Planning A Family Trip: The Basics

Planning a trip involves weeding through a lot of details. I cover many different topics elsewhere (how to book hotels, how to find cheap airplane tickets and 29 Tips for Traveling the World with Kids), but here I’ll discuss the initial idea of your trip and how you begin to makes some decisions about where to go and what kind of trip you want to have.

Important: If you’re even thinking about taking a trip then apply for your passports. The application process for passports varies quite a bit in each country (in the U.S. it’s usually quite speedy, in Canada surprisingly slow) but regardless where you’re from it’s an uncertainty that can derail even the best planned vacation.

Planning Your Vacation

There are many variables that define a trip: the duration, destination, activity level, and — for family travel — the age of your kids.

What Kind of Trip?

Unless you have a specific destination in mind deciding what kind of trip you want to have is probably the first order of business.

Sun, Sand and Swimming

On the beach or by the pool, this is the most typical vacation getaway — a week or two lounging around the pool and playing in the sea. It’s simple, easy and — depending how you do it — can be very cheap and budget-friendly. Even parents that love the water can be surprised just how much time kids can spend playing in the pool.

Action and Adventure

Canoeing, kayaking, snowboarding, camping, hiking, wildlife safaris — and that’s just a start of some of the crazy fun to be had out there. Activities can range from one day outings to themes that can form the backdrop for the entire trip. If you have kids that love to be active there are an uncountable number of great destinations that will fit the bill. From kayaking around Thailand’s cliffs and coves to snow boarding in Europe and body surfing Costa Rica’s shores you can keep your family very busy and very happy.


This can sound boring — and you’re first thought might be, “my kids would hate that kind of trip.” And, well, you may be right. But I wouldn’t assume that immediately. You might be surprised how engaged your son or daughter will be at some of the wonderful museums, exhibits and cultural events that are hosted in different cities around the world. Many are simply fantastic! Try taking your children to a kid-friendly museum in your home city or country before deciding whether it will work — many parents, myself included, are apt to ignore local attractions and only visit museums when they’re traveling.

Package Tours and Resorts

You can get some great deals when you book hotel and plane together so if a cheap holiday in the sun is what you’re after then this might be the way to go. One drawback can be a feeling of isolation and boredom as some resorts are so self contained that little interaction with the surrounding area is required. The best resorts involve a friendly and active environment with intriguing kid-friendly day trips that take advantage of the nearby sights and attractions.

Round the World Tickets

RTW trips take a lot of planning: they cross different climates, require different clothes, and can involve questions on what to do with work, the house, and where to get all that money. On the other hand many people are choosing a shorter version of the typical RTW trip that takes in few countries and perhaps takes just 2 or 3 weeks. Kids, of course, will love the idea of go all the way around the globe and will probably come away from the experience with a greater sense of the world and its dimensions and layout.

Further Reading for RTW Trips:

How Long to Travel

Most people are limited by how much vacation time they get. Here are some thoughts and ideas to consider if you do have the freedom to choose the length of your trip.

1 or 2 Week Vacation

  • Maximize happiness: take many short trips instead of one big one. Experts who study happiness, will tell you that you’re much better off doing many small short things than doing one or two big things. Many little purchases (e.g. a few books or cd’s every week) will make you happier than one big purchase (say a new sports car). The same applies to travel and vacations.
  • Don’t underestimate how much you can do in 1 or 2 weeks. As someone whose first few overseas trips lasted between 6 weeks and 4 months, I would have scoffed at the idea of taking a 2 week trip. But since then – on trips both with and without children – I’ve seen how much you can do in just 7, 10 or 14 days. Western Europe’s big cities, for example, are so close and well-connected by air and rail, you could easily see 3, 4 or 5 cities in a 2 week trip across the Atlantic.
  • One obvious drawback of a shorter trip is that you don’t have as much time and perhaps want to narrow your choices to destinations you can reach in a reasonable amount of time. (Reasonable being different for everyone.) If you’re going somewhere that requires a few long flights — say a trip to Thailand from Los Angeles, it can seem like you arrive at your destination, just begin to get settled and then have to pack your bags and start making your way home.

