
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?
Comments are closed.
Caylee
August 27, 2019 at 3:50 pmThese tips are great! My husband and I always have a hard time deciding where to travel so this list of questions and things to think about will really come in handy!
Lina
August 27, 2019 at 4:17 pm“How much time do you have” is the principal issue when choosing a travel destination, so the best way to figured it out is by planning very well the flight hours, layovers… and think if it’s worth it to go to that destination!
Beth
August 27, 2019 at 4:55 pmThese are great things to think about. My daughter often vacations with one of her best friends, they live on opposite sides of the country, so they have a lot of logistics to work out. They went through the same sort of conversation trying to decide where to go on their most recent trip together.
Kat&Phil
August 27, 2019 at 10:05 pmSimple but completely effective! We’d really like try the ‘throw a dart at a map’ method someday 😉
Kileen
August 28, 2019 at 2:39 amThese are such awesome tips on choosing a travel destination! There are so many factors that should be considered, these tips are a great way to narrow it down!
Kileen
cute & little
Crickette, The Things I Have to Say
August 28, 2019 at 12:36 pmI love going on and planning trips. I love organizing stuff so I love building itineraries and planning outfits. Yeah, outfits. HAHA. Choosing where to go can be really hard when there’s so much to see in the world. So usually we just go with the flow.
My sister just wanted to go to Vietnam for her bday, so there, we booked a flight for next week. And I’m so excited. I haven’t finished planning my outfits, though. HAHAHA.
Lilia
August 28, 2019 at 2:19 pmThese are some really great tips and things we often take for granted when travelling, especially as a mum of young children. I’m literally making notes for our next trip.
Mary
August 28, 2019 at 5:09 pmthanks for the tips, now we can start planning our out of the country travel with our two kids.
Summer
August 28, 2019 at 7:11 pmSuch great tips – all foundational conversations to have when deciding on where to visit next!
Stephanie
August 28, 2019 at 7:13 pmThis was really helpful to read through. My husband and I are trying to plan a trip for our first wedding anniversary in November. But with two trips for weddings in October, and tight finances, we’re having a hard time deciding where to go that’s within driving distance, new to us, and still interesting haha!
Subhashish Roy
August 29, 2019 at 1:44 amVery good practical tips. Every vacation is different and hence requires good preparations to experience the best. I too am a passionate planner.
Indya | The Small Adventurer
August 29, 2019 at 3:51 amI’ve always had a LONG list of places I want to go (in order of preference, too!), but have only really thought about the fact that the “when” is also super important! Japan is my number one destination for example, so do I go when they think the Cherry Blossom Season will be? Or should I go during Winter and witness a blanket of snow for the first time? It’s so hard! I see lots of pro and con lists in my future before I ever make a decision.
Khushboo
August 29, 2019 at 8:08 amThese are some cool and helpful tips you shared. I will remember this for my next travel.
Chocoviv
August 29, 2019 at 6:17 pmMy partner does the choosing of location and I decide what to do there…
Karla
August 31, 2019 at 5:45 pmThis is very helpful! My boyfriend and I are planning to have a vacation before the year ends. I’ll definitely consider the tips you mentioned. Thank you!