I woke up and booked the cheapest same-day flight out of the country

What if you woke up and bought a same-day flight without knowing your destination?

For years, I’ve had a tradition of leaving the country for my birthday. One day, undoubtedly, I will take this up with a therapist and not my preferred airline. As with many things, the pandemic abruptly put an indefinite pause on this birthday ritual, but with travel now back, I was keen to buy myself a birthday present: a round-trip ticket to anywhere.

What I was craving above all else was a stomach-dropping sense of serendipity, a trip unburdened by an overwrought itinerary. Even though international travel has returned, it’s not without its complexities. It’s expensive, and travelers often book far ahead and budget carefully to score the best deals on flights, hotels and even rental cars — which can still be notoriously pricey compared to pre-pandemic rates.

Suffice it to say, as my birthday approached, I hadn’t pieced anything together.

And so I wondered: What would happen if, instead of meticulous advance planning, I woke up and booked the cheapest flight I could find departing that same day? Would there even be a cheap flight to book? Could I surrender to spontaneity without having a crippling anxiety attack?

I could think of no better way to resurrect my tradition of leaving the country on my birthday.

Planning without a plan

Sometimes, even impulsiveness requires a bit of planning. Sure, it would sound far more fearless if I said I boldly showed up at the airport with an overnight bag in tow and asked for the cheapest flight out of the country (and maybe that would be fun for another day), but for this, I needed to set some parameters.

This was my birthday, after all — I didn’t want to spend it at the airport watching unclaimed baggage circle on carousels for 12 hours.

I knew I needed to book a round-trip flight (no point getting a great deal one-way if it costs you a fortune to come home) with a single carry-on bag included. I was willing to fly out of any airport in the New York City area with any airline, though I admittedly prayed to the birthday gods for a Star Alliance flight to earn points toward renewing my United MileagePlus status.

Another consideration was entry requirements: My passport is current, but destinations that demand visas would be off-limits for this trip.

And though I wouldn’t exclusively shop for nonstop flights, I also wouldn’t book a trip with an outrageous layover or a dizzying series of connections. With only a couple of nights to spend abroad, maximizing my time at the destination was a priority.

Destination, unknown

As the clock struck midnight, just as I slipped firmly into my 32nd rotation around the sun (better than turning into a pumpkin, I suppose), I hopped onto Google Flights and switched to map view. I knew I would likely have the most luck finding a cheap flight to the Caribbean, Canada, Mexico and Central or South America.

I’d done some online flight browsing the previous week and had seen some great deals on flights to Europe (comparatively speaking). Still, the cheapest overall fares were routinely to Colombia, Costa Rica, Toronto and Montreal in Canada, and, interestingly, even Turks and Caicos.

By the morning of my birthday, I found the cheapest round-trip flight out of the country after zooming in on the Baja Peninsula. There was a $383 round-trip fare with JetBlue departing from New York-JFK for Los Cabos (SJD) at 9 a.m.

I was lucky enough to snag nonstop flights in both directions — perfect for a quick two-night trip. That aforementioned Turks and Caicos deal sometimes comes with a mood-killing day-long layover or an airport change. No, thank you.

Thanks to the time zone shift, I’d land at SJD around noon — allowing plenty of time to check in to my hotel and spend the rest of the day sipping celebratory mezcalitas.

To put things in perspective, last-minute, same-day fares to Miami were approaching $600, and even a quick hop to Boston would have cost more at $394 round-trip. I was leaving the country for a beach paradise for less.

If you’re dicing with last-minute bookings, you’re basically playing roulette and will either land a bargain or a fare astronomically higher than usual. By contrast to my Los Cabos fare, for example, flights to Mexico City cost a staggering $1,001 that morning, and Edinburgh fares were nearly $2,000.

Once my flights were booked, it was time to find a place to stay.

I’d considered HotWire’s last-minute Hot Rates, which allow travelers to book a property based on star rating at a deeply discounted price (think: 40% off). But I wouldn’t know exactly which hotel I was getting until the reservation was booked.

Instead, I opted for HotelTonight and glanced at properties around Los Cabos. HotelTonight is a hotel booking app that focuses on deals for last-minute stays and is a fun, almost game-ified way to reward yourself for, well, not planning too far ahead. (Once I “level up,” for example, I’ll start getting additional 10% discounts.)

A quick search for my dates surfaced a “daily drop” deal at the top of my feed. Users get one of these deals per day and only have 15 minutes to lock in the price.

