
aka “How to still like your family after you vacation together”
Traveling with other people can be fun, or it can be anxiety inducing, especially when you have a large family or new members you’ll be meeting for the first time.
🎯 We get it!
Tyann’s family has done a 4+ night Branson trip every year for the last 15 years. When we say family, we mean her parents, her siblings, the spouses, and all the kiddos.
In the beginning, that was 19 people. Fast forward through the years as the family has grown, now they would be a total of 37 people if everyone can make it!
There are many personalities that you’re traveling with, and some may clash with your own personality. It’s good to be aware and give one another grace as there will for sure be times that you get on each other’s nerves.
Here are our tips to not only survive a family trip but to enjoy it and still like everyone at the end of the trip:
1. Set expectations
Expectations will make or break your trip!
Misaligned expectations equals an unbearable experience, but clear and transparent expectations will help make this trip a repeatable one with your family.
Talk with your family about what your trip will look like. There’s no right or wrong answer, the most important part is listening to and considering all the different personalities that will be together.
👉 What is the expectation on how much time the family will spend together?
🔥 Will you be spending every moment together?
🥾 Or choose one activity a day to be together?
Setting boundaries and expectations of time will lend to a more harmonious time when you are together, whether it’s for several hours on a hike or a bit of downtime to choose a movie to watch in the family room or a book to read on the deck.
Consider the various needs of:
- family members who have limited energy
- kiddos who take naps
- eating schedules
- those with low blood sugar
- who have travel anxiety
- limited mobility issues
- needed alone time to reenergize
2. Discuss the most important needs and features for the place you stay
So. Many. Choices. On where to stay with your family.
Each trip is different, and the type of lodging will depend on your destination, the personalities of your family or group, and the features you desire for the stay.
As you discuss what will work best for your trip, consider these and decide what is important to you and what is a low priority:
💤 Sleeping
- How many bedrooms do you need?
- Who will share a bedroom and who needs their own space?
- What size and types of beds will best accommodate your family?
- If you’re considering bunkbeds for the teenagers, young adults, or even the kiddos, keep safety in mind:
- Is the top bunk railing and ladder per regulations?
- Will the person sleeping in the bunk be within the weight limit for that bed?
🍽️ Eating
- Is there a large dining area for everyone to eat together?
- Are there enough seats at the table for everyone or will you need to eat in shifts?
- Will you be making any meals during your trip?
- Is the kitchen equipped with enough pots, pans, dishes, glasses, utensils for your whole family?
🔥 “Must-haves”
- Are there specific “must-have” amenities for the trip: swimming pool, hot tub, game room, fire pit, bbq grill, deck with a view…?
- Does the location need to be within a certain distance to an activity: marina, hiking trails, groceries, restaurants, golf course, fishing…?
- Do you need extra space for the kiddos (and adults) to be kids and to play?
Figuring out the most important pieces for your stay will help you to narrow down your lodging choices while ensuring that you’ve considered all the various needs of your family.
3. An organizer, a wallet, and a contact walk into a bar…
There are 3 important roles that your family would be wise to assign as you plan your big family trip.
These roles could all be assigned to one person, or you may decide to have different people take on the responsibilities.
When our family went on our big Alaska cruise, Tyann took on all three roles.
Choose what works best for your family, but make sure that these roles are taken on by people who will be responsible and communicate with everyone going on the trip.
Because if one of these roles goes incommunicado, your trip could be in jeopardy.
✅ Role 1: The organizer
This person is most likely you who is reading these tips, or you’ve received this link from your organizer.
You enjoy researching all your options, keeping track of them, and steering the conversation back to the decisions you need made.
As far as first dibs on bedroom assignment, that’s usually you.
(And if you were assigned this role against your will, just give us a call at 417-213-3828. We’ll help you and make you look like the rock star you are.)
💰 Role 2: The wallet
You’re the one who is in charge of collecting all the monies if you’re splitting the costs with your family, or you’re the grandparent paying for it all.
Either way, everyone trusts you to make the payments and secure the trip. And you get second choice on bedroom assignment.
📣 Role 3: The contact
This role is the given to the one who is the best communicator in your family, the one who receives all the information about where you’re staying and what you’re doing. And then you share all the info with your family.
