The Art Of Crafting The Perfect Family Vacation: A Comprehensive Travel Planning Guide

We believe that traveling is one of life’s greatest pleasures. However, planning a trip can be overwhelming, especially if you’re not doing it often. We are often asked to share our tips on travel planning, so we have decided to share a series of posts outlining our approach to family travel planning. With a little preparation and organization, you can plan a stress-free vacation that will leave you with lasting memories. Here are some tips and tricks for travel planning that we have accumulated during our travels.

Table Of Contents

Chapter 1: WHERE AND WHEN (to travel)
Chapter 2. WHO (is traveling)
Chapter 3. WHAT (actual planning)

Chapter 1: WHERE AND WHEN (to travel)

Before any travel plans materialize you need to choose where and when you’re going. There are at least three different approaches to this (obviously critical) part.

Family Travel Planning: When dates are locked

The first approach to choosing when and where to go is one that many families would be almost forced to use – that is when your dates of travel are locked – most likely due to school schedules. School breaks are often the time when you can travel freely with no unexcused absences. That might include longer breaks like winter or spring break, but you can also travel around long weekends – in the end, it all depends on your tolerance for kids skipping school 🙂 We have historically been a bit more relaxed about truancy (our kids are in Kindergarten and 5th grade, so maybe that will end soon). In the last few years, we’ve pretty much used every long weekend as a chance to do a 9-day trip – a long weekend gives you 3 days, then you skip 4 days, and then there are 2 days of the next weekend. But 9 days is enough to fly across the world and have an amazing vacation!

Update at Sep 2023
As we have entered the new school year, and our older daughter started middle school, above statement is no longer valid, at least in our school/district. So this particular way of planning is becoming even more important for us now as we likely will only travel during school holidays for the foreseeable future. Dammit.

The caveat of this approach? Everyone and their mom are traveling during those dates too – that will likely make your trip more expensive. As Scott Keyes from Going.com (formerly Scott’s Cheap Flights) wrote in his book (highly recommended btw) – there are two variables affecting the price of airfare: dates and destination. If both are locked you are highly unlikely to find any cheap tickets. If one is locked but the other one is changeable – you might be able to get lucky.

So in the case when your dates are locked, you got two choices: if you are not willing to pay a lot you will have to be flexible with your destination, or if you insist on going to a particular place – be ready to pay for that. We’ll cover the latter in the “destination locked” part of this, so let’s focus on choosing your destination to travel to during specific dates.

While hotel and food prices could vary from destination to destination, in our experience those differences are not as significant as the spread of what you will have to spend on getting there, so we almost always start with booking our flights.

Searching for and booking flights when your dates of travel are locked

Most of us have bucket lists, so your first order of business should be checking the prices for flights to each of your dream destinations. As of now, there’s no better tool to do that than Google Flights.

Few tips on using Google Flights:

Choose multiple origin airports (if there are multiple you can quickly access – whether by driving or with a short and cheap flight you can always book separately, e.g. SFO->LAX)
Check if you can choose multiple destination airports as well – but be careful with results as they might have an outbound flight departing from a different airport than the inbound flight. Or you could use that to your advantage in some trips by arriving in one part of the area and departing from another.
Even though your dates are locked in this scenario, check the prices for flights that depart a day before or after. Sometimes the price difference would be enough to justify an extra day or shortening the trip a bit.

If you are a member of airlines’ loyalty programs – check if you could get to your desired destinations by booking your flights with miles. Make sure to compare the dollar prices to the miles amount before booking to not waste your miles. Or use those miles and be happy anyway – your choice.

There are more complex strategies you could use if you’re really keen on some specific destinations – we’ll cover that below too.

But since our original idea here was around being open to different destinations – you could use Google Flights in a more open-ended way: just put a continent (e.g. Europe) as your destination on Google Flights, set your dates and any other parameters that are important to you and explore the world map with prices for flights to each city on the map. Choose the one you like and book. Unfortunately, this method only works for specific dates so if you want to play with +/- days of departure or arrival you will have to repeat this exercise a few times to get the full breadth of the results.

