The trips that go well share a small number of planning characteristics.
Fewer destinations
Time in places rather than between them.
Which is the most common improvement available.
Requirements checked early
Entry, health and documentation with lead time.
Which prevents the avoidable problems.
Realistic budget
Including local transport, food and activities.
Unplanned time
Space for what you did not know about.
Which is where most of the memorable things happen.
The four things that matter most
Fewer destinations than you want, requirements checked with enough lead time, a budget that includes daily costs, and unstructured time deliberately left in the itinerary.
Which is a short list and covers most of the difference between a trip that works and one that does not.
Everything else, the specific properties, the exact routing, the equipment, matters considerably less than any of those four, despite receiving most of the attention.
Booking order
Requirements and health first, then transport, then accommodation.
Which avoids committing to something that turns out to be impossible.
Leaving room
A day with nothing planned in each place.
Which is where the unplanned happens.
Asking locally
The best source of information once you arrive.
A general note
Requirements and conditions change; check official sources close to departure.
What actually makes a trip go well
Very little of it is the things travel content concentrates on. It is not the property, the itinerary or the equipment. It is preparation on a small number of specific points, a pace that leaves room for things to go wrong, and enough humility to ask people who live there.
The trips that go badly are usually the ones where something checkable was not checked: an entry requirement, a health preparation, a transport connection, or the assumption that a place would be like somewhere else. All of those are answerable in advance and none takes long.
The preparation that repays itself
Entry requirements from the destination’s own authority. Travel health advice with enough lead time for vaccinations. A realistic daily budget including local transport, food and activities. Twenty words of the language. Somebody at home who knows roughly where you are.
That is an hour or two spread over the weeks before departure, and between them those five things prevent most of the situations that turn an ordinary problem into a serious one.
What travel writing tends to leave out
Most of it is written to inspire rather than to inform, which means it emphasises the extraordinary and skips the logistics. That is a reasonable commercial choice and it produces a systematic gap: the things that determine whether a trip works are rarely the things written about.
Entry requirements, health preparation, realistic budgeting and what a place is actually like on an ordinary Tuesday are all more consequential than any recommendation, and considerably less photogenic.
A general note
Entry requirements, health advice, safety conditions and local law differ enormously by destination and by nationality, and they change. Official sources for your own nationality and your specific destination are the only reliable reference.
On the destinations themselves
Almost every place is more ordinary and more interesting than its reputation. The reputation is built from a handful of images that a great many people have now seen, and arriving expecting them produces a disappointment that has nothing to do with the place.
The parts of a destination that people remember afterwards are generally not the ones they went for, which is an argument for leaving room in an itinerary rather than filling it. Whatever you plan, the unplanned hours are where most of it happens.
The travel that seems to be worth most
Longer stays in fewer places, some contact with people who live there rather than only with people paid to serve you, and a willingness to be uncomfortable occasionally. That is what the research on attitude change points at, and it is also what people describe when they talk about trips that mattered to them.
None of it requires money. Some of the most valuable travel is the cheapest, which is not something the industry has any interest in saying.
Where to get reliable information
Foreign ministries publish entry requirements and safety advice for their own nationals. Travel health services publish destination-specific medical guidance. National tourist boards publish practical information without a commercial interest in any particular property.
All three are free, current and specific to where you are actually going, which is more than can be said for most of what a search returns.
One habit worth adopting
Ask someone who lives there. Accommodation staff, drivers, shopkeepers and people at the next table know things no guide contains, and most of them are pleased to be asked.
It is also the part of travelling that people remember afterwards, which is a reasonable argument for it beyond the practical one.