Choosing the Perfect Vacation Destination

Tips and advice to help you pick the perfect spot for that all-important annual recharge because we all know what a daunting task choosing the perfect destination to spend your holiday (and your hard-earned savings) can be…

You leave the airplane, head to baggage collection, go through customs, grab a cab, check into your hotel, and take the first shower of your well-deserved vacation in your dream destination. Then you leave the hotel, ready to explore and get all those Instagram shots you’ve been dreaming of for weeks, or even months. This is a vacation. You feel like you’re living on a natural high.

And then it all falls down…

It’s hurricane season. It’s monsoon season. The Trevi Fountain is under maintenance. You can’t get close enough to see the main attraction, because there is a political rally going on. The museum you wanted to visit is closed for the duration of your stay. The painting you wanted to see is currently on display at a gallery in another country.

These small things have ruined several dream holidays. And though you’ll always make the most of a situation like that, the knowledge that you could have avoided these mishaps is haunting. So I’ve compiled five tips to help you pick the perfect holiday destination and avoid these vacation mishaps.

The weather

These things seem simple and easy. Yet, when you’re browsing the internet and a sale on the trip of a lifetime pops up, the last thing you consider is the weather. This is how people get booked on Caribbean cruises during hurricane seasons, or why we visit top beach locations at the height of winter! But the cold and rainy weather isn’t the only issue… if you’re not a fan of heat, or you get sunburned easily, you should probably avoid destinations known for extreme heat during local summers, especially if you are planning to visit a location where A/C might not always be available.

Getting a glimpse of Christ the Redeemer in Rio is rather tough on a misty day…

Is it the busy season?

You might like standing in lines to get into tourist attractions. You might enjoy having to push your way through a crowd just to see Van Gogh’s Starry Night. I don’t.

This is why I always try to find out when the peak season at my travel destination is. And then I plan my trip for a month before or after that period. It makes your holiday a little more hassle-free when you don’t have to constantly readjust your schedule due to the lines you’ve been cueing up in.

There’s a downside to this as well, though… If you’re heading to a destination during the offseason, always check the websites or Facebook pages of the attractions you’d like to visit. Some museums, restaurants, galleries, and even major public attractions close down for maintenance, renovations, or an annual break during these periods. Consequently, I once really did visit Rome without seeing the Trevi Fountain…

Tourists flogging around the Trevi Fountain… good luck getting that million dollar shot!

Events calendar

I have a couple of items on my bucket list that are very calendar-specific. I’d like to see New York’s Manhattanhenge (a phenomenon where the setting or rising sun is aligned with the east-west streets of the main street grid of Manhattan); I want to see a great band perform at Red Rocks Amphitheatre, Colorado; I’d like to visit Svalbard, Norway, to see polar bears and narwhales. These things only happen during certain times and seasons of the year, often not the time during which you can afford to take your big holiday from work.

More examples? The party capitals of the world (think Ibiza) are only really vibrant, and therefore fun, during the peak season. No use planning to see American democracy in action while you visit Washington, D.C. if the Senate will be in recess during your trip… or for that matter, hoping to do a quick tour of the Capital sites while angry Americans are marching against Trump (I have some personal experience in this area).

One more thing… when there are big events taking place in a city (St. Patrick’s Day in Chicago or Boston; Pride Parade in San Francisco; Cannes Film Festival in the south of France) hotel prices tend to skyrocket. Just another reason to check the events calendar before booking your trip!

Arriving in Chicago for St. Patties… one day after…

Location and General Distance

Sometimes we assume that it will be easy to drive from one city to the next, to catch a quick train, or that we can explore an entire city on foot.

Unfortunately, not all places have Uber (please check this before you visit a foreign country), not all destinations have great (or any) public transport, and sometimes the attractions you really want to see are very far apart. For instance, when I went to Nashville, I really wanted to visit the Bluebird Café and the Grand Ole Opry at night time. But these places are very far from the downtown area, which is where my hotel shuttle was dropping guests. I ended up missing out on the two experiences I most wanted during my stay in the home of Country Music because of this…

Another example – Australia is more or less the same size as the U.S. – if you’re in Sydney, Melbourne is literally on the other side of the country! Canada? Same story… you need flights or DAYS if you want to travel from Vancouver to Toronto, as these are on opposite sides of a very large country.

When Uber isn’t really an option… discovering Colombo, Sri Lanka on a tuk-tuk.

Consider your fellow travelers

While traveling on your own brings a whole set of challenges (check out my top tips for solo traveling), so does traveling with someone else, and especially traveling in a group. Make sure you pick a holiday spot that will satisfy everyone from the beach bum to the art aficionado, the history buff to the professional shopper, the jock to the foodie… most importantly, make sure that YOU will be happy as well! You’re paying a lot of money to visit someplace exciting; you should leave feeling like you got everything you wanted from your trip!

Traveling in groups can be tricky… that’s why I usually prefer traveling on my own!

Basically, it comes down to planning… And as a person who detests planning, it’s hard for me to admit. Here’s the best way to do it: choose the time you can go on holiday, and then pick the destination you most want to see. Now, jump online and research all of the things mentioned above. You don’t need to book ridiculously far in advance (though this is the budget-friendly thing to do), or plan a detailed itinerary for each day (unless that’s your thing J), just make sure that you’ll be in the right place at the right time!

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