We all know the feeling of going back and forth on where to travel next for weeks or even months on end. When we should actually go is often a secondary concern and sometimes just not even up to us. We take whatever holiday days we can get and we also might be limited by school holidays. Sometimes we realise too late that timing can really make or break a place. The same place that gives you empty beaches and golden light in one month might greet you with packed streets, closed restaurants, two weeks of rain or even a monsoon in another.
So should we just go when flights are cheap or ask friends for their experiences? What do we do when we're limited to certain periods of the year and don't have the freedom to choose to go whenever?
'When to go' is a question you can answer just as systematically as 'where to go'. Sometimes your dates are fixed and you have to find a destination that makes sense for that specific time of the year. Sometimes it's the other way around. Both cases can be handled with a bit of strategy.
Step 1: Figure out which is fixed, your dates or your destination
Before anything else, it's important to look at what factors you can actually change. For a lot of us, holiday days depend on school holidays, company shutdowns or whatever weeks our colleagues haven't yet claimed. If you find yourself in such a situation, there isn't much point in falling in love with a destination whose best season you can never reach. The dates you have at your disposal become your starting point and the question turns into which places are at their best when you can actually travel.
If it's the other way around and you've already set your heart on a destination, you're in luck if you have flexibility when it comes to taking holiday days. In that case, just find the window when that place offers the things you're going there for. If both dates and destinations are flexible, you're in the luxurious position of having the most options. Your biggest pain point will only be having so many options that it's hard to decide what to go for.
No matter what scenario you find yourself in, our Trip Finder can help you narrow down your options and find the perfect destination and dates for your trip. If your dates are fixed, you can filter for your desired climate in the specific month you're travelling. Whether you're looking for warm and dry weather in November, snow in March or mild temperatures in January, our tool filters the destinations according to your preferences. If you already have a place in mind, you can also look for it via our search bar and the destination page will show you the best times to go.
Step 2: Understand what 'good weather' actually means for you
There's no such thing as universally good weather, only weather that fits your preferences and plans. Hot, sunny weather and a cloudless sky sound great until you're trying to do a city walking tour. A bit of drizzle might ruin a beach week, but if you're going for museums, food markets, shopping and thermal baths, you might not even mind a little bit of rain.
So instead of asking yourself when the weather is good in a certain place, ask yourself when the weather is good for what you want to do. Look at the whole picture from average temperatures to rainfall patterns, humidity and water temperature. If you suffer from allergies, aspects like pollen count can also play an important role.
Step 3: Decide where you stand on the peak vs. shoulder or off-season question
Peak season is peak season for a reason. It's usually when the conditions are at their most reliable, but also when the prices are at the highest levels and everywhere is incredibly busy. The shoulder season, meaning the weeks just before or after the main rush, is when a lot of experienced travellers decide to go instead. You often get most of the good conditions at a much lower price. This strategy can be a very smart way to avoid the crowds and enjoy a destination in a calmer setting.
Off-season can be a bit of a gamble. It can mean wonderfully quiet streets and low prices, but it can also mean a higher chance of rain, limited ferry schedules, closed restaurants and the one museum you really wanted to go to being closed for renovation. If you're considering a trip during off-season, especially to an island or a resort town, it's a good idea to check what will actually be open when you arrive. Some people will happily accept a higher likelihood of rain in exchange for having a famous viewpoint almost to themselves. Others want the guarantee of a cloudless sky even if they have to put up with the crowds.
Step 4: Check the calendar for the things climate charts won't tell you
While climate is arguably the main factor when it comes to choosing travel dates, there are other aspects that shouldn't be neglected when you're planning a trip. Local holidays, festivals and big events can change a destination completely in ways that you might not expect. Sometimes a festival can be the main reason to go somewhere in the first place, but often it might be wiser to plan around it. Random trade shows that you've never even heard of might just triple hotel prices or a city might be effectively closed for a public holiday you didn't even know existed. The same goes for school holiday periods and for religious seasons that change opening hours and the whole daily rhythm of a place. A quick check of what's going on locally during the weeks you've picked doesn't take a lot of time and can prevent unpleasant surprises.
We've made it quick and easy for you to check the local holidays at destinations you're considering travelling to. On every travelfilters place info page, you'll find a 'Quick Facts' box that lists the holidays of the specific destination.
Step 5: Match the timing to your route, not just to one place
If your trip covers several destinations, the timing question gets a bit more interesting, especially for a longer trip. After all, the best month for one stop isn't automatically the best month for the next. A route that combines mountains and coastline or two different climate zones might only have a short window where everything works at once. Sometimes it's simply a matter of putting the stops in the right order, so that each place gets its better weeks.
This is where it really pays off to plan the 'when' and the 'where' together. On travelfilters, you can save destinations to a list, check each one's best travel times on its place info page and finally turn the list into a travel route. We even give you estimated travel times between the stops, so you know how much time it will take you to get from A to B.
Step 6: Run a final check on your dates
Before you book, give your chosen window one last honest look. Are the flight prices for those dates still within your budget? Does the length of the trip really make sense for the travel time involved? Did you leave a buffer day at the start or the end, so a delayed flight or a slow first day doesn't throw off the whole plan? For the flights, the place info page of your destination can help, since you can check prices and connections from your home airport right there.
If the dates pass the test, go ahead and book them. If they don't and you have the flexibility, shift the window a week or two and check again. Even small shifts can make a surprisingly big difference in price and experience.
Don't overthink it
The right travel dates aren't a matter of luck and they aren't the same for everyone. Start by asking yourself what you actually want out of the trip, like the activities, the atmosphere and the budget. Then you can check the destinations you've picked against the seasons and the local calendar. If your dates aren't flexible, work with the more limited options you have and see which of those are a fit for what you're looking for.
No matter what travel planning scenario you find yourself in, travelfilters can do the heavy lifting for you. You can find destinations by activities and budget, filter places by your desired climate in the exact month you're travelling, check the best times to travel and detailed climate info right on the place info pages and turn your favourites into lists and routes.
Your ideal travel window is out there for you to find. Try our Trip Finder now to do just that.
