How to plan a family holiday like a pro is about putting into action all the things I have learned since I started traveling with my son full time 2 years ago. I have combined handy techniques with fantastic apps and websites that will help you plan a family like a pro.

How to plan a family holiday CHOOSE A HOLIDAY GOAL

Choosing one goal for your trip is the perfect way to ensure the perfect family holiday. With one goal in mind you can focus your search and really feel you nailed it when you look back. Writing down a priority each will work wonders in planning your perfect family holiday and in my experience avoids conflict and disappointment. Getting a tan used to be high on my list of holiday goals but planning the perfect family holiday must involve everyone. I have discovered that Oscar Chang can not sit and bake in one place but we do share a love of swimming, animals, wide open spaces and climbing just about anything. A simple goal like “to teach my kids to build sand castles” or something more adventurous like learning to surf are a great family holiday memory. Whatever your goals are, make sure your whole family is on the same page.

How to plan a family holiday RESEARCH YOUR DESTINATION

Whether you have a country or a particular activity in mind masterminding a perfect family holiday should involve lots of research. Research can not only show you the best a place has to offer, it can also help you avoid disasters. National or religious holidays, monsoons season or in my case even travel sickness. My first starting point is always good old Google.  When looking up tips for travel on the Huatulco to San Christobal de las Casas bus route in Mexico I noticed a few people mentioned travel sickness. I’m presuming the two sets of parents sitting behind me who “borrowed” all my wet wipes  on this particular 7 hour journey did not. Sorry gross story but you get my point. This isn’t my only form of research as it can be superficial if you don’t get past the first page. I also follow a ton of family travel blogs which I find particularly useful for handy children’s activities. If you have a special travel interest, guaranteed there will be a travel blog dedicated to it.  Other great research options are the big players like The National Geographic and The Guardian Travel. Recent additions to my inspiration station are AFAR and Monocle for more off beat destinations. I even dip into more backpacker orientated sites like Matador Network which I honestly think is excellent. The family travel community on Instagram is also huge and offers an opportunity for great personal insight, they all tend to be open to conversations and sharing great tips on where to go and what to do. I love Pinterest as a research tool too, so many writers, bloggers, and publications have a presence here it’s a great aggregator of all of the above. You can check out our boards from previous trips to Mexico, Croatia and more or our next adventure an epic American road trip. Of course, we have a bucket list too everyone should have one of those. Get your kids involved with the research too it can be a really fun activity for the whole family.


How to plan a family holiday RELAX

I have so many conversations that start with; “We want to go somewhere warm, but not too far away, it has to have a beach with sand and really amazing food, oh and Jim wants to spend a few days in such and such a city”. Ok. Well, all of those things sound amazing but are you going to produce a movie or have a family vacation? I know the way we are wired these days is to constantly have options and more choice and infinite possibilities but at some point holidays really should be about enjoying the simple things in life.  One person’s dream trip to a sunny beach is anothers idea of hell, with sunburn, sand and mosquitos thrown in as an extra horror.

How to plan a family holiday PACK LIGHT

This is such straightforward advice but oh boy this can make or break the “perfect family holiday” dream. If like me you travel alone with your child, packing light is everything. There is nothing more miserable than lugging too many heavy bags and a screaming toddler. It’s exhausting and lets not even start on the acupuncture bills. If you are traveling as a big family nothing is worse than lost bags and inflated excess baggage fees. I challenge you to find a location these days that doesn’t provide almost all the items you need for a successful holiday. I mean unless you are visiting a tropical island with no inhabitants. Ok maybe they don’t use Kheils products or wear contact lenses but within reason, many items are now available in your seaside location of choice. Part of the travel experience for me has always been to try some local products too. I still maintain the best conditioner to tame my wild curly hair was bought in El Salvador. I get it they are humidity experts. Consider your packing list carefully, do you really need beach towels for a family of 4?

