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That Time I Let Fate Decide Our Vacation

I’m a planner. And I’ve basically been a travel writer since way before I was a travel writer, filling journals and photo albums with surprisingly detailed notes (what did I think I was going to do with them), odd observations and funny stories from over thirty states, twelve countries and three continents.

So how did an obsessive planner wind up letting fate decide her next trip? I’ll get to that.

First, you should know that I love the travel planning process. I adore every moment of preparation. I’m basically a giant nerd about it.

I read guidebooks (as many as I can find) and take notes to get an idea of what to see. I stare at mass transit schedules and Google Earth street views to decide which neighborhoods to stay in so we don’t need to rent a car.

I scroll through Yelp and TripAdvisor reviews to see which restaurants and attractions people are talking about and which hotels and guesthouses are the most fun. I follow local blogs, get inspired by travel writers and research the customs of the country before we even book our tickets. And speaking of tickets, I sign up for fare alerts and spend hours leisurely comparing prices so we can score the best deal.

It was a massive relief to meet other travel writers and realize that they do the same things. It’s a beautiful moment when you meet someone new and immediately start dorking out over packing tips and comparing your favorite local street food stops. I’ve clearly found my people.

And just so you know, I don’t do this so that I can torture my travel companions like an overzealous tour guide once we get to where we’re going. It’s exactly the opposite, in fact.

I do my research so that when we land, I’m confident that we’ll have time to see what we want to see and plenty of time to wander. I do my research so I don’t need to bury my face in a map or clearly mark myself a tourist by lugging a guidebook around to figure out our next move.

This approach anticipates problems ahead of time so we arrive with exact change for the bus and know where to go for late night eats when our flight gets in after 10 p.m. There are enough unexpected hiccups when you travel, so I figure I’ll just save my energy for the stuff I can’t prevent.

And I’m proud when people ask me to help them figure out the subway or request a restaurant recommendation. Not only does this mean that I don’t look like a tourist, it also means that I can meet people in a real, organic way. Preparation means that I get to feel confident, fully experience a place and make my time and money go further.

So yeah, I’ve got my tricks. I’ve got this system down. Which is great. Except when I can’t use it.

That happened this year. Derrick is a union driver and his vacation request is based on a complex web of requests and seniority. To make a long story short, the only available vacation week that would work fell in mid-February (yay!) and he was told about it in late January (wait — what?). Clearly, my typical leisurely, shop around planning strategy (complete with flexible dates and multiple airport options to maximize our budget and our options) wasn’t gonna cut it this time. Our dates weren’t even remotely flexible — and they were coming up fast.

Since our limited budget and lack of time meant we couldn’t be picky about our destination, I got the romantic idea that we should give up control (ha!) and let the flight gods decide our 2016 vacation. “We’re going to book the cheapest flight to somewhere we haven’t been and just see what happens,” I chirped on Twitter during a chat about 2016 travel goals, full of optimism and untested bravado.

I wanted to get an apartment somewhere and just live like a local — no resorts, nothing fancy. Derrick just wanted to go somewhere warm. We decided to focus on the Caribbean, Latin America and South America. It seemed doable.

A quick scan of the travel sites (ones where we could compare a ton of options at a glance — SkyscannerKayak and Google Flights, if you’re curious) told me we were going to have to book as soon as possible. I never do that, but rates were climbing and flight options and hotels were disappearing incredibly fast. We decided to do the most affordable flight that wasn’t ridiculously inconvenient.

That can be a challenge in and of itself. We fly out of a small airport in Fargo where four airlines offer direct flights to ten cities in the U.S. We wanted to at least get off the mainland, so those ten cities were out. And our travels had already taken us to a lot of the more affordable connections from said cities, so a super cheap fare just wasn’t in the cards.

Puerto Rico made the final cut. The flight itself wasn’t technically the cheapest — that honor went to Belize and then Guatemala, which would have been cool, since I have a thing for Mayan ruins.

