Our Favorite Tips for Planning a Multi-Family Vacation

Younger generations never forget taking a multi-family vacation. If you were lucky enough to travel with extended family or friends as a kid, you probably remember that trip like it was yesterday. You get to spend quality time with family and enjoy a fun vacation. Win-win! But organizing a multi-family vacation, especially for those with large families, is not easy. It requires careful planning from the get-go, compromise, and almost zero expectations. Especially if the trip is for family members of all ages. Here’s how to navigate planning a successful multifamily trip so that you don’t make mistakes, have fun, and even want to plan future group trips!

How to Plan a Successful Multi Family Vacation

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Tips for Planning a Multi-Family Vacation

1. Choose Someone To Be the Organizer

There’s a reason why ships only have one captain, businesses have one CEO, and orchestras have one conductor. There is no chance of miscommunication or mistakes between the organizers if only one person is planning this trip.

Since you’re reading this article, you clearly care about the whole family having a great time on this multi-family vacation. Chances are you’ll be the organizer unless someone else is happy to step up!

If so, you will be the point person. Expect, and encourage, the entire family to ask you any questions. You will know everything about transport, accommodations, dining, and activities. All bookings will probably be in your name unless you decide otherwise. You will need a lot of patience and, at times, it can feel overwhelming. Remember: it’s so much better that people ask questions so they aren’t confused later and forget to bring an essential item, show up late, etc.

trip planning vacation planner

Just because you should know everything about the trip, doesn’t mean you have to plan everything yourself. Conductors don’t play the actual instruments! It will be your job to create a list of tasks and delegate them to other family members. 

It’s a good idea to delegate a particular job to someone who will care the most about that task. Maybe your mom can help you pick activities because she might use a cane and is concerned about being on her feet too long. Maybe your friend can help you choose restaurants if their kids have allergies. If your husband is driving the rental car, let him pick the car! This is a great way to keep the peace when planning a multi-family vacation.

But there still needs to be one overseer. For example, you need to ensure your husband chooses a large enough car. Look up your friend’s dining options on Google Maps so they don’t pick places that are miles outside town.

2. Survey the Group 

After you’ve declared someone the organizer, this is a great time to survey the group. Different generations and larger family groups mean a lot of perspectives. You need to wade through them in the most organized way you can!

Create a survey with a program like SurveyMonkey. It might seem formal, but it’s much easier than asking endless questions to potentially dozens of friends and family members. Here are some considerations when creating your survey:

  • Length of vacation: Long weekends (4 – 5 days), one week, 10 days, or two weeks are probably adequate for the length of the vacation.
  • Date of vacation: Ask everyone to input the best months for them, and then the best dates within those months separately. Hopefully, you already have an idea of the time of year you want to travel.
  • Style of travel: Road trips, cruises, city breaks, national parks/state parks, theme parks, and resort vacations should cover most options
  • Destinations: Most people will have strong opinions about whether they want to stay in the United States (if that’s where you’re based), North America, or abroad. If people choose ‘abroad’, insert a suggestion box for countries (or a region, like the Caribbean) where they would like to travel. You may need to do a follow-up survey to narrow down a vacation destination.
  • Budget: You can use thresholds i.e. $2,000 – $3,000 per person, but many people struggle to visualize budgets like this. Few people have a clue exactly how much they spend on an entire vacation! Instead, break it down by item. Offer thresholds for flights, accommodations, food, and activities. You can always shake up the math if you’re traveling somewhere like Mexico, where the flights might be pricey but the other costs are lower. Always be clear on whether the budget suggestions are per person or not.
  • Logistics: Ask your family members if they have a valid passport and know they need to purchase travel insurance, especially if you are traveling abroad. It might sound patronizing, but your friends or family members may not travel much. They may appreciate the reminder! You’ll also feel confident that you did your due diligence by asking the question.

Always include ‘I’m flexible’ as an option. Most family members won’t be flexible, but it’s better not to force people into a choice if they don’t mind. For example, retired grandparents with a healthy pension will be less concerned about the budget than your newlywed best friend. They also won’t have to take paid time off, so the length of the trip will be less of a concern.

You can’t always go with the majority. Over half of the group may choose ‘theme parks‘, but that might not be much fun for grandpa in his mobility scooter. Several people may have entered their favorite destination of ‘Napa Valley’ into the suggestion box. Visiting wineries isn’t much fun for younger children! Always consider ages, accessibility issues, and allergies. 

Unless it’s unworkable, aim for the lowest suggested budget. Your priority is to spend quality time together, not spend everyone’s savings. Major cities, or destinations a short drive away from major cities, are an excellent choice when you all live in different states. They’re easier (and often cheaper) to travel to. Choosing a big city usually gives you more date options.

Don’t worry if you need to create a follow-up survey once you’ve narrowed the options. If most people want to go on a road trip, you need willing drivers. If everyone wants to travel abroad on your multi-family vacation, get specific about where. Find out exactly what everyone expects so you can manage those expectations.

