Finding the spontaneous, yet scheduled, happy medium that (almost) guarantees getting the most out of travel
There’s no sign over the door. No menu in Portuguese and English accented with over-stylized photos or waiter perched outside, wooing potential customers with a smile and sing-song recitation of the specials. Indeed, the only clues that this windowless room just steps from Cais da Ribeira—the colorful stretch of umbrella-crowned tables and high-end tapas bars overlooking the Douro River in Porto, Portugal—was a restaurant were the six tables inside, a one-sided menu plastered to the counter, and the platters of food being served to a boisterous group of Portuguese men drinking pitchers of Super Bock and arguing about whose fútbol team was best.
I’d just finished touring Graham’s Port Lodge, the 1890 cellar, tasting room, restaurant, and museum of one of Portugal’s most renowned port producers, located across the river, and I was starving. My plan had been to eat at a restaurant specializing in bacalhau (cod fish, the star of Portuguese cuisine) near the lodge, but when I arrived and looked at the menu—high prices, predictable entrees—I meandered on, determined to find somewhere more authentic and less tourist-laden.
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Sweaty from the surprisingly hot October sun and slightly tipsy from the port, I strolled back across the Dom Luís I Bridge and turned onto Cais da Ribeira. I paused to eye the various plates perched in front of the groups of Spanish, French, and Italian speakers (all of Europe, it seemed, was on vacation, and everyone had chosen this riverside promenade as their place of escape), but instead of settling for a made-for-tourists lunch like my fellow travelers, I pressed on. Just as I was about to give up, I spotted it: a single door blending into the cool shadows of the stone walls, the promising smell of fresh onion and frying fish floating from it, hanging thick on the salty, humid air.
Outcomes like this are what make taking risks while traveling worthwhile. But for as valuable and, sometimes, rewarding as it can be to shirk plans in favor of the “whatever happens, happens” approach, chance doesn’t always rule in one’s favor. Forgoing booking tickets ahead of time can end in missed connections or increased prices. Waiting to see what lodging is still available upon arrival can lead to sleeping on a moldy futon in a sketchy neighborhood. And choosing the cheapest option for flights, trains, or buses can result in extremely early or late arrival times, which can mean limited transportation options and difficult lodging situations.
On the other hand, over-planning a vacation can be just as detrimental. Cramming each day full of tours, shows, and reservations can result in spending more time looking at your watch than whatever it is you scrambled across town to see; passing on an authentic dining experience; or never getting to know a city beyond its tourist-friendly facade. And while those outcomes aren’t the worst things in the world, they also aren’t as satisfying as allowing a city to reveal itself in its own way, on its own schedule.
Which leaves us at that ever-elusive place of finding the happy-medium between the too-little and too-much planning approaches. But take heart: It is possible to be spontaneous and well-prepared at the same time. It just takes a little foresight and a willingness to embrace the unexpected, even if—and especially when—the unexpected interferes with the planned.
The easiest way to start a trip off right is to take care of the things that can be taken care of ahead of time. Namely: lodging, transportation, and mapping out your top can’t-miss destinations.
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Where you stay can have an enormous impact on how you experience a city. There are more options for lodging today than ever before—hostels, hotels, Airbnbs, VRBO—and it’s well worth your time to look into each one to make sure you get the most out of the time you have in your destination of choice, as well as the most for your money.
It’s tempting, especially when traveling on a budget, to pull up Expedia or Hostelworld.com, find the cheapest room, and click “confirm.” However, what appears to be the least expensive option on paper can actually end up costing more in the long run in terms of transportation fees, peace of mind, and a good night’s rest. Many hotels and hostels are cheap because they are located far from the city center. In places with great public transportation—New York City or London, for example—this isn’t a big deal: just buy a multi-day subway or bus pass when you arrive, look up the routes you need, and arrange your daily schedules accordingly. But there’s a lot to be said for exploring a place on foot, and, in my experience, paying a few extra dollars a night in exchange for the freedom of not having to wait for a bus or a train is more than worth it.
The same goes for amenities and the guarantee of a good night’s sleep. If you’re someone who is blessed with the ability to fall into a deep sleep regardless of sound, light, temperature, and bedding, then by all means, book that shared room in the hostel or Airbnb. But if you’re like the rest of us and require more than just a space to lie down in, be honest with yourself about what you need to sleep well and find a place that suits those needs. While it’s possible to explore a city on limited sleep, it’s usually not pleasant. Better to budget for a quiet room and warm bed than wind up sick and exhausted a few days into your vacation, loathing the thought of returning to your room at the end of the day.
Once you know where you’ll be staying, the next step is to figure out how you’re going to get there upon arrival. Taking a taxi is almost always an option, but more often than not you’ll end up paying a hefty sum for the convenience. Instead of wasting your money, look up the metro, bus, or walking routes you can take to get your place of accommodation ahead of time, take a screenshot of the information, and enjoy the feeling of being a step ahead of the game when you arrive. At the very least, write down the address of your destination: that way, if you need to ask for help or get a taxi, you can show someone where you’re headed.
Finally, you’ve likely chosen your destination for a specific reason, and therefore have an idea of the things you want to see and do while you’re there. To avoid missing out on something due to odd schedules or already full tours, look up the opening times, prices, and locations of your must-see places ahead of time, then plan the rest of your trip—including time to wander without an agenda—accordingly. This will give your trip structure without being overly rigid, and guarantees that even if every spontaneous trek you take leads to a dead end, at least you’ve seen the things you came to see.
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There are plenty of other ways to plan ahead and help make a trip go more smoothly: calling your credit card company and bank before heading overseas so they don’t shut down your cards, having cash on hand so you don’t get stuck being unable to pay for that pint of beer in a place that doesn’t have a credit card reader, knowing the norms for tipping and a few common phrases in the language of wherever you’re traveling. But really, no matter how much you plan, it’s impossible to anticipate how a trip will turn out. Buses get off schedule. Restaurants close. Sunny mornings turn into rainy afternoons. In the end, as long as you do your best to make the most of whatever happens, you’ll be guaranteed an adventure—even if it’s not the one you planned on having.
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