy for the activity stop.

One reason this trip works well is that it doesn’t try to cram everything into the first hour. Instead, it gives you time to settle in—find a spot on deck, grab a drink, and look for movement out on the water. In multiple trips, the dolphins are part of the fun, and even when you don’t get a dramatic sighting, the sea ride still feels like a real change of pace from a bus-and-stops day.

You should also know the sailing is part of the experience. On some returns, the day can shift into lighter, quieter conditions as you head back, so the cruise can feel relaxed rather than strictly “transfer from A to B.”

Dia Island time: Saint George Bay and all the water fun

Dia Island is where this tour turns into a true beach-day-at-sea. You’ll drop anchor in Saint George Bay, and you’ll have around 3 hours at the island for swimming and activities.

Here’s what you can plan for once you’re anchored:

• Swim and snorkel in clear water (snorkeling masks are provided)
• Try SUP paddleboarding to explore the bay at your own pace
• Sunbathe on deck between dips
• Fishing opportunity with the included equipment

The SUP factor: you’re not just a spectator

The SUP is one of the best “why this is worth it” items because it gives you a chance to move around the bay rather than just float in one spot. If you’ve tried SUP before, you’ll appreciate the freedom. If you haven’t, you’ll still likely find it doable because it’s focused on exploring the bay rather than doing anything technical.

I like that the day is structured so the SUP isn’t a one-minute demo. You actually get time.

Snorkeling and the water depth reality

Snorkeling is popular here, and the water clarity is usually a big part of the appeal. Since the water can be deep, the crew helps you feel more comfortable with flotation support. In practice, you can expect life jackets and float aids (like pool noodles) to be available, which makes it easier to enjoy the stop without worrying about staying perfectly positioned.

If you hate gear fuss, don’t worry: it’s all handled onboard. You can focus on the water rather than sorting equipment at the dock.

Fishing: a bonus, not a guarantee

Fishing is included, and the crew will help with the setup. You’re not promised a trophy catch, but the chance to reel in something big is part of the charm. If you’ve ever wanted to try fishing in a place where the sea is the main event, this gives you that shot without having to plan anything yourself.

Lunch and drinks onboard: Mediterranean comfort, with real options

About halfway through your island time, lunch gets served onboard. The menu is simple, Mediterranean, and built for being eaten while you’re not sitting in a restaurant chair.

What you can expect:

• Greek salad
• Pasta with shrimp
• Fruit salad
• Unlimited drinks: white wine, beer, soft drinks, and water

One practical thing I appreciate: this isn’t “bring your own snacks” territory. The meal is part of the schedule, so you’re not stuck hunting for food later or trying to time it between swims.

Dietary needs: gluten-free and vegan options

Good news if you have dietary restrictions: gluten-free and vegan options are always available onboard. That means you’re not gambling on whether the pasta has hidden ingredients or whether the salad is safe.

What the lunch feels like in the real world

Let’s keep it honest. The lunch is convenient and satisfying, and it hits the spot after swimming. It’s not trying to be fine dining. If you’re expecting a restaurant-level meal presentation, you might be slightly underwhelmed. If you want filling, fresh-feeling comfort while you’re out at sea, you’ll be happy.

Back to Heraklion: the return sail and where the day lands

After Dia, you’ll sail back for about 80 minutes. This is another chance to relax on deck and take in the coastline again. Depending on your exact departure time, you may catch that softer late-day light on the return. Even without a dramatic sunset moment, sailing back tends to feel smoother once you’ve done the swimming and ate your lunch.

Then you’ll head back to the drop-off process. The activity ends at the same meeting point, Old Anchor monument near the Marina Cafe.

If you booked an option with transfers, you’ll typically be returned via van to many drop-off points across the island. That list is long, including areas like Heraklion, Hersonissos, Malia, Stalida, Gouves, Ammoudara, Agia Pelagia, and more.

Price and value: why $67 can make sense in Crete

At $67 per person, you’re paying for more than a quick boat ride. You’re basically buying a full package: yacht cruise + anchor time + multiple water activities + lunch + unlimited drinks + equipment, all without you arranging taxis, snorkeling gear, or meal stops.

Here’s where the value usually lands well:

• You get time on the island (not just a photo stop)
• Swimming + snorkeling + SUP are included together
• Fishing gear is part of the deal
• Unlimited wine/beer/soft drinks reduces the “nickel-and-diming” problem that can happen with day trips
• Insurance is included, which is a quiet but meaningful benefit for a water-based activity

The main “cost” isn’t the money—it’s that you’re giving up a chunk of the day to one focused plan. If you love doing things yourself—solo kayaking, independent boat hopping, and long beach wandering—this might feel structured. If you want a well-run day where the sea is the headline, it’s a strong value.

What to pack and how to avoid small mistakes

You’ll want to bring:

• Passport or ID card
• Swimwear
• Towel
• Comfortable shoes

Avoid high-heeled shoes—they’re not allowed onboard. It’s a boat. Think traction and comfort.

If you’re sensitive to the sun, bring sunscreen and a light layer for when the breeze kicks in. Even in a sunny Crete day, the open water wind can make you rethink your outfit.

Who this trip fits best (and who should choose something else)

This is a great match if you want:

• A small-group sailing experience (up to 8 people)
• A mix of active time (snorkel/SUP/fishing) and downtime (deck relaxing)
• Included food and drinks so you’re not juggling plans

It might not fit as well if:

• You’re traveling with a wheelchair (this trip is not suitable for wheelchair users)
• You want a party vibe. This is more “easy day on the water” than club music at sea.
• You’re very picky about lunch quality. It’s convenient and tasty, but it’s not an ultra-high-end restaurant meal.

Should you book the Heraklion to Dia Island sailing trip?

If you’re staying in or near Heraklion, Hersonissos, Malia, or the nearby coast, I’d put this on your short list. The big reason is simple: you get a full day of water time—swimming, snorkeling, SUP, and fishing—plus lunch and drinks, without you doing the logistics.

Book it if you want a relaxed, well-paced day where the crew handles the gear and timing. Skip it if your ideal Cretan day is mostly land-based exploring, or if you want a more luxurious food experience than an onboard Mediterranean lunch.

FAQ

Where is the meeting point for the Dia Island sailing trip?

You meet at the Old Anchor monument near the Marina Cafe in Heraklion. A Set Sails representative will be there to lead you to the boat.

How long is the tour?

The total duration is 6 hours.

What happens first when I arrive at Heraklion Port?

You’ll check in at the meeting point, walk to the boat, and get a safety briefing before sailing begins.

Are drinks included?

Yes. Unlimited white wine, soft drinks, beer, and water are included onboard.

What activities are included at Dia Island?

At Dia Island you can swim and snorkel, try SUP paddleboarding, and fish using the included equipment. You’ll also have time to sunbathe and relax on deck.

Is lunch included, and what does it include?

Yes. Lunch onboard includes Greek salad, pasta with shrimps, fruit salad, and dessert. Meal is served during the island stop.

Do they offer gluten-free or vegan options?

Yes. Gluten-free and vegan options are always available on board.

Is pickup available from outside Heraklion?

Pickup is optional and available from selected areas such as Hersonissos, Malia, Stalida, Gouves, Heraklion, Koutouloufari, Piskopiano, Anissaras, Analipsi, Ammoudara, Agia Pelagia, and Lygaria.

Is the trip wheelchair accessible?

No. It’s listed as not suitable for wheelchair users.