Gone with the Grins

How to Plan a Family Trip

Here are the tips, tools, and apps you need to plan a vacation.If the thought of planning a family trip to an unfamiliar place makes you break out in a cold sweat, you’re not alone. That’s why they make travel agents, after all. Like a lot of people, I’ve gone that route before, and while it was certainly easier, I never felt like I had any real investment in the trip before it came time to hustle everyone onto the plane. (Monetary investment, definitely… personal investment, not so much.)

For those of us who remember life before the World Wide Web, I can tell you, planning and executing a trip now is a breeze compared to the Dark Ages of, say, the 1980s. It just takes time and perhaps a laser-focused, Type A personality. Guilty, as charged. In the end, you’ll probably come out ahead financially, you’ll have more control over your flight times and itinerary, and become so much better acquainted with your destination in the process. (I highly recommend that at least one adult brain in the group contains all this big picture stuff.)

If that sounds like your kind of fun, fire up a search engine, and follow these 10 steps that will make it easy to plan a family trip all by yourself. 

#1: Choose Your Destination

It may seem obvious, but the first hurdle is to figure out where you want to go. Then you can tackle when you can manage said trip, and how much you can afford to spend. Have a family powwow and answer questions like…

  • What does everyone like to do? City sightseeing? National Parks? Lazing on the beach? Cruising?
  • What destinations & activities are on your bucket lists? Niagara Falls? Disney World? Skiing in the Alps? Legoland?
  • How much vacation time do you have? Even if you only get 10 days a year, a week in Costa Rica is better than the other 50 spent at the office. 
  • When are the kids out of school? Yes, it is always crowded during school breaks, but if that’s your only choice, find out which places are a little less popular and go there. See what we thought of our Spring Break visit to Universal Studios Orlando instead of that other park.
  • How far do you want to go? Do you have the time or inclination for an overseas flight or would you rather go some place a little closer?
  • How much culture shock can your family handle? Think about language barriers and picky eaters.
  • How much will it cost? Remember, plane tickets will probably be your single largest expense, but they are usually bought and paid for much earlier in the planning process. Food, lodging, and other transportation costs often come due after you get home, which helps space out the financial hit.

#2: Research, Research, Research

Now that you have a place in mind, plant yourself in front of a computer and start Googling. Find out what there is to see and do, what the adults will like, what the kids will hate, and how much you can afford to blow on, say, a whale-watching tour. You can also…

  • Watch videos.
  • Listen to podcasts. (Rick Steves has some great ones for Europe.)
  • Haunt the travel forums if you have specific questions.
  • Buy a few travel magazines.
  • Request brochures.
  • Maybe read a book or watch a movie set in your destination of choice.

#3: Buy a Guide Book and Map

Now that you’re familiar with your location, pick up a guide book on Amazon or Half Price Books. Besides the obvious tourist draws, most of them also dedicate at least the first chapter to things-you-really-need-to-know like the weather, currency, departure taxes, rules of the road, and maybe a little history thrown in for good measure.

I especially like the ones that include a pull-out map. Even with all the gadgetry available for trip planning these days, nothing quite beats a good ol’ paper map that you can spread out on the floor and sticky note to death while you’re trying to figure out how to do everything you want in the time you have allotted. (Google Maps will also let you do this virtually. Simply “Save” each potential location and little stars will appear, marking all the spots you want to see.)

#4: Plan Your Route and Make An Itinerary

Which brings me to task Number 4… using that map to plan your sight-seeing extravaganza. Some things to consider…

  • Estimate how many days it will take to see all there is to see in each destination. Then use Google Maps to determine how long it will take to travel between locations, whether it’s by car, train, bus, bicycle, rickshaw, or plane.
  • Pick the most reasonable airport to fly in and out of. It’s usually cheaper to use the same airport, but sometimes it just makes more sense to start in one place and end in another, like we did on our California road trip.
  • Make an itinerary. I usually start with a simple Word document that breaks down each day with notes on lodging, possible activities, and travel time. It’s a constantly changing beast, and rarely looks the same post-trip. But it’s usually pretty close and a nice guide for our vacation days. Eventually I turn my itineraries into something like this for everyone’s viewing pleasure.