The arrival info, where to park, the house rules, the pool hours…it’s all placed in your hands (or in your email).
Being the one responsible can be stressful, but we’ve worked to make it easier for you. After you book, we’ll send you our digital guide that you can then share with everyone.
And if you want your family to get the fun info we send by text leading up to your stay, just let us know who to add to the communication flow!
4. The budget and payments
More than likely, your family members each have different priorities on their budget allotment for the trip.
When it comes to money, it’s wise to understand each person’s boundaries on how much they want to spend and how they want to spend it. Then respect those boundaries!
👉 Are you splitting the cost evenly across the board for the place to stay?
⬆️ Is someone willing to pay more for an upgrade or first choice of bedroom suite?
Consider transportation, food and activities in your budget outline also. Is someone willing to skip an attraction to put more funds towards a better place to stay? Or someone may prefer to make more meals at the vacation home to have more in the activities budget line.
If you’re renting a vacation home for your trip, you’ll probably have one person collecting all the funds and then submitting payment for the home. See the wallet role above.
Will you be doing the same for other activities like a show so that you can order the tickets together to confirm sitting together? Will a restaurant bill be split at the time of payment or will it be paid all together as a single bill?
Making these budget and payment decisions ahead of time will avoid confusion and tension at the time of paying a bill. And if you need a way to track costs, consider a simple spreadsheet or an app like Splitwise.
💡 We’ve even had some families make contributions to a shared bank account throughout the year and then all expenses for the trip are paid out of that bank account.
There are several ways to manage the money and payments, the key is to sort out and establish expectations ahead of time to ensure fewer bumps on the trip.
5. Leave hangry at home: meals, snacks, beverages
Figuring out the food plan is especially important for the foodies. And by “foodies” we mean those who:
- ❤️ love food, period
- 👋 obsess over food
- 🎯 get hangry if they don’t eat regularly
- 💯 must eat for survival
Guess that’s all of us. And, yes, we said food plan!
Here are the important food questions to ask your family:
- Is each family on their own for groceries and meals?
- Will you split the grocery bill?
- Will you make meals for the whole group?
- Which meals will be at the vacation home and which ones will be at a restaurant?
- Do you need to make any reservations?
- What about bringing in a private chef or having a meal catered?
Double check with your family on their current eating habits and styles:
- Is someone doing their best to stay away from sugar?
- Is another eating all proteins?
- Another one non gluten or is Alpha-gal?
- Maybe someone doesn’t eat breakfast?
- Do you have teenage boys who are bottomless pits when it comes to food?
@bransonfamilyretreats #recipe #secret #family #ricekrispietreats #nobake @Jif @Kellogg’s Rice Krispies @Rice Krispies Treats ♬ Little Things - Adrián Berenguer
When Tyann’s family does their annual family trip, they put each sibling’s family in charge of a meal or two. That means each sibling will choose the meal they’ll make for the whole family. They do this for 2 meals per day and for that other meal everyone is on their own.
They’ll let everyone know ahead of time what the planned meal is and also include what variances might be made for eating habits that the main dish might not accommodate. But beyond that, if someone simply doesn’t like the planned meal, they’re welcome to eat previous leftovers or take care of their own meal.
For snacks and beverages, everyone contributes their favorites. But if it’s a special item that they aren’t willing to share, they’ll hide it so the siblings don’t find it. Some things simply don’t change even when you grow up, do they? 😆
But don’t forget about the snacks and treats you can make while on your trip. Bake chocolate chip cookies with Grandma, mix up some Rice Krispie Treats with Auntie, or slice up some fruit with Dad.
🎯 The important part is to always have snacks available to satisfy the hunger between planned meals.
One of our guests holds a cooking competition between the families, trying to outdo one another with the meal they serve to the whole group.
Another guest hires a private chef for one of the dinners so that no one has to prep or make a large meal that day. Cooking is a lot of work, and you’re on vacation!
6. Communicate the house rules and arrival info
Sharing this crucial information can be simple and a sanity saver for yourself.