3. Choose Lodging

Once you’ve decided on a great destination, the next thing to book is a home base. This is easy if you’re planning a cruise, and most difficult if you’re planning a road trip to remote destinations! Choose somewhere with activities suitable for older adults and little kids. 

Pueblo Bonito Resort Los Cabos

Here’s a general guide to the types of accommodation you might pick:

  • All-inclusive resorts
  • Non-inclusive properties
  • Hotels
  • Bed & Breakfasts/Guesthouses
  • Self-catered cabins, apartments, and villas
  • Motel-style accommodations

All-inclusive resorts aren’t common in the US, but they’re a perfect choice for a beach break in Mexico. Self-catered accommodation is usually great for large families, but don’t just consider the number of beds. The best places for a multi-family vacation have at least one bathroom per family. 

Keep accessibility in mind. If anyone in your group has limited mobility, ensure there are no steps up to the front door or that there is a ramp. Check that there is a step-free, first-floor bedroom. Run the accommodation you have in mind past the person with extra needs before anyone else.

Check and double-check that the amenities you need are included. At a minimum, everyone will expect free Wi-Fi, air-conditioning, hair dryers, comfortable beds, and clean hotel rooms. Some may expect a swimming pool, spa, onsite bar, onsite restaurant, a kids’ club, hot tub, free breakfast, and free parking. Expectations can make or break a multi-family trip. If there is no air-conditioning in the hotel you booked, it will be the last year you will be allowed to organize the group vacation!

Choose lodging with as many amenities as possible, but you’ll never find the perfect place that ticks every box. Keep everyone’s budget in mind from the first survey. Always run the final price by everyone before booking.

4. Discuss and Plan Meals

Next, plan meals. Your lodging will help dictate whether you are primarily eating out, ordering in, or cooking. Don’t forget to take dietary needs and budgets into account.

group dinner pizza

Staying in self-catered family vacation rentals will require the most planning (here are some easy meals to cook on vacation if you need them). Set up a spreadsheet that everyone can access with the days and mealtimes and ask everyone to sign up for an evening meal. You may also need breakfast foods, lunches, and snacks. As the point person, you will probably be responsible for the groceries. Ensure everyone is set up to reimburse you (either with Venmo, Zelle, PayPal, etc.) before the trip. Keep receipts and take photos of them so they are easy to share with your family. You could also use an app like TriCount to keep track of group expenses.

If you’re a larger group, research restaurants and make reservations. It’s unlikely that a larger group of 10+ people can show up at a restaurant and find a free table or dining room! Splitting up for some meals on multi-family trips is ideal, especially if you’re spending a week or longer together. It’s easier to cater to dietary needs and tastes and you’ll find more options.

5. Create a Group Chat 

Creating a group chat through Facebook, WhatsApp, Slack, or group messaging is a great option for keeping in touch. Choose a method that works for everyone. Ensure everyone knows how to use the ‘search’ function on your group chat so you’re not repeating the same information.

Set up the chat at the beginning of your planning phase and run all communications through this chat. This is where you can link the surveys, send reminders, and upload grocery receipts and restaurant bills. If everyone uses Google Maps, you could also create a trip map to send to everyone. Pin your accommodation, parking lots, dining options, and activities onto the map so everyone can look up the addresses.

You can also send photos you took of your great vacation and share what a good time you’re having on your group chat!

6. Plan Activities (But Don’t Overplan)

It can be tempting to plan a lot of activities so that no one complains that the trip was boring. In reality, everyone likes free time! The great thing about multiple families traveling together is that you probably have tons of things to talk about.

Before you plan, again, discuss budgets. Never book an activity (or spend any money in general!) without getting the ‘okay’ from everyone. Let everyone in the group know that they don’t have to participate in all family activities. Some people are introverts, others may like to sleep in, and some have different interests.

group hiking multi family vacation

That being said, book at least one or two activities everyone can and wants to do. Depending on the activities, one in the morning and one in the afternoon is usually enough. You can often find group discounts at a lower rate by organizing activities in advance. Have a couple of last-minute activity options in your back pocket in case of bad weather. Find activities with different options for different age groups. For example, if the older children want to go rock climbing or horseback riding, are there playgrounds or short hikes for younger children? 

Plan a special group activity towards the end of the trip, ideally something private. It’ll be a nice send-off! Booking a day trip can be one of the best ways to do something together and enjoy a change of scenery.

7. Be Flexible When Planning a Multi-Family Vacation

It can be surprising how people we are friends with can be so different when we travel together! While it can be fun, there will inevitably be hiccups and disagreements. At the very least, someone will forget their swimsuit for water activities and someone else will complain about the menu at a restaurant. Choosing the perfect spot, with the ideal accommodation, and cost-effective restaurants won’t do anything to thwart these incidents.

The most important thing to remember is that you’re all there to spend time together and make memories. Be flexible and encourage everyone else (as much as possible!) to be flexible too. 

Take a Multi-Family Vacation with Your Friends

Booking any trip for large groups with different ages, budgets, interests, and dietary requirements is a challenge. It’s even harder when you don’t spend extensive amounts of time together! But planning a multi-vacation is worth it and doable. If you follow these tips, we promise, it could even be fun!