Holiday Nerd

    A Guide to Planning a Holiday

    Planning a holiday is essentially an exercise in balancing constraints. Everyone has limits of some sort, and understanding yours upfront will help you plan more effectively, save money, and get more enjoyment from the trip. Broadly speaking, the fewer constraints you have, the more flexibility you have to optimise for value. The more fixed your constraints, the more creative you need to be.

    Understanding Your Constraints

    Before you look at destinations, flights, or hotels, it’s worth being honest about what is fixed and what is flexible. The main constraining (or maximising) factors tend to fall into four categories.

    Money

    Money is usually the most obvious constraint.

    • Absolute constraint: This is a hard limit. For example, “I cannot afford to spend more than £2,000 in total.” Once you hit this ceiling, the trip simply doesn’t work.
    • Value-maximising constraint: Here, the budget is flexible, but the goal is to get the best possible experience for the money you’re spending. You’re less concerned about the headline cost and more about “bang for your buck”.

    Being clear on which of these applies will shape every decision that follows.

    Dates

    Dates are often fixed due to external factors:

    • School holidays
    • Industry-specific busy periods (e.g. retail over winter, finance around year-end)
    • Coordinating with others’ availability

    If your dates are fixed and fall in peak season, this is one of the biggest constraints you can face. If they’re flexible, even by a few days, you can often unlock significant savings.

    Length of Trip

    The amount of time you can be away is typically constrained by:

    • Annual leave allowances
    • The ability to step away from work (particularly if self-employed)
    • Family or caring responsibilities

    Trip length matters because it affects flight economics (long-haul trips are harder to justify for very short durations) and accommodation costs.

    Destination

    Sometimes the destination itself is non-negotiable:

    • Visiting family
    • Attending a wedding, birthday, or christening
    • A long-held desire to go somewhere specific

    When the destination is fixed, flexibility has to come from elsewhere—dates, airports, or accommodation type.

    How Constraints Shape Your Planning Approach

    Your mix of constraints determines how you should plan.

    When Constraints Are Minimal

    At one end of the spectrum, you may have no real constraints, or only a budget/value-maximisation goal. This is the ideal scenario for deal-driven planning.

    In this case:

    • Start with flights, as these are usually the most expensive and volatile element.
    • Use comparison and inspiration tools such as Skyscanner, Google Flights, and Kayak.
    • Search broadly: “Anywhere” destinations, whole-month views, or flexible dates.
    • Let price guide the destination rather than the other way around.

    The British Airways Cheapest Fare Finder is another useful tool—it allows you to search by destination and is particularly easy to use.

    It’s also worth looking at:

    • Package holidays and cruises, which can offer excellent value in off-peak periods when operators are trying to fill rooms or cabins.
    • Providers such as TUI often have strong late deals.
    • Flight deal sites like Secret Flying and Jack’s Flight Club, which highlight low fares and occasional error fares.

    Once flights are locked in, accommodation and activities can usually be shaped around them at relatively predictable costs.

    When Constraints Are Tight

    At the other end, if you must go to a specific place, at a specific time and for a specific length then you are more of a captive audience. Prices will generally be higher, and the scope for savings is more limited. That said, savings are still possible with smarter planning. When flexibility is limited, creativity becomes your main tool.

    Alternative Airports

    Especially in Europe, flying into or out of a different airport can make a big difference.

    • Consider airports slightly further away from your destination and travel onward by train or car.
    • This is particularly effective if you were planning to hire a car anyway.
    • Examples include flying into one country and travelling across a border (e.g. flying into Geneva for France, or Brussels for parts of northern France or the Netherlands).

    The extra travel time is often outweighed by cheaper flights and sometimes cheaper car hire.

    Adjusting Around Other Constraints

    If:

    • Dates are fixed → focus on airports, flight times, and accommodation type.

    • Destination is fixed → experiment with nearby regions or secondary cities.

    • Length is fixed → optimise flight timings to maximise usable days (early outbound, late return).

    Even small adjustments—changing departure airports, shifting accommodation by a few miles, or altering check-in days—can meaningfully reduce costs.

    Creating a Plan

    Once you understand your constraints, create a simple plan. This doesn’t need to be fancy—a Word document, Excel spreadsheet, or even handwritten notes will do.

    Start with:

    • Outbound and inbound flights
    • The days in between

    Map out where you’ll be on each day, particularly if you’re travelling around, and decide how long you want to stay in each place. Do this before booking accommodation or internal flights.

    For inspiration on pacing:

    • Look at tour company itineraries (bearing in mind they often move more slowly and include buffer days).
    • Use online resources and AI tools such as ChatGPT to sense-check your plan and spot any obvious issues or gaps.

    Once your itinerary is set, accommodation is usually the next major cost. We have a fun separate guide on booking hotels.

    Think about the purpose of each hotel:

    • If you’re arriving late, leaving early, or spending most of the day out, a cheaper option may be better value.
    • Save your budget for places where you’ll spend more time and want to relax.

    For example, if you’re budgeting £150 per night:

    • Consider spending under £100 on a night before an early flight.
    • Use the savings to spend £200+ on a hotel where you’ll have a full, relaxing day.

    After accommodation, you can start pencilling in activities. Platforms like Viator and GetYourGuide are useful, but remember to leave room for spontaneity. It is worth checking providers directly as you can get better value given the high charges these site charge providers, however at least with Viator and GetYourGuide you have a level of protection, the comfort of which can be worth the extra cost.

    For must-do activities or very popular attractions, book in advance to avoid disappointment, especially at peak times.

    Bringing It All Together

    The key to planning a good holiday isn’t finding the “perfect” deal—it’s understanding where you have flexibility and where you don’t.

    Start by identifying your constraints, decide which are absolute and which are preferences, and plan accordingly. The fewer constraints you have, the more you can let price and value lead. The more constraints you have, the more important it is to think laterally.

    Either way, a thoughtful approach almost always leads to a better holiday for the money you spend. And importantly, the more time you plan a trip and travel, the more confident you’ll become. Each holiday teaches you what works for you, what doesn’t, and where you can push or relax your constraints next time—making every trip easier and better planned than the last.