Dia Island from Heraklion feels instantly special. This small-group yacht cruise pairs clear-water swimming time with real sailing—plus a lunch that’s more than just a snack. I love that the crew keeps things friendly and hands-on (without hovering), so you can float, swim, or paddle at your own pace.

I also like the mix of activities packed into the Saint George Bay stop: snorkeling, SUP paddleboarding, and even fishing gear so you can try your luck. Guides like George and Vaso show up as the kind of team that makes the day run smoothly, and you can get helpful tips fast—especially if you’re new to snorkeling or fishing.

One thing to plan for: it’s not a wheelchair-friendly outing, and the water temps can feel cool depending on the day—so bring swim layers if you get cold easily.

Key things you’ll notice

• Small group (up to 8): more room to relax and move around the boat
• Dia Island stop (about 3 hours): enough time for multiple swims and a proper lunch break
• Onboard activities: snorkeling kit, SUP paddleboard, and fishing equipment are included
• Unlimited drinks with lunch: wine, beer, soft drinks, and water
• Sunset potential on the way back: sailing in fading light can be stunning
• Transfer options from Crete: pickup at selected locations instead of only port access

Heraklion to Dia Island: the recipe for a great sea day

This is one of those Crete trips that makes the day feel longer than six hours—in a good way. You start in Heraklion, sail out across the Aegean, anchor at Dia, then return with time to relax again on deck. The value sits in the balance: you’re not just watching the sea, you’re using it.

What makes Dia Island work is simple: the water is clear enough for snorkeling, the bay gives you calm swim time, and the shorelines look dramatic from the boat. It’s also a mythology-steeped stop, but you don’t need a textbook to enjoy it. If you like myth and swimming, it’s a tidy combo.

Meeting at Old Anchor: fast start, easy finding

You meet near the Marina Cafe at the Old Anchor monument. A “Set Sails” representative meets you there and leads you to the boat, and there’s parking close by. The setup is straightforward: show up with your ID (passport or national ID), bring a towel, and you’ll be onboard without drama.

If you don’t want to deal with port logistics, you can choose an option with a transfer. Pickup is listed for various areas such as Heraklion, Hersonissos, Malia, Stalida, Gouves, and several nearby resort zones. That matters on Crete, where “getting to the port” can turn into a half-day if you’re not close.

The sail out across the Aegean: what you’ll do in the first 80 minutes

After the walkaround and a safety briefing, you’ll set sail from Heraklion Port. The outbound stretch is about 80 minutes, and the point isn’t to rush—it’s to settle in and watch the coast change. This is when I’d look up and notice how the rugged shoreline drops toward the sea.

And yes, there’s a chance to spot dolphins. Even when you don’t get a dolphin sighting, you still get that “moving viewpoint” feeling: deck time, wind, and photos that are actually about the coast rather than just the boat. On a small vessel, you can usually find a comfortable spot fast.

Dia Island at Saint George Bay: swimming, snorkeling, SUP, and fishing

Your main “do things” block is the Dia Island stop, roughly three hours in the Saint George Bay area. This is where the trip earns its keep, because the schedule gives you multiple ways to spend the time rather than a single rushed activity.

Snorkeling and swimming with real included gear

Snorkeling is built into the stop, and you’ll have equipment available onboard. The water can be warm or cooler depending on timing, so I’d treat it like a “bring patience and enjoy the clarity” situation. In practice, the included setup makes it easy even if you’re not a confident swimmer.

Also, you may have extra float support such as pool noodles and life jackets on hand. That’s a comfort detail that makes it less stressful to go in when you’re still getting comfortable.

SUP paddleboarding: explore under your own power

The trip includes SUP paddleboarding, and this is one of the best ways to explore the bay without needing a guide for every minute. The island is close enough to feel like you’re doing something, but far enough that you’ll get that “wow, I can see it from here” effect.

Bring water awareness: SUP time is active, so pace yourself. If you’re newer to paddleboarding, expect a bit of wobble, then it clicks.

Fishing break: try for a big one

Fishing equipment is included, and the crew will help you get set. This is not a guaranteed “caught a trophy” moment, but it’s a fun change from swimming and paddling, and it adds a little challenge to the day.

If you like trying local activities even when you’re not an expert, you’ll probably enjoy this. And if you’re the type who gets bored doing the same thing for hours, fishing gives your brain a new task.

Lunch on board: Mediterranean food, unlimited drinks, and dietary options

Lunch is served onboard during the Dia stop, and it’s a proper Mediterranean spread—not just bread and olives. You’ll typically get Greek salad, seafood pasta, and fruit salad. Drinks are unlimited, including white wine, beer, soft drinks, and water.

This part is a big deal for value. For a beach day, most “cheap” tours make you buy food separately or hunt for something nearby. Here, your lunch and drinks are folded into the outing, which keeps your day from turning into logistics.

