I Failed My Own Group Trip (Here’s What I Learned)

JaQuay Young El

7d • General discussion

Okay so I need to tell you about the time I completely messed up a group trip.

This was years ago - way before I said “I’m done, I’m only booking party adults-only travel from now on.”

I was booking a trip for friends and family. People I actually knew. Should’ve been the EASIEST trip to plan, right?

Nope.

**Here’s the thing:**

I’m used to traveling with MY friends and family - the people I ALWAYS travel with. We carry our own fun. There’s literally never a dull moment with us. We bring the energy no matter where we are.

So when I booked this trip for a DIFFERENT group - people I knew but hadn’t traveled with before - I just assumed it would be the same vibe.

Wrong.

**Here’s what I did:**

Booked this beautiful eco-friendly villa. Remote area. Had a pool. Gorgeous views. The photos were stunning.

I’m thinking: “We’re a fun group. We’ll bring the vibes. We don’t need clubs or bars. We’ll make our own party at the villa.”

That’s how it works with MY usual crew. So I figured it would work with this group too.

**Here’s what actually happened:**

First night? We had some fun. But it wasn’t like the trip I’d planned the year before where everyone was HYPED.

The energy just felt… off. People were bored after dinner. There was literally nowhere to go. Nothing to do. We were just… stuck at this villa.

By night two, people were on their phones. By night three, I could FEEL the disappointment in the air.

I messed up.

**So what went wrong?**

I forgot to treat them like clients.

When I book trips for my actual clients, I ask a million questions:

- What’s this trip FOR?

- What do you want out of it?

- What’s your ideal night look like?

- You want nightlife or you good staying at the property?

But this group? I just assumed. I thought “I know how to travel with friends and family. I’ve done this before. We always have fun.”

Yeah - with MY usual people. Not with THIS group.

**This was my first time traveling with them. I should’ve done what I do with my clients from JUMP.**

Big mistake.

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### **Here’s what I didn’t do:**

**I never asked: Why are we even going on this trip?**

Like is this supposed to be chill and relaxing? Or are we trying to turn up?

I just assumed everyone was like my usual travel crew. Never asked.

**I never asked: What vibe are y’all expecting?**

Turns out some people wanted to PARTY. Some wanted to relax. Some wanted nightlife.

And I booked right in the middle - which made nobody happy.

**I never asked: What’s your perfect night look like?**

If I’d just ASKED, I would’ve known half the group wanted to hit clubs. The other half wanted a pool bar with music at minimum.

The eco villa? Had neither. Just… nature sounds and a pool.

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### **What I should’ve done:**

**Treated them like clients from day one**

Just because they were friends and family didn’t mean I could skip my process.

**Asked the questions BEFORE I booked anything**

Even with people I know, I should’ve done a quick group chat survey:

- What’s this trip for? Celebration? Relaxation? Turn up mode?

- What do you wanna do at night? Stay at the spot? Go out?

- What vibe you expecting? Party? Chill? Both?

**Not assumed this group was like my OTHER travel groups**

Every group is different. Every trip has a different vibe. You can’t just copy/paste what works with one group onto another.

**Picked a place that matched what THEY said**

Not what worked for my usual crew.

If they wanted nightlife → Book near clubs and bars

If they wanted chill → Book the remote villa

If they wanted both → Book a resort with a bar + close to nightlife

**Set expectations before we even got there**

Tell everyone what’s around. What we can do. What to expect.

No surprises. No disappointment.

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### **What I learned:**

**Just because you travel well with YOUR people doesn’t mean you know how to travel with THESE people.**

My usual crew? We bring speakers, games, our own energy. We don’t need anything external.

But I can’t assume EVERY friend group operates like that.

**And just because you KNOW someone doesn’t mean you know what they want from THIS specific trip.**

Your friend who’s always down to party might want to chill this time.

Your cousin who’s usually low-key might be ready to turn UP on this one.

**You can’t assume. You gotta ASK. Every single time.**

Even if it’s your own friends and family. ESPECIALLY if it’s your first time traveling with them.

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### **How you can avoid what I did:**

Before you book any group trip - even with people you know - just ask these questions:

**1. What’s this trip for?**

Celebration? Relaxation? Bonding? Party?

**2. What’s your perfect day look like?**

Beach all day? Excursions? Just vibing at the pool?

**3. What’s your perfect NIGHT look like?**

Staying at the spot? Going out to clubs? Dinner and drinks then done? Early to bed?

**4. What vibe you expecting?**

Turn up energy? Chill mode? Mix of both?

**5. Do you NEED nightlife around?**

Or you cool with just whatever’s at the resort?

**Get those answers BEFORE you pick where to go.**

Not after you book. Not when you’re already there. BEFORE.

**Especially if it’s your first time traveling with this specific group.**

Don’t assume they operate like your OTHER travel groups. Ask.

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### **What happened after that trip:**

I literally said “I’m done. I’m only booking party adults-only travel from now on.”

Because I learned:

- When you mix different vibes = someone’s gonna be disappointed

- Party people NEED nightlife access or they get bored

- You can’t just assume - even with friends and family - ASK the questions

- Every group is different, even if you’re a “fun” person who travels a lot

That’s when I developed my whole location-first method. So I’d never book another group trip where everyone’s sitting around after dinner like “now what?”

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### **Your turn:**

Have you ever planned a trip and realized way too late you picked completely the wrong vibe?

What happened? What did you wish you’d known before you booked?

Drop your story below. Let’s learn from each other’s mistakes.

~ JaQuay

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