Tips for Choosing a Travel Destination

It might seem like a non-issue when you’re thinking about traveling, however sometimes you need to figure out a starting point to determine the best spot to visit. For example: I’m getting ready to meet a friend for a long weekend and we’re 1/2 way across the country from each other. If you saw our text conversations trying to figure out where to go you would understand why I wrote this! The Cliffs Notes version went something like this:

• “What about Toronto?” “Eh, I was just in Canada in July.”
• “Portugal?” “I can’t, I’m going to be planning a trip there in the fall.”
• “Iceland?” “I don’t really want to go during peak tourist season.”
• “Mexico, specifically San Miguel de Allende?” “It will take me too long to get there, I’ll spend half the weekend in transit.”
• “New York?” “I’m super close to NYC and would prefer to go somewhere farther away from home!”
• “Savannah?” “Not really into Georgia right now. Next.”
• “Charleston?” “I was just there.”
• “Napa?” “Next.”

We did ultimately decide on a location (that we’re both excited about!) after several days of back and forth. Want to know where we’re headed? You’ll just have to follow me on Instagram and keep an eye on my stories!

So it’s not always as easy as saying “Japan has been on my bucket list” or “I’ve never been to Colombia but really want to go” (although sometimes it is!). Sometimes you’re traveling with your SO or your family. You might be meeting a friend at a destination that’s new to both of you or traveling with a group. You might want to plan a solo trip or only have three days before you have to go back to work. Whatever the reason, sometimes the feeling of wanting to travel can be anxiety inducing due to decision making but don’t let that keep you from having a good time! Check out some basic tips to help you narrow it down and select the best place(s) for your needs.

Who is going?

Is it just you? Are you traveling with your SO who happens to hate the beach? Your bestie who doesn’t have a passport? A family member with mobility issues? Getting a loose outline of who is coming and any major likes/dislikes they have is essential. You can ask

• Any aversion to certain climates/temperatures?
• Do they have, or are they willing to get, a passport?
• Any major medical issues that need to be taken into consideration?
• Are they comfortable with traveling or have they rarely left the state?
• Any severe dislikes, i.e. humidity, the beach, the snow?
• What kind of traveler are they? Do they only prefer 5 star accommodations or have they backpacked & stayed in hostels?

The easiest way to ruin a trip with someone (or several someones) is to not take into account what they like and their hard bottom lines! Thinking about camping with your dude who hates nature? Probably not going to be a win.

If it’s just you going solo you need to take a bit to think about where you would feel comfortable vs. where you wouldn’t want to go solo. Is the destination known to be safe for a solo traveler (especially ladies)?

How much time do you have?

Regardless of whether or not you’re planning on going solo or with others you should figure out how much time you actually have. It wouldn’t make sense to try to get to Indonesia from Boston if you only have four days off and need to back in the office on the fifth day – you would spend almost half that time in transit and would have jet lag like crazy on your return! This is an especially important question to ask if you’re meeting someone (who’s coming from a different destination) for a trip. Just because it’s a three hour flight from you doesn’t mean it’s a similar time commitment for them.

What’s your preferred method of travel?

Hate flying? Taking a long weekend across the country is going to be pretty impossible. Get car sick easily? Road trips are probably not the way to go. This goes for anyone you’re traveling with, too! If your partner gets anxiety on flights and really doesn’t enjoy them then that 18 hour nonstop to Australia is probably not high on their to-do list.

How much money are you looking to spend?

Traveling with a bunch of friends that only get one vacation a year, have kids and budget down to the dollar? Or are you solo, saved up and ready to spend? You need to not only determine the cost of getting to/from your destination but also transportation when you get there and lodging. Don’t forget about food and activities! While traveling with friends can definitely ease the total cost it makes a huge difference where you travel to. If you’re heading out of the country you should check out how far your money will go.

Hopefully these tips are helpful if you’re feeling a bit lost (before your trip even starts!). Looking for trip inspiration? Check out my Santo Domingo guide and my 3 Nights in Montreal guide for a few ideas. Also stay tuned for an update on where we decided for our above mentioned meetup (or watch my IG stories if you can’t wait!).

Have you ever run into issues or challenges when decided on a travel destination? If so, how did you work through them?