By ensuring everyone has the House Rules and Arrival Info handy for themselves, you don’t have to become the nagging enforcer. Here are a few things you can do:
- Forward emails to your family
- Share the link to the digital guidebook with your family
- Encourage your family to look at the info
And when your family asks about the info that you’ve already sent them, you can answer their question by referring back to the emails or digital guidebook.
Here’s what that might look like…
Additionally, consider assigning bedrooms ahead of time before arrival. Ask for a floor plan of the vacation home you’ve booked if you don’t see it on the property website, and then assign bedrooms.
Think about which room:
- might be the quietest for littles going to bed early
- should be awarded to the person who organized or paid for the trip
- has the bed set up that works for each family unit
Then bring door hangers to place on each bedroom so there’s reduced confusion on who’s room is whose. Plus, you don’t want anyone accidentally going into the wrong room at a poor time.
Bonus: we’ve made some door hanger templates you can print off, personalize, and even color as an activity!
- Template with hole punch, add string or ribbon (write your names)
- Template with cutting lines (write your names)
- Canva template to add your names then print
7. Create an itinerary
At minimum, have a rough idea of the main activities you expect your family to participate in.
For Tyann’s annual family trip, the expectations include one activity per day with the whole family. One day is usually an adventure activity, another day is usually a show, and another day is Family Game Night.
Our tips to ensure you have a smoother group activity time:
- Each family choose one activity that’s important to them
- Consider ability levels of all family members
- Build in waiting time to gather everyone
With traveling as a large family and even multiple vehicles, it’s also easy to mistakenly leave someone behind. You might think that could never happen, but it does!
Consider having assigned buddies, especially with the kiddos, so someone isn’t forgotten back at the vacation home or at an activity. We’ve had some guests even charter a bus or rent a large passenger van so that everyone can ride together.
8. Make space for downtime
Downtime is the time to recharge energy.
Everyone needs it, and making space for it will give the opportunity for happier attitudes when it’s activity time:
😴 quick nap for the littles and gramps
🕹️ video games or a movie for the teenagers
📖 curled up on the deck with a book
🎣 dropping a line in the water for some fishing
🌅 glass of wine and sister conversations as the sun sets
🎱 shooting some pool with the brothers and the football game on
🐶 taking the dog for a walk
Recognizing that each person simply needs their recharge time and space is an excellent way to show love and care for your family.
9. Be flexible, have patience, give grace
Even the best laid plans aren’t foolproof. Having back up plans and being flexible will help ease disappointment when something isn’t perfect.
Maybe the day you planned to go boating on the lake ends up being a rainy day. Consider rescheduling your boat reservation to another day and then spend the day in your jammies making cookies, playing board games, swimming in the indoor pool and dancing in the rain.
Did the show you were hoping to see sell out before you could get tickets? Consider catching one of the other newly opened shows and experiencing their amazing talent.
Or there’s a 90 minute wait for the restaurant you picked for dinner, maybe that means getting snow cones while you wait for your table. Flexibility is key.
You will one hundred percent run into traffic during your trip. It is what it is!
You can use Waze app to help find a route around the traffic. Or ahead of time get directions on Google Map and input your expected departure time to check if it’s during a normal heavy traffic time of day.
Have that one family member who is always running late? There’s nothing wrong with telling them that you’re meeting 15 minutes earlier than the actual time to create a buffer.
Whatever you do, bring your patience with you. Traveling with family, and even more so when you’re a large group, you’ll need your patience for survival as well as be ready to heap out lots of grace to others.
10. Book a stay with us
We’re all about family traveling together and do our best to provide the little details for comfort and ease that are usually overlooked.
Including but not limited to:
- 🔌 Bedside charging ports for easy access
- 📺 TV in every bedroom for downtime
- 🧼 En suite bathrooms for nearly every bedroom
- 🍪 KitchenAid mixers for baking
- 🐶 Dog-friendly for your four legged family members
- ♿️ Wheelchair-friendly for all abilities to join you
- 👋 Personally answer your calls and texts for the utmost care
Remember to book early for best availability of popular dates.
And as soon as you make your decision on which vacation home and your travel dates, book ASAP. We’ve seen families get everything lined up except booking the home and literally minutes before they push the button to confirm their stay, another family has booked the dates.
We don’t want that to happen to you! Search your dates now




