8 Simple Rules for Picking a Holiday Destination

Planning a family vacation can be difficult, but it’s a great way to get the family on the same page, looking forward to an enjoyable vacation together. Family vacations are a great time to bond with the family and forge memorable experiences. The key to a successful family holiday is in the location.

Here are 8 Simple Rules for Picking a Holiday Destination.

I’ve followed this method since 2008 and with family, friends, and even work colleagues, and it hasn’t let me down yet.

Hopefully, you will find it useful and help you plan your next epic vacation!

Tip: Start planning 6 months prior for your next family vacation.

Vacation Time

For me, the duration of your vacation is the most important factor. It directly impacts your budget, the type of holiday, and the travel distance. Are you going for a weekend, 2 weeks or even a month? 

For example, a weekend getaway, you won’t travel more than 3 hours which means you have more time to spend at your destination. While a 2-week trip or a month means you can stay in multiple places for a few days each and take in the local sights accordingly! 

When we went to Switzerland for 14 days, we stayed in 5 cities for 2 or 3 days each. And because of their well-connected transportation system, we occasionally managed day trips to nearby towns.

Type of Holiday Experience

To have a memorable trip, choose a destination that allows you to have the experiences you enjoy.

  • Relaxation or adventure
  • Beaches or mountains
  • Summer or winter
  • Cities or countryside
  • Resorts or road trips
  • Festivals and culture
  • Shopping or food experience
  • Luxury, mid-range, or budget
Outdoor Adventure Holiday Experience

Are you the type of person who likes to sit by the pool all day with a book? Or would this bore you to death? Are there enough child-activities to keep your kids entertained during the entire holiday?

Sit down with other members of your traveling group and discuss your ideas and interests. Memorable trips are those where each member gets to experience something they love.

Travel Distance to the Holiday Destination

A basic rule of thumb for travelers: the longer it takes to get there, the longer you should spend there. If you spend more time traveling than you do exploring & relaxing, chances are you’re not going to come home satisfied with your trip.

I once made that mistake a few years back and I can honestly say it was one of my worst experiences. We decided to do a day trip and ended up having a 12-hour round drive just to spend three hours at our destination. Definitely not worth the effort or time.

Personally I prefer the quickest route to the destination so I can spend the most amount of time at the destination.


Travel Budget

For most people, this factor tends to be the biggest influencer on their choice of destination. If you are on a strict budget, pick a budget-friendly country. There are hundreds of lists of cheap countries you can look but I suggest compare their currency value to the one you earn in to get a good idea.

If you are going to be spending most of the time away from the hotel, pick a mid-range accommodation which includes the complimentary breakfast. Most travelers eat out every meal, making food one of the biggest day-to-day expenses while traveling. You can cut your travel budget significantly if you’re willing to do your own cooking (at least sometimes). 

Similarly, you can save some money with your flights, by flying on off-peak days, into alternative airports, and having a layover. It’s one way of seeing another destination on the way to your final destination.


Mode of Travel

If you are traveling internationally, the default choice of travel is flight, however, your final destination may involve – a few flights, a bus ride, a couple of train and tram rides, and then a 20-minute walk. If you traveling light that may be okay for some but if you got 4 suitcases, 4 carry-on bags, and whatnot, it’s a bloody nightmare.

Remember quickest route to the destination is sometimes the best option

When to Travel

Weather and crowds play an important role when you plan your trip. For your chosen destination, do you know when the high season and low season is? Check the weather as well. You may not want to visit Jamaica during the hurricane season or Dubai in the middle of summer!

The Language Barrier

A few years ago we visited the eastern European country of Georgia for 3 days. Beautiful country, great food and very welcoming, friendly people. Being a former soviet state, the large majority spoke Georgian and Russian, while a very tiny minority spoke English. For the first day, we tried to go on our own but in the end, we had to hire a local tour guide to help with the translation. It was just impossible to go anywhere or do anything without knowing the local language.

So when you are looking at a destination, make sure they speak your language or consider it as an opportunity to learn a new language. A crash course specifically! 

Follow your Friends

Another way to help filter down your destination choices is to follow your friends. You may have friends who live in different cities, states, or even countries, go visit them. The bonus is you may save on accommodation if they let you stay with them or at the very least you have a local tour guide!

Save Your Sanity!

Picking a holiday destination is part of the enjoyment of the vacation itself. It builds excitement and anticipation, allowing you and your children to dream about the great time you’re going to have. Even more importantly, a well-planned family vacation is going to go more smoothly and be more enjoyable than one that was largely unplanned. Keep in mind everyone’s expectations and the activities they enjoy, and you’ll be better able to find a holiday destination that makes everyone happy.

A lot of work goes into planning the perfect vacation. From spending hours on review sites to asking friends and family for recommendations, we often spend a lot of time trying to get everything just right. Hopefully with these 8 simple rules, picking a holiday destination should become a lot easier!

Additional Reading

In case you missed the first two parts of the series, here they are again – Can we go on a vacation in the COVID-19 era? and How will the Travel & Tourism resume after COVID-19?


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10 thoughts on “8 Simple Rules for Picking a Holiday Destination”

  1. I just love your advice. It’s all spot on. We travel with our kids, now teens, often and the perfect vacation for us really comes down to the length of time we have and the type of vacation we’re looking for. We aim for at least 10 days but more is always better!

  2. You’ve got so many important points here. There’s nothing worse than a vacation where the kids’ expectations are different from the parents’. So good to involve them.

  3. Nice tips. The language barrier reminds of the very first time I visited Hamburg in 1982 and went to the drug store to get some medicine for migriane! Thanks for sharing these tips.

  4. I so agree that where you plan to go on holiday depends on the length of your holiday. Also when it comes to flying (which most of sadly can’t do this year!), the longer the flight the more it costs, so unless money’s no issue, the longer you stay the more worth it it is!

  5. Great post on how to pick your next destination, I agree it’s important to know how far a destination is. So many people have said to me “I didn’t realise the flight was that long” especially when they have gone on a 5 day trip.
    Thanks for sharing


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