2 to 4 Week Vacation

  • A longer trip can take in more regions in their prime time to tour. For example a trip through the Mediterranean could take in Greece in late September, Turkey in mid-October and Egypt in early November — catching each of those countries at it’s best.
  • The longer you go the more you spend, but the less you’ll spend on a per day basis. 4 weeks touring Southeast Asia will probably cost only 1/2 as much more as a 2 week trip — owing to the fact that the airfare to Bangkok or Singapore will be the same and that the longer you’re in a place the smarter you usually travel. You’ll bargain better for things in the market, know where the locals eat lunch, and can get a better deal on accommodations if you’re staying at a particular hotel for more than a few days. In general you’ll know what things cost and make better decisions when it comes buying things and looking for the best price.
  • It will be more of an experience with more time to travel, enjoy the local environment and become accustomed to your destination. This applies especially if you’re traveling with kids. You’ll get in a groove, establish a routine (even if you’re bouncing between different cities), and quickly discover what works and what doesn’t. If you’re traveling with more than one child they’ll probably really bond as they are each other’s only consistent playmate. All these aspects won’t be as firmly established on a short trip.
  • Many tickets are 4 week or 30 day max so before planning a trip like this check to see the airline tickets will suit your budget.

More Than A Month

  • Like a 3 or 4 week trip, but more so. You’ll be able to rent a house if you want, really get to know the locals, find the best markets, and make your locale feel like a second home. If you’re inclined to take some language courses that can be a great way to feel involved in local life and give the trip a very special feel. Most people who try to learn foreign languages notice a big increase in ability after the 3rd or 4th week of trying to communicate. (Not that you’re fluent at this point but simple phrases, greetings and questions start to feel more natural and vocabulary starts to increase dramatically.)

Age of Children – What to Expect when you’re Exploring

One argument that you can dispel immediately is the “if we wait a few years they’ll remember more” — this is an argument for people looking for an excuse not to travel. Yes, they’ll always remember more when they’re a little older. They’ll remember more of a book you read to them when they’re 10 instead of when they’re 2 — that’s isn’t a good reason to avoid reading to them when they’re toddler.

Traveling with a newborn

  • I encourage everyone to travel but even I might hesitate with a newborn. Unless it’s a short trip to visit family (less than 6 hours total on a plane) I’d defer your travel plans until after the baby is 3 months old. We took our first-born from San Francisco to Northern Canada when he was 6 weeks old — and while it all worked out fine — the planning and preparation required an insane amount of time and energy.

Traveling with a baby (2 months – 12 months)


  • Baby is not moving around much yet, so parents need not worry (as much) about unsafe environments — electrical outlets, 3rd story hotel windows, etc.
  • Baby sleeps a lot so parents can visit museums, cafes, and nicer restaurants that may be off-limits in just a few more months.
  • Don’t need an extra seat yet on the airplane, and baby still can sleep in the bulkhead bassinet at the front of the plane.
  • Great bonding time. Many parents (in the U.S. in particular) have limited maternity and paternity leave so a week or two away from home — together — can be a great opportunity to leave well-meaning grandparents, neighbors and friends behind and have some uninterrupted family time.
  • Babies are easy to carry and move around compared to a grumpy and tired toddler.


  • Parents of first-borns are still getting used to the rhythms and requirements of their little ones. An unusual setting and hectic travel itinerary could be unnerving for some.
  • Baby may not have received all of his or her vaccinations yet.
  • Formula, diapers and many changes of clothes. All these need to be packed — or purchased — for your trip so you’ll need to pack accordingly.
  • You will need to pack or plan for unique sleeping arrangements (e.g. travel crib).