But because we waited a not-so-whopping six days to book, the only remaining flights to these destinations required an overnight stay during one leg of the trip, which would actually make them more expensive overall. Plus, I was not going to spent my birthday in an airport hotel in Houston. Oh, did I mention that our random vacation dates just happen to include both Valentine’s Day and my birthday? Yeah. No pressure….

So I booked our Puerto Rico flight in an uncharacteristic frenzy, still kicking myself because the flight option with the shorter layover had disappeared overnight. If you can’t book early or be flexible, you at least have to be decisive. And it turns out I was right to panic — all flights would be booked by that afternoon.

We’d fly into the capital city of San Juan super early in the morning. I had absolutely no clue about what we’d find there. I attempted to research neighborhoods, but the info I found told me a lot about about San Juan’s attractions, but was more than a little vague about how to get to them. And it was largely silent about how and where the locals live and how they get around.

It seems that most people who visit San Juan arrive via cruise ship or book a giant luxury resort and take pre-arranged tours if they want to leave the grounds. There’s nothing wrong with that, but we just weren’t going to do either. I found myself scribbling more questions than answers. “Where is this neighborhood?” “Where does the train actually go?” “Why do tourists hate the bus?” This was not a particularly auspicious start.

I didn’t want to book a place to stay until I narrowed down an ideal neighborhood, but (in keeping with our theme) we were running out of time. I needed somewhere affordable, centrally located and convenient to public transportation. It also needed to have a flexible cancellation policy in case my Puerto Rico contacts came through and I ended up covering another part of the country. (Spoiler alert — they did!)

I booked my first ever Airbnb room (what haven’t I done this before?!) in a guest house partially because it looked pretty, partially because a review mentioned a bus stop and partially because, well, it was available. We needed to stay for a week and it’s the high season in Puerto Rico. It had good ratings and I decided good enough was, well, good enough. But I didn’t really believe that yet.

“Ugh,” I vented to Derrick as I sent the confirmation. “I hope this be okay. I just don’t understand this place yet. I don’t get how it works.”

My husband, who does not share my fear of missing out, just shrugged. “We can go to the beach, right?”

“Sure,” I told him, “There are couple nice ones within the city limits. And there’s a gorgeous historical district that I want to check out, some cool art galleries and some fun looking bars. It’s a brilliant place to score rum and coffee, so that’s about perfect.”

“Is there food?”

“Yeah, of course,” I said, giving him a weird look. “It’s a normal city.” We love cities. We are pretty enthusiastic urban explorers.

“And our room has a door and a bed and everything?”

“Yes. Obviously. Why wouldn’t it?”

“Then I really don’t get what you’re worried about. That sounds awesome.”

Yeah. It does. The downside to being a planner is that it’s easy to get distracted by the idea  of creating “The Best Trip EVER!!!!” — the most exciting, authentic, relaxing, once-in-a-lifetime, budget maximizing extravaganza possible.

And as a travel writer, my travel planning also needs to help me create and pitch stories so I can, you know, get paid. And my trip needs to combine what I need to do and what I want to do. The stakes are high and there are a lot of factors in play…which is sort of the opposite of how vacations work for most people.

So I made a concentrated effort to chill the heck out. And guess what? I picked up my guidebooks at the library, found a few local bloggers I liked and my Twitter friends shared some of their favorite places. And just like that, the pieces fit together. Puerto Rico seemed like a place to me. I could break down San Juan into neighborhoods and see how to lay out our time there. I was back in my element. The trip is coming together. And I’m really, really excited about it.

We’ll be spending a ton of time in San Juan, strolling through the old city, checking out the city beaches, shopping, eating and sitting around on our guesthouse’s veranda. Then we’ll head to Vieques, a sleepy little island (yes, an island off of an island) where we’ll snorkel, check out the bio bay and hopefully do a whole lot of nothing.

Because doing a whole lot of nothing is, after all, what what all this work is for.

How about you? Are you a planner? Or do you prefer to sit back and let someone else handle things? What planning tips do you recommend? Have you ever let fate decide where you travel? Would you ever try it?

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