#5: Get a Fare Watch App

Once you’ve picked your dates and gotten time-off approval from your boss, add them to a fare watch app like Hopper or Skyscanner. You’ll get regular alerts about your upcoming dates and when they think it’s a good idea to book your flights.

If your dates are somewhat flexible, checking their recommendations against a site like Google Flights is a good idea to see if you can save money by leaving a day early or coming back a day later.

#6: Book Your Plane Tickets 

There’s no real magic formula for booking plane tickets. About the best you can do is look at fares often, get a feel for what they cost, and buy your tickets several months before your trip. CheapAir.com puts the prime booking window at three weeks to three-and-a-half months from your departure date on U.S. domestic flights. But even the absolute lowest fares can show up a full 11 months out. Bottom line… if you’re traveling with a family, in a limited time frame, AND you want to sit together, do not wait to get your tickets two months before you fly.

For flight comparisons, I use the big search engines like Kayak, Travelocity, and Google Flights. Then I head over to the airline’s website to buy my tickets.

(Speaking of plane tickets, if you’re traveling out of the country, this would be an ideal time to check your passports. The bigger lead you give the government to process a new or out-of-date passport, the better.)

#7: Reserve Your Lodging

Now that your e-tickets are safely tucked away in your in-box, it’s time to start researching and booking your lodging. Here are some things to consider… 

  • Do you like having a “Home Base”? Or do you want to move every few nights? How hard will that be on the kids? On you?
  • Do you want to cook? Do you love the idea of someone making you breakfast, or are you looking forward to shopping in a foreign supermarket?
  • Do you prefer the convenience of hotels? While they’re often the most expensive option, sometimes you can’t beat a hotel right in the middle of town. You might also earn rewards points, to boot. 
  • What about a family hostel? They’re not just for backpackers anymore. Read about the one we stayed at in Luxembourg. 
  • Or something even more unusual? Like a tree house or a luxury safari tent? If you can afford to splurge, these are the most memorable digs, for sure.

The choices abound, so finding the right fit for your vacation will take a bit of time. Some good sites to check include HomeAway, Hosteling International, Airbnb, and TripAdvisor.

#8: Arrange Your Transportation

Next on the list… figure out how you want to get around. Two adults with one amenable child can probably navigate short-hop flights and intercity trains with ease. But additional kids not only add to the expense, but the stress level, as well. If renting a car in your destination is relatively simple, get one. We’ve done it both ways, and have found that having our own wheels is really ideal for a family trip. Go where you want, when you want, and carry around all the snacks, jackets, books, pillows, blankets, and toys you want.

RentalCars.com is one of many U.S. consolidators. Europcar is popular in, you guessed it, Europe.

#9: Protect Your Investment

Let’s face it. Kids do crazy things. They jump, they fall, they break parts of their bodies. Even Weekend Warriors sometimes end up in the Emergency Room.

Seriously… think about buying some trip insurance. At the very least, get it just for the plane tickets. Most everything else (rooms, car rentals) can be cancelled right up to a few days before your vacation, at which point you’ll probably know whether you’re going or not. We’ve used Travel Guard before (though we’ve never had to make a claim… thankfully) which covers you whether you lose your camera or cancel your trip altogether — for very specific reasons they lay out in the fine print. Be sure to read it.

Check your credit card, too. The better ones offer some decent (and free!) coverage as long as you charge your trip to the card.

#10: Back Up Your Documents

Just in case you misplace your resort agreement or a pickpocket makes off with your Mastercard, take pictures of all your documents before you leave. Passports, health insurance cards, itineraries, train tickets, hotel confirmations, credit cards… keep them all in a Cloud-based storage system like Dropbox where you can access them remotely in an emergency. 

Aaaaand… that about covers the big stuff. See? That wasn’t so hard! Now stash all your documents in one easy-to-find place, pat yourself on the back for a job well done, and dream about tropical beaches or amusement parks or wherever you’re headed next!

If you’d like to see our past itineraries to Europe, Hawaii, Costa Rica, and Universal Orlando, click here.