Yet another option is looking for deals – and it could be quite useful in this situation.

Searching for airfare deals

Airfare deals are often the best solution if you are flexible enough in your travel plans. But even if you’re locked on the dates (just dates) it still could be a great option to have in your arsenal – and sometimes the best option too.

What are the airfare deals? There are multiple types of those – could be just a sale that an airline does for whatever business reason they have, could be a human error, a currency conversion issue – or just a result of a mistake in overly complicated pricing mechanisms used to determine the final price of a ticket. But in the end, you don’t really care much – as long as you can get a good deal, right?

The easiest approach to finding those deals is to rely on experts. Going.com (formerly Scott’s Cheap Flights) is one of the best flight deal websites in the US. In the UK, there’s Jack’s Flight Club, and in Canada – Next Departure. You can always use Google to find the most reputable one in your country too. These services often employ a team of experts searching for the deals all day every day – and deliver their findings on their website, or app – or send it to your email (if you subscribe). Oftentimes there’s a fee to get the deals fast – and it might be worth it as some of them are short-lived (especially if they are caused by a mistake in pricing).

Other reputable sources in US would include Secret Flying, Airfarewatchdog, and Thrifty Traveler. Most likely you won’t need all of them, let alone paid subscriptions to all of them – but it’s your choice – and sometimes they have overlaps but they also might find unique deals too.

Once you’ve selected your sources you can browse the recent deals to see if there are any interesting destinations that have deals for your dates. We do that by using a filter in Gmail to group all the deal subscriptions in one place and then look at what might be interesting from time to time.

Is it worth it? It might very well be. A few years ago we flew to Singapore from San Francisco for $260 per person round-trip on Singapore Airlines.

Last but not least – the better the deal – the faster it will be gone, so book quickly if you find something that interests you. To protect you, most airlines have a 24-hour penalty-free cancelation period, and in US it’s actually the law for them to offer that period. So book first – and then decide if you want to keep those flights or not.

Choosing your travel dates for a particular destination

If you’ve set your mind on visiting a particular place – and if you have enough freedom with your work and kids’ schedules – here are some tips on choosing the dates and flights.

First, make sure to check the best time of the year to visit your destination. There’s rainy seasons, extreme heat, freezing temperatures and many other factors that might make it less pleasant to travel. You can check that by simply googling “when is the best time to visit <Destination>” – but make sure you look at more than one answer as they usually vary a little.

If after this your plans are still on – head to Google Flights (https://flights.google.com). Choose your departure airport (or airports), select your destination (again, make sure to select all possible airports you could use). Once you do that and click Search (for any dates), you will see two other options on the upper right of results list: Date Grid and Price Graph. These are your best friends for this quest.

Start with Price Graph – this tool will show you prices for your trip across the dates months ahead. If you’re lucky and you see a good option – we’re done.

Date Grid allows you to look at a matrix of prices for flights departing and arriving +/-3 days from your preferred dates. This could be used as a fine-tuning tool once you have a ballpark idea of when you plan to travel.

Now, the tricky part is that the above tools are separate. And since you have to select the trip duration in Price Graph, you might be missing some dates with great prices. So at the very least play with the trip length in Price Graph (+/-2 days from your original duration) to see the full picture.

Aside from that, make sure to check if you can get to your destination with miles. If you’re booking in advance you might get great miles pricing and avoid spending much money on flights.

Choosing your travel dates and destination based on budget

If you’re open to traveling anytime and interested in going pretty much anywhere – this might be your approach. Or if you’re tight on budget but can be flexible with dates – this would work too.

And this one is at the same time easy and not – there are only two approaches that we know to work.

The first is combing through Google Flights. Select your departure airports, enter a continent (any), and go to the map. Once you’re in the map mode your initially selected destination continent doesn’t matter as Google Flights will show you prices for any airport that is within the map area. Set an upper limit for the price (along with any other parameters you care about, e.g. total flight duration, or the number of stops) and browse the map. This was the easy part. The hard one is finding a good set of dates – and there’s, unfortunately, no good way other than just playing with all the combinations of travel dates you might be open to – and repeating the exercise. It might be exhausting – but some find it almost meditation-like 🙂 You’ll never know until you try.

