How to Plan a Family Reunion Vacation

A family reunion vacation brings together loved ones spread across the country or world. But where to begin planning a destination family reunion? As with any important project, there’s only one way to tackle it: one step at a time. Plan a memorable multigenerational holiday with these eight helpful tips for a family reunion trip. 

This website sometimes receives compensation, hosted travel, or products related to blog posts. This article may include affiliate links at no extra cost to consumers. As an Amazon Associate, we earn money from qualifying purchases.

1. Start early and choose dates.

It can be a challenge to plan a vacation for one family unit. Throw into the mix additional ages and abilities, strong personalities, various preferences, differing budgets, and assorted travel logistics. A family reunion vacation can seem daunting to organize, but it’s worth it for the quality time spent together and lifelong memories made. Start planning early, ideally one year or at least a few months in advance.

The first step is choosing definitive vacation dates that work for everyone. Once these dates are selected, everyone involved must truly commit. That means requesting those dates off from work, putting them on the calendar, and not changing the dates unless there is a medical emergency. I played by these rules and wound up missing one of my best friend’s weddings, which she scheduled to take place after I had already promised to attend my family’s destination reunion.

2. Designate leaders.

Since you’re the one reading this article, the main family reunion leader is probably you. But maybe not. If you’ve recently had a major life event (had a baby, started a demanding new job, enrolled in graduate school, gone through a divorce), then you may not have the time or presence to do the heavy lifting. The leader should be someone who has the interest, organizational skills, and, most importantly, perseverance to get the trip from the “wouldn’t it be nice” phase to fruition.

Each family unit needs a leader or spokesperson as well. As you get further into the planning process, you may want to assign one person to plan meals, another to be in charge of organizing activities, and another to arrange accommodations.

3. Pick the best destination for your family reunion vacation.

Next up? You need a destination! This sounds like the fun part, and it might be. Or it could prove difficult indeed. Ask each family unit to narrow down their suggested destinations to three to five places. You can brainstorm via email or text. Eventually, though, you’ll want to set up a Zoom call attended by all family members or each family unit leader to hash out which place makes the most sense.

Keep travel budgets in mind.

Some family units may have much more expendable income than others. If someone has deep pockets and a generous heart who wants to pitch in to pay a portion (or all expenses) for others who can’t afford as much, then that might solve the problem. But, this may not be feasible or other family members may not be comfortable accepting such financial help. It works best to choose a destination that works for all budgets and allows those with extra cash to choose upgrades and more expensive experiences as desired.

Don’t forget travel logistics.

Air travel and other forms of transport can greatly affect costs. Therefore, do some research on how much it will cost each family unit to reach destinations before making your final decision. It’s also obviously much more expensive for a family of five to reach a faraway destination than it is for a couple without kids. Plus, travel time can really eat into vacation days. It’s probably best to choose a destination in the middle of all participants, if possible.

Think about activities for all ages.

You also want to consider the variety of activities available for each attendee. On a family reunion vacation to lovely Los Cabos, Mexico years ago, my family unit wound up feeling left out. That’s because my husband and I spent most of our time managing naps and mealtimes for our toddler at the resort by ourselves. Meanwhile, the rest of our crew’s older kids and adults were out enjoying activities together, like surf lessons and horseback riding. 

Avoid too much sightseeing.

It can be difficult to manage many people in a destination where the focus is on sightseeing, like New York City or Washington DC. You may end up spending a lot of time wrangling your extended family or exploring separately. A destination with lots of options for large group activities, as well as some smaller spin-off fun, works best.

Plan to compromise.

For our most recent family reunion vacation, some of us wanted to fly to Hawaii, but this tropical locale proved too expensive for some family members to reach. Walt Disney World was shot down because we worried this destination’s pace would be too hectic and not allow enough downtime together. We also considered embarking on a Caribbean cruise, but my brother-in-law detests the idea of cruising. Others suggested a San Diego vacation, but my family of four lived there at the time and we argued we wouldn’t be able to truly relax in our hometown.

After much debate, we all agreed on a summer trip to Keystone, Colorado. This outdoorsy destination offered tons of activities for all sorts of ages and personalities, allowing everyone to pick and choose the things they wanted to do.

4. Choose the right accommodations.

The right accommodations can make or break a vacation. This is never truer than when planning a multigenerational holiday with lots of attendees.

Consider an all-inclusive resort.

If you want to stay in a hotel or resort, then consider an all-inclusive option. All-inclusive resorts make budgeting easier, meals easier to organize, and provide lots of things to do. Be sure to ask for a group discount if booking several rooms.

Book a cruise.

A multigenerational cruise may be the easiest route for planning a family reunion vacation. Cruises offer a ton of activities for all ages and interests. Also, you can request that your entire family be seated together each evening for meals. That way, groups can set off on various shore excursions during the day and then come together each night over dinner to swap tales of adventures.

Stay together in a vacation rental home.

In Keystone, all 13 of us stayed together in a vacation rental house. Our temporary home was outfitted with seven bedrooms, a pool table, air hockey, a hot tub, and a fireplace. All of this added to the fun of our family reunion trip. It may sound daunting to have so many family members under one roof, but we planned plenty of daytime activities with smaller groups or alone time as needed. 

If sharing accommodations, then figure out how you’ll divvy up costs before leaving home. You could pay according to bedrooms used or number of people per family unit (with a potential discount for children aged 12 and younger). Be sensitive to budget constraints here, too!

5. Plan meals in advance.

If you plan to dine out often, then be sure to make dining reservations in advance. This is especially true if you’re traveling with a large group, which cannot be easily accommodated at the last minute. You may also want to designate a couple of nights in for takeout or delivery dinner. Being on the go-go-go all day and evening can be tiring for vacationers, especially children, and older family members.

