There is a reason most families talk about planning a reunion for years before actually doing it. Getting 10, 20, or 50 people to agree on dates, a destination, a budget, and an itinerary is genuinely one of the hardest coordination challenges in group travel. You are dealing with toddlers and grandparents, picky eaters and adventurous foodies, tight budgets and deep pockets, all wrapped in the emotional complexity that only family can deliver.

But when a family reunion trip works, nothing else compares. Cousins who have only met on video calls become real friends. Grandparents watch their grandchildren play together in person. Stories get passed down that would otherwise be lost. The trip itself becomes a family heirloom.

Here is how to plan one that actually happens -- and that people actually enjoy.

Step 1: Appoint a Planning Committee (Not Just One Person)

The single biggest mistake in family reunion planning is putting all the work on one person. That person burns out, gets resentful, and the trip either falls apart or succeeds at their expense.

Instead, form a small planning committee of 3 to 5 people, ideally representing different branches of the family and different generations. Assign clear roles:

Logistics lead: Handles venue research, booking, and travel coordination
Finance lead: Manages the budget, collects payments, tracks expenses
Activities lead: Plans events, games, and outings
Communications lead: Sends updates, manages the family group chat or email chain, maintains the RSVP list

Meet virtually every two weeks starting six months before the trip. Use a shared Google Doc or Notion page to track decisions and action items.

Step 2: Choose Your Dates Strategically

For large families, you will never find dates that work for everyone. Accept this early. Instead, aim for dates that work for the most people, especially the key family members whose presence matters most (the matriarch, the patriarch, the cousin everyone loves).

Best windows for family reunions:

Memorial Day weekend (late May): Three-day weekend, warm weather, summer pricing has not peaked yet
Fourth of July week: Many people already plan to take time off, but prices are high
Labor Day weekend (early September): Another three-day weekend, slightly cooler, kids are often back in school but can miss a Friday
Thanksgiving week: Everyone is already in travel mode, but this competes with individual family traditions
Summer (June-August): Longest window for school-age kids, but the most expensive

Send a poll with 3 to 4 date options at least 8 months in advance. Give people two weeks to respond, then lock it in. Waiting for 100% consensus means waiting forever.

Step 3: Pick the Right Destination Format

The destination format matters more than the specific location. Choose based on your family's size, budget, and personality.

All-Inclusive Resorts

Best for: 15-40 people who want simplicity and predictable costs

All-inclusive resorts remove the biggest headache of large-group travel: paying for things. Meals, drinks, activities, and entertainment are bundled into one price. Everyone eats when they want, does what they want, and nobody argues about the dinner bill.

Top picks for family reunions:

Beaches Resorts (Turks and Caicos, Jamaica, Curacao): Specifically designed for families, with kids clubs, water parks, and family suites. Group rates start around $250 per person per night.
Club Med (various locations): Strong kids programs (called "Mini Clubs"), sports, and evening entertainment. Group rates from $200 per person per night.
Moon Palace, Cancun: Massive property with something for every age. Group rates from $180 per person per night.

Drawback: Less flexibility, and some family members may find the resort environment too contained.

Rental Villas or Large Homes

Best for: 10-25 people who want a home base and a communal atmosphere

A large vacation rental (or a cluster of smaller ones) gives the family a shared gathering space -- a big kitchen, a living room, a pool -- that becomes the heart of the reunion.

Where to look:

VRBO and Vacasa tend to have more large-property listings than Airbnb
Search by group size, not just bedrooms. A 6-bedroom house might sleep 14 comfortably or 20 with air mattresses, depending on the layout.
Look for properties with outdoor space: a big yard, a pool, or proximity to a beach or park

Estimated costs: A large lakeside home sleeping 16 in the Smoky Mountains runs $400-$800 per night total, or $25-$50 per person per night. A beachfront compound in the Outer Banks sleeping 24 runs $800-$2,000 per night total.

Drawback: Someone has to manage cooking, cleaning, and shared spaces. Assign chore rotations from day one.

Cruise Ships

Best for: 20-50+ people with varying interests and budgets

Cruises are secretly one of the best family reunion formats. Everyone books their own cabin at whatever price tier they can afford (interior cabin to suite). Meals are included. Activities span toddler splash zones to adult-only lounges. And the ship handles all the logistics.

Group booking perks (usually available for 8+ cabins):

One free cabin for every 8-16 booked (varies by cruise line)
Private event space for a family dinner or gathering
Group shore excursion discounts
Dedicated group coordinator from the cruise line

Recommended lines for family reunions:

Royal Caribbean: Best activity variety (rock climbing, surf simulator, water slides)
Disney Cruise Line: Unmatched for families with kids under 12, but pricier
Norwegian Cruise Line: Flexible dining, good freestyle approach for groups

Drawback: Port days scatter the group, and some family members may get seasick or dislike the cruise environment.

Campgrounds or State Parks

Best for: 10-30 people who love the outdoors and want affordability

State parks with group camping sites or cabin clusters offer a back-to-basics reunion that strips away distractions and forces genuine togetherness. Campfires, hikes, fishing, and stargazing cost almost nothing.