The second approach is still combing – but at this time combing through the deals subscriptions or websites (we outlined those above). If you’re using email to aggregate the deals, they usually have all the necessary information (dates and destination) in the email title – which makes it relatively easy to spot a good one that would work for you.

How to actually choose a destination?

Some people have a very clear idea of where they would like to travel, and they may have even had these plans in place for a long time. However, for others, the decision of where to go can be a difficult one, as there are so many destinations to choose from. For those who have already been to all the places they wanted to see, they may be looking for new and exciting places to explore. They could look into previously undiscovered locations, or they could try something completely different, such as a different type of holiday or a different mode of transportation.

You can always let the randomness of the world choose for you. When you are not sure about your destination – and regardless of whether your dates are locked – just wait for the next flight deal to a place you haven’t been to. Double-check if it fits your criteria (on budget, safety level, or type of the trip) and book it right there. That might simplify the process a bit, especially if your bucket list is the entire world – though it gets more and more rare to find deals once you have traveled a lot.

Another option is having or maintaining your bucket list – and choosing from the destinations on your list every time you plan a new trip.

You might have a note or a doc somewhere to list the destinations you hear about that you are interested in. See a great place on Instagram? Add it to the doc. A friend mentioned having a blast during their last trip? Add that destination to your list.

Sometimes you have themes that might help you choose the destinations too. Knowing that our older daughter Christine is a big ABBA fan, we have planned trips around her birthday specifically with that in mind – first was to the island of Skopelos in Greece where Mamma Mia movie was filmed, and the second one was to Sweden, the birthplace of ABBA, and followed up by an ABBA concert in London (just a short hop from Stockholm)

Or just get an existing list. It could be just a list of all countries on the planet. Or all National Parks in the US. Our favorite one that we often use as a source of inspiration is the “Ultimate Travel” list from Lonely Planet. Another good one is “Destinations of a Lifetime” by National Geographic. Both are available as books – and we suggest getting one to keep on your coffee table so that you can always dive into the travel mood!

Surprise travel

Surprise travel is a great way to inject a bit of excitement into your life. It involves a spontaneous trip, with no advanced planning, and can be a great way to experience a new destination and culture. A surprise trip can involve anything from a weekend getaway to a longer vacation.

It is a great way to get away from the stress and monotony of everyday life, and can be a great way to surprise a loved one. It can be as simple as planning a few days away and not telling your partner until the last minute, or it can involve a more elaborate surprise, such as planning a surprise destination and activities.

How do you organize that?

Well, the easiest way is for one member of the family to organize the trip by themselves. We’ve done that multiple times – last year when we went to Bora Bora – Roman only told us to pack for a beach vacation and we only found out the destination when we came to the gate at the airport. Same way Roman and Natalia traveled to Mexico City couple of years ago – Natalia didn’t know the destination until the very end. The Mexico City trip showcased another interesting aspect of surprise travel. One of the experiences Roman booked was the hot air balloon ride, and Natalia admitted later that she would have never agreed to that if she was asked.

If you want it to be a surprise for everyone – you can hire specialists who would do it for you. We’ve used Pack up + Go once and were very satisfied with the trip they planned (Mom and daughter long weekend getaway that ended up being in Houston).

Pack up + Go can offer a variety of options: from short weekend getaways to full-sized longer trips, they could plan a road trip for you, or even a staycation to experience your hometown in a new way. To book a trip you will have to answer a questionnaire, and then few days before the departure date you will get an envelope from them containing all the details. Ideally you would open the envelope as late as possible so they would also send you a weather forecast at your destination few days before the trip starts so you can pack accordingly.

Another reputable company offering surprise trips is Surprisit. They offer trips across US, Canada, Caribbean, or Europe.

Most travel agents and agencies would happily take on a challenge to book a surprise trip for you as well. This might give you a more tailored experience, but obviously will come at a higher price.