It was nearly 1 a.m., so I was determined to find something fast so I could rest up before departure. There were plenty of great deals, including a basic Hampton Inn & Suites in San Jose for an average of $115 per night and a deeply discounted room at the Hacienda Encantada Resort & Spa (normally $559, now $218). But since this was an exercise in impromptu behavior, I decided to add one more element of uncertainty to my trip.

I swiped to reveal a $144 average per night stay at Drift San Jose. This hip boutique property is in San Jose del Cabo’s colorful Gallery District and has a sleek, minimalist aesthetic. Best of all, rooms have freestanding soaking tubs hewn from poured concrete and industrial steel accents offset by neutral-hued textiles. My cost for two nights came to $342 — perfect.

With my flights and hotels booked, I tumbled into sleep, ready to wake early, grab my passport, toss a swimsuit in a carry-on and head to the airport.

No place like somewhere else

Since my flight departed from JFK, an hour away by car on a good day (and when is it ever a good traffic day in New York City?). I had to leave plenty of time to get there. I could have cut costs and taken public transportation, but that’s a deeply unpleasant experience with luggage and frankly, I didn’t have time. The ride set me back $156 with a tip.

The next time I try to leave the country without notice, I’ll likely only look for flights out of my home airport, Newark Liberty International (EWR), instead of expanding my search to the surrounding metro area. Even if the flights cost a little more, I’d save time and money by avoiding costly Ubers and taxis. After I deplaned at JFK two days later, I found myself in a $170 taxi home, meaning I spent $326 on rides to and from the airport — nearly as much as my flights to Cabo just to schlep from the airport and back.

My devotion to EWR and, therefore, to United, means I rarely find myself flying other airlines, and it had been more than a year since the last time I boarded a JetBlue flight. But when I arrived at my seat to find a series of messages on the seatback screen wishing me a happy birthday and promising a complimentary alcoholic beverage, I felt almost like I had Mosaic status.

I treated myself to a birthday bloody mary (the recipe is a standard bloody mary with a dash of impending mortality) and settled in for the roughly five-hour flight.

Navigating customs when I reached Los Cabos was an hour-long sloth-like slog, which may not be how most people want to spend their birthday. But I generally love being in airports in foreign countries, and very little could dampen my spirits that day.

When I finally stepped out of the airport, however, the chaos hit me as quickly as the stifling heat. Chauffeurs and taxi drivers clambered for attention at every turn. A veritable wall of signs with last names and hotel logos filled the small outdoor space while travelers — seemingly unable to step past the commotion — stumbled into seats at the outdoor bars flanking the airport. The vibe was boisterous and upbeat, but I was overwhelmed and wished I’d had more time to arrange a pickup. I wanted nothing more at that moment than to find a sign with my name on it that would shepherd me through the bedlam.

Thankfully, Uber is available in this area, so I ordered a ride, thinking it would be the fastest way through the pandemonium — particularly since I didn’t have any cash on me. Big mistake.

It turns out Ubers are not allowed into the taxi and chauffeur pickup area, and finding my (incredibly patient and helpful) driver, Gustavo, required a miniature expedition. After attempting to beg my way into a gated hotel parking lot, I found myself making a terrifying mad dash across a busy two-lane road with no sidewalk, accompanied unexpectedly by a man named John, who founded Twigs, Minnesota’s stick crayons (literally crayons that look like sticks).

With my rollaboard suitcase in tow, we dipped down a sandy embankment to find Gustavo waiting on a service road. He graciously dropped John at his Airbnb before taking me to my hotel.

In short, I would advise against taking an Uber from this airport.

By the time my heart stopped palpitating, I had arrived at Drift San Jose, the surfer-chic 29-room hideout spread across two contemporary buildings overlooking a small courtyard with a sleek plunge pool. I couldn’t wait to order a cocktail and curl up in a woven hammock suspended between palm trees.

After I checked in, I was directed to my room on the second level, up two flights of stairs (no elevators of which to speak). That was more than fine for me, but it’s certainly something to keep in mind with a last-minute trip: If I’d needed an accessible ground-floor room, I might not have been able to snag one with such short notice.

Fortunately, my room was ready when I arrived. After fawning over the space, with its micro-library of thematic hardcovers (the “Eat Like a Lunchador” cookbook, William Finnegan’s memoir, “Barbarian Days: A Surfing Life”) and pedal loom-woven Minna bathrobes crafted in Chiapas, I drifted downstairs for lunch at the hotel’s restaurant and mezcal bar.

I received a welcome hibiscus mezcalita and ordered the tuna ceviche with corn chips. As I snacked, I admired the immaculately decorated brick courtyard, shaded by sun sails and decorated with artfully arranged cacti in terracotta pots piled on cinderblocks, as Talisco’s cinematic “Thousand Suns” emanated from the bar. I had made it.

