5 Tips for Planning That Ever-So-Important First Family Trip 

Family times in Toronto, Canada

There’s little more rewarding than pulling off a successful family vacation. 

Although nobody wants to dwell on the “what-ifs,” there’s a lot that can potentially go wrong from temper tantrums and budgeting to simply being underwhelmed by your destination. And so planning that very first family trip can be equal parts exciting and exhausting. Because hey, that first trip only happens, well, once. Naturally you want to make it count, right? 


Relaxing at Sandbanks with my family in 2005

First-time planning might seem totally daunting, but doesn’t have to be. Granted you’ve picked out a destination and have done some homework already, it’s all about focusing on the fine details of travel and expecting any potential problems before they arise. As such, here’s a quick checklist to guarantee your vacation planning is on-point. 

Make Sure to Dress the Part 

This might seem like a no-brainer, but don’t forget to do a double-take of the forecast of wherever your destination. 

Will it be snowy? Are you prepared to layer up or dress down for a flight? How do you typically handle humidity? 

To ensure that you aren’t miserable, packing layered outfits is a smart move. Travel is a prime time to prioritize comfort over style, after all. 

But most importantly, if you’re going somewhere that’s going to involve tons of walking (think: NYC or Disney World), a proper pair of shoes is not something you can afford to do without. If you’re in need to some new kicks for yourself or your family, check out this Foot Locker coupon 

Choose Your Lodging Carefully 

Travelling families have no shortage of options when it comes to where they stay on their next adventure. 

Of course, you can find sweet hotel deals via sites like Hotwire. If you’ve never booked through deal-hunting services before, it might make more sense to book directly if you don’t want to get stuck somewhere with less-than-stellar amenities. 

AirBNB can be a cost-effective option, although you need to do some research to ensure that your temporary home is in a safe area and likewise nearby attractions you’re looking to hit up. Searching AirBNBs specifically for families can help narrow down your options. 

Dinner with my family in 2011 – all together.


Ideally, though, staying with a relative or family member is ideal for a first-time vacation given that you can pack lighter and save some serious dough in the process. 

Figure Out How You’re Going to Get Around 

Depending on where you’re staying, a rental car may not be necessary. This can save you some stress, but in this case you need to ensure that your transportation is reliable. 

For example, let’s say you’re taking a theme park vacation. Anyone staying on Disney property can take a shuttle from Point A to Point B and to the airport, but bear in mind that you might have to wait up to twenty minutes for them at any given time. 

Meanwhile, if you find yourself in one of the most walkable cities in the United States, you might realize that hoofing it is totally fair game granted your kiddos can handle the journey. 

Schedule Activities in Advance – But Don’t Overplan 

In terms of your day-to-day activities, don’t go anywhere without a gameplan. Sightseeing. Attractions. Restaurants. The list goes on and on when it comes to when you should have mapped out beforehand. 

But do note that overplanning can ruin vacations if you fail to leave wiggle room in your schedule. You should have some activities lined up on a daily basis, but not in such a way that you’re constantly trying to stick to a timetable. After all, you might be more inclined to just relax once you’re on vacation rather than constantly shuffle from attraction to attraction. 

Don’t Forget to Make Some Memories 

Lastly, don’t forget to kick back and enjoy your vacation.  

Of course, take the time to document as much as you can via photos and social media so you can cherish these moments. Just understand that vacations can be unpredictable and sometimes you just need to roll with the punches. As long as you’re spending quality time with your family, that’s what really matters, right? 

If you’re obsessing with making your first big family trip “perfect,” take a step back and relax. All you can really do is plan to the best of your ability, and these tips can help you do exactly that. No matter where you’re headed, this checklist is more than enough to set you up for a successful trip. 

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