Chapter 2. WHO (is traveling)

Determining who is going to travel is an equally important part of the planning process. This may affect your decisions regarding the WHEN and WHERE, so you may need to reconsider those steps after this one. The default option here is your entire family – so we won’t really cover that part.

1 Parent – 1 Kid travel

While not 100% “family” travel, going on vacation with just one parent and one child can be a wonderful and rewarding experience. It allows for quality bonding time with just the two of you and gives you the opportunity to explore new places and experiences together. Depending on the age of the child, there are many fun activities to explore and enjoy. You could go to the beach and build sandcastles, explore a new city and take in the culture, or take a hike in the mountains. It can be a great chance for the parent and child to make memories that will last a lifetime.

It is important to ensure the child is comfortable and happy during the trip and to discuss with them any plans or expectations in advance. If possible, involve the child in the planning process, so they feel a part of the experience. This can also be a great opportunity for the parent to teach their child about safety, responsibility, and independence.

Or, instead, you can make that a surprise trip for the child. If you are absolutely sure of some place or experience they would enjoy, you could plan it without telling them a thing and just let them enjoy the moment!

The most extreme option is when both travelers have no idea where they’re going. Roman once planned a trip for Natalia and Christine (with the help of Pack up + Go) where they both didn’t know their destination until they opened an envelope with a printed trip plan in the taxi on the way to the airport. To pull that off you need to know the travelers’ preferences better – so be careful with this as you might end up taking too many risks 🙂

Solo parent travel

Even though this would technically not be a “family” travel in the way we’re usually talking about it – it is an option worth considering every now and then. After all, parents are people too, right? Having a trip that is just about the two of you, and not having to deal with diapers, or tantrums, or moods (depending on what stage your kids are at) is a great opportunity to unwind and replenish your parenting powers.

You could choose your destination the same way as you would do when traveling with kids, but when the trip is just for adults there are few other options that get “unlocked”:

Adult-only resorts. It doesn’t have to be Hedonism – but if your goal was to take rest from the craziness of life with kids then you might choose a place where even other’s kids won’t be present
Destinations with tougher conditions. Extreme cold or altitude, trips involving long hikes or any other type of strenuous physical activity – anything that you’re not ready to do with your kids.
Destinations that might not be kid-friendly. Vegas is a great example for most people (though a lot of families make it work) – sometimes you might not want your kids to be around all the drinking and smoking and whatever else happens in Vegas.
Not-so-safe destinations. Again, everyone’s level of tolerance is different – so it’s up to you to define your safety boundaries. But there are places on Earth where each one of us might be uncomfortable traveling to with kids.
Convenience-related limits. We personally would probably challenge this the most and encourage you to #takeyourkidseverywhere but if there are destinations you want to go to and you’re not sure your kids would enjoy it a lot – consider going without the kids 🙂

Choosing or finding travel partners

When we talk about family travel we might not necessarily limit that to just one family. Traveling with family friends makes it more fun especially if the kids in another family are friends with your kids. It also is a great way to make your vacation more affordable as you can split some of the costs (group tours often have a flat fee, ½ of a price of a bigger AirBnb is usually lower than the entire price of a smaller AirBnb, etc).

Now, you might have some friendly families who you often travel with – then you might even do the entire planning together. Depending on the respective families’ travel habits and histories it might be easy – or might be not. In cases when both (or more, if there are more) families agree on the dates but not necessarily destinations – you could either alternate the choosing party or split the trip in half and let each one direct the entire travel crew during their part of the trip.

The second option – plan (or start planning) a trip and invite other families. You could do that before you book anything, or maybe after you booked the tickets. Sometimes you might find great travel partners that way from the friends you have never traveled with before and maybe never discussed it. Just blast anyone you might be interested in traveling with a message saying “We booked flights to X for the dates of Y, want to join?”. 99% will politely thank you but eventually, someone will agree 🙂

Or you might have more people in your extended family who would be willing to travel with you – cousins, grandparents, etc. This route is obviously different depending on how close you are with your family – both in terms of relationship as well as distance. But traveling together might present a chance to improve both. If you live far away from your family – consider meeting half-way for a reunion. If you want to get closer to someone in your family – invite them on a trip.

