Last Minute Trips to Anywhere: Finding the Best Deals

Shawn Forno

Have you ever awakened 45 minutes late for work? Your eyes pop open and your stomach goes cold. Your heart lurches into motion and pumps adrenaline through your veins. You are awake and alert in a way you never thought possible.

Now, have you ever thought to yourself, “I gotta get me some more of this?” If so, you might have what it takes to master last-minute travel.

I’m a huge procrastinator—always have been—(just ask my editor!) I can bang out a 20-page Chaucer retrospective the morning it’s due, slap together a set list on the way to a gig, and of course, I’ve packed for a six month around the world trip in three minutes while the cab to the airport is waiting in the driveway.

Whether it’s late bookings, packing the night before (or day of), or misplaced itineraries; we all procrastinate in our own ways when it comes to travel. But what about actually planning a trip—the entire trip—at the last minute?

What does same-day travel look like? More importantly, what does it really cost?

To find out, I packed a bag, grabbed my laptop, and headed to the airport. Here’s what happened:

Step 1: Pick a Trip, Any Trip

last minute travel
This first step of last-minute travel is actually a lot harder than it sounds. You have to make a very deliberate (some might say “foolish”) choice, and you have to mean it.

When people find out what I do for a living, all the trips I take, they inevitably ask (with a hint of whimsy in their voices), “How do you do it? How do you travel to so many places?”

To which I always respond (with a deadpan tone), “I think of where I want to go, then I buy a ticket.”

It’s always seemed pretty straightforward to me, but I understand not everyone is like that.

That’s the beauty of last-minute, or same-day, travel—whether you’re pulling the trigger and going to that wedding you didn’t think you had the money, or time, for, surprising an old high school friend on their birthday, visiting your mom on a whim, or just exploring a destination that’s been eating at you for years, the exhilaration of travel can only be surpassed by the instant gratification of traveling unscripted, unleashed, and at the last minute. Spontaneous travel feels like nothing else.

Inevitably at some point during the flight you will be hit with an overwhelming sense of accomplishment—bordering on self-indulgence—that goes something like this:

“I can’t believe I’m actually here! Six hours ago I was in my crappy apartment, now I’m on the way to Fiji. I.AM.IN.THE.AIR.ON.THE.WAY.TO.FIJI!!! I was supposed to work tomorrow. Oh well.”

Step 2: The Red Tape (Passports & Visas)

Last-minute travel sounds romantic—you hop on a plane and get whisked away to Greece. However, nothing can ruin spontaneous travel like passport and visa restrictions. So, here’s a quick rundown of the hangups you’ll likely come across when you travel at the drop of a hat.

Last Minute Visa Requirements

A lot of countries require a visa to get in. Crazy, right? You can’t just go to Russia or China, and if you try you’ll just waste a lot of money and time arguing at the airport.

For most travel visas you need a passport that is valid 6 months after your return date—not your departure date– not to mention at least 6 weeks of processing time for you passport to travel to and from the foreign embassy. For most people this isn’t an issue, but if you’re a long-haul traveler stringing one-way tickets together, the expiration date on your passport becomes a lot more relevant, and multiple visas can become a logistical nightmare. Make sure you give yourself tons of lead time and that you’re covered for the entire trip!

U.S. Territories & Disputed Areas: No Visa Required & VOA

If that all sounds exhausting, you’re right. The easiest way to travel at the last-minute is just to avoid the whole visa headache and visit countries that don’t have any visa requirements.

Dozens of countries across Europe, Asia, Africa, and South America have, essentially, waived the visa restrictions for American passport holders (for trips less than 90 days)—and others simply require a visa on arrival (VOA) fee. However, the holy grail of the last-minute travel game is U.S. territories, disputed countries, and partially recognized states.

Here’s a list of island nations that Americans can travel to visa free (Bold denotes U.S. Territories):

Traveling With a Damaged Passport

One final hangup that might surprise you is traveling on a damaged passport. Just minutes before I headed to the airport, heart set on Ibiza, I realized that my passport was severely damaged (I’d accidentally put it through the wash and dry a few weeks before). You can’t travel on a damaged passport.

According to the U.S. State Department website:

If your passport has been significantly damaged, especially the book cover or the page displaying your personal data and photo, you will need to apply for a new passport.”

Disqualifying passport damage includes:

Normal wear and tear—like bending and a little foxing on the edges—is fine. If your passport is damaged, the fastest way to get an expedited passport is to apply in person. If you don’t live close to these agencies, you can pay the passport expedition fee ($110), mail in your damaged passport and wait 2-3 weeks (expedited) or 4-6 weeks (standard) for the new passport to arrive.

Since I can’t get a same-day passport, it’s time to explore the good ol’ USA.

