How to Pick Your Next Memorable Vacation Destination

There can be a lot of pressure when planning your next vacation destination. You only have a limited amount of PTO and money, and you want to make the most out of your trip. With so many options, how are you supposed to choose?

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I’ve compiled a list of the most important questions to ask yourself when considering a future trip. These questions will help you narrow down your search and pinpoint exactly what you’re looking for in a vacation.

Nova Scotia

When You Close Your Eyes, What Kind Of Vacation Do You Imagine?

Do you imagine relaxing by a pool or strolling the streets of a famous city? 

Will you want to sleep in or wake up for sunrise?

Will you spend days with friends and family or by yourself on a solo trip?

These are also really important questions to ask the members of your party. If you are all thinking of a different idea of what you’ll do on your vacation, it’s going to make planning your trip that much harder. 

Maybe you just want to have a relaxing-do-nothing sort of trip. Awesome! But just know that a trip like that is very different from a trip exploring Europe. 

Read More: How do you plan a trip from start to finish?

What Pace of Travel Are You Looking For?

Expanding on the first question, how active do you want to be on your trip? Do you want to make the most out of your short time and see as much as possible? Or are you looking for a more laid back and relaxing trip where you don’t plan many activities. 

I like to fall somewhere in between these two preferences. I often try to plan for 1-2 big activities throughout the day and keep a lot of wiggle room for unexpected adventures. 

Freeport, ME

What Regions of the World Are Calling Your Name?

Do you have a passport? Are you wanting to go international? Are you looking for a bit of a change of scenery but not too crazy of a culture shock?

There are regions of the world that will be similar to where you live and there will be regions that are vastly different from where you live. 

I often feel pulled to different regions of the world based on photos I’ve seen and experiences I dream of doing. I often think of the Pacific Northwest where I can do a kayaking trip with orca whales. 

Maybe you are drawn to the charming towns of Europe or the exotic streets of Asia. Dive deep into why you’re drawn to certain areas. 

Read More: How to Travel More with a Full Time Job

How far are you willing to travel?

Are you wanting to fly somewhere or a road trip close to home? How long do you have for a vacation? 

If you only have a few days, it will only make sense to either drive somewhere close to fly direct to your destination. 

While we would love to fly across the world for every vacation, that takes a huge time away from your trip. 

What do you value? How do you like to spend your free time?

We choose our vacations with our values in mind. We value wildlife experiences, nature-based destinations, and places that aren’t packed with tourists. 

When you think of past vacations, which ones were your favorites? And which ones did you not care for as much, and why?

Thinking back, the vacations I’ve loved the most have been the ones that help me reconnect with nature and my family. (Thus, the name of this blog). I’ve loved exploring small towns and the quieter sides of cities, and I’ve loved any chance we’ve gotten to see wildlife. 

Savannah, Georgia

If you could only pick three words to describe your ideal vacation?

This is a great activity to do with all members of your party to be sure you’re all on the same page. 

When we were planning a recent trip with my husband’s family, we knew we wanted the beach, but we realized that even that is not clear enough. 

Did we all want a beach vacation with amusement parks close by? Did we want a beach vacation within the US or internationally? Were we planning to spend the whole trip at the beach, or did we want day trips as well?

Are you interested in a particular activity or hobby?

Our favorite activities are hiking, kayaking, going to the beach, and exploring small historical towns. 

Knowing what’s important to you makes it a lot easier to search for destinations. You can search directly for the best hiking spots or the best beaches of a particular country. 

Are there any festivals or events you’re interested in? 

We don’t typically go to festivals or large events but as an avid knitter, I’ve always wanted to go to one festival in particular, the New York Sheep and Wool festival. I know, very specific and a bit geeky, but we all have our thing. 

So, knowing that this was high on my bucket list, we made sure to carve out 2 days of PTO just for this trip. 

Custer State Park, South Dakota

How much are you willing to spend?

Even if you are drawn to a safari in Africa, you may not have the budget needed to experience a safari the way you’re imagining. 

I truly believe you can visit any destination on any budget if you’re willing to sacrifice aspects of your trip. 

But if what you really have in mind will be outside of your budget, planning your trip may leave you feeling frustrated. It may be better to set aside money for your future bucket list trip and focus on the trip you can afford. 

Read More: How to RV in the US for Less than $2500

Are you flexible with your vacation dates or do you need to go during a specific time frame? 

This is really important to know because it will influence the cost of your trip, what season you will travel in, and what you will do on vacation. 

If you are able to stay flexible it will really open up the possibilities. If you’re thinking of visiting Italy, but can’t quite swing a budget during peak season, you might be able to make it work on the off season or shoulder season. 

Once you’ve narrowed down your destinations, it’s time to narrow down even further.

Why are you interested in the destination? 

What exactly are you looking to do in each destination? 

If you can’t clearly answer those questions, then do some research and get inspiration. 

My favorite ways to get a sense of a destination is to read blogs and watch YouTube videos. 

Once I’ve narrowed down a few things I’d like to do in each destination, I use Google Maps to see how far away these activities are from each other. And I like to use Google Maps to visually see which regions have the most activities. 

For example, if you choose Maine as your destination (you definitely should go to Maine!) you may find after research that you’d love to go to Portland, ME to explore the numerous restaurants and the easternmost point in the US in Lubec, ME. These places look close on a map but in reality, it’s a good 4 hours away. 

Are you willing to drive 4 hours between the two towns? If not, narrow down even further as to what is your biggest priority. 

A Few Other Ways to Pick a Destination 

Pick From a Hat

Pick your top 10 destinations and select your destination at random.

Point to a Spot on a Map

This is how we picked our first international trip! I was so indecisive of where to go in Europe, so I presented my husband with a map and told him to point to a country with his eyes closed. 

I also think this is a great way to go to an underrated or lesser-known location. 

Let a Surprise Travel Company Pick for You

Companies like Pack Up and Go are a really great option for those that aren’t especially thrilled about having to plan a vacation. You don’t find out where you’re going until you get to the airport! 

I’ve used Pack Up and Go twice now and loved both trips! 

The first trip was with my mom, and we ended up going to Chicago. 

My second trip with the company was to Atlanta with three of my girlfriends. (We couldn’t wait until getting to the airport to find out where we were going!)

I highly suggest looking into the company!

Pack Up and Go sent us to Atlanta!

Final Thoughts

There is no wrong way to pick a vacation destination. You can pick a popular place and have a blast, or you could pick a destination that no one has ever heard of and still have a wonderful time. 

The key is to not let the process of picking a vacation destination hold you back from actually taking your vacation. Even with all of these questions, don’t think too hard, just go!