Let's Take a Day Trip

CHICAGO — It’s June! Long gone are the days of cold, snow, ice, and wind, and we welcome the warm days on the horizon. This is the time of year you and your friends want to take a trip.

Many of you haven’t been on vacation since 2020 when the world was shut down. With the global pandemic behind us, it’s time to venture out there and explore the world.

Why not do it with your best friends or your favorite family members?
Nevertheless, if you’ve ever attempted to plan a “Guys’ Trip” or “Girls’ Trip,” you may have noticed it’s not as easy as it seems. But after reading this post, you’ll walk away with the keys to plan accordingly and understand how to navigate the hurdles of planning such a trip.

Finances varies person-to-person

The above seems obvious, but in reality, money is the most complicated issue when it comes to planning a trip. Before picking a destination and host of events, you’d like to do while out of town, you must have a deep, serious conversation with your friends about their finances.

You’re probably thinking, “Oh, this is easy,” but trust me, it’s not. Social media makes everyone believe that working 9-5 or making 5K a month is pointless and unsustainable. Facebook and Instagram tell us every day we’re all broke and poor and everyone else in the world is living their best lives.

All of this is to say you may think you know your friends’ financial situation, but you don’t.

This is why it is vital to have those conversations. A person making 70K with a modest lifestyle with no children – in theory, is doing “well.” While another person with two children, a mortgage, and a high car note – is struggling.

At the same time – if a person making 70K is financially irresponsible and the person making less with two children budgets their money very well – the latter could be doing way better than the person making 70K.

The point here is to talk to your friends about their finances and do so in a direct yet respectful way. Just because your bro might seem like he got money – he could be on the struggle bus. And your home girl’s hair may stay laid, and she has a million side hustles – nevertheless, she’s hurting.

It’s important to discuss this because when the planning starts, those with financial hardships tend to go quiet in the group chat or start back-peddling, and that causes unnecessary disruptions.

You can still include those friends on a trip but consider doing something more affordable. I’ll conclude this part of the conversation with this thought –
What’s the difference between a beach in Cancun and one in Milwaukee?
They both got sand, people, and water. In Cancun, you’ll bar-hop and go to the club. In Milwaukee, you can visit the East Side and do the same – and there’s a casino, if that’s your thing.

So, you can enjoy all of your friends in Milwaukee and have as much fun, right?

Go together, but go alone

That might sound like an oxymoron – but stay with me for a minute. While staying at an Airbnb sounds fun, splitting a hotel room can be more cost-effective – unless you and your friends are “perfect matches,” it’s okay to have your own while out of town.

I love it that way. I’m quiet, and one of my best friends is loud. He loves playing music in the morning and watching TV at night. Not me, so how can I be comfortable if I’m not?

If you’re like me, get yourself a hotel. You can enjoy the peace and quiet, and alone time is good, especially on vacation. It is also just as important to experience the break and do something you may like that your party doesn’t.

I love baseball, and most of my friends don’t – so if we’re going to a city with a baseball team and the tickets are cheap, I might enjoy an afternoon game while they’re doing something else. That doesn’t make me anti-social. I am also getting a chance to do things I like to do while on vacation.

Keep in mind; it is your vacation too. So, enjoy it. Do something you like by yourself while you’re out of town. Just communicate that with everyone, leading to our next and final topic.

At this big age, we should know how to communicate

We are all grown here. So, let’s keep it real. Communication is the foundation of everything in life. You must be able to communicate the good, the bad, the ugly, and the indifferent.

Everyone must be able to communicate the plan when it comes to traveling.

This could mean doing a weekly Zoom or daily group chat. But keep the group chat on task. If you’re planning a trip to Texas, the group chat can’t discuss who won the game last night, or did you see Nick and Sharon on Young and the Restless? Okay, I know, ain’t nobody watching Y&R but me – nevertheless, the point is to be communicative about what you all plan to do.

It’s okay to “wing it,” but have somewhat of a plan. It can be simple, like “We’re doing dinner at 8 p.m. at this place,” or “Friday night is ‘Ladies Night’ at this club, so we’re going there.” The goal is to ensure everyone knows what is happening.

In Conclusion

In order to have an ideal trip with a group, you must discuss finances openly and honestly, and you should enjoy some alone time. To do this successfully, you must communicate accordingly.

A group trip can end friendships and create unnecessary drama and tension – when the goal is to have fun. So, do those three things and tell me about your trip!