Offsite Horror Stories (and How to Avoid Them)

Everyone loves a team retreat. 

But let’s be honest, when things go wrong on a company trip, they go really wrong.

The group dinner that turns into a stomach bug epidemic, the “easy hike” that somehow becomes a six-hour survival test, or the Wi-Fi that “totally works” (spoiler: it doesn’t).

Every team has at least one retreat story they tell in hushed tones. And if they don’t… It’s only a matter of time.

Today, we’re serving up a few real-world offsite horror stories and, more importantly, how you can avoid slipping into your own.

The Wi-Fi Was… Decorative

The Horror:
A big planning retreat derailed when “fast internet” turned out to mean barely emailing.

Avoid It:
Get real upload/download speeds in writing. If it’s critical, book a coworking backup.
Pro Tip: Airport hotels often have the best Wi-Fi if you’re stuck. Make sure to install a VPN before accessing, you and your CSO will thank us later.

The Great Ceviche Incident

The Horror:
Team dinner ended with half the group fighting food poisoning instead of team bonding.

Avoid It:
Stick to busy restaurants with lots of locals, and prioritize cooked meals in hot climates.
Pro Tip: Plan at least one “safe” dinner to reset everyone’s stomach.

We’re Stranded. Again.

The Horror:
No rides. No shuttles. Missed dinners and lost team members.

Avoid It:
Pre-book transportation for bigger groups. Even a rented minivan beats 8 frantic Uber calls.
Pro Tip: Confirm all pickups, especially in remote areas.

Oops, No Insurance

The Horror:
An injured cofounder + international hospital bill = $2,300 emergency Venmo.

Avoid It:
Travel insurance is your safety net, build it into the budget early.
Pro Tip: Group coverage is cheap and easy.

Too Much Agenda, Not Enough Fun

The Horror:
Wall-to-wall meetings = an exhausted, resentful team by Day 2.

Avoid It:
Leave space to breathe. Free afternoons = happier humans.
Pro Tip: One half-day of pure free time works wonders.

Final Thought:

Great retreats don’t happen by accident.
Plan ahead. Expect some chaos. Build in flexibility.

And if you want to skip the horror stories altogether?
Vamos is here to help you plan smarter.
→ Join the beta at govamos.io