9 Top Tips from Travel Writers for Stress-Free Last-Minute Vacation Planning

Instead of months of grueling, high pressure planning, spontaneous trips allow vacationers to stay more in the moment and explore at their own pace. Free of strict timetables and lists of tourist attractions, travelers open themselves up to new opportunities and unique encounters that they otherwise might have missed. To ensure you can enjoy the perks of spontaneity with as little stress as possible, two of Islands’ seasoned travel writers have shared their top tips for putting together trips with little warning. Kristi Roe-Owen has drawn on her many years of impromptu traveling with kids, while Tess Kazenoff has weighed in with her favorite strategies for keeping costs low when booking transportation and accommodations on short notice.

Kristi: Vacations with our family of five can be just a little chaotic even when they’re carefully planned out. And with our family’s busy schedule, that’s not always a luxury we have. Between school, work, and various other obligations, we’ve had more than our share of last-minute vacations from short-notice Disney World trips that put our airport parenting skills to the test to a long list of impromptu road trips through just about every stage of our kids’ development. In many ways, I’ve found that traveling last minute can serve as something of a teamwork endurance test for a family.

Tess: Last-minute travel can be pricey, but if you’re flexible, it’s surprisingly affordable — and often less stressful than you’d think. Over the years, I’ve taken a number of last-minute trips, and always on a budget. These are the strategies I incorporate to find the best deals without sacrificing too much comfort and still having an amazing travel experience.

Tess: When it comes to trip planning, most people start with a destination already in mind and then go from there. But if you’re up for some extra spontaneity, try starting with the best flight deal instead. There are plenty of flight deal tools, but I mostly use two free favorites: Google Flights and Skyscanner. Both allow you to see all the best flight prices across the world.

I also follow lots of airlines on social media to stay up-to-date on any sales, which has allowed me to purchase a number of last-minute flights. Additionally, you can sign up for travel newsletters (Going and Thrifty Traveler are two to check out) to get alerted about deals as soon as they pop up. Sometimes airlines have “mistake fares” that go away within hours — so if you have the flexibility, jump on these deals to travel on short notice for less!

Tess: When time is short and flights are expensive, picking destinations where the dollar goes further can stretch your budget without extra effort. This is how I was able to start traveling in my late teens and early 20s when I didn’t have much expendable income at home in the U.S., and it’s how I continue to make the bulk of my travel decisions today. I’ve found that you just end up with so much more flexibility when it comes to accommodations, dining out, and travel experiences, which just makes for an all-around more memorable — and less stressful — trip.

Plus, there are so many amazing vacation possibilities where the U.S. dollar goes far. Some of my favorite trips have been to places like Brazil, Argentina, Mexico, and Thailand where you can make your dollars stretch to experience more for less. All of these spots have a ton of culture, delicious food, incredible nature, and interesting cities, and are generally far more affordable than places in the U.S. or Western Europe. It’s necessary to note that when traveling to more budget-friendly destinations, please be mindful of local communities and the dynamics at play which impact affordability. Often, a place isn’t nearly as affordable for locals as it is for foreign tourists, so it’s always important to be respectful of this.

Kristi: I’ve never gone wrong overpacking and overplanning for my kids’ comfort on any vacation, especially when we’re planning it on the fly. Anytime you’re pulling together a last-minute trip, there’s a good chance you won’t get a lot of time to lock down every detail, which can mean having to navigate where to eat or what to do next on the fly. And the last thing you need while you’re trying to iron out your plans for the day is a roomful of bored or hungry kids underfoot.

And it’s not just about keeping everyone distracted while the grown-ups talk — it can also be really good for everyone’s morale to pack everything you need for chill time in your hotel room. Taking time out for a midday nap or even a do-nothing day can go a long way when it comes to preventing crankiness from setting in and giving everyone the opportunity to be emotionally and mentally present.

For all of those reasons, packing a chill bag is one of my favorite last-minute vacation tips for traveling with kids. When they were little, that might mean bringing noise-canceling headphones and a few favorite toys. Now that they’re teens, I pack items like trivia cards, art supplies, and plenty of easy grab-and-go food like granola bars and fruit snacks. Every kid also brings a personal “on-the-go” bag or backpack with their favorite comfort items, books, and treats.

Tess: Travel insurance can feel like an annoying extra cost up front, and it’s something I didn’t think to do on my first few international trips. But when I had traveled enough times to have a thing or two go wrong — which is a possibility every time you set out — I knew I had to change my ways. I now make sure I get travel insurance every time I travel internationally. I always purchase coverage that encompasses all types of travel emergencies, from medical costs (if you’re abroad, your normal health insurance will typically not cover you) to flight cancellations and lost baggage.

So far, I’ve luckily only had to use my travel insurance twice. Once, I got COVID while in Brazil and needed to reschedule my return flight. A couple years later, due to a storm, my flight home from Guatemala was canceled right when I was about to board. I had to book a new last-minute airfare and a hotel room for the night.

