The Annual Trip or Reunion
Thirty-two easy ways to plan an annual trip or reunion, the yearly highlight that anchors a friendship.
A yearly trip is a big warm anchor. Plan it with care.
28 tips that really help
These ideas come from The Good Life (Robert Waldinger and Marc Schulz), Friends (Robin Dunbar), Platonic (Marisa Franco), and everyday practice. Pick one tip and try it today.
Why an annual trip
A regular reunion gives friendships something to look forward to and a deep well of memories. It anchors the year.
Plan one.
Pick a repeating time
Same weekend or season each year. Predictable dates make planning easy.
Choose.
Start small
A day trip or one night counts. Grow it later.
Start small.
Agree on a budget
Talk money early. Choose options that suit everyone.
Be clear.
Choose a place together
Offer three options and vote. Fair choices build goodwill.
Vote.
Share the planning
Divide tasks: travel, stay, food, activities. Fairness matters.
Share.
Book early
Early booking saves money and ensures dates. Commit.
Book.
Plan some free time
Allow solo time and rest. Space helps closeness.
Allow it.
Plan a few shared activities
One or two special activities create memories. Do not overpack.
Choose a few.
Capture memories
Take photos, keep tickets and write notes. Make an album.
Capture.
Plan the next one
Before leaving, decide next year’s date or place. Keep the tradition.
Plan.
Script: proposing
Shall we plan a weekend trip together next June? Say it brightly.
Use it.
Script: budget
What budget would feel comfortable for everyone? Say it kindly.
Use it.
Script: sharing
I will research places if you check dates. Say it cheerfully.
Use it.
Script: flexible
I am easy about where, so tell me what you prefer. Say it gently.
Use it.
Script: closing
Thanks for planning with me, I can not wait. Say it sincerely.
Use it.
Mistake: avoiding money talk
Hidden costs cause stress, so be clear.
Talk.
Mistake: inviting too many
Large groups are hard to organise, so choose a core.
Keep it small.
Mistake: dropping the tradition after one miss
One miss is fine, so restart next year.
Continue.
Mistake: ignoring different budgets
Pick options that suit all, so be fair.
Be kind.
Troubleshoot: when schedules clash
Offer rotating dates or a flexible season. Stay open.
Adapt.
Troubleshoot: when money is tight
Choose cheap or free options like camping or local trips. Fun is not costly.
Go cheap.
Troubleshoot: when someone cannot come
Include them by video or share photos. Keep the bond.
Include.
Troubleshoot: when planning stalls
Pick a leader and a deadline. Gentle leadership helps.
Lead kindly.
Troubleshoot: when travel is hard
Meet halfway or use a central place. Be creative.
Compromise.
Drill: pick a yearly date
Choose a repeating weekend for a friend trip and invite them. Put it in the calendar.
Choose.
Drill: write three place ideas
List three possible places and prices. Share with friends.
List.
Drill: start a shared album
Create a shared photo album for your trips. Add the first photo.
Create.
Easy things to say
When you are stuck, pick one of these. They work in many everyday friendships.
“Shall we plan a trip next summer?”
“What budget feels comfortable?”
“I will research places.”
“I am easy about dates.”
“Thanks for planning with me.”
“Can not wait.”
Your first week
One small action a day. Each day is only a little bigger than the last.
Pick a time of year
Pick a budget
Pick a place
Share tasks
Book early
Plan flexibility
Make memories
Further reading
- The Good Life (Robert Waldinger and Marc Schulz)
- Friends (Robin Dunbar)
- Platonic (Marisa Franco)
The tips above are written in our own words and are general guidance. The books are suggestions for further reading.
More lessons in “How to Maintain Friendships”
Keep going. Small steps every day make a big change.
← Previous: Gratitude Messages for No ReasonNext: Monthly Dinner or Game Night →
- Why Good Friendships Fade Without a Fight
- Time, Distance and Busy Seasons
- Life Stages and Friend Drift
- The Silence Spiral
- Why It Is Never Too Late to Reconnect
- Friendship Needs Maintenance Like Anything Else
- What Long Friendships Have in Common
- The Five-Minute Check-In
- Share Something That Made You Think of Them
- React to Their Posts Meaningfully
- Send a Voice Note on Your Walk
- Keep a Standing Weekly Call
- The Birthday Habit
- Gratitude Messages for No Reason
- The Annual Trip or Reunion
- Monthly Dinner or Game Night
- Holiday Traditions With Friends
- Book Clubs and Shared Projects
- Walk-and-Talk Dates
- Create a Friend Group Chat Worth Keeping
- Celebrate Milestones Together
- Make Time Zones Work
- Video Calls With Purpose
- Watch, Play or Cook Together Online
- Send Letters, Cards and Surprises
- Plan Visits Well in Advance
- Make Every Reunion Count
- Keep the Daily Life Connection
- Reach Out After a Long Silence
- Apologise Sincerely and Simply
- Forgive Without Forgetting Yourself
- Resolve a Misunderstanding
- Rebuild After a Disagreement
- Make Peace With Friends Who Have Changed
- Nurture a Circle, Not Just a Few People
- Make New Friends at Every Age
- Be a Friend to Older and Younger People
- Leave Room for Change
- Let Go Kindly When You Must
- Your Lifelong Friendship Plan
