Why Online Itinerary Advice Often Misses the Mark for Sailing Holidays

As someone who has skippered yachts and arranged charters for decades, I often speak to clients who have done their homework, but based that research on unrealistic or ill-suited recommendations. Here’s why it happens, and how you can avoid disappointment.

Cruise Ship Routes Aren’t Sailing Routes

Many itinerary suggestions you’ll find online are borrowed from cruise ship marketing, most often the mini cruise ships that cover the same region but are fully crewed and have a very different agenda. These big vessels move fast, overnight, and tend to only stop at main ports. A bareboat holiday by contrast, is about relaxed days, shorter hops and avoiding busy ports where possible.

For instance when in Korčula on a Croatian sailing holiday, I would anchor on the opposite side from the town and run a stern line ashore. I find that better than going into the port or marina or even anchoring in the middle. Arriving early gets the best spot, and over the course of the afternoon others will do the same, forming a line of boats along the shore. You maintain privacy, your boat is secure, and you can explore ashore by dinghy or water taxi knowing everything is safe.

What works for boats carrying many passengers on a schedule rarely suits a small group of friends and families sailing under their own power.

Day Tour Hotspots Are Often Best Avoided

The next common pitfall? Places that are heavily promoted by one-day excursion operators. These locations often make for great brochures and Instagram posts, but they’re not always suited to overnight stays. Even if they are, you likely don’t want to be there.

• Unsafe or exposed to weather
• Overcrowded by mid-morning
• Lacking in real charm or authenticity

I’ve personally seen many clients plan their route around these "must-see" stops only to find they detract from the experience.

Beautiful and very popular Korčula, Croatia

A Society Islands itinerary requires thought

The Risk of Overpacking Your Itinerary

Marketing content often sells the dream of squeezing in everything: more stops, more sights, more sailing miles. But on a bareboat holiday, trying to do too much is a recipe for fatigue, stress, and even risk.

What many online guides miss is that good sailing involves adding a margin: for weather, for flexibility, for unplanned swims and longer lunches. The best memories come not from racing the clock but from finding your rhythm on the water.

I’ve found this problem is getting worse as each company tries to make their offer look better than the competition. Charter operators’ marketing departments aim for engagement over realism, while the operations teams are left to manage disappointed clients. Unfortunately, marketing often sits closer to management, and operational concerns don’t always get the respect they deserve.

Why First-Hand Advice Makes the Difference

When I speak to clients just before their departure, I draw not only on my sailing knowledge of the region, but also on what I’ve come to understand about them: their group dynamics, preferences and comfort levels. That’s something no AI, no blog and no brochure can replicate.

It’s often during those short pre-trip calls that I help clients:

• Avoid pushing through risky passages
• Reshape an itinerary that’s too ambitious
• Discover less-publicised anchorages and stopovers
• Understand local quirks that only come from experience

If you've booked a charter with Sail Connections, I always recommend a call before you leave. We'll talk through what you're hoping to get out of the trip and I'll share tips that suit your specific plans, rather than a generic version of them.

A Final Word

Information is everywhere now. But experience still counts. And when you're heading out on the water, that's what matters most.

If you’d like to discuss your charter plans or get a realistic sense-check on your itinerary, give me a ring or send me an email for feedback. I’m always happy to share what I’ve learned based on real-world sailing, not marketing copy. One conversation can make the difference between a good trip and a great one.

In the Cyclades, watch out for the Meltimi, and the crowds

When it's well-planned, it's plain sailing

Photo credits:

• Huahine, by Dream Yacht Charters
• Milos, Cyclades Islands by David Tip on Unsplash
• Korčula, Croatia by Joanna on Unsplash