The Destination

Where were we traveling to?

Beautiful beaches with crystal clear water, exactly as pictured in the brochures
The local food scene was much more diverse than we expected
Historical sites were less crowded in the morning
Packing

What needed to be done beforehand?

Created a shared packing checklist which helped tremendously
Should have packed more comfortable walking shoes
Forgot power adapters for international outlets
Lost Luggage

What issues did we encounter on the way?

Flight delay caused us to miss our connection
Language barrier made local transportation confusing
Hotel reservation was missing from their system
Vacation Snaps

What were the highlights of our journey?

Sunset dinner cruise exceeded all expectations
Making friends with the local tour guide made everything special
Spontaneous decision to join the cooking class was amazing

What is the Vacation Retrospective?

The Vacation Retrospective takes the retro format your team already knows and points it at a trip. It works for a family holiday, a team offsite or a business trip: anything where several people traveled together and you'd like the next one to go more smoothly. The board has four columns. The Destination covers what the place was like compared with what you expected. Packing looks at the preparation, from documents to the shoes you wished you'd brought. Lost Luggage is for everything that went wrong on the way, like delays, missing bookings or jet lag, and Vacation Snaps collects the highlights. Because everyone adds their own notes, you hear about the trip from each person's point of view. That matters when the kids, the planners and the people who went along for the ride had very different experiences. You finish with a short list of things to do differently, and a few good memories on the record.

Vacation Retrospective Format

The Destination

Where were we traveling to?

Start by asking what people expected from the destination and how it compared. Cover the surprises, good and bad, from the food and weather to how easy it was to get around.

Packing

What needed to be done beforehand?

Look at the preparation: documents, bookings and what went in the bags. Ask what turned out to be essential and what could have stayed at home, so the next packing list is better.

Lost Luggage

What issues did we encounter on the way?

Go through the problems on the trip, from minor annoyances to real setbacks. For each one, ask whether you could have prevented it or planned around it.

Vacation Snaps

What were the highlights of our journey?

End on the best moments. Invite people to share the stories they'll remember, especially the unplanned ones.

When to use this retrospective

  • After a team retreat or business trip, to plan the next one better
  • After a family vacation, to capture lessons and favorite moments
  • Before planning a new trip, so you don't repeat past problems
  • When you want feedback from a group about how a trip was organized

Suggested icebreaker questions

  • If you could instantly teleport to any destination right now, where would you go and why?
  • What's the most unusual food you've ever tried while traveling?

Want a warm-up your team plays, not just answers out loud? Browse free icebreakers →

Ideas and tips for your retrospective meeting

  • Run it within a week of getting back, while memories are fresh
  • Ask people to bring photos to jog memories and start conversations
  • Make it clear that both good and bad experiences are welcome
  • Spend your time on what you can change next time, not on things nobody could have controlled
  • Write down specific recommendations for the next trip, such as a shared packing list
  • Expect different views. Travelers often care about different things, and each perspective counts

Frequently asked questions

What is a vacation retrospective?
It's a retrospective for looking back on a trip with your family or team. The four columns are The Destination, Packing, Lost Luggage and Vacation Snaps.
When should you run a vacation retrospective?
Within a week of getting back, while memories are fresh. It suits family holidays, team retreats and business trips, and it's useful again when you start planning the next trip.
How do you run a vacation retrospective?
Give everyone a few minutes to add notes to each column, then go through them together, starting with The Destination and ending with Vacation Snaps. Finish by writing down two or three things to do differently next time.
Can you use it for a team offsite?
Yes. For an offsite or retreat, use Packing for the logistics and agenda planning and Lost Luggage for anything that disrupted the event.
How long does a vacation retrospective take?
For a single trip, 30–45 minutes is usually enough.
Ready to run this retrospective?Try this retrospective live