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Vacations vs. Trips - 6 Questions to Ask Before You Travel With Someone

Soooo.... I was talking to one of my dear friends about how “particular” I am when it comes to traveling with other people.

As I proceeded to trip her out about all of the factors that need to be considered, she said, “Yeah, you should write about that. That would be entertaining to read!”

three women sitting on shore near trees at daytime
Photo by Jovaughn Stephens / Unsplash

Travel compatibility is extremely important!

Traveling with someone is a short-term, committed relationship that can potentially make or break your trip and/or your friendship.

I personally have experienced and witnessed some horror stories!

Ladies and gentleman, I am not about that life! I don’t spend my hard-earned money on vacations just for it to be spoiled by someone that I have chosen to travel with.

What I have also realized in recent years is that I have always had “particular” tastes, but I had not been confident enough to advocate for myself.

However, that is no longer a problem for me. It’s not about being nice when it comes to my vacation needs.

It’s about having straightforward, honest and mutually communicative discussions about what everyone wants from their holiday.

woman with her right hand on shoulder of another woman standing on beach
Photo by rawpixel / Unsplash

The 6 main questions I always ask are:

What’s your budget?

Always an important question. It gives me the information I need to start investigating potential vacation spots and will determine what methods I will use to search for deals.

If they have money already saved up, then I can look for vacation packages. If not, I know we are purchasing the accommodations separate from the flights and it gives everyone more time to save money.

Depending on the hotel, you can either make a deposit to hold the rooms or give your credit card information and pay the entire balance upon arrival.

Each person can look for flight deals and purchase the flights when they have the money.

What kind of vacation are you looking for?

Are you looking for something relaxing? Do you want to party from the time we get to the airport to the time we return? Do you want to do a lot of excursions or tours at the destination?

It’s very important to either want the same things or be ok with doing things independently while on vacay. I’ve had it work out quite well both ways, but communication is key!

Is there a theme to the vacation?

I have planned and gone on birthday trips for myself, sister trips, runcations and a divorce celebration trip. They are all different types of trips with different focuses. Everyone has to be on the same page about who or what the focus is on.

For example, when I planned a trip for a friend celebrating her divorce, I mapped out a variety of activities she would enjoy while having enough time in between to just chill on the beach.

However, if the focus is on me because it’s my birthday, then I make it clear to anyone considering going that I’m going to do what I want to do and they have to agree to that.

three sun loungers on seashore near woman in bikini
Photo by Sarah Louise Kinsella / Unsplash

What kind of vacationer are you?

Are you laid back? “Particular” like me? An adventurer? What type of hotels do you like? Are you looking for romance during the trip?

Do you snore? (I warn all potential travel boos that I am a life long snorer, LOL)

When sharing space during vacation, you gotta know these things in advance because it plays a significant role in the type of accommodations selected.

Another great example: Your travel companion may be interested in hookin’ up during vacation. No judgements, but all parties sharing the space have to be ok with that.

You may decide to get a 2 bedroom AirBnB instead of a hotel room or agree to let the other roommate have the room for a couple of hours while you go have fun at the bar.

Whatever you decide, it’s good to have that discussion BEFORE you go on the trip so everyone is on the same page.

What temperature do you like your hotel room to be?

This may seem like a very trivial question, but it is very important to me. I can’t stand to be cold, so I really try hard to travel with someone of a similar temperament or have a discussion about the air conditioning/heating situation.

Some of my friends are naturally hot blooded or go through their own “personal summers” during the night, so it’s a conversation worth having.

Are you serious about going?

The most important question of all! Are you ready to put your money where you mouth is? Please let me know because I will start searching for travel deals as soon as we get off of the phone, LOL!

This is one of the main reasons why some trips never happen.

When it’s time to put the money down, your friend cannot be found or life happens and they can’t afford to go.

It saves a lot of time, heartache and pain when everyone is certain that they can get the time off, get a babysitter and have the money to go.

So this is my little questionnaire I do with anyone I’m considering traveling with. All my friends know how “particular” I can be. I am upfront about my needs and I still manage to get takers that want to travel with me.

silhouette of three woman with hands on the air while dancing during sunset
Photo by Levi Guzman / Unsplash

Bottom line - when the communication is good, traveling with others can be a wonderful experience!

What’s important to you when you travel with others? Like, share and leave a comment on my Facebook page.