How to Plan a Stress-Free Vacation as a Military Family

So you want to plan a family vacation? Great! What’s the problem? Oh, you’re a military family and have no idea what your schedule looks like for the next 6-12 months because the squadron, manning, and operational tempo is constantly changing. I get it. I think a lot of us in the military community have been there a handful of times. A lot of travel clients of mine serve with the military in some capacity, and a common question is, “how to plan a stress-free vacation as a military family?”

What if I told you I’ve cracked the code on how to plan a magical vacation for your military family and keep it stress-free?

Here are my top five tips & tricks to do just that:

1. ALWAYS LOOK FOR DISCOUNTS

I refuse to buy or purchase ANYTHING without first seeing if there is a discount code or promotion out there. Chances are, there is. The same thing goes for travel, especially as a military family! Now, the goal isn’t always to find “the cheapest rate” because, let’s be real – sometimes the cheapest = low quality. Military discounts are available for many different types of travel destination, and using those discounts can help you and your family afford a better quality vacation at a lower price point! Read my blog post all about, “Military Discounts for Your Next Disney Vacation,” for more details.

2. STAY FLEXIBLE

A phrase we have heard all too often as military families, “don’t make plans, things could always change!” Ain’t that the truth! We don’t get the luxury of planning 6-12 months out, so make sure you manage expectations and assume the “No Plan, Game Plan” (as my pilot husband likes to refer to it.) If you see a chunk of free calendar space, keep an eye on hotels, airfare, and your military member’s schedule. Write down a list of a few different options so that when the time comes to book, you aren’t disappointed if you have to modify or significantly alter your big travel plans!

When booking travel, always make sure to look at the cancellation and reservation modification policies (and read their fine print) before putting any money down. You’ll want to make sure that you have the absolute best chance of making changes with little to no penalty should your service member’s schedule change last minute.

3. BOOK DIRECT AND CONSIDER TRAVEL INSURANCE

A lot of the big vacation package deals can certainly be appealing, especially if you want to book through a third-party supplier. I always recommend booking directly through the travel supplier (theme park tickets, hotel room reservations, cruise itineraries, etc.) to have one line of contact should something go awry. Most of the time, the policies for modifications & cancellations are lenient with military members, especially if leave is recalled or if your service member gets called to last minute duty or deployment.

If your family decides to book through a third-party supplier, please consider purchasing travel insurance. Typically you can purchase the travel insurance offered through the supplier, but another option is to look at a secondary supplier like Allianz or even through USAA! Travel insurance will cover the cost of your trip for delay or cancellation, but also in the event of a medical emergency or even severe weather that could affect your vacation! Honestly, if the past few years in the travel industry have taught us anything – buy the travel insurance!

4. GET CREATIVE WITH YOUR BUDGET

Most travel suppliers often times offer the ability to pay off your vacation over time leading up to your actual trip! How nice is it that you can arrive for your Disney vacation, cruise or relaxing all-inclusive getaway with not a single penny left on your balance due?! Research these options before making your deposit, as a payment plan is not always available. You can also develop a savings plan 6-12 months before your vacation to set money away so that when the balance finally is due, you aren’t stressed about paying it off right before your trip.

Another tip I like to share is purchasing discounted gift cards when you see them on sale! Did you know that you can use Disney Gift Cards towards the total cost of your vacation? Did you also know they go on sale at Target from time to time? I just gave you my secret roadmap to getting a Disney discount without hunting the Internet for one. You’re welcome!

5. WORK WITH A TRAVEL AGENT

I know you have a lot of choices when it comes to your vacation, but working with a travel agent isn’t as archaic as it used to be. Some of us may even remember our parents making appointments with the local brick & mortar travel agencies in the 80s & 90s to book vacations. Note to self: it’s not like that anymore!

Enter, a travel agent specializing in Disney, cruises and luxury vacations beyond the theme parks! A modern, virtual, personal travel assistant to help you with everything you need in order to plan your next vacation and keep it stress free. Have you figured out by now that I am one of them?

When working with a travel agent as a military family, make sure you hire someone who is well-versed in travel for military families! There is nothing worse than working with someone who is a travel expert, but not familiar with the unique challenges the military community faces. A travel agent is your point person to adjust your travel plans should you need it, while you focus on the home front. Rapid deployment orders came through and your stuck figuring out if, how, and when you’ll get to actually take your vacation? No worries. A travel agent (like me) specialized in working with military families will handle everything while you worry about more important matters, like getting your service member and your family ready for what is sure to be a stressful and emotional change for everyone. I’ll handle the trip – don’t worry about it!


The military always keeps us on our toes, but with the right strategy and the right game plan, you won’t be asking yourself how to plan a stress-free vacation as a military family, and instead you will be able to just do it! Use these tools, and onward you go! I hope you picked up a few tips & tricks along the way. Better yet, reach out to me if you’re interested in working with a travel agent. As I always say, “Travel is on the horizon, and the magic is just beginning…


*This post is an excerpt of a larger piece originally written for the Wives of the Armed Forces Blog – you can read it in it’s entirety here!*

Similar Posts