We may earn money or products from the companies mentioned in this post. At no additional cost to you, clicking in these links go to support our blog. As an Amazon Associate, I earn from qualifying purchases.
Hi, I’m Tonya, the Travel Publisher on Detail Oriented Traveler. The Moms in the Trenches team occasionally get to travel together on a one big happy multifamily vacation. A while ago, we did just that. You can read my review of Encore Resorts, here.
The following is our advice on how to travel as a large group and originally appeared on Detail Oriented Traveler.
Have you ever considered traveling with a large group of friends? When we were younger, that was easy to do. Grab a bunch of girlfriends or a couple of other couples and off to the beach or theme parks we go.
Now that we have families of our own, traveling with a group presents its own set of challenges. The following is our comprehensive list. How to make your multifamily vacation a successful one!
Make Sure You’re Travel Compatible
Before you head out on to a big trip together, discuss what your travel styles are like. Do you stick to bedtimes on vacation or is it a free for all? Do you structure and plan activities, or are you more spontaneous? These companions are your best friends and family that you’re willing to travel with, make sure you stay that way after the vacation.
Discuss budgets. Yes, it’s not a great topic. Yet you don’t want to travel with someone that could put a financial strain on your family or vice versa.
A good way to test your travel compatibility may be to do a day trip together. Go to the zoo or the beach. Pay attention to each other’s dynamics.
Pick a Leader
You want to have one person that’s the point of contact when your friends or family have questions or when things go wrong. The leader makes the reservations, communicates with the families, arranges the travel dates. This person can change if you travel together yearly.
Alternatively, get a travel agent to be the leader. It costs nothing extra and can take the stress of finding suitable airfare and accommodations out of the mix.
If you’re traveling to Florida, I recommend Best of Orlando for all your theme park needs.
Do Something for Everyone
This can be tricky on a multifamily vacation. Maybe start with a resort that has plenty of activities and amenities for kids, as well as locations that offer popular attractions. This is not the time to hike the Grand Canyon if your entire group isn’t into it. Think Great Wolf Lodges or Kalahari Resorts for their indoor waterparks.
If you’re going to the Orlando area, we recommend Encore Resort at Reunion. It’s the comfort of a home rental, so plenty of space, with the convenience and amenities of a resort. You can read our full review here.
Compromise and Communicate
This is not the time to get everything you want. Be ready to compromise on some aspects of the multifamily vacation. The idea is to spend time with your friends or family in a new location. A compromise now is worth the quality time you get during the vacation.
Communicate often. If you have questions before, ask. If you’re concerned about something, ask. If …whatever, ask.
And if you’re the leader, communicate often. Be detailed and let everyone know what’s up and when.
Decide how finances will be tracked
Are you traveling with a group of 3 other families and splitting everything 4 ways? Or are there 15 of you and you need to split by the person? Decide ahead of time what the parameters are so no one feels like they are paying more than their fair share.
Splitwise is a fantastic app to keep everyone on the up and up when it comes to finances. If you pay for and your BFF covers activities, no need to figure out who owes what. Splitwise does the math for you.
Stay in a big home rental
If you’re traveling with a group, getting a large multifamily vacation home is one of the best ways to spend quality time together. Not only do you have a kitchen, but you also have a common space for the kids to play games and the adults to hang out after they go to bed.
Staying in a home with a pool provides even more common areas to hang out in various groups.
Assign bedrooms ahead of time
And speaking of bedrooms, it might make sense to communicate and figure that out ahead of time too. If there are two masters, but three families, who gets a smaller room?
The same can be said for the kids. Do you want siblings together or similar ages? Discuss this ahead of time so there aren’t any fights.
Get groceries delivered
Even if you have a car on vacation, it’s worth it to getdelivered. Why spend that precious time with your friends and family in a grocery store? is my choice for this. Sign up at for 2 weeks free!
Rent a home with a pool
If you’re going someplace warm, try to find a rental with a pool. This is a great place to relax at the end of the day and come together as friends or family.
Choose a home with game tables
If you can, in the larger markets, many home rentals come with game tables. We enjoyed having an air hockey and video game console at our Encore Resort home. This provides something to do in case it rains. Alternatively, it gives the kids something to do while the adults are getting everything ready for the day.
If you don’t have games in the home rental, or you’re staying in a hotel, pack some games. Whenever we’re traveling as a group, it’s fun to interact in new ways that board games and card games provide.
Decide on Days Apart
With all this together time, you may want to plan for days apart. Maybe do a child swap and each couple gets a night out on their own. Or one family group does Disney while the other heads to Universal. Whatever it is, communicate ahead of time that these are options. Don’t feel left out if some members of the family need alone time.
Have a list of Allergies and Dietary Restrictions
Orderingand factoring in allergies and dietary restrictions can be challenging with a big group. Plus, going out to eat with that many people may also be a challenge. Plan ahead and know what meals you want to cook or what restaurant’s have on their menu. Make a list for every adult in the group.
Related – How to teach kids budgeting with Groceries.
As well as dietary restrictions, you need to talk about general food preferences before you set off. The last thing you want is to book up a sushi restaurant and then get there and realize that half of you don’t like fish. It’s especially important to think about what the kids will eat, so even if you want to go somewhere adventurous, it might be better to stick to a pizza restaurant because you know that everybody will be happy with that. If you do some research and you find restaurants that you really want to try, put it to the group and see what they say. If nobody else is interested, there’s no reason why the families can’t eat separately for a night or two and meet up afterwards.
Establish Adult and Child Rules
Are you comfortable with your best friend telling your child what to do? Let’s face it, kids are going to act up even on vacation. In a large group setting, you may not be nearby to discipline your kid. Establish what the rules are in your family and try to abide by those for each group.
Planning a group trip should also come with planning for emergencies. Should someone get sick or have to back out of the vacation, protect your finances with a trip cancelation policy. Often a multifamily vacation is a greater overall expense split between the families. If one family has to back out, don’t burden everyone else with the added costs.
Depending on your needs, travel insurance can cover trip cancelation, medical emergencies and weather-related delays. We’ve used Allianz Travel in the past with tremendous success.
Traveling together with your friends and family gives you the opportunity to connect with them on a level you can’t do day to day. And while planning a multifamily vacation takes a few extra considerations, the memories you make will be priceless.
Above all else, remember to have fun!