5 Tips: How To Choose The PERFECT Vacation Destination

As much as I travel for work, I like to carve out time for a vacation (ironically, my job is not a vacation!). When I do have the time to plan a vacation, I’m in the same boat as you. Where do I start? How do I choose the perfect vacation destination for my next trip?

Choosing a destination to spend your next vacation is not easy. There’s an incredible amount of great places, making it hard to decide where to go. It’s like going to an ice cream parlor and stressing over what flavor to get. It can be overwhelming.

To make life easier, we created a check-list of five questions you should answer to help you choose the perfect vacation spot for your next trip.

How to Choose The Perfect Vacation Destination

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5 questions to ask yourself when planning your next trip

Sedona, Arizona.

Sedona, Arizona.

1. What are your top ten fantasy trips at this point in time?

Kimpton Tryon Park – Charlotte, NC

Your list doesn’t necessarily have to include your “bucket list” (places you have to see before you die). Think of the places you want to visit now. Why? These are the places that will definitely make you instantly satisfied.

Picking the top ten is possibly the hardest part, but think about where and why you want to go. City? Beach? Private island? Skiing? Down Under? A new luxury hotel you’ve been dying to check out? A food truck in a jungle everyone has raved about?

When you ask yourself why you want to go, if you can’t find a good enough reason, it should not be on your list right now. I highly recommend visiting a place you’ve never been to rather than a place you already love (you can always go back there.. why not try something new?). Also, be as specific as you can be. For instance, don’t think “Hawaii” but rather “Maui.”

Write down the top ten. Now cut that in half. It’s tough, but this will help you identify the five places you really want to visit.

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The beaches of Riviera Nayarit, Mexico.

The beaches of Riviera Nayarit, Mexico.

2. How much time do you have?

Unfortunately, America has a notorious low percentage of passport holders because Americans have very little vacation days. If you plan on going overseas, get your passport NOW. Based on the five places you want to visit, you should figure out what makes sense in terms of how much time you can spend there.

Amantaka in Laos.

If time is not an issue, you’re golden. If it is, narrow your list even further down to destinations easiest to get to (for instance, if Hawaii and Thailand are on your list, go with Hawaii for now, as you lose two days going to Thailand). If money is not an issue, and you can group your vacation with Christmas (when hotels are at their most expensive) or Thanksgiving (when flights are expensive), you can have a longer vacation using your vacation days.

This is one of the best ways to choose the perfect vacation destination.

Four Seasons Bora Bora in Tahiti.

Four Seasons Bora Bora in Tahiti.

3. Is now the best time to go?

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High-season destinations will be more expensive to travel to than off season (for instance, in winter, high-season would include tropical destinations like Mexico and Hawaii. Off season for winter would be cities that will be crazy cold like Copenhagen or southern Italy).

Also, are there cheap flights? Can you get good hotel rates? Is there a big city event that has all the hotel rooms sold out? Within your five top destinations, figure out which ones pass all these questions and are places realistically suitable to visit now. This will help you choose the perfect vacation destination.

Underwater restaurant in the Maldives.

Underwater restaurant in the Maldives.

4. Who do you want to travel with?

Trust me. It’s better to decide who you want to travel with AFTER you pick the destination.

Think about who you’d want to be with on this vacation. Lover? Family? Kids? Grandparents? The guy that works at Dunkin Donuts? Or do you want to be alone?

Make sure your travel companion is someone who will appreciate where you’re going. They are also great in helping narrow down the top five. Chances are they’ll want to visit at least one of those places. Again, choose your travel companion after you have the top five (or, if you have someone in mind, agree to choose your top five together). It’s so much easier that way.

Sunset at Four Seasons Papagayo, Costa Rica.

Sunset at Four Seasons Papagayo, Costa Rica.

5. How much planning do you want to do?

Now that you’ve likely narrowed down the top five to your fantasy vacation spot, think about whether you want to do all the planning or leave it to someone else. Travel agents have made a huge comeback and, in most cases, it doesn’t cost you a penny to use them.

Virtuoso agents are the most qualified in terms of luxury travel, and customers get free room upgrades, breakfasts, etc, just from working with one (they get commission). Otherwise, you can hit the ground running as soon as you arrive with recommendations on restaurants and attractions from locals, concierge and friends who have visited.

Resort at Pedregal in Los Cabos.

Resort at Pedregal in Los Cabos.

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Do you have any tips on how to choose the perfect vacation destination? Let us know in the comments below!

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Jimmy Im has traveled to 113 countries, stayed at over 600 hotels and clocked millions of air miles. He currently lives in New York City.

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