How to Plan a Family Reunion Trip

By Sophie Friedman. May 10, 2023 · 6 minute read

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How to Plan a Family Reunion Trip

The hardest part is knowing where to start. We’ll walk you through planning timelines, money-saving tips, and ideas for when, where, and how long your reunion trip should be.

Benefits of a Family Reunion Trip

The benefits of a family reunion trip are many: It’s a rare chance to reconnect, strengthen relationships, and make new memories. Sure, you’ll see one another at the next wedding, graduation, or funeral, but a dedicated family reunion is an opportunity for multiple generations to simply be together, without the pressure of pre-scheduled events.

Family reunions are especially important for the oldest and youngest family members. Grandparents and great grandparents won’t be around forever. Little ones may not immediately appreciate the time they spend with older relatives, but they will be sure to appreciate these memories — and group photos! — years down the line.

How to Plan a Family Reunion Trip

Organization is crucial when it comes to destination family reunion planning. After all, you’re planning a vacation for potentially dozens of people of varying ages and interests. Maybe you’re a spreadsheet and travel aficionado, in which case, bon voyage! If not, read on for everything you need to consider when planning a family reunion trip, then divide and conquer.

Where, When, and How Long: Guidelines

Every family has diverging interests. Maybe the younger generation love long hikes, but Uncle Mike prefers antiquing, your grandmother could splash in the pool all day, and your brother is practically a vampire. A well-planned destination family reunion vacation will offer something for everyone.

Recommended: How Families Afford to Travel

How Long Should A Family Reunion Trip Be?

Is your family thinking of a week-long vacation or a weekend getaway? Keep in mind that not everyone has the same vacation time from work, and some people may have other obligations they must allocate vacation days to. It’s also important to find out which families may be traveling with pets.

The length of a reunion is often determined by budget. Whoever the lead organizer is should simply ask the group (more on how to do that below) what everyone’s maximum budget is and go from there.

When and Where to Take a Family Reunion Trip

Agreeing on a time of year for your reunion may be easier than you think. First, take into account how many attendees have school-aged kids. For them, winter and summer breaks will be the most convenient times to travel, but also the most expensive. Instead, consider using a shoulder-season school holiday, like Indigenous Peoples’ Day in October or Memorial Day in May, and taking a long weekend trip. Bonus: The weather in many destinations will be pleasant, but prices won’t yet be sky-high.

When evaluating destinations, contemplate: How many people are coming? Will you fly or drive? Is it easier to stay somewhere walkable, or does the group prefer renting cars? Ask select family members for their top (realistic) destination ideas.

Recommended: How to Balance the Urge to Travel and the Need to Save

How to Save On A Family Reunion Trip

Accommodations tend to take a big bite out of travel funds. For most groups, sharing one or more houses or apartments will be much more affordable than booking hotel rooms. In Montana, for example, you may well find two nearby houses that can hold a dozen people each. In Fort Lauderdale, you’re more likely to find three- to four-bedroom condos.

Sharing accommodations can also make it easier to prorate costs, allowing those on a tight budget to select a smaller room or pull-out couch. (Also keep in mind credit card rewards, which are sometimes applicable to vacation home sites.)

Other advantages of a rental house are space to spread out, doors that can be closed when kids are sleeping but adults are up late talking, and the ability to prepare meals — another huge cost saver.

Family Reunion Planning Timeline

Your planning timeline will vary depending on your destination. If the gang is flying to Hawaii from across the country, you’ll want to book flights many months in advance and keep your eye on hotel prices. If everyone is driving, you can book accommodations a few months out and then wait to plan activities.

6–12 months out: Use a free online poll tool or the poll feature in messaging apps like Whatsapp and Telegram to vote on when and where to go. The group chat can be your best friend and worst enemy (btw, you may want to mute it), but it is useful for soliciting opinions. It’s important to confirm budgets and expectations now.

4–5 months out: Once a destination is decided, pull a few accommodation options to fit the group’s needs, whether that’s a block of hotel rooms, a few condos, or a rental house. Reconfirm everyone’s budget, as financial circumstances can change.

If your family reunion trip requires flights, compare the price of a ticket in miles vs. cash so you can decide whether to use a credit card that gives credit card miles vs. cash back.

2 months out: Keep the momentum going by booking any activities, whether you need lift tickets, plan to take tours, or want to go snorkeling. With major logistics out of the way, this is the fun part.

1 month out: Everything that needs to be booked in advance is done, and the countdown is on. Now is the time to look into nearby grocery stores, where people might eat if they arrive late, whether strollers and carseats can be rented or should be packed, etc.

Do’s and Don’ts for a Fun, Memorable Reunion

•   Don’t overschedule your family reunion trip: Try booking only one major activity per day for those who want to participate, whether that’s a beach excursion, a museum, or a walking tour.

•   Do respect peoples’ natural rhythms: Aunt Sue may be ready for 5am bird-watching, but your college-age cousins are more likely to roll out of bed several hours later. Everyone is more cheerful when they get enough sleep, so don’t wake people at the crack of dawn with a megaphone.

•   Don’t feel compelled to capture every moment. The pressure to take a million perfect photos is very real, but try to live in the moment. You may not see some of these people again for several years.

•   Bring an instant camera: These tangible memories are the perfect family reunion souvenir, and instant camera film colors are universally flattering.

•   Pack games: Uno, travel Scrabble, Code Names, even simple packs of cards provide entertainment after dinner and on rainy afternoons.

•   Make videos: Film older relatives talking about their lives. Prompt them with questions about their childhood, who their friends were, what they ate, what they dreamed their adult lives would be. This is a wonderful way to memorialize older generations.

After the Event

•   Create a place for everyone to share photos, like Google Drive or Dropbox.

•   Print a few of the best photos and mail them to your family with a short note; it’s a treat to get snail mail.

•   If people have suggestions for the next family reunion trip, note them.

•   Use an expense tracker to organize who owes whom for shared costs.

The Takeaway

A family reunion is a unique chance for relatives across generations to meet for the first time or reconnect. Summer is generally the easiest time for families with young kids to travel, but it’s also the most expensive. If your family reunion trip works for a long weekend within driving distance, this is the most budget-friendly option. While it takes some coordination — and maybe a little stress — be assured that it is worth the trouble.


Photo credit: iStock/ferrantraite


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