One of the questions I’m asked most often is how I choose where to go and then once I’ve settled on a destination, how I set about planning the trip. Of course, it would be much simpler to let someone else take care of the details, but that’s where a lot of the fun is, and who wouldn’t want to create a bespoke trip without the bespoke price tag that comes with it. I’ve saved tens of thousands of pounds over the years going it alone, so I plan to continue travelling independently as much as possible.

Now I’m writing for a living, I am offered press trips on a regular basis. While I have accepted some of these and am very grateful for the generosity of the tourist boards involved, I don’t like to travel like this all the time. I’m fortunate to have worked with some lovely PRs who have gone out of their way to deliver a tailormade experience within the confines of the programme that’s been agreed. But on a group trip, everyone has to compromise. When I travel solo, I can do as I please and it’s extraordinarily liberating.

How I go about choosing my next destination

Now a big trip for me these days, with family commitments, is just two weeks. This blog won’t be relevant if you’re planning a gap year and need to stretch a budget or find annual insurance cover. (However, you can apply some of the same principles and concentrate on the first and last week of a longer period of travel.) Instead, I’m talking about choosing the destination that’s likely to be your main holiday.

This is often a fluid concept. I do have a loose wish list of places I’d like to visit. Right now, for instance, Sao Tome & Principe, The Azores and Tobago are on that list, together with Tajikistan, Madagascar, Belarus and Algeria. However, I’ve found that being more flexible enables me to take advantage of better flight deals that might present themselves. Often, flight costs form a large part of a trip, particularly if it’s to a long haul destination. Keeping abreast of flight sales and last minute offers is a good idea. But although I have that list, I almost always end up travelling somewhere else – this year it’s Grenada.

Next steps after I’ve found my flights

Finding a well-priced flight is a start, but it doesn’t necessarily mean I’m going to book. But if there’s a chance that the cost of that flight will increase, it’s important to act fast. It is possible with some airlines to pay a small amount to hold the fare. I’ve never needed to do so, but it does quite literally buy you time to get your other arrangements tentatively in place before committing to the full whack.

A case in point

I recently found a sub £100 return fare from London to Algiers. Algeria is on my travel B list at the moment, a place I expect I would enjoy. The fare was a great deal, far lower than usual, with BA. The dates worked too. A quick scour of accommodation via booking.com indicated that I could find something central and reasonably priced that didn’t look like a dive. Photos from the road from the excellent Simon Urwin via my  Twitter feed only served to fuel my interest.

It all fell apart when it came to the visa. I’ve never been turned down for a visa – and I’ve bought a fair number in my time. Sadly, it would seem the Algerians are hard to please and turn down many applications. As a freelance writer on an unreliable income I might or might not match their criteria – who knows? But to meet the visa criteria I would need to buy the flight and arrange the accommodation in advance. The latter I could achieve with minimal risk on a free cancellation basis, but the former would be an unrefundable outlay. So, I decided not to take the risk and have not applied. Algeria is a destination probably best left for another time.

Back to the drawing board

Having shortlisted a destination with affordable transport, it’s time to look at geography. Use a guide book such as Lonely Planet or a comprehensive online guide to identify some of the key places and sights that interest you. Don’t over-plan, but also don’t be the person who realises once they return home that they missed out something they’d love to have seen because they didn’t do any research. The trick is to do just enough planning to make sure it’s possible to fit in all your must-dos. Fine tuning can come later.

I sometimes take a look at the itineraries of tour operators such as Explore or Intrepid, as they tend to be balanced and well thought through. Then I weed out the parts that don’t interest me and mentally replace them with what I’d prefer to do. But don’t assume that because an area doesn’t feature on most tours, it isn’t worth bothering with. If I had relied solely on such sources of information, I’d have missed out wild and wonderful Svaneti in Georgia which was the highlight of my time in the country.

Considering open jaw itineraries

Is a round trip fare to and from the same airport a smart decision or would an open jaw be more sensible, saving unnecessary backtracking? For instance, I’ve used this for a rail holiday in the US, booking Amtrak services to link the two cities at either end. I also looped through a few countries on a longer journey, beginning in Cape Town and ending in Johannesburg but going the long way round via Namibia, Zambia, Zimbabwe and Botswana. Alternatively, I’ve flown into one capital, for example Panama City, and out of its neighbour, San Jose, using the two cities as bases for point and spoke excursions. (That’s when you stay in one place and head out and back in a different direction each day.)

If you are going to opt for an open jaw flight, try flipping the two destinations around. Sometimes when I’ve looked into following the same itinerary but in reverse I have saved a whole heap of money. It’s also worth thinking about whether to avoid somewhere on a particular day of the week. For example, there’s no use planning to be in a city on, say, a Monday if the main reason you are going there is to visit a museum that’s closed on that day. Kick off dates for seasonal attractions might vary from year to year so always check. Finally, if the place you intend to visit stages a big festival of some sort, such as Day of the Dead in Mexico, make sure you’re booking early enough to make sure transport and accommodation isn’t already sold out.

The overland bit

One final thing to look at is overland transport. If I plan to start and finish in two different cities, I always research what the public transport is like between. I look into whether I can take a bus or train and if so, how far in advance I can book my ticket (many companies have online sites). In some cases, demand outstrips supply, so make sure there’s a plan B before committing to expensive flights.

Don’t rule out domestic flights, which in some places can be cost (and certainly time) effective. I always leave a day clear between any inbound transport and my international flight home, even if that means splitting the sightseeing between the early and later part of my trip. Delays do happen, and you don’t want the added stress of worrying about missed connections. Another thing I’ve learnt the hard way is to reconfirm flights with regional airlines or carriers that you’re not sure you can trust. I didn’t, in Argentina, and had to make hasty arrangements to bus it across the country to make Buenos Aires before my next flight left. Look what I would have missed!

Now factor in the weather

This one’s important. Once I know that my potential trip is a possibility – the flights are available, the accommodation suits my needs and I have a vague plan of the order in which I’ll see places –  I just double check the weather. It helps that I was a geography teacher for years, so I’m unlikely to make the mistake of unwittingly timing it to arrive right in the middle of hurricane season or the monsoon. Do that, and not only will your triup be a washout, but you might find yourself stranded if public transport on the ground is adversely affected.

Consider how you’re likely to spend your time. Is it still going to be OK if the temperature’s on the chilly side? There’s not a lot of point in booking a beach resort if it’s going to be too cold to swim in the sea or snooze beside the pool. But if you’re keen to explore a city, then those same cooler temperatures will make sightseeing a whole lot more pleasant. Shoulder seasons are a gamble with their promise of cheaper flights but a higher chance of inclement weather. Of course, you can’t predict the weather even in peak season, so there’s always going to be that chance of it scuppering your plans.

That’s almost it

By the time you’ve got this far, I expect you’ll probably fall into one of two camps. Some of you will be thinking that it would be so much simpler just to let a tour operator take care of all this time-consuming planning stuff. But if like me, you love that kind of thing, just think of the many happy hours you can spend travelling vicariously through blogs and magazine articles while you craft a trip that’s perfect for you. Book those flights, make sure you have insurance from the get go and start making your dream a reality.