A dilemma I’m approached with by my clients, friends, and family is actually quite a common one. The majority of people that need my help are those who have the time and/or money to take a vacation but have no idea where to go. Maybe they’re open to every continent or just don’t know what the best choice is, but nearly everyone has trouble selecting the destination for their big vacation. The world is a pretty big place, so it’s no surprise one may need a little help being swayed.

So being a professional travel planner, I’m going to spill some of my secrets on how I help my clients choose the best destination for their vacation.

Here’s How to Pick the Destination for your Next Big Trip



Let’s start broad and work our way down. Start by choosing what general areas of the world you’re interested in. It’s ok to be feeling a pull towards Asia, but from there decide if you want Southeast Asia, Central Asia, Indian subcontinent, or maybe just China (well not just China, China is huge). Checking visa requirements and processing times should be done right off the bat.

Then, select an area of the world that you can get a reasonable flight to/from with respect to the time off you have. A country that requires 2 days of flying each way to visit when you only have 10 days is not making the most of your vacation time. Consider inter-country travel time and time changes as well. The Philippines and Thailand may seem near each other so you want to visit both, but travel once in the countries is tedious, lengthy, and uncertain.


How you want to interact with the destination is one of the most important factors in choosing your next trip and it should be based on what’s best for you mentally and physically.

If you work like a dog, it may be a good idea to relax a little and choose somewhere that’s less of a “challenge”. If you’re a bit out of shape or ill, maybe put off trekking Mt. Everest til you’ve trained up. Let’s continue with the example of Asia. For sun, beach, and partying, Thailand, Vietnam, and Bali are best. To soak in history, sightseeing, and food, China and Japan are perfect. Picture how you want to feel during and after the trip and keep this in mind throughout the planning process.


The actual sights in a city or country can help you choose where to go. If you have a monument or festival on your bucket list, give that option more weight. Perhaps you want to sightsee as much as possible on your trip or you live for architecture and famous sites; try selecting a region that has a lot to offer so you won’t feel like you’re wasting precious vacation time.



People tend check the weather patterns of where they’re thinking of going, but they forget about researching the social season. By this I mean weather and peak travel times – both can have a huge impact on how you enjoy your trip and the destination. Perhaps it’s not the best idea to visit the Greek Islands or Ibiza in January when everything is closed, dead, and its too chilly to get to the beach. Save certain places that are particularly fun during certain times for when you can actually savor them at their best. “Shoulder seasons” can be a wonderful time because it’s cheaper but still great weather. For example in Spring, the tulips are blooming in Amsterdam and the Wisteria and Cherry Blossoms come alive in Japan.

Don’t forget to check the festival schedules of the countries you want to visit as well. There’s an abundance of holidays all year round so choosing a place with this in mind could be great fun and a once-in-a-lifetime experience.

Bear in mind that visiting a city or country during a festival can mean prices are higher and availability is slim — book in advance!


Take into account how much you actually want to see in the time you have. If you decided you wanted a relaxing style of travel, then trying to speed through 10 different cities in 2 weeks may not be the best choice. You don’t want to finish up your trip not even remembering what you saw in the first half of it because you crammed too much in. You don’t want to wear yourself out nor be too bored.

Make sure you choose an area that you can navigate at the speed that coincides with the style of trip you’d like to have.


Doing a bit of research on what I’ve mentioned – seasons, festivals, sites, travel time, visas, etc. – will help you gather the facts to make a decision. Search for discussion boards on Lonely Planet and in various travel Facebook groups. Create a Pinterest board to help with organization. It’s also fantastic for finding inspiration, travel tips, and city guides from locals and fellow travelers. I create boards categorized by getaway type and region of the world for my clients to check out. Have a look:

Instagram is an amazing tool for inspiration as well. Be wary of accounts that may drastically photoshop or alter pictures to the point of overdramatizing. My feed is full of shots from my travels for inspiration and personal recaps/reviews. Here’s mine:


Maybe you have a hefty amount of time for the trip but you don’t want to spend every dollar from your savings. Average daily cost to visit a country should be a last resort to deciding where go. For example, Japan can cost $75-$100 a day to visit whereas Thailand and Vietnam cost around $30. If you want a taste of Asia but don’t have the spending money after booking the flights, weigh which will help stretch your money farther. I don’t like money to dictate where I go, but if I’m truly stuck between two places then I’ll use this as a tool to choose.

If you’re still stuck after using these tips, you have two options: Flip a coin or give me a call and I’ll help!

pick the destination

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16 Thoughts on “How to Pick the Destination for Your Next Trip”

    • That totally depends! Do you want to be surrounded by lushness and green or be WOWed by wildlife? I loved my trip to Norway last year specifically for the lushness and expansive nature! Patagonia is amazing for that too or try a safari in Tanzania or Kenya. Feel free to message me if you’re stuck and need more help!

  • Hi! I needed your article, as I’m now thinking where to spend my vacation… And I’m still in the “thinking” phase, and still haven’t decided on the continent… Sooo with Your help I think I’ll first decide my budget,and then there will be less choices 🙂

  • Oh yes, thanks to our criteria, it’s so much easier to actually think of your next possible destination. Some people really need this kind of advice before they can decide where they wanna travel! Such a nice, helpful post. I like the place to be sunny and not really in a full season 🙂

  • Thats a great post! Ive always struggle where to go for my next holidays but the only reasons for it is that I wanna go everywhere haha so I am just choosing where to go first. But am sure this post is very helpful for many people thanks for sharing!

  • These are some great tips, especially planning around the social calendar. I don’t like a lot of crowds, but sometimes the best experiences come during those busier social times of the year. And budget is always a concern. We’re always looking for the best deals. I’ll have to check out your Pinterest boards for some of our upcoming destinations.

    • Thanks so much and yes I completely understand! You can (and should) get some great deals and should always be looking out, but don’t miss out on something amazing just to stay in the budget! Enjoy your travels!!

  • Great tips. I always go for sights. On what I really want to visit. Then if I’m decided, I look for cheaper flights 😀 Then from that, I will plan how much or estimate expenses

  • great tips, especially about understanding the time it takes to travel within a country. Sometimes I’m surprised by how much people plan to travel in a country that is actually really hard to get around in! nice food for thought 🙂

  • I decide depending on the time we have allocated and take it from there – it is quite easy in Europe but we are now in Australia and the distances are huge! If we drive anywhere is can take up half the holiday so we have to plan very carefully! Good tips!

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