How to plan a family holiday GET ADVENTUROUS

There is so much travel information available to the average traveler these days why not get creative and choose a holiday off the beaten track. When choosing a 4 generation family holiday traveling from the UK we decided on France as a destination purely for its proximity. Rather than choose a popular resort or busy tourist destination I chose the lesser populist town of Montpellier. It turned out being the perfect option. We didn’t jostle for beach space or restaurant reservations and our accommodation was affordable and exactly where we wanted it to be, in the city center. You can check out what everyone enjoyed in a little Montpelier round up here. For our next multi-generational trip we are taking a road trip. A road trip across America. The excitement this has generated in the planning process alone is making this holiday memorable before it has even started! Want to know where we are going? Sing up for our newsletter for more news.

How to plan a family holiday AGREE ON A BUDGET IN ADVANCE

The biggest expense every holiday has are flights and accommodation. Agree on this first. Make sure you stick to it and that everyone is aware of any additional costs. Having money for treats like a great family dinner at the local hot spot or an extra excursion to see some turtles makes holidays extra memorable. Bickering 3 Christmases later about who paid more for their room just plain sucks. If you are cooking family style gather a kitty together and work out a daily budget that everyone is happy with. The same goes for activities. Agree in advance what everyone can afford. No one likes to tell their kids “No you can’t go with uncle Peter on the fishing trip today, you’re staying with mom.” Make sure it’s everyone or no one.

How to plan a family holiday PLAN

Perhaps this should have been number 1 but then planning to the tiniest details is not my jam. What is important is planning the most important stuff.

Airport Transport – Nothing sucks more than rushing for a flight. Plan a route and a budget and get organized. This can make or break a trip as a family.

Book or bookmark a few restaurants – We use some fantastic app’s to both book or bookmark restaurants, cafes and most importantly pizza and ice cream joints. You may have other priorities, great seafood or vegetarian options. After a long day site seeing or soaking up the sun it’s a great feeling to have a booking somewhere especially in the school holidays when top spots are busy.

Organize your currency and budget – Of course, most destinations are now credit card friendly but not all. Arrange some local currency in advance so that you have cash when you arrive. When it comes to credit cards and travel there is so much choice out there now with banks offering no charges on currency withdrawals and credit cards with travel insurance included. I have been traveling with an American Express Platinum card for most of my adult life. Lounge access, Travel insurance and a concierge service for a small fee. Choose what works for you but always make sure you let your bank know you are traveling to avoid temporary blocks.

How to plan a family holiday BE SAFE

VACCINATE –  Oscar Chang has been vaccinated on 3 continents and we have had to visit a doctor exactly twice during 2 years of travel. Ironically both times were during down time in the UK and here in Berlin.  It’s important to follow the latest outbreaks and updates, I always check the WHO website for worldwide warnings and vaccinations.

INSURANCE – No ifs or buts. If you want the perfect family holiday. Buy great insurance.

COPY DOCUMENTS – I copy my documents in three ways. I save them in a cloud such as Dropbox, I save them on a USB stick and I photograph essentials on my phone. This way even if the very clothes off my back are stolen I can go to an internet cafe (trust me, they have those everywhere now!) log into my remote storage and print a copy. I also copy those essential numbers to cancel all my cards on to a document and save it in my remote storage.

How to plan a family holiday SHOP AROUND

There are a so many ways to budget, save, hack and scam your way to a cheaper holiday but who has the time! I try I really do but I can safely say that the sites below have kept me feeling like I got a great deal. In all seriousness though being creative about your planning can really help. Choose destinations that aren’t always the big names. There are so many beautiful places to discover in the world. The Four Seasons and Biarritz will be there when you have the budget don’t worry. We spent 3 months in Croatia last year but explored the lakes and waterways rather than the overpriced beaches. We also visited Montenegro, Croatia’s less explored yet equally stunning neighbor. Consider housesitting over hotels, or even a family home swap. I chose Airbnb 9 out of 10 times over hotels. Choose from 100’s of family-friendly homes and soon to come home swaps on sites like Kid and Coe.

