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The idea of friends, family and kids vacationing together sounds great, at first. What isn’t on the itinerary is a trip full of stress and hurt feelings. Below I am answering a few common questions to help on how to navigate the intricacies of traveling with others.

Who takes the lead when you have multiple planners who want to research and make trip decisions?

While there isn’t really a set rule of thumb on this, my recommendation is to have an honest, open dialog about expectations. Once you’ve determined who is taking lead or which parties are responsible for the various aspects of research, it’s critical to stick to what you’ve determined. If you have something to contribute or a concern about an aspect of the travel and you’re not the lead, don’t circumvent the other person by doing your own research. Take the issue directly to them so that you can respectfully come to a solution together.

Starting early is also wise. When things are down to the wire, it can greatly increase the potential for chaos. Plus, when you book travel nine months to a year in advance, you’re more likely to score the best deals. The longer you wait, the more expensive it will be for everyone.

What if you reach your destination and each family wants to do different activities?

Communication is key in these scenarios. As long as everyone is up-front about their expectations, this really doesn’t have to be an area of contention. If you want to break off and do a separate activity, have a clear plan when you went to reconnect for a shared activity. This will continue to create consensus for a trip that allows for individual exploration as well as time for shared community. Also, if your vacation is with friends instead of a family, be sure to select who you want to travel with wisely. Plan trips with individuals who you not only get along well with, but also have similar interests.

Who gets the master bedroom?

Typically, the person or family handling the bulk of the trip planning gets the master. It’s only fair. They’re doing the lion’s share of the work. If it’s unclear, flip a coin.

How do you handle deposits and payments when splitting a rental?

Handling payments can be one of the trickiest aspects of travel planning. In our digital age, we have many resources to make this process more seamless. Here are two apps that could be especially helpful. The first is The app has a calculator to help you determine how to divvy expenses for multiple travelers. You can break it down per night, per traveler or equally so everyone pays the exact same. The second app is Venmo, a mobile payment service owned by PayPal. It allows users to transfer money to one another using a mobile phone app or web interface. It provides great documentation to reference back to if needed. Plus, great news for those of you who love Airbnb. In 2017, they launched payment splitting for group travel.

Meals can be tricky too. Who cooks? How are groceries split?

Regarding food, devising a plan beforehand is crucial. Map out your time so you can determine how many meals you plan to eat out and how many you plan to cook in the rental. Then determine who will be responsible for meals made. Planning ahead will ensure all the responsibility and expense are not falling on one family but can be truly shared.

Overall, when it comes to group travel, it’s best to have clear expectations and express them so everyone is on the same page. When it comes to money matters, always be prepared to pay deposits and fees when due. Delays in payment can create a strain on the other parties. You don’t want to start your trip on the wrong foot before it even begins. For a vacation filled with memories and few mishaps, my top two pieces of advice are to communicate well and plan intentionally.


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