Make some of your own meals, if possible.

A vacation rental home can save your family lots of money and stress when it comes to planning meals. Even if you don’t have a full kitchen at your accommodations, buying some groceries for easy snacks and breakfasts saves on money and time. You can also handily pack lunches for hikes and other outdoorsy activities. In the evenings, come together as a group for dinners. 

Take turns choosing meals.

For those staying in hotels or who don’t like to cook, have each family choose a restaurant for a specified night. This spreads the responsibility and the joy of selecting where to eat. If family units pay for the group on their designated night, then that alleviates some of the worries of selecting dining options that meet various budget needs.

When renting a vacation home, I suggest scheduling who will make dinner each night. During our Keystone family reunion trip, our extended family ate two dinners at restaurants together, but different family units took turns as chefs the rest of the nights. 

Host themed dinners.

We upped the fun by decorating our rental cabin differently for three festive dinners. First, we celebrated milestone birthdays that had taken place throughout the year (my 40th, my sister’s 50th, and both my parents’ 70th birthdays). Another evening, we commemorated my triplet niece and nephews’ graduation from high school. Finally, we honored my parents’ 50th wedding anniversary.

My sister-in-law thought ahead by packing decorations in her suitcase. Meanwhile, the rest of got creative searching for candles, balloons and other merry touches at local stores. Even if you’re not celebrating anything in particular, it would be exciting to choose different themes for each dinner — like luau, jazz club, or French bistro.

6. Consider childcare options.

If you’re hoping your family reunion vacation will mean relief in terms of childcare, then be sure to make your wishes known before you leave home. You might hope your in-laws will watch the kiddos every other night, but this might make them feel stressed out. You’re better off discussing expectations in advance.

Childcare was one of the reasons I originally pushed for a cruise before we decided to vacation in Keystone. My children love kids clubs on cruise ships, and I didn’t want to miss out on grown-up fun. Staying together in a rental home, however, meant that my kids got to choose a different family member to read their bedtime stories each night. Then, it was time for the adults to play board games, sip their beverage of choice, and laugh a whole lot.

7. Organize activities before leaving home.

Once you’ve chosen travel dates, selected a destination, and booked accommodations, it’s time to plan what your family will do each day. Winging it when traveling with a large group will eat into precious vacation time and leave you scrambling to make the most of your trip.

To keep this all organized, I recommend making a spreadsheet. In my family of type-a personalities that includes two professional accountants, it was easy to find someone willing (and excited about!) creating a spreadsheet of our daily activities.

Sign up for activities in advance.

We actually had two spreadsheets. I created one with various activity options including pricing, which I asked (hounded!) each head of household to fill in all desired activities for every member of their family unit. Once I had this information, I was able to make arrangements for every event.

Plan mornings, afternoons, and evenings.

For the second spreadsheet, my dad broke each day into three parts: morning, afternoon, and evening. Everyone filled in who was doing what for each segment of the day. This made it easy to keep track of who would be where at any given time. It also helped ensure no one felt left out because they could join in or opt-out. Dinners were included in the evening section, noting which family unit was making what meal.

Spend time together and apart.

Advanced planning meant that our focus was on having a good time and connecting with each other, rather than trying to figure out where to go and what to do. Some things we all did together, like our Wagon Ride Dinner. Most things we did in smaller groups like fly-fishing, mountaintop yoga, and summer snow-tubing. I recommend making time for one-on-one activities as well. I loved hiking and talking with my 19-year-old nephew one day during our trip. Of course, introverts and ambiverts will want to schedule some alone time, too. 

8. Apologize and forgive.

Something crazy happened during my family’s multigenerational trip to Keystone: we apologized and forgave when we screwed up. This was revolutionary for my family. With so many people spending so much time together, the vacation easily could have been ruined by arguments, silent treatments, and slammed doors. Our week was not without drama. A few times people said insensitive things to others, and there were a couple of minor arguments. But that’s where this trip marked a turning point in how our family operates. A couple of hours later or the next morning, we said we were sorry. And we accepted the apologies. We hugged and moved on.

On the last day of our family reunion trip, all four family units had packed their rental cars and were ready to drive back to Denver for flights home to our different corners of the country.

Often, after several days of family togetherness, we’re all tense and ready for some time apart. Not this time, though. Everyone lingered, going back for one more hug. We all had tears in our eyes. Because we knew we’d never have this specific, special time together ever again.

Even though we knew we’d see each other in the future, there was something magical about this vacation that we didn’t want to end. It was a sense of appreciation of family and love that is often buried below busy lives and hurt feelings.

I hope you’ll plan a family reunion vacation, too, so you can experience what it feels like when love among extended family is the top priority.

Learn more family travel tips!

Want to experience Keystone, Colorado with your family? Read about these things to do in Keystone in summer. 

If you want to focus on nature play during your trip, then take a look at these outdoorsy vacations for families.

For even more travel ideas, discover my family’s picks for the best family vacation destinations.

Take this travel quiz: where to go on vacation.

Save these family reunion vacation tips!

Are you considering planning a multigenerational trip with your family? Save these tips for planning a successful family reunion trip. Simply pin the image above to Pinterest. We hope you’ll follow Travel Mamas on Pinterest while you’re at it!

Have you ever embarked on a family reunion vacation? Share your questions or tips below!

A Note from The Travel Mama: Keystone Ski Resort and other providers hosted some of my family of four’s activities and meals during our Keystone vacation. All opinions are mine, as always.

Sharing is caring!