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Bridget Gleeson Travel Writer

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Return of the native son (plus one)

My boyfriend and I are planning a last-minute vacation to Spain and Portugal. Or perhaps it’s more accurate to say I’m planning a vacation while he tries to get a word in edgewise.

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The kicker? The trip was his idea. And we’re going to his native land, so to speak -  his grandparents emigrated to Argentina from Europe in the 1930s.

Hi, my name is Bridget, and I have travel control issues.

Just for fun, let’s break it down. He has uncles and cousins eagerly awaiting him at beachhouses in Faro and apartments in Barcelona; I don’t know anyone from Spain who is actually living there right now. He is a native Spanish speaker and converses fluently in Portuguese; I know how to make a delicious white sangria. He has a map pinpointing the tiny coastal town where his grandmother was born; I have a Google Earth app on my new Macbook.

Clearly, this trip is his thing.

So why do I feel like I need to call the shots? Why can’t I help myself from looking over his shoulder and thinking – often aloud – ‘oh, but wouldn’t it be better to fly into Lisbon and then rent a car instead of trying to fly into Madrid where everything is more expensive?’

It’s an occupational hazard, pure and simple. I’ve made a living out of planning long trips with difficult logistics and explaining to travelers how to follow suit. Ever thought about how to get to Tierra del Fuego overland without driving your own vehicle? I’ve done it twice. Stuck in a dusty Bolivian village and trying to get to Sucre without boarding the scary public bus? I’ve done that too. How to travel from Rome to the Greek island of Corfu when you don’t have enough cash for a plane ticket? Cross the Strait of Magellan on a ferry during a snowstorm? Just try me. I love the challenge. I guess it’s just exciting to me that there are still so many open roads and unexpectedly blocked passages and unchartered territories that are never covered in Travel & Leisure.

When I’m on a long trip for work, I plan the route well ahead of time because I have so many specific destinations on my checklist. I choose the hotels; I decide whether  to splurge on a short flight or whether it’s safe to walk around in the dark. Anyone who’s with me on one of those trips – my mother, one of my sisters – usually sticks with the plan because they know I have to figure this stuff out for my job. In these cases, my travel companions seem to be more relaxed because they don’t have to know how we’re getting to the next place. I’ve been in their shoes. My first time in Santiago, I just followed my sister’s Chilean husband around and did whatever he said because, let’s face it, he definitely knows best.

When we travel, the options are overwhelming. I guess we all want a local authority – or at least someone who knows more than we do – to tell us what’s best.

On this upcoming vacation, neither one of us is an authority, and we’re looking at a complicated itinerary involving remote coastal towns, multiple airports and Smartcar rentals.

I know it’s very uncool of me to be so power-hungry. For once, the challenge isn’t getting from point A to B – it’s figuring out how to put a sock in it and fasten my seatbelt on the passenger side.