How to Plan a Holiday Around the Way You Actually Travel

Two people can book the same destination and have completely different holidays. One wants to be up at dawn for a hike. The other wants a long breakfast, a pool and a novel. Neither is wrong, but a trip planned for the wrong kind of traveller can feel like hard work.

Before you start comparing flights, it is worth asking a simple question: how do you actually like to travel? The answer shapes everything from your itinerary to what you pack and how you prepare.

The solo adventurer

Travelling alone gives you total control of the schedule, which is both the joy and the challenge. There is no one to negotiate with, but there is also no one to share the planning, the luggage or the decisions when something goes wrong.

A few things make solo trips run more smoothly:

• Plan the first and last day in detail, even if everything in between is loose. Knowing how you will get from the airport to your bed takes the pressure off arrival.
• Share your rough itinerary with someone at home and check in regularly.
• Build in sociable options, such as a cooking class or small group tour, for days when your own company wears thin.

Solo travellers often pack more activity into a day. If that includes trekking, diving or hiring a scooter, check those activities before you go rather than assuming they are covered by your arrangements.

The family holiday

With children, the pace of a holiday is set by the youngest member of the group. A day that looks manageable on paper can unravel by mid-afternoon if there is no time for snacks, naps or a run around.

Families tend to have the best trips when they plan for slower days. Pick accommodation with a bit of space, ideally with a kitchen or at least a fridge, and keep the first day light while everyone adjusts. One main activity a day, with something flexible around it, usually works better than a packed timetable.

Practical preparation matters more with a family, too. Pack a small bag with medicines, chargers, a change of clothes and copies of important documents. Make sure everyone’s passport has enough validity left, and keep a note of the nearest medical facilities at your destination.

The couples’ escape

Couples often say they want to relax and then plan a trip that looks suspiciously like a work schedule. The trick is to agree on priorities before you book. Is this about food, scenery, culture or doing as little as possible?

Choose a base that suits the shared priority and leave room for a few spontaneous decisions. A restaurant recommendation from a local or a beach you spotted from the bus can end up being the highlight. If one of you loves museums and the other does not, a half-day apart is not a failure. It often makes the evening together better.

Matching insurance to the trip

Whichever kind of traveller you are, travel insurance is one of those things that is easy to buy in a hurry and harder to understand later. The cover that suits a family beach holiday may not suit a ski trip or a solo trek.

When comparing policies, look closely at:

• Which activities are included, and which need adding.
• How pre-existing medical conditions are handled.
• Cover for cancellations, delays and lost luggage.
• Whether the policy suits the length and destinations of your trip.

Read the product disclosure or policy wording rather than relying on a summary. If you are travelling from Australia, for example, providers such as Freely offer travel insurance for every kind of traveller, which is a useful reminder that cover should reflect how you travel, not just where. UK travellers should look for the same flexibility from providers available to them.

A quick planning check

Before you book, run through a few questions:

• What pace suits everyone travelling?
• Which days need firm plans, and which can stay open?
• Are there activities that need special preparation or cover?
• What would you do if a flight is cancelled or someone falls ill?

None of this needs to take the fun out of planning. If anything, it removes the small worries that tend to surface halfway through a trip.

The best holidays are not the ones with the most impressive itinerary. They are the ones that fit the people taking them. Plan for the way you actually travel, and the rest tends to fall into place.

This is a collaborative post.