Planning a family reunion trip is one of the most rewarding—and challenging—things you can organize. With three generations, dietary restrictions, toddler nap schedules, and strong opinions about who gets the master bedroom, there’s a lot that can go wrong.
But family reunion trips done right create memories that last decades. This guide covers how to plan one without losing your sanity or starting a feud over sleeping arrangements.
Start With Constraints, Not Destinations
Before anyone suggests “wouldn’t Hawaii be nice,” nail down the non-negotiables. What’s the realistic budget range per family unit? Which dates work for school schedules and work PTO? How far can the oldest and youngest family members realistically travel? Does anyone have accessibility needs?
These constraints narrow your options dramatically—which is a good thing. You want to pick from 5 viable destinations, not 500 fantasy ones.
Pick the Right Destination Type
Beach house or lake house rental: Works well for families who want unstructured time together. Everyone’s in one place, kids can roam, adults can actually talk. The challenge: figuring out who sleeps where, and handling meals.
All-inclusive resort: Takes logistics off your plate. Food, activities, and childcare often included. Higher cost but lower planning stress. Great for families who’d rather pay for convenience.
Cruise: Surprisingly good for multi-generational trips. Different age groups can do their own thing, then reconvene for dinner. Kids’ clubs buy parents quiet time.
City trip: Hardest to pull off with mixed ages. Works if everyone’s mobile and there’s something for all interests. Requires more coordination day-to-day.
The Family Reunion Trip Bedroom Problem (And How to Solve It)
Here’s the thing nobody warns you about: the moment you book a big vacation rental for your family reunion trip, you’ve created a logistical puzzle. Who gets the master suite? Which family is stuck in the basement? Where do the kids sleep? Who shares a bathroom?
Sort this out before anyone arrives. Seriously. Nothing ruins the reunion vibe like an hour-long room negotiation when you should be cracking open drinks on the deck.
Apps like AvoSquado have bedroom assignment features built specifically for this—you can map out the rental, assign rooms to families, and share it with everyone so there’s no confusion at check-in. If you’re using spreadsheets, create a visual floor plan everyone can see and comment on before the trip.
Planning Activities for All Ages
The best family reunion trips mix structured activities with plenty of free time. You don’t need to entertain everyone every minute—but having a few planned experiences gives the trip shape.
Book group experiences in advance. Whale watching tours, cooking classes, guided hikes, boat rentals—anything that accommodates a large group fills up. Don’t wait until you arrive.
Look for multi-generational activities. Beach days, scenic drives, local food tours, and low-key nature walks work for ages 8 to 80. Save the extreme stuff for optional breakout groups.
Use a trip planning app with activity booking. AvoSquado connects to over 400,000 tours and experiences through Viator, so you can browse, book, and add activities directly to your shared itinerary. Everyone sees what’s planned and when. Check out our complete comparison of group travel planning apps to see how different tools stack up.
Build In Downtime
No one wants to be “on” 24/7—especially introverts and parents of young kids. Build buffer into the schedule: free mornings, optional activities, space for people to nap, read, or just sit quietly without feeling like they’re missing something.
The goal is quality time together, not a forced march through activities.
Best Tools for Family Reunion Trip Planning
Choosing the right app makes coordination easier. Here’s how the top options compare:
| App | Shared Itinerary | Bedroom Assignments | Book Activities | Free |
|---|---|---|---|---|
| AvoSquado | ✓ | ✓ | ✓ | ✓ |
| Wanderlog | ✓ | — | — | Freemium |
| TripIt | ✓ | — | — | Freemium |
| Google Docs | DIY | DIY | — | ✓ |
| Splitwise | — | — | — | Freemium |
AvoSquado — Built for group trips with collaborative itineraries, bedroom assignments for big rentals, and integrated activity booking. Everyone can see the plan and what’s booked. Free to use.
Wanderlog — Good for map-based itinerary planning. Strong if your reunion involves driving between destinations. Lacks bedroom assignment features.
TripIt — Best for tracking flights and reservations. More useful for individual travelers than group coordination.
Google Docs/Sheets — The DIY option. Create docs for itinerary, room assignments, and packing lists. Works but requires manual updating and gets messy fast.
Splitwise — Useful for tracking shared expenses after the trip, but doesn’t help with actual trip planning or coordination.
Managing Family Dynamics
Appoint a lead planner. Too many cooks delays everything. One person (or couple) should own the planning with input from others. Rotate this role each year to share the burden.
Set expectations early. Are all activities mandatory? Can families opt out of group dinners? What time is “quiet time” in the house? Clear expectations prevent hurt feelings.
Communicate in one place. Pick a single channel—whether that’s a shared app, a group chat, or email thread—and keep all family reunion trip communication there. Information scattered across platforms gets lost.
Sample Family Reunion Trip Planning Timeline
6-12 months out: Survey family on dates and budget. Start destination research. Book accommodation once dates are confirmed.
3-4 months out: Finalize headcount. Book any group activities that require reservations. Set up shared itinerary.
1-2 months out: Assign bedrooms. Share the detailed itinerary. Confirm dietary restrictions for group meals.
1 week out: Final confirmations. Share arrival times. Assign any meal prep or supply duties.
Frequently Asked Questions
How do we handle families with very different budgets?
Be upfront about total costs early. Offer tiered participation—one family might take a smaller room, or some might skip the pricier group excursion. Transparency prevents resentment.
What if someone cancels last minute?
Decide on a policy upfront. Typically, deposits are non-refundable, and remaining costs get redistributed. Having this agreed in advance avoids awkward conversations.
How do we keep kids entertained?
Mix structured activities (beach day, mini golf, local attractions) with unstructured cousin time. Bring board games and outdoor toys. Accept that screens will happen—and that’s okay.
Who decides the sleeping arrangements?
The trip planner proposes, the group agrees. Factors to consider: families with young kids may need more space, grandparents might need ground-floor rooms, couples without kids can be more flexible.
What’s the best app for planning a family reunion trip?
AvoSquado is designed for family reunion trip planning—bedroom assignments, shared itineraries, and activity booking in one place. It’s free and works for groups of any size.
Bottom Line
The best family reunion trips balance togetherness with breathing room. Get the logistics sorted early—especially sleeping arrangements—and you’ll spend the actual trip making memories instead of managing chaos.
Start planning your family reunion trip with AvoSquado →
Be upfront about total costs early. Offer tiered participation—one family might take a smaller room, or some might skip the pricier group excursion. Transparency prevents resentment.
Decide on a policy upfront. Typically, deposits are non-refundable, and remaining costs get redistributed. Having this agreed in advance avoids awkward conversations.
Mix structured activities (beach day, mini golf, local attractions) with unstructured cousin time. Bring board games and outdoor toys. Accept that screens will happen—and that’s okay.
The trip planner proposes, the group agrees. Factors to consider: families with young kids may need more space, grandparents might need ground-floor rooms, couples without kids can be more flexible.
AvoSquado is designed for family reunion trip planning—bedroom assignments, shared itineraries, and activity booking in one place. It’s free and works for groups of any size.