How to plan a family holiday ASK FOR ADVICE

A few weeks ago I met up with some mom friends and we talked about travel and holidays. As the resident nomad its hard to avoid the subject! Two friends who had known each other for a long time admitted they had gone to the same destination without actually asking one another any tips or advice. What a shame they agreed, they could have solved so many little problems. You would be surprised how helpful family travel bloggers can be. A message on Facebook or a post on Twitter or Instagram will pretty much always elicit a response from either the writers themselves or a helpful member of the community. Families who travel can’t wait to tell others all about it, they want to encourage people to travel more and are surprisingly relaxed about sharing the most awesome tips! So just post a comment. Go on, give it a go below 🙂

How to plan a family holiday  TOP RESEARCH SITES.

TRIPADVISOR – Not sure what we did before this came along. Check what’s popular in any world destination, from accommodation to attractions this is by far the most contributed to network.

PINTEREST – Guides, Maps, Tips and Experts all in one place. A great aggregator for destinations and hobby,s. A fun way to inspire the whole family.

INSTAGRAM – The experts are here and they are sharing their tips and favorite spots every day. Most are responsive too so advice can be easy to come by on this great app.

THE GUARDIAN TRAVEL – Consistently well-written content with some great and original family-friendly destinations.

AFAR – Great and original content. One of the best Apps too.

MY TINY ATLAS – Beautiful photography to get you inspired. Small but perfectly form online magazine.

How to plan a family holiday FLIGHTS

SKYSCANNER – Flight comparison sites are truly fantastic, what I love about this one is the option to check out an alternative airport too. The flight alert newsletter is really good too. Lots of savings here.

KAYAK – Much like Skyscanner but with the added bonus of searching some budget airlines too.

DIRECT TO AIRLINE – Dont forget to check the airline web site too. Deals are to be head exspecially with upgrades and points.

Seat Guru – I would be lost on long-haul without this site. We have scored great leg room, bulkhead seats aka play area and yes when you fly with kids ever extra inch of space matters.

The Points Guy – The messiaha of point hacking. I love to read this site even when I’m not thinking about using points. So well researched and the reviews are honest and helpful. The airline nerd Narnia.

How to plan a family holiday ACCOMMODATION – Don’t overlook this ugly looking site. They list apartments too which are a fantastic alternative to hotels. I have rented some of the nicest places on here when I have been in a jam. The choice is vast.

Airbnb – A fantastic alternative to hotels. You may get the opportunity to meet a particularly knowledgeable local or discover a historical home. Use our link to get a 25% discount on your next booking.

Agoda – Although Agoda now offers booking for accommodation worldwide it’s particularly good for the Asian market. I used it all through Japan, Thailand, and Cambodia with excellent results. The awards points are a really nice bonus too!

Kid and Co – Wonderfully stylish family homes to complete your family holiday experience. This will keep your luggage to a minimum with homes fully equipped for the little ones.

Sabbatical Homes – If you’re a teacher and looking for a house swap for the entire family holiday this is your savior. I have been recommended this site many times, now I just have to get a teaching job!

Trusted Housesitters – Can you imagine a holiday with totally free accommodation for the entire family. If this is your dream then this is your site. House sit, discover how people live and save masses of money.

How to plan a family holiday JOIN AND SAVE

SECRET ESCAPES – If you’re looking to holiday like a family in style but at a fraction of the cost sign up asap. I love this site, the international content is excellent.

VERY CHIC – Another sign and save site with exceptional hotel deals in some top international destinations. Paris, Milan luxury with huge savings.

TABLE HOTELS – The original lux hotel saving site. The newsletter is well worth the sign up for some stylish mega savings on hotels.


My Well Traveled Friend's guide to the perfect family holiday

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