Estimated costs: Group campsites run $50-$150 per night total. State park cabins run $75-$200 per cabin per night.

Drawback: Requires more physical ability and tolerance for limited amenities. Not ideal if the family includes elderly members with mobility issues or very young children who need climate control.

Step 4: Set Up a Financial System That Actually Works

Money is the number one reason family reunions fall apart. Here is how to handle it.

Collect Deposits Early

Require a non-refundable deposit (typically $50-$100 per family unit) within 30 days of announcing the trip. This separates the committed from the "sounds fun, maybe." Use Venmo, Zelle, or PayPal -- whatever is easiest for your family.

Create a Transparent Budget

Share a simple spreadsheet showing:

Total cost of accommodation
Per-family or per-person share
Shared food/activity fund contribution
What is and is not included

Handle Income Disparities with Grace

In most families, financial situations vary enormously. The cousin who is a doctor and the cousin who is a teacher should not be expected to contribute equally to a luxury venue.

Options that work:

Tiered pricing: Larger families or higher earners pay a slightly higher share. This only works if the family culture supports it.
Core costs only: Everyone pays for accommodation and shared meals. All extras (excursions, upgraded rooms, alcohol) are individual.
Scholarship fund: The family members who can afford more contribute to a general fund that quietly subsidizes those who cannot. The logistics lead handles this privately.

Use a Shared Expense Tracker

Splitwise is the standard tool for this. Create a group, add all families, and log every shared expense. At the end of the trip, Splitwise calculates exactly who owes whom.

Step 5: Plan Activities for All Ages

The key to multi-age activities is offering layers. The same setting can work for a 5-year-old and a 70-year-old if you plan it right.

Activities That Work for Everyone

A family talent show or trivia night: Low physical demand, high entertainment value. Make trivia questions about family history for bonus connection.
A group cooking competition: Split into teams across generations. Grandma's expertise pairs with a teenager's energy.
Beach or lake day: Toddlers splash in the shallows, teens swim out to the platform, adults read on the shore, grandparents sit in the shade.
Photo scavenger hunt: Teams roam the area completing photo challenges. Adjust difficulty by team.
Family Olympics: Relay races, egg tosses, three-legged races. Assign teams that mix ages and family branches.

Build in Down Time

A packed schedule exhausts a large group fast. Plan one organized group activity per day, and leave the rest open. People will naturally cluster into smaller groups -- the runners will find each other, the board game crowd will set up in the living room, the nappers will disappear after lunch. This is fine. Reunion does not mean doing everything together every minute.

Step 6: Manage Dietary Needs Without Losing Your Mind

With 20+ people, you will almost certainly have vegetarians, gluten-free eaters, nut allergies, picky kids, and that uncle who only eats steak.

Survey dietary needs in advance. Add a question to your RSVP form. Then:

For shared meals at the rental, plan dishes that are naturally flexible: taco bars, build-your-own bowls, grilled proteins with multiple sides
For restaurant dinners, choose places with varied menus and call ahead about allergies
Keep a stash of safe snacks for kids and allergy-sensitive family members
Label everything at potluck-style meals

Step 7: Create Communication Channels That Work

Before the Trip

Use email for official announcements (dates, costs, deadlines). Not everyone checks group chats.
Use a group chat (WhatsApp or a family-specific app) for casual coordination and excitement-building.
Create a shared Google Drive folder with the itinerary, packing list, dietary survey results, and emergency contacts.

During the Trip

Post the daily schedule on a physical whiteboard at the main gathering spot. Not everyone will check their phone.
Designate a meeting time and place each morning (breakfast at 8:30, main patio). Announcements happen there.
Use walkie-talkie apps (like Zello) if the venue is large and cell service is spotty.

Step 8: Capture the Memories

Hire a photographer for one afternoon if the budget allows. A one-hour family photo session ($200-$500) is worth every penny.
Set up a shared Google Photos album and ask everyone to upload their pictures throughout the trip.
Designate a "family historian" who records short video interviews with older family members, asking about their memories and stories.
Create a time capsule with notes from each family member, to be opened at the next reunion.

How TripGenie Can Help

Coordinating a family reunion trip means managing more moving parts than most people deal with outside of their actual jobs. TripGenie can help you build an itinerary that accounts for your group size, budget, and activity preferences -- then share it with the entire family so everyone knows the plan without you having to answer the same question forty times.

The Bottom Line

A family reunion trip will never be perfect. Someone will complain about the food. The kids will have a meltdown. Uncle Ray will tell the same story three times. But ten years from now, what everyone will remember is not the hiccups -- it is the afternoon the cousins spent hours in the pool together, the night Grandma taught everyone her card game, and the morning everyone sat on the porch with coffee and nowhere to be.

Plan the logistics well enough that they fade into the background. Then let the family do what families do: make memories that outlast all of us.

Planning a Family Reunion Trip That Actually Brings People Together