Planning Your Annual Charter Route

How to Design the Perfect Sailing Itinerary—Your Way

If you scroll through social media, you’ll find endless questions about sailing routes around the world. People often expect to find a ready-made itinerary online, assuming that if someone else did it—it must work for them too.

Sure, it’s great to ask for recommendations, but remember: your dream route should fit your crew, your pace, and your style. Use the wisdom of others—but chart your own course.

This guide will help you plan a charter itinerary that’s truly yours (charter route planning).

Essential Tools for Charter Route Planning

🧭Navionics (Garmin)

A must-have for any skipper. Navionics provides up-to-date nautical charts, distance calculations between islands, local weather, and marina details (subscription required).It’s perfect not only for planning—but also for real-time navigation if your charter boat doesn’t have a plotter on board.

⚓ Navily

Think of Navily as the social network for sailors.It’s packed with community reviews, photos, and ratings for anchorages and marinas, plus direct chat with other skippers in the area.A goldmine of real-world experience.

🤖 ChatGPT (yes, really)

AI tools are now part of every skipper’s toolkit.If you know how to ask the right questions—clearly define your timing, preferences, and information sources—AI can save you hours of research.Just don’t trust it blindly; treat it as a smart assistant, not a skipper.

🌐 The Internet at Large

Online sailing forums and Facebook groups are full of insights—but also misinformation.Learn to filter and cross-check before you anchor your trust there.

Step One – Get to Know Your Sailing Area

No voyage or vacation is truly enjoyable without a bit of research first. Understanding the region adds excitement and helps you start the adventure long before you leave the dock.

Here’s what to explore before you go:

• Weather patterns – Is the seasonal wind suitable for your experience level and crew? Learn about local conditions like the Meltemi, katabatic winds from the mountains, or sudden squalls—and note daylight hours.

• Must-see spots – Research highlights, ask focused questions in forums, and talk to other skippers who’ve been there. Tools like AI can help summarize all this info, but remember: how you phrase your questions shapes the answers.

• Marinas and anchorages – Use Navily or Navionics to identify great bays, affordable marinas, and service points for fuel and water.

Practical Checks Before You Set Sail

Paperwork & Regulations

Make sure local cruising taxes are covered. In Greece, for example, there’s the TEPAI (cruising tax). Most charter companies handle it for you—but confirm it’s valid for your charter dates.

Bridges & Channels

Some passages require prior coordination, such as:

• Corinth Canal – Must be booked and paid online at least 24 hours in advance.

• Rio–Antirrio Bridge – Contact the bridge operator for clearance.

• Lefkada Bridge – Opens only at scheduled times—plan your crossing accordingly.

Charter Crowds & Timing

Most European charters start and end on Saturdays, creating high congestion near base marinas.If you get your boat early—sail straight to a more distant anchorage.If you board late, stay at the marina overnight, get familiar with the boat, and train your crew.Night sailing is often prohibited for charterers, so enjoy the marina vibe, grab a local meal, and start fresh at dawn.

Pro tip: if you’re fully provisioned, consider anchoring out your first night nearby.Waking up at sunrise on your first morning—already at sea—is priceless.

תעלת קורינטוס מחייבת תאום מוקדם, מילוי טפסים אונליין ותשלום

גשר ריו-אנטיריו ביציאה ממפרץ קורינטוס לים היוני מחייב תאום מעבר בקשר

Water, Power & Supplies

Many monohulls don’t have a watermaker or generator. Check your tank capacities and plan refills accordingly. In most European cruising areas, supplies are easy to find on nearly every island or village, so there’s no need to overload the boat.Buy bread, fruit, and vegetables fresh every day or two—like a local.

Weather Forecasts

No single weather app is 100% accurate—especially in Greece. Always compare at least two sourcess\Algorithm, morning and evening, and monitor Navtex alerts if your yacht has one. Reliable options include:

• The Hellenic National Meteorological Service (HNMS)

• POSEIDON marine models (for wind and wave maps)

• And of course, Windy, my personal favorite for clarity and detail.

Anchoring & Mooring

If you’ve never done Mediterranean mooring before, invest in a short training session at home with a local instructor. It’s not difficult—but mistakes can cost you hours untangling anchors. A good instructor will also teach you how to free a fouled anchor.

When you want to explore ashore, plan to arrive early (around 11:00 a.m.)—you’ll find better spots and more time to enjoy the island.

Your Crew

Every crew has its mix of experience and expectations. Keep the first sailing day short to let everyone adjust. If someone is prone to seasickness, bring medication and take it before leaving port, not after.

Now You’re Ready to Design Your Route

Ask yourself:

• Do I want to visit every highlight, or savor fewer places in depth? If you’re unlikely to return, go for the full circuit. If you might come back, divide the area into sections—explore one half this year, the other next time.

For example, in the Saronic Gulf, you could:

• Rush through Athens–Aegina–Poros–Hydra–Ermioni–Spetses in one go, or

• Divide it:

  • North loop – Athens, Aegina, Perdika, Moni, Agistri, Epidaurus, Methana.

  • South loop – Poros, Hydra, Ermioni, Spetses, Porto Heli.I prefer the second approach: explore slowly, return for more.

Next, decide whether you prefer marinas or anchorages. Marinas offer comfort and power, but require early arrivals. Anchoring gives freedom and silence—but less access to town life. The best trips blend both.

Once you’ve chosen your destinations, plot them on Navionics and use auto-route to estimate distances and sailing times.Tweak manually until the daily rhythm feels right—your route should breathe, not rush.

מסלול רגוע במפרץ הסרוני באמצעו נוויונקס

🗺 Example: A Relaxed Saronic Gulf Route

A sample Navionics map might show an easygoing circuit with short daily hops, perfect for enjoying swims, tavernas, and sunsets instead of long engine hours.

In the End – It’s All About Rhythm and Flow

Sailing rewards those who rise early, drop anchor early, eat well, and listen to the wind.Plan your route—but stay flexible.Weather shifts, moods change, surprises happen.That’s the beauty of the sea: it teaches you to adapt, to breathe, and to let the journey guide you.