Hiring a Skipper in Greece: What to Expect and How to Choose

I've been a skipper for over a decade. It's the best job I've ever had — and I get asked a lot of questions about how it works. Here's what clients really need to know when hiring a skipper in Greece.

When You Need a Skipper vs When You Don't

You need a skipper if: you don't have a sailing license, you're not confident in your skills, you want to relax and learn, or you're chartering in challenging waters (Cyclades in August) and prefer an expert. You don't need one if: you have a valid license and experience, you're comfortable in the conditions, and you want the freedom of being your own captain. Simple. Many of our clients start with a skipper for their first charter, then go bareboat the next time.

Qualifications to Look For

RYA Yachtmaster (Coastal or Offshore) is the gold standard. I hold Yachtmaster Coastal — it's recognized worldwide. Greek commercial licenses are also valid. Ask for proof. A good skipper will have their credentials ready. Experience matters — someone who's sailed Greece for years knows the anchorages, the weather patterns, the best tavernas. I've done hundreds of charters here; I know which bay to duck into when the Meltemi kicks up.

Typical Cost: €150–200 per Day

That's the going rate. It usually includes the skipper's time, their expertise, and sometimes their food (they eat with you). Accommodation is on the boat — the skipper gets a cabin. It's not extra. If you're paying significantly less, ask why. If you're paying more, you might be getting a premium service — some skippers offer cooking, provisioning, or specialized itineraries.

What's Included and Skipper Etiquette

The skipper handles all sailing — docking, anchoring, navigation. They'll brief you on safety, show you the boat, and plan the route. They eat with you — it's part of the experience. Think of them as a knowledgeable crew member, not staff. They share a cabin (usually the smallest one). Be respectful of their space. A good skipper is flexible — they'll adapt to your pace, your interests, your energy level. I've had groups who wanted to sail at dawn and groups who wanted to sleep until noon. Both are fine.

How a Good Skipper Transforms the Trip

We know the secret anchorages. We know which taverna has the best octopus. We know when to leave early and when to wait. I've turned nervous first-timers into confident sailors. I've helped families create memories their kids still talk about. The best part? When someone says "I never thought I could do this" — and then they're helming, tacking, loving it. That's the magic.

How I Plan Routes Based on Group Personality

Adventurous group? We'll go further, try new spots, maybe push into the Meltemi when it's safe. Relaxed group? Short hops, long lunches, plenty of swimming. Families? Kid-friendly beaches, early anchorages, simple dinners. I read the room. I ask: "What do you want from this week?" And I build the route around that.

Communication Tips and Red Flags

Communication before the trip matters. Tell your skipper about experience levels, dietary needs, preferences. A good skipper will respond promptly, ask questions, and make you feel prepared. Red flags: someone who doesn't respond to emails, who can't show credentials, who promises things that sound too good (e.g., "guaranteed dolphin sightings"). Trust your gut. If something feels off, it probably is.

I love this job. Every charter is different. Every group teaches me something. I'm lucky to do what I do.