Step 3: Finding Your Flight

last minute travel

Once you narrow the field to visa-free destinations, choosing a last-minute travel destination is pretty easy. Odds are good that you’ve already got somewhere in mind, since most last minute travel is event driven (wedding, reunion, spring break), but there are a few great online tools to help you keep the trip from costing an arm and both legs. Here are the tools I use:

ITA Matrix

Have you ever used Google Flights, Expedia, Kayak, Hipmunk or one of a dozen other flight search engines? Then you’ve used the ITA Matrix.

last minute travel

Developed by some smart people at MIT, the ITA Matrix is the algorithm hell beast (aka “software”) that processes millions of pieces of constantly shifting travel data to power basically every flight search tool on the internet. The ITA Matrix single-handedly democratized travel overnight, yet no one really knows about it, mainly because the site looks like something of Geocities from 1997.

last minute travel

It’s just a boring screen where you enter search criteria and get prices. Open the calendar view—with prices 30 days from today. Data, information, output. MIT design at it’s finest. All those other fancy deal sites just skim the exact same data from the ITA Matrix and slap some user friendly design on the page. The information is literally exactly the same. In fact, most search engines that use ITA Matrix software actually omit a lot of budget or regional airlines, so the prices can be significantly higher.

The catch with ITA Matrix is that you can’t actually purchase the tickets there—it’s just a search tool. However, I still begin every flight search there because it’s the fastest, cleanest, most comprehensive way to find out how much a flight really costs.

Google Flights

Google Flights is a much more streamlined (aka pretty) version of the ITA Matrix that connects you with options to purchase your flight then and there—which is great. I get why people like it.

last minute travel

The coolest part about Google Flights is the “I’m Feeling Lucky” option—a throwback to their generic search—that lets you see select destinations based on a few simple filters like dates, stops, and price. Even if you’re not planning to travel, set your price limit to something low—like $500 round trip—and see how far you can go if you fly on the right day. I found a round trip flight from NYC to Dubai for $497!

It’s a great way to get the creative travel juices flowing and see that exotic foreign travel really isn’t as expensive as you think.

Priceline Express Deals

I tried a new booking tool for this last minute trip, and I’m actually pretty impressed with it. After searching through the Matrix (get it?) I was a little disheartened that last minute flights to Austin were so expensive—upwards of $650 for a quick 4-day trip. I could have tweaked my destination, but I wanted to see how cheaply I could get there so I turned over a few stones and discovered Priceline Express Deals.

last minute travel

Basically, this service lets you book a last minute trip (within 7 days of the purchase date) for a substantial discount—typically 50-60% off the lowest listed price. The only caveat, you have very little control over the time of day that you fly.

The way it works is that you enter your destination and dates, just like normal, in the Priceline search engine. Then, since you entered a date that is the same day, or within seven days, of your search; you’ll be presented with a Priceline Express Deal as the #1 result. The price should be significantly less than the next best price.

Click on it, and pick your flight window—typically 8 hours either from:

If you select a flight on the same day you’ll be given one option—after 5pm (unless you get up super early).

last minute travel

When you book the flight—and not before—Priceline will tell you exactly when your flight leaves (you don’t have to actually wait at the airport all those hours!). That’s the scariest part because you won’t have any control over the time you’re given until you’ve paid. You just pick a time slot that works and hope for a good flight time.

Pro Tip: Be packed when you book since you might get a flight that leaves really soon!

The upside is that Priceline Express Deals gives you a cheap viable option for last-minute flights, the downside is that you have a big departure window and you’ll most likely get stuck with a middle seat (I did on both of my flights), since you’re a last minute fare.

If you can live with that, you’ve got a powerful new tool in your same day travel toolkit!

Step 4: Last Minute Accommodation

The undisputed king of last-minute accommodation is Airbnb. There’s simply no contest.

The Instant Book feature on the site is amazing, easy to use, and combined with the vetted rating system, you can rest assured that your room will be available and ready to accept you with open arms no matter when you land.

I made my booking for Austin at the airport while waiting for my flight to board. It took a few seconds to see which part of town is the coolest place to stay with a bunch of walking options, and I was prompted to look at a lovely multiple 5-star rated “Urban Farm” right in the middle of downtown Austin.

I’m actually writing this article from my private room, next to a backyard with a bunch of chickens in it. It’s amazing, and I couldn’t have planned for a place this unique. When you travel last minute, serendipity is built in. It’s easy to “Keep Austin Weird” when you’re flying by the seat of your pants.

I’m paying $65 a night (plus service fees) for a 5-star rated private room in a great location (with free breakfast and bike rental). I could have easily gotten something else for half the price ($31 was the cheapest good option I found), but I’m fancy.

The prevalence of Instant Book and the reliability of the platform makes Airbnb my only real option for booking last minute accommodation.

Last Minute Packing Tips

Let’s be honest, you always pack last minute, don’t you? I thought so. Well, packing for a completely thrown together trip isn’t all that different from your normal “procrasti-packing.”

Pack in Layers

The key to comfort in any foreign clime is layers. Tank top + t-shirt + long sleeve + light jacket. Airplanes are either blazing hot or arctic freezers, so wear a few layers to stay flexible and comfortable on your flight.

Tank tops are my layer of choice if things get really warm, and it’s a great idea to bring one long sleeve button up.