Both incidents were some of my most stressful travel experiences ever, but a huge weight was taken off my shoulders knowing that I was covered and wouldn’t have to pay for all the medical costs, last-minute flights, and extra hotel nights myself. Of course, the hope is always that you don’t need to use it. But when it comes to eliminating stress — and possibly saving you thousands of dollars — insurance is a must.

Kristi: Traveling at the last minute can mean that everyone doesn’t get to do everything they want to on a trip. As the parent of three neurodivergent teens, I’ve learned that preparing everyone for what to expect can go a long way in terms of preventing disappointment and ensuring we remain on the same page. But even if you don’t have the neurospicy factor on deck, that seems to be true with most kids. Just taking a little time out to let your group know what you’re going to be doing — things like where you’re going to spend your time and when you will eat — can help reduce complaints and ease the stress of traveling without much notice, which can feel disruptive to some kids’ schedules and lead to irritation and anxiety.

I like to sit everyone down and review the full plan so everyone knows exactly what to expect, answering any questions they might have and taking the time to acknowledge and validate their feelings. Kids aren’t always great at understanding their own feelings, so try to read between the lines — sometimes what looks like pushback is simply a desire to check in with their friends or take a quiet time out. Our youngest kiddo tends to feel a little stressed and even anxious when plans change without much notice. But usually, just by setting aside a few minutes to set expectations, answer any questions, and read between the lines to check her emotional temperature, we have been able to assuage her concerns and get her hyped about our plans for the day.

Tess: To save on your last-minute flight and stress less about your trip budget, don’t limit yourself to flying out of your closest airport or taking a specific route. I live in Long Beach, California, so I typically depart from Los Angeles International Airport (LAX), but I always look for flight options from John Wayne Airport in Orange County as well as smaller spots like “America’s coolest airport” in Long Beach.

At the very least, always check out every airport within driving distance. If you’re not located near a major travel hub or you just want to take this tip one step further, consider reviewing airfare options from other major cities and flying there first. If you find a ticket that’s $400 cheaper from New York, for example, and it would cost $100 to fly to New York from your city, that could be worth it for you.

This is also an opportunity to add extra destinations to your trip. Maybe you want to go to Italy, but you find an amazing flight deal that gets you to Paris, and then you can take a cheap flight a couple days later to get to your final destination. Though I haven’t tried it yet, airline stopover programs even let you add bonus destinations without any extra flight costs. Copa Airlines, for example, will allow you to stop in Panama City for free, Icelandair allows free stops in Iceland en route to destinations throughout Europe, and Japan Airlines lets you add extra Japanese cities to your itinerary, just as a few examples. These programs are so cool, and I can’t wait to try them out.

Kristi: Our family loves impromptu summer road trips, and we’re lucky enough to live near Route 66 where there are tons of unique little Roadside America stops to check out. But one of the biggest pitfalls we’ve run into when we take these last-minute drives is blowing our budget on dining out. With a family of five where even a stop at McDonald’s can easily run upwards of $30, dining is one of our biggest travel expenses.

And even when your budget isn’t an issue and you’re fine with doing full-service meals throughout your trip, all of that dining out can start to wreak havoc on your digestive system after a few days. It’s something we experienced too many times when my mom used to generously treat our entire family to Disney World buffets. Don’t get me wrong — I love Disney dining. But dinners out tend to be heavier than most of us eat in our regular everyday lives, and frankly, all of that dining out can really start to sap the enjoyment out of what might otherwise be truly special meals.

As our crew has gotten older we’ve started to embrace hotel room dining, bringing a collapsible cooler to fill with simple, healthy items like sandwich supplies and yogurt. This keeps everyone feeling better and saves us from blowing our food budget. And in the era of grocery delivery services like Instacart, it’s a perfect solution for families who don’t have a lot of time for trip planning. Just pack your cooler, then hop online while you’re en route, place an order, and have food ready to go for your hungry crew as soon as you’ve arrived at your room — no dinner reservation required.

Tess: Using points and miles is my new favorite travel hack that I’ve only really gotten into in the past couple of years. But just through my normal spending, it’s already gotten me a week-long hotel stay in Mexico City’s vibrant downtown, the cutest boutique hotel in Antigua, Guatemala, and a beachside stay in the iconic California beach town, Santa Barbara, not to mention some flights to the East Coast to visit my family. Keep in mind that this isn’t the simplest tip. It takes some research to choose your credit cards, some strategy to most effectively earn points and utilize them, and time to earn the points you’ll need.

But ultimately, it’s 100% worth the extra effort required. While which card is best for you depends on lots of personal factors like your spending habits, I recommend starting with a card that has flexibility — meaning you can transfer points to a variety of airline and hotel programs. And although you can typically find the best deals when booking further out, you do occasionally stumble on a great last-minute option through partner airline and rewards programs. But if nothing else, you can use your points and miles to save a ton of money on your pricier last-minute flight, or on your hotel stay. This has been the biggest game-changer for me, and can help eliminate stress over paying for your impromptu vacation.