Holiday Heaven, Holiday Hell: Why There’s No One‑Size‑Fits‑All Getaway

At a recent networking event, the group warmed up with an icebreaker called “Holiday Heaven, Holiday Hell.” It sounded lighthearted enough, but as people shared their answers it became a neat little case study in something that plays out all the time in travel: there is no single, universal idea of the perfect holiday.

In any given week, the mix of people planning trips is incredibly varied. Some want non‑stop activity and entertainment; others crave silence, space and very little on the agenda. For one person, a bustling resort feels like heaven. For another, the same place would be something to endure rather than enjoy. The exercise made visible just how personal travel really is, and why a tailored approach has become so important.

One Person’s Dream Is Another Person’s Nightmare

As part of the activity, everyone had to write down their idea of holiday heaven.

One person chose a big family trip to Disneyland Paris with their wider family: rides, parades, character meet‑and‑greets and shared memories. It was a holiday they were genuinely excited about, full of anticipation and planning.

A few minutes later, someone else shared their holiday hell. Top of their list? Disneyland Paris.

Neither view was “wrong”. In fact, both were entirely valid. What feels magical, nostalgic and joyful for one person can feel noisy, overwhelming and stressful for another. The same destination, seen through two different sets of expectations and preferences, becomes either a dream or a nightmare.

For anyone working in travel, this contrast is familiar. The role is not to decide what a “proper” holiday should look like, but to understand each traveller’s version of heaven and help them move towards that, rather than towards someone else’s ideal.

From “No Idea” To Something That Fits

Travellers tend to arrive at the planning stage in very different places. Some have a fixed destination in mind. Others can only describe how they hope to feel:

• “We want somewhere relaxing, but not boring.”
• “We need things for the kids to do, but not full‑on chaos.”
• “We like good food, a bit of culture, and somewhere that still feels authentic.”

Quite often, people are not sure whether what they are picturing actually exists. They bring a list of criteria, a sense of what will not work, and a hope that there is something out there that does.

This is where professional knowledge makes a difference. The “must‑haves” and “absolutely‑nots”, the budget, the timing and the personal quirks all become useful information. With that, it is possible to filter out options that are almost guaranteed to disappoint and to highlight the ones that are more likely to feel right.

At its best, this process turns uncertainty into a clearer sense of direction: not towards a generic “perfect” holiday, but towards a trip that makes sense for a specific person or family at a specific moment in their lives.

Creating “Holiday Heaven”

If you laid out ten people’s versions of “holiday heaven”, they would probably have very little in common. For one, it might be:

• A luxury resort where the kids are entertained and the adults can genuinely switch off.

For another:

• A small adults‑only hotel with a quiet pool and sunset cocktails.

For a third:

• A villa in a peaceful location with space for the whole family to spread out.

Others might choose:

• A city break full of galleries, markets and food tours.
• A once‑in‑a‑lifetime adventure somewhere they have always dreamt of.

Their “holiday hell” lists would be just as varied: loud nightlife when someone wants tranquillity, feeling isolated and bored when they actually love a buzz, or finding themselves in a hotel that does not reflect their style or standards.

Seen through this lens, there is no single template for a good holiday. There is only the question: what feels right for this particular traveller, in this particular season of their life? The most satisfying trips tend to be the ones that start with that question, and stay honest about the answers.