Pashmina

Ladies, a pashmina does wonders on the plane and is one of the most versatile things you can pack. It’s a scarf, a blanket, a towel (in a pinch), and I’m gonna try to start the trend of men wearing them #pashminaman2017

Light Rainproof Jacket

As I already mentioned, a nice lightweight jacket is key to comfortable last minute travel. Barring my unisex pashmina, I always pack a light jacket in case things get chilly or rainy. It’s easy and usually worth it.

Boat Shoes

As always, I wear boat shoes to keep my carry on bag as light as possible (no extra shoes), while providing me with the comfort, style, and durability to walk the city streets by day and dance away the night.

courtesy Sperry Topsider

Boat shoes are a cinch in airport security (you’ve got a last minute flight to catch), and are great to kick off on the actual flight and let your puppies breathe. Yeah, I’m that guy.

Daypack

A light, easy to stow, daypack is a must. I love the Tortuga daypack because I can roll it into a tight ball in my carry on and use it for exploring.

Wool Cap

A wool cap is surprisingly versatile. It makes a great eye cover to catch some zzzs on the flight, it’s a great way to stay dry, or beat the windy chill if your destination gets cold, and I hang it off my belt to use as an extra pocket or impromptu daypack if I’m walking around town with a few small items and want to keep my hands free. Find a good one and you’ll bring it everywhere.

Bathing Suit

Always bring a bathing suit. Always. There is no exception. I would pack one for the moon.

Laptop

Usually, I bring a laptop with me, even on short trips. Because I work from the road I need mine, but for last-minute trips a laptop is a handy tool for anyone. Things can go wrong, your phone can die, your cell service might drop off, or any number of other things. Having a laptop handy for making last minute changes can be an awesome get out of jail free card.

Portable Battery Charger

Anker Battery Cell Charger

I always travel with the Anker 6700mH travel battery charger. When you travel last-minute, you’re going to be doing important stuff on your phone—booking a place to sleep, looking at maps, as well as checking your flight times and gate info. You really, really, don’t want your phone to die. Bring a fully loaded charger.

Last Minute Travel Apps

Now that you’re booked, packed, and ready to explore, here are just a few digital enhancements you can download to make your last minute trip a success!

Magic Seaweed Weather App

travel app

Yahoo Weather is a great basic weather app with reliable results and a 5 or 10-day weather graph, but if you’re looking for more detailed information like trends, ocean temperature, and offline maps, Magic Seaweed (a surfing app) is for you.

Tinder

travel app

If you’re single, there’s no better travel app than Tinder. Seriously. I used Tinder while traveling through Iceland to get recommendations for live music, cool bars, festivals, off the grid hot pools, and more. Make it very clear in your short bio that you’re just passing through and looking for a friend or some recommendations. Don’t ask for a “tour guide,” since it’s rarely an effective way to meet people.

If you play your cards right, you can have the ultimate local tour of a destination where you know no one. And all for free.

Podcasts

Power Trip Travel Podcast logo banner

Podcasts are freaking awesome (we even have one!). Aside from the obvious benefit of killing time on long flights, podcasts are a great way to get information about your random destination. Just search the city you’re going to, download a few episodes, and learn a few things before you land. Easy.

Spotify Discover

travel apps

Streaming music is great, but did you know that Spotify has a concert feature? Simply click on the Browse tab, select Concerts, and allow Spotify to use your location for a list of upcoming concerts in your area. You can also search through podcasts and radio for local playlists for a better understanding of the music scene wherever you are.

Facebook a.k.a. “Your Online Network”

The second I knew I was flying to Austin, I jumped on Facebook and texted a few friends looking for recommendations. Use your network and you’ll be stunned by how many options fall into your lap. I’m going swing dancing on Thursday, eating some epic bbq later today, and I’ve got a list of vintage shops that I absolutely “have to hit up.” All within a few minutes. The internet really is great.

Airbnb

Short of a network of friends, asking your Airbnb host for recommendations (or a quick look at their guidebook if they have one) is a great way to get the local tips, and is another reason why Airbnb is really my only choice for traveling last minute. The opportunity cost of looking up a hundred different things to do adds up and wastes your time.

Get the tips and get out there!

Focus is Key

The guiding principle for any trip, but especially a hastily planned excursion, should be focus. It sounds like a paradox to champion focus on a last-minute trip, but it’s key. You can’t try to do everything. Pick a topic and indulge.

If you want to see museums, take your time and enjoy them. Interested in the nightlife? Do a deep dive into the concert calendar and club scene for the best nights and locations. Want to vintage shop? Jump on the forums and find out where the best selection and deals are. Every city has something unique to offer, but you have to prioritize your time or else you’ll skip across the surface like a well thrown stone.

Narrow your focus. Don’t be a tourist.

TL;DR

Last minute travel can be intimidating and costly, but if you use the right search tools, prioritize your time, and reach out to find the right information you’ll have the most unexpected time of your life!

If you take a last-minute trip using any of the tips or tools above, tweet at me to let me know how it went. And, if you take a last-minute trip to New York, let me know. If I’m in town, we’ll grab a beer and I can tell you about that time I got stuck in a hurricane in Austin.

Photo Credit: RondellMelling, Pixabay