You’ll also have vegan and gluten-free options available. One more practical note: there can be pasta substitutions like pesto pasta, which is helpful if you don’t want to eat the seafood option. If you have any strict needs, it’s smart to mention them before you’re seated.

Sailing back with wind, sunset glow, and that quiet Crete feeling

The return sail is also about 80 minutes. What you’re looking for here is the mood shift: the pace slows, the deck becomes a front-row seat, and the island memories start to settle in.

Many crews take the return route under sail when conditions allow, and you can end up seeing the day turn into sunset light. If you’ve never watched a sailboat move under wind while everyone else is stuck on shore, you’ll understand the appeal fast—quiet, steady, and just a little dramatic.

Even if you arrive late in the sunset cycle, the light still hits the sea and coastline well enough for photos. And because the group is small, the boat doesn’t feel like a floating party.

Price and value: why about $67 can make sense here

At around $67 per person, this feels like good value if you care about three things: time in the water, included equipment, and not having to pay for drinks and lunch separately.

Here’s what you’re buying with that price:

• a yacht cruise with a captain and crew
• a three-hour anchored island stop
• snorkeling gear plus SUP access
• fishing equipment
• a full lunch with unlimited drinks

The only cost “gotchas” are the ones that apply to almost every day trip: you’ll likely want sunscreen, you might buy snacks or extras for personal cravings, and you won’t want to show up in the wrong shoes. High-heeled shoes aren’t allowed, so stick to flats with grip if you’re walking around the boat.

Small group dynamics: attentive crew without the pushy vibe

One of the most consistent themes is that the crew tends to be friendly and attentive, but not overbearing. That matters more than people think. On some tours, staff are everywhere, always talking, always directing. On this one, the tone seems to be: you’re safe, you’re set up, and then you’re free to enjoy.

You’ll also meet a multi-person crew model, with captains and guides who run the day. Names that come up include George, Vaso, Spiros, Marina, and others. You don’t need to remember names to enjoy the trip—but it’s a good sign that different crew members can handle different guests and needs.

The “small group” cap (up to 8 participants) helps a lot with this. You’re not sharing every decision—where to sit, when to go in, how to find a calm corner—among dozens of people.

Who should book this Heraklion sailing trip

This is a strong pick if you want:

• a water-focused day on Crete (swimming, snorkeling, SUP)
• a guided experience that still gives you freedom
• included food and drinks so you can stay relaxed
• a small-group vibe without loud chaos

It’s also good for couples. The pace supports easy conversation without needing constant entertainment. Families might enjoy it too, as long as the kids are comfortable with water activities (and remember the trip isn’t suited for wheelchair users).

You might skip it if you’re looking for a full-on history tour or a long walking day. This trip is about the sea and the bay time, not a museum schedule.

Practical tips before you go (so the day stays fun)

Bring swimwear and a towel. Comfortable shoes help, especially if you’ll step around the dock area. The tour also lists bringing passport or ID, and it’s wise to carry it even if you think you won’t need it.

One important admin detail: you may be asked for complete names, passport numbers, and countries of origin for everyone on the trip, since port authorities require it. That’s normal for ports, so handle it early if you can.

A couple comfort tips:

• water can feel cooler than you expect once you’re in, so plan for that
• if you’re doing SUP, keep an eye on your energy level so you don’t burn out early
• high-heeled shoes are a no-go—wear something stable

Should you book this Dia Island sailing trip?

If you want a relaxed, active sea day that includes everything you’d normally pay for separately, I’d book it. The combination of three hours at Dia, snorkeling + SUP + fishing equipment, and an included lunch with unlimited drinks is where the real value lives.

I’d also book it if you like the idea of sailing out and back with a small crew, where you can actually enjoy the deck instead of fighting for space. Just go in knowing it’s not a “tour of Crete on land” day. It’s a sea day, and that’s the point.

FAQ

How long is the sailing trip to Dia Island?

The total duration is about 6 hours, with the itinerary designed around an extended stop at Dia Island and sailing time in between.

Where do I meet for the Heraklion boat trip?

Meet at the Old Anchor monument near the Marina Cafe. A Set Sails representative will be there to guide you to the boat, and the tour ends back at the same meeting point.

Is lunch included, and what’s it like?

Yes. Lunch is served onboard and includes a Mediterranean menu such as Greek salad, seafood pasta, and fruit salad.

Are drinks included?

Yes. Drinks are included and are listed as unlimited white wine, soft drinks, beer, and water.

What activities are included at Dia Island?

You’ll have snorkeling and swimming time, SUP paddleboarding equipment, and included fishing equipment.

Are vegan or gluten-free meals available?

Yes. Gluten-free and vegan options are available onboard.

Can I cancel and get a refund?

Free cancellation is available up to 24 hours in advance for a full refund.