Traveling with a group? Here’s how to plan and stay friends

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Traveling with a group? Here’s how to plan and stay friends
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Investigating group deals may be a bit time-consuming but the research can save you money. (Source: Getty Images)

Lauren Sloss

From bachelor parties to family reunions, group trips are opportunities to explore the world with the people you love. They also have the potential to be planning messes, with scheduling, decision-making and sorting-out finances coming together in a seemingly endless and possibly disappointing snarl. But they don’t have to be. We’ve rounded up tips, tricks and tools to help plan your next group getaway, hopefully allowing everyone to focus on the fun, not the logistics.

— Understand your group dynamic

The first step in planning a successful trip: Ensure the travellers will get along well together. “Is it a group of friends, or is it a couple of families travelling together? Is it a multigenerational trip with a big age range?” said Kate Doty, managing director of premier access at the adventure travel company, Geographic Expeditions (GeoEx). “These factors all come into play with activity level, comfort zones and rooming.”

Understanding individual roles within the group is big, too. “There will be someone in the group who will be the natural leader,” Doty said. “Be candid about this! Find opportunities to talk through these topics with humour and lightness.”

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Group dynamics can play a big role in determining where to stay. Families might prefer the ease and facilities of a hotel or resort. Big groups of friends might opt to search through home rental sites like VRBO and Airbnb. Ali Killam, Airbnb’s consumer trends expert, recommends creating a shared wish list and inviting group members to add listings and vote on favourites.

“Determine what’s most important to the group when it comes to accommodations — a pool, a big kitchen, proximity to town, the beach — and filter the search accordingly,” she said.

— Shared apps are vital

Once you’ve decided on the group, figure out when everyone is available. Doodle allows users to create a poll online of possible travel dates and then vote on preferred options. Tried and true Google Sheets is a decent way to organize options for destinations, housing and more in a spreadsheet and track when and how people will be travelling.

Katrina Kagan, the partnerships and marketing associate at the weekly newsletter Girls’ Night In is the designated planner in her group of friends, who try to take group trips at least once a year. She created a trip planning spreadsheet that gathers travel details, expenses, meals and more for the purpose; her colleagues were so impressed that they shared it with the newsletter’s 150,000 subscribers.

“If you’re a planner like I am, this spreadsheet is a way to get organized enough that you can feel personally at ease during your trip. Why not take half an hour beforehand to get organized?” she said. “If you’re not a natural planner and are looking to step into that role, this can be a starting point.”

Beyond the spreadsheet, TripIt is an itinerary-building app that allows you to collect details for flights, hotels, car rentals and more into a master itinerary — the app’s Inner Circle feature allows you to share your itinerary with other members of your group.

Other ways to communicate, beyond unwieldy email chains: set up a private Facebook or WhatsApp group to send messages both while planning and when travelling. Google Docs make for a shared repository of events and suggestions and other vital information. And, if you plan on Instagramming your travels, a fun group hashtag is a nice way to keep track of the memories.

— Figure out finances

Tracking expenses is doable via spreadsheet, but still requires a fair amount of work to properly divvy up shares and figure out who owes what. Splittr and Splitwise are popular mobile free apps for tracking, prorating and ultimately balancing expenses, available offline and in multiple currencies.

“I was travelling a lot with friends, and I was the one who did the spreadsheet after the trip. I thought, ‘This should be easier!’” said the Splittr founder and developer, Raphael Wichmann.

Splitwise was originally created with roommates in mind, but translates to the travel space — it also integrates directly with the payment app Venmo, allowing you to make payments and receive money directly.

“We’re looking to helps reduce stress and awkwardness when it comes to finances,” said Jon Bittner, the Splitwise chief executive. Bittner suggests creating a group as soon as the first big expense, like a house or hotel rooms, has been booked, and continue adding expenses as you go.

Looking to treat your friends or family to free rides during your trip? Uber Events allows you to set up a code to cover transportation for your crew, with options to customize the time window, location and pickup radius (we particularly like this option for weddings and family reunions).

— Getting group deals

Investigating group deals may be a bit time-consuming but the research can save you money. Amtrak recently launched Share Fares, which earns you greater discounts on tickets the more people you travel with. If booked at least three days in advance, this program can reduce ticket prices up to 35% for groups of four.

Brian Kelly, The Points Guy, has made a career out of understanding the intricacies of airline and credit card loyalty programs. On his site, he published a free article, the “Ultimate Guide to Points, Pooling and Sharing,” for applying airlines miles and credit card points to group travel.

To begin with, he warns about transferring points and suggests instead on combining them.

“Airlines will generally charge you one cent per point or mile to transfer, which negates the value,” he said. He also suggested savings could be had by taking a “look at your trip in terms of one-ways instead of round-trips, and look at it based on availability.” If flying together is a priority, consider letting members of your group with the most available points purchase individual legs of the trip. This allows for booking through multiple airlines, too.

Some domestic airlines offer perks for groups booking together, including discounted fares and flexible ticketing options (while other apps and services for booking group flights exist, we found they were neither streamlined nor consistently well reviewed).

— In doubt? Leave it to the professionals

Kelly may be a points expert, but he decided to use a travel agent for a recent group trip to Iceland. “The number of options when planning a trip can be overwhelming,” he said. And when one of his friends left a piece of luggage at the airport, the tour company was able to have it delivered to the group.

Not being responsible, he said, “felt like an actual vacation!” Others are making similar decisions: A return to travel agents and advisers is on the rise. A recent report from the MMGY Global marketing agency noted a growing number of millennials, especially millennial families, planned to use travel agents for trip planning during 2018 and 2019.

Cece Drummond, the managing director of destinations and experiences of Virtuoso, a global travel adviser network, noted that VIP treatment, better value and free benefits are some perks of using travel agencies.

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“They can easily be frustration because there’s too much information available,” she said. “Our advisers can help sort and sift through that.”

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