Lost in Los Cabos

Considering I had no idea I’d be eating my birthday dinner in Cabo just the day before, I hadn’t really considered where I’d eat — or even what I’d do — once I settled in.

During my Uber ride to the hotel, Gustavo pointed out various restaurants and bars. He recommended a few places within walking distance of the hotel, including La Lupita — a suggestion echoed by Lucy, who worked at the hotel, when I asked for dinner recommendations upon check-in.

Gustavo also told me that, since it was Thursday, I should check out Art Walk that evening. San Jose del Cabo is one of those rare utopias where you can order margaritas to go and sip them while you meander in and out of galleries, admiring local artworks and enjoying the convivial atmosphere during the weekly event.

After lazily exploring the shops and galleries and contemplating the line at Margaritas To Go (that is the name of the bar, people!), I went to La Lupita for dinner. The host told me I couldn’t be accommodated that evening, particularly since there was a private event. So, I wandered up the street to Jasmine, which Gustavo had also mentioned, and was told it was also fully booked.

Despite having multiple recommendations, I found that without reservations, I didn’t have anywhere to go during one of the busiest nights of the week. For the first time, I could see how spontaneity, under certain circumstances, might be a little pointless.

Hungry and jet-lagged, I went back to the hotel to regroup. One of the hotel’s neighborhood recommendations, in addition to La Lupita, was Lumbre — “the most authentic cuisine in Cabo,” the website claimed.

Well, OK then.

Just a three-minute walk from the hotel, Lumbre was — perhaps initially worryingly — able to accommodate me immediately. But the moody, dark space with its exposed brick walls and open kitchen felt like the perfect spot for my birthday party of one.

I ordered the restaurant’s signature Collins — a smoky mix of tequila, soda, butterfly pea flower, local Damiana liqueur and mesquite syrup — and tucked into plates of seared fish tataki, grilled romaine with avocado and seaweed, and fresh-caught fish with ladrillo mole and cauliflower puree.

I left the restaurant so satiated I could hardly drag myself past the live DJ performing at the hotel bar and up the two flights of stairs to my room.

The next day, after breakfast at Cafe de Lolita around the corner, I decided to walk to Costa Azul, a stunning stretch of beach about 30 minutes from the hotel on foot.

After living in New York City for a decade, my sense of what’s walkable might be skewed: If it’s less than an hour away by foot, it always seems like a reasonable stroll. Usually, my compulsion to walk works out just fine, and I discover hidden corners of cities in my wandering that are too often skipped over by public transport or whizzed past in cars.

Occasionally, I’ll admit, I end up at a highway entrance ramp, looping around a parking garage or, as was the case upon landing in Cabo and trying to find my Uber, scurrying across busy arteries and slipping between slashed barbed-wire fencing.

Thankfully, the stroll to this particular beach was easy and lovely, with pedestrian walkways, sidewalks, and occasional horse grazing along the road. I spent a delightful part of that afternoon with my feet in the sand, watching as a flying fish navigated the cresting and crashing surf like a silver torpedo.

For my final dinner away, I once again tried to grab a table at La Lupita, and this time, I could elbow up to the bar for tacos and tamarind margaritas. Was it touristy? Absolutely. Beside me, two couples eagerly exchanged Peloton usernames. (I wish I could have seen my face.)

But with a live band performing from a lofted stage, I stuffed my face with grilled nopales, and I couldn’t have been happier. After all, I’d woken in Jersey City the day before, with the first hours of my birthday spread before me like potential flight paths arching across a flattened map of the world.

Travel is in many ways more convenient than ever, but it can also be tedious, inflexible and information overload: We read reviews before booking anything, use apps to compare prices, and our sense of adventure sometimes shrivels down and shrinks until it’s more like a small kernel of anxiety than excitement.

Sure, I had no time to plan activities, like a surf lesson or sailing trip, or make restaurant reservations. But I had no trouble filling my time with what seemed right in the moment — and I could easily forgive myself for exceptionally lazy mornings drinking coffee by the pool. There is nothing more liberating than being unburdened from decisions and schedules made weeks or months earlier.

And though I didn’t have time to invite a friend on my spur-of-the-moment getaway, I brought serendipity along instead.

Serendipity never complains or doubts and worries. It never fails to meet expectations. Instead, it emboldened my decisions, led to new discoveries and made my birthday trip that much more exceptional.

It was the perfect travel companion for what turned out to be one of the most memorable birthday trips yet.

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