How to Maximize Fun on Group Vacations
- Aug 7, 2025
- 6 min read
Written by Amy Spofford, Pre & Postnatal Coach
Amy Spofford is well-versed in pregnancy, birth, postpartum, and mom life. She is the founder of Eat What Feels Good, LLC, a platform promoting healthy preparation for and healing from birth so new moms can enjoy their little ones.
Let’s get real about traveling with others. Vacations with family and friends, while exciting, can be mentally taxing at times. People may disagree on what to do, where to eat, and when to put the kids to bed. These small issues can add up and leave vacationers feeling annoyed or resentful toward their loved ones. If things get particularly inflammatory, it won’t feel like much of a vacation at all. Whether we take these trips enthusiastically or out of family obligation, there are ways we can ensure a genuinely enjoyable trip that will leave our hearts full and resentment at a minimum.
Preparation helps
Spreadsheets are our friends! While there are plenty of people out there who resist them due to feeling boxed in by guidelines, it’s true that lists and itineraries allow for organization. Having a plan, as long as it’s not too rigid, usually eliminates some of the annoying things about traveling to a new place. Those who are typically not spreadsheet-inclined may romanticize the idea of a freestyle vacation, not thinking about how idle time and indecision can lead to tension among group members. There is something to be said for someone doing research and making the decisions, or for options being chosen ahead of time to avoid input from everyone in the moment. Organization makes way for unencumbered fun!
100% togetherness is unnecessary
We go on group vacations because we want to be with these people, right? Well, sure, but too much constant togetherness leaves no room to breathe and can end up being a detriment to the group fun. When any two or more households come together for an entire week (or more), the clash of different routines becomes apparent. People like their routines, and too much deviation is stressful. A great solution to this is allowing for time apart. After all, it’s everyone’s vacation, so it doesn’t feel fair to be following an itinerary made by one person the entire time.
Some of the kids want to take a walk? One or two parents can take them while others stay back. Some people want pizza, and others want to make tacos. That’s fine! You will meet up later to play card games. The kids want to go on rides at a park, but some babies are ready for bed. Everyone can get what they want. Sure, this means not everyone will be together all the time, but that makes the full-group times that much more special.
There is often one person in the group who feels responsible for everyone having fun and being together. This is usually the person who has done the most planning, researching, and organizing for the trip. Because they have put in so much effort to make everything amazing, people splitting off and making separate plans may stress them out. Having a conversation ahead of time can smooth this over, and the planner can get on board once they understand they do not have to bear this burden. I have been on both sides of this issue, and I am happy to report that people can change, and this can become a non-issue!
Vacation is in the eye of the beholder
Different routines and family dynamics aside, people have different perspectives on what feels like a vacation to them. For example, while one person loves to cook every night on a beach vacation because it saves money (among other benefits), another person may want to take advantage of local fare or have a break from cooking. In this case, a combination of group meals in and out of the house could work, or the group can decide to split up for meals.
The key is to communicate what you want to do. Martyrdom, in this case, backfires big time, because if it’s been settled that everyone can get what they want but you don’t speak up, you’ll be the one constantly sacrificing, and no one else will know. You will ruin your own time. If you feel like you’re constantly the one giving so others can have fun, make sure to check yourself. Tell the group you want to go for a pedicure, shop for souvenirs, or whatever is on your list of fun things to do. This only works when you embrace the fact that you deserve your version of a vacation, too.
Talk about finances ahead of time
We all know money issues cause tension within groups. This is part of why spreadsheets can be helpful ahead of a vacation, because they highlight the fairness of contributions like food, booze, and supplies, and lay out other costs clearly, in writing. When dining out, it’s helpful to set the expectation of whether families will take turns paying, use separate checks, or send money to the payer for their individual portion of the bill. Things to consider will be whether kids are involved, whether a household is single or dual income, and whether alcohol is being ordered or brought. While it’s fun to be generous, no one likes to pay more than their share when they’re short on cash. Be careful of phrases like “it all comes out in the wash,” because this isn’t always the case.
Vacationing with children
On a kid-free vacation, people typically feel more comfortable stating what they want to do, but with children present, kids’ needs often win out. Kids need adults to get ready for the day, apply sunscreen, fix their meals, and supervise them. Partners need to have conversations about the delegation of duties if both parties are going to have fun on vacation. If there are multiple sets of parents on the trip, collective parenting tasks, like making a batch of the kids’ favorite foods or having shareable snacks on hand, can be helpful and give other parents intermittent breaks. Setting ground rules and giving permission for the redirection of kids who aren’t yours can reduce tension as well. No one likes another adult disciplining their child in front of them, but when on a group vacation, not every parent will be present when corrections need to be made in behavior. Being on the same page about rules, respecting all adults present, bedtimes, and allotments of screens and sweets can be helpful. Tension among children transfers to tension among their parents, and when the mama bears come out, relationships can be strained. Remember to be kind to your friends’ kids even when you need to be firm, because their parents will remember if you aren’t.
Make memories by adding whimsy
Group vacations can be the source of memories that last a lifetime. Some ways to elevate the experience can involve bringing games, crafts, matching outfits, and merch dedicated to the trip itself. Card games, board games, tech-based fun presentations, and homemade trivia rounds with personalized questions are some of the hilarious and thrilling ways I’ve passed the time with friends and family while away. We have brought crafts and other children’s activities for the kids to stay occupied and bought matching items ahead of time just for the fun of feeling coordinated. We have even made our own tie-dye shirts that we then wore for family photos! Koozies, printed tees, and beach bags can all be personalized for vacation merch that you can use for years to come. Making it fun and not taking yourselves too seriously truly contributes to endless memories that will keep you coming back for more, year after year.
Read more from Amy Spofford
Amy Spofford, Pre & Postnatal Coach
Amy Spofford is a Pre & Postnatal Coach, a Nutritional Therapy Practitioner, and a mom of three little ones. Practicing as a speech-language pathologist in a nursing home rehab setting during a pandemic made pregnancy and early parenthood beyond difficult. Amy used her holistic nutrition certification and research skills to dive deep into all things pregnancy, birth, and postpartum, thinking there has to be a better way to navigate this season of life. This led to her becoming certified as a Pre & Postnatal coach. Her mission is to reduce the incidence of perinatal mood and anxiety disorders by providing education and support to pregnant women through their transition into postpartum.