Traveling with a toddler and preschooler (1 year to 4 years old)


  • Children this age are really starting to interact and learn. Countries, maps, learning new words and phrases.
  • Trips are definitely more fun and engaging than when they were babies.
  • Interesting activities, events and performances abound for kids this age in different cities and countries: playrooms, parks, exhibits, science museums and much more. Some are absolutely amazing!
  • Can walk on their own, giving parents a little break from the constant carrying and pushing.
  • Start them when they’re young, they really will retain something from this trip and probably be a lot less intimidated by future trips when they’re preschoolers and older.
  • A toddler will have had most vaccination shots.


  • Parents will have to worry about “what they will get into”.
  • Weather is a bit more of an issue with toddlers (I think) Paris in February is fine with a baby, with a toddler or older you might feel confined inside without the usual resources of schools, play dates and favorite activity centers.

School age kids (5 to 17 years old)


  • Kids this age are even more engaged with their surroundings. If they’re learning a second language at school this can really re-enforce some of that learning and make a foreign language seem cool and worth learning.


  • This is not so much a con but you really need to plan ways to keep them entertained and engaged. When you have a 3 year old you can pretty much do what you want. When you have an 8 year old they’ll insist on some input.
  • Missing school, exams, and friends becomes more of an issue for this age group. Be prepared for some grumpiness – at least for a few days – from your 16 year old missing their boyfriend back home.

Choosing a Destination – Vacation Ideas

Where to go? In the end it all comes down to a destination. Here are a few thoughts on certain destinations that I find really work for kids and families.

Cities – Urban Adventures

Perhaps a little surprising to the uninitiated, cities are great destinations for kids: lots to do — museums, aquariums, parks and unique restaurants with fun themes. Everything from cupcake shops to licorice specialty stores. And shopping of course, for those interested. Big urban destinations will often have some very engaging city tours that are equal parts comedy show and educational talk.

Most cities usually have subway systems (think New York, London, Paris and Tokyo) that most kids will find thrilling — especially if they come from communities without urban transportation. Whizzing around the city and beneath the streets — popping up to the street to visit a restaurant and then back down the stairs only to emerge somewhere else a few minutes later — is the stuff of dreams for an imaginative youngster.

Beaches — Seaside Vacations

There isn’t a whole lot to explain here. Swimming, sand castles, running on the beach, kayaking, water jet rentals and parachute rides behind a boat just begin to name some of the activities that await those on a family beach vacation. for those old enough, and most places have a pool as well.

Islands — Compact Adventures

Islands come in all different shapes and sizes of course, but most have a unique feel to them that differs markedly that the nearest mainland. Islands are usually easy to get around and give a vacation a very distinct feel. Whether it’s Ireland, Sicily, Crete, Koh Samui or Bali visitors tend to come away from their trip with a feeling that they really know the place they were. A visit that covers a larger territory can leave families feeling rushed as they breeze through sites and towns. Vacations are best when they have a unifying feel or common theme and this is almost built-in when you choose an island destination for your holiday.

Jungles, Rain Forests and The Great Outdoors

Kids thrill to the opportunity to see wildlife and outdoor settings form the backdrop of their vacation. There’s an immense amount to do and experience and a good tour company will be able to show you a wide range of activities for your trip. From hikes and bungee jumping to rafting and safaris — the allure of adventure travel is not just for 20-somethings any more.

Great Destinations for a Family Vacation

There are an incredible number of great destinations out there for families looking for an adventure, a great city or a deserted beach. Here are some of the most popular places to vacation with children and a few thoughts about what you’ll find there.

Belize, The Yucatan or Costa Rica
These Central American destinations share a common theme: great beaches, diverse wildlife and scenery, lush green jungles to explore, and a relatively short flight from the U.S.

The Bahamas or Hawaii
Islands are great destinations. Island groups are better. These two collections of islands have everything you’ll need for a superb sun holiday: fantastic kid friendly beaches, lots of water fun activities, a small town vibe to many beach locations and good deals on flights and accommodations outside of high season.