Finally, you can always ask family and friends if they know of any families looking for travel partners. This is a great way to get recommendations from people you trust, and it can help you find the perfect buddy family for your vacation.

Chapter 3. WHAT (actual planning)

Now, the “real” planning part. The planning of the trip itself.

Flights

We’ve covered the flight search quite a bit above, as part of choosing the destination and dates of travel. In short, Google Flights, using miles, and looking for airfare deals are your best friends here.

It’s important to know that there is no silver bullet when it comes to searching for flights. There are a lot of myths we want to dispel first:

There is no _optimal_ time to book.
First, Tuesdays are not the best days to book.
Second, generally few months before the trip is when prices are the lowest. But that is not guaranteed. So don’t wait if you’re ready and prices seem reasonable. They might go down or might go up. You will never guess
Third. There is [almost] no way to predict prices. Some services try to do that by making a guess. Maybe it’s an educated guess – but they can’t be sure. However, there are certain trends that repeat year over year so you might consider them – most major destinations will almost always have a sale once a season. Just don’t rely on that – it might not happen.

Now, you are looking for flights and have some set of destinations and dates you are considering.

Look for the award tickets first. That would be either with an airline you have miles with or if you have credit card points (e.g. Chase Ultimate Rewards or AMEX Membership Rewards) you might be able to transfer those to an airline of your choice. Award flights are usually cheaper upfront – but as with everything, that is not guaranteed.

Then look for deals. We’ve covered it above as well.

And then look for buying those tickets with your own hard-earned money. Google Flights and its friends (SkyScanner, or even Expedia) are good helpers here. Just make sure to set all the limits that are important to you but be flexible too. Consider multiple nearby departure airports or multiple arrival airports. Think about whether you want to have any stops – this one will greatly depend on your own and your kids’ tolerance of air travel.

Don’t forget about low-cost carriers. Some of them might not be listed on other websites (Southwest is a good example) so you will have to check those manually. Watch out for the fees very carefully though – that’s how these carriers make their money. If you’re diligent enough though – it could be a great option.

There are a few more complex approaches too

Complex approaches to flight search

Booking multiple parts of your trip separately. All the aggregators will usually offer you routes that can be purchased in one ticket (Google Flights can do separate tickets, but it’s not ideal). Time to think: where can you make a convenient stop? As an example: for flights from US to Europe that might be one of the major airports (London, Paris, Amsterdam, Frankfurt). Search for flights to those airports first, and then separately search for flights to your destination. But don’t forget about the caveats of this:

you need to make sure you have enough time between the flights
you need to make sure you can get from the arrival point to the departure point (they might be in different terminals or even airports)
Be aware that if your first leg gets delayed you are going to lose your other booking.

Go crazy with stops and airport changes. If you go to matrix.itasoftware.com (direct web interface for the booking engine Google Flights uses) you can have the ultimate flexibility of search. There are dozens of options that would be impossible on a traditional flight search engine. 2 stops, but first one not less than 120 minutes, not longer than 300 minutes, and only in London or Frankfurt? Sure, you can do that. Limit all that to only options where first flight is directly operated by either United or Alaska Airlines? Done. Exclude connections in France? Easy. Well, you get the point. Their help center is great at explaining all the options too.

There’s also a service called kiwi.com that searches for flights using all sorts of tricks mentioned above – but consensus among travelers and reviewers online is that you shouldn’t book with them as it might not work as they promise. It could still be a good discovery tool though.

One of the craziest tricks is booking so called “hidden city” flights. It’s not unheard of to find a situation where a flight from San Francisco to London would cost more (sometiems much more) than a flight from San Francisco to Dublin with a stop in London. So theoretically why can’t you book that Dublin flight and just leave the airport in London? You can, but it gets rather complicated here. If you skip that second flight, airline will cancel the rest of that trip – so you can only book one way. You cannot check bags as they will be automatically sent to final destination. And overall airlines really don’t like you doing that – so using this trick too often might get you banned. A website called Skiplagged is a great tool to find such deals.

Reminder: you got to be sure you know what you’re doing with the methods above. So proceed at your own risk – but also please share with us any great fares you find!

Route

Once you know your general destination, how do you choose where to go exactly?

Sometimes it’s obvious (going to a resort and going to stay at that resort the entire time, or it’s a long weekend trip to a city and there’s no way you will have time to get out) – then you might skip this part.

Here are a few options you would want to consider

Must-see locations. List those first of all – as you must see them so you will have to put your route together including those.
- * Right after this first step do a reality check. Are you trying to do too much in too little time? General rule we recommend is not more than two (preferably one) activities or attractions a day, and at least two nights (preferably three) in each location if you’re moving around your destination. Repeat this step after every other step. And accept upfront that you might not be able to see all you wanted to see and do all you wanted to do.
Depending on where you’re going – decide if you are going to be staying in just one place (e.g. city) or you will move around the region, taking your trip duration into account. With some destinations, it’s more obvious (in Singapore you will likely stay in Singapore the entire time lol). If not obvious, you need to do some research.
- * (see above) reality check
A great way to research routes in the destination of your choice is googling. But googling for something like “itinerary in Italy” won’t help you much as most of the results you will get are going to be travel agencies and booking websites advertising. Simple trick we use is adding duration (you can play with it – if your duration is 7 days you can google for 5 days and 10 days too), but also adding “+blog” at the end of your search query. “10 day itinerary Italy +blog” gives you much more relevant results than “itinerary in Italy”, try it!
Now open as many of those search results as you have time to, and read them. Or if you’re lazy – stop at the first one you like and just follow it – that would work too. We’re usually planning quite a lot so we might look through dozens of results before proceeding. General approach is to start a Google Doc with specific locations and collect notes on each of them. So since we started with Italy as example, you might have Venice, Rome, Sorrento and Cinque Terre as your locations. Try to overshoot at this point to have more wiggle room later.
Once you’re done with browsing all the search results you will likely have an idea of your itinerary
- * (see above. yes, again) reality check
This part of planning is the most creative one where no single best solution exists, so you might go back to the beginning few times as you change some parts of the plan. Just be ready for this 🙂

The algorithm above is universal but could be very time-consuming. You could usually take shortcuts by identifying (or knowing) top destinations around the area you’re traveling to, so you could quickly have a draft itinerary by dividing your trip evenly between those destinations.

Don’t forget that this is not final until you go through the next steps in planning anyway. So just get to the point where you feel like it’s a good start, and let’s continue to figuring out where you’re going to sleep 🙂

Accomodation

By this point you have (at least the idea of) your flights and your route, so it’s time to know where you will live during your trip.

Even though for ourselves we’re almost always recommending AirBnb, the choice is not so simple sometimes. In general, you have two general options: Hotels or AirBnb.

Let’s look at pros and cons for both:

Hotels:

Pros

More integrated experience (breakfast and restaurants in the same place, room service, gym, swimming pool etc)
Potentially more central location
Concierge support, baggage service, housekeeping
Easier to get to and from
Guaranteed room quality (you get what you pay for)
You can book with points or earn points for your stay
Easy to cancel without penalty

Cons

Might be pricier for a family as you would need two rooms or a suite. You can try living in a single room with 1 kid, but then none of you have privacy or space for parents to hang out after kids go to bed (we once had a parents party with friends in a large bathroom of a hotel)
In the case of two rooms might be hard to have connecting rooms. In Europe and Japan we’ve seen many hotels that don’t have that option at all.
Cookie cutter rooms, rarely a chance for the rooms to be too interesting
In most cases no kitchen to cook in
Noise. Much more likely to hear other guests than in an AirBnb

For you to decide (it’s a pro for some while a con for others)

You will see and meet other people. A lot 🙂

AirBnbs