London, Paris, Rome, and Barcelona
Maybe the best family trip there is: fly to London, with at least 3 or 4 days to enjoy that incredible city. Then train to Paris and its bevy of parks, playgrounds, museums and markets. Next, make your way south (perhaps with a stop on the French Riviera) to either Rome and its phenomenal collection of tourist attractions — or to Barcelona and its surreal sights and family friendly beaches.

Greek Islands or Croatian Coast
Island hopping, beaches, great weather, small crowds (if you know where to go) and a feeling like life just couldn’t be any better. These two countries mix kid friendly fun and adult attractions as well as anywhere.

Egypt, Turkey or Morocco
You’ll want to put a lot of thought and planning into what cities and attractions to visit in these three potentially challenging, but ultimately rewarding countries. They can work well in conjunction with an off-season trip to Europe. See London, Paris or Rome at a discount in the spring or fall, then make your way south if you need a break from the Europe’s grey skies.

Thailand or Vietnam
These two countries just keep getting more and more family friendly. Great value for the money make them a good destination if you have more than 2 weeks to wander and explore. You’ll probably come for the beaches, but you’ll end up remembering the food and hospitality.

Singapore, Hong Kong or Tokyo
Three big bustling Asian cities with enough to do and see to easily fill 2 weeks of holiday fun. Zoos, museums, theme parks, teeming markets, funky restaurants and shopping, shopping, shopping.

If there’s a culture that loves kids more than Bali it’s yet to be found. If you come with young kids be prepared to be set upon by some of the friendliest and funnest people around. There’s so much packed into this little island most people leave with a long list of all the things they didn’t have time for but plan to do on their next visit.

Vancouver and Vancouver Island
A great summer or winter destination: beaches, hiking and mountain biking in the summer months, snowboarding, skiing and kid-friendly museums and attractions in the winter months. Come with a lot of energy and you’ll leave with a bucketful of memories.

The quintessential family vacation destination. A mind-boggling array of attractions will keep all the members of the family happy for weeks on end. The biggest challenge will be narrowing the to-do list down to something manageable. San Diego, Los Angeles and San Francisco could each keep a family busy for more than a week – a drop down the coast between all 3 will combine the best of California into a very manageable 2 week holiday.

Saving Money

-> Travel during the low season. Consider traveling to certain countries during the off-peak season. For some countries this can be an unattractive time: rainy, cold and uninviting. But for others there can be little or no difference between high and low season — except for the number of tourists and the price of hotels.

Hawaii is a great example. The weather in during low season (September and October) is just as nice as the high season (December and January), so a visit here during the fall will save you a lot of money. Of course many people come to Hawaii in the winter to avoid the harsh North American winters, so that’s certainly a consideration. But if the idea is more specifically about Hawaii and having a great trip then there’s little reason avoid the low season.

It can also depend on what you’re planning to do at a destination. Most people visit Greece to swim in the ocean and relax on the beach which is why July and August are so busy, but if you’re a family that loves to hike then the Greek Islands in April can be great.

-> Be flexible with your destination. Look and search for different airport, cities and countries to fly to. A year back we entertained the idea of vacationing in Greece, Thailand or Vietnam. As the dates grew closer the flights to Vietnam fell fairly drastically and we booked return tickets for a month long trip to Vietnam for less than $700 each. Thailand was at least $400 more and Greece another $300 on top of that even though all 3 of these destination are usually about the same price. Flexibility and a wide search allowed us to choose the one that saved us a lot of money.

-> Check to see what’s included in your hotel price. Even a simple continental breakfast can save a family of four $30 or $40 a day by erasing the need to buy breakfast every morning. If you rent a house, you can stay in and cook breakfast (or any other meal) yourself in a fully equipped kitchen instead. Day trips from your hotel (especially if it’s an all inclusive resort) can add costs or save money to your bottom line depending on what’s included.

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