10 Ways To Organize and Save With Group Vacations

Summer 2021 travel is heating up and closing in on pre-pandemic levels from two years ago, according to some of the latest Transportation Security Agency travel checkpoint numbers. On June 20, TSA reported 2,030,577 travelers, while exactly two years earlier, the agency reported 2,716,428 travelers.

And people are planning group trips once again, too. “Now that restrictions are loosening up, my friends and I — all travel enthusiasts — are planning to go on a summer vacation to Fiji since it’s near and just a few hours away from Australia,” said Immanuel Debeer, founder of Flight Hacks. “We’re going as a group not just because we miss the outdoors and each other’s company, but because group travel can be a lot cheaper.”

Group travel can be cheaper, according to travel industry experts, but you need to know how to get group-related discounts and savings. Additionally, it’s helpful to have some tried-and-true tips for successfully planning and organizing a group trip so that you can avoid common pitfalls and create an enjoyable experience for everyone involved.

Here’s your go-to guide for organizing and saving with group vacations.

Last updated: June 23, 2021

Grace Poole, the founder of Parenting Under Pressure, and her husband have been designated as the official group travel planners among their respective families because they happen to live in the most central U.S. location out of everyone involved. “Essentially, that means a lot of group trips and a lot of tedious planning,” Poole said. “We’ve found that one of the easiest ways to organize a group vacation is to choose one person/family to be in charge. That way, everyone going on the trip knows who needs to be informed about all of the decisions and any last-minute changes.”

“Planning a group vacation is fun; getting people to commit and pay for it never is,” said Chris Atkins, owner and founder at Central America Fishing. “It’s easy to envision you and your family or friends enjoying a private villa on the beach somewhere, but oftentimes the reality is that not everyone will have the same vacation funds to play with. It is a waste of everyone’s time and emotions to get your hopes up about group vacations that are unrealistic, so defining a realistic budget before you start planning your trip will save you loads of time, heartache and possibly resentment.”

“I’ve found success in arranging group itineraries well in advance of the proposed departure dates, meaning group travelers can secure 2021’s rates for a trip in 2022 or 2023 — or beyond,” said Shy Bredewold, director of client engagement for Odyssean Travel. “Cruises and scheduled itineraries often increase 5%-10% per year, which means a group rate for a trip secured today can be paid over the next 12-24 months, and even some late joiners can enjoy savings when they’re ready to commit.”

Erin Clarkson, travel guide and author of Savannah First-Timer’s Guide, believes that vacation rental properties are often a better choice than hotels for group travel. “When you split the cost of a vacation rental, it often costs less per person than the cost of a hotel, which often means you can extend the length of the trip,” Clarkson said. “Both Airbnb and VRBO offer discounts if you book for a certain number of nights (usually 7).”

Clarkson especially likes the idea of vacation rentals because they can provide common areas exclusively for the group, where everyone can gather to eat, chat, share purchases and relax. Plus, she has another tip: “Look for vacation rental properties that have a pool, which is an added perk. It’s much nicer to share a private pool amongst a group of friends than to have to share a large hotel pool with a group of strangers.”

Dr. Terika Haynes, the owner of Dynamite Travel, has this suggestion for transferring from the airport:

“Instead of booking individual transfers/transportation, consider booking a van or Sprinter vehicle that can transfer the entire group at one time,” Haynes said. “This will take a little extra work in coordinating similar flight times, but this will help to decrease transfer costs.”

Haynes also has this advice related to booking activities: “As it relates to tours and excursions, inquire about private group tours and boat charters,” she said. “Sometimes this is also cheaper than booking the individual/per person ticket. Sometimes vendors will also extend a group discount if the number of people in the group is large enough.”

“It takes a lot of time, effort and patience to pull off a group trip,” Atkins said. “When it happens, the group leader should be rewarded for it. If you lead a group, you should have no shame in asking a hotel or tour company for a free spot for you as the group leader. Most times, they will be appreciative of the business you brought them, and from their side, they will have already made their necessary margins from the others in your group, so go ahead and leverage that by asking for a free spot.”

“It is helpful to have a balance of days with organized activities and days that are completely free so people can do whatever they want,” said James Ian, the founder of Travel Collecting. 

And Jackie Becker, a travel agent for luxury brand Inca Expert, agreed. “Add in a free day, especially in larger groups. People have varying passions and things they want to see on a vacation,” she said. “Setting a day aside for people to do what they want will help keep tensions cool while traveling.”

“It’s a lot of work to get everyone to agree on a destination, transportation, and expenses, but I use trip-planning apps like Travefy to discuss and approve our plans,” said Debeer. “We also use Splitwise to do the math for us when sharing our expenses.”

If apps are too involved for some members of your group, consider creating a shareable document that all parties can access online or printing out a hard copy for everyone, like Candice Criscione of The Tuscan Mom recommended.

“Create a document (simple or detailed) to distribute to everyone before the trip,” Criscione said. “It should include important details like emergency contact numbers, things to know about the accommodation (rooming arrangements, wi-fi password, etc.) and important dates or activities on the vacation.”

“Another trick is to plan your holiday for off-season times in your target destination,” said Darko Ivanoski, founder and CEO of ESTAForm. “Prices for hotels and other excursions can halve during the quieter months as operators are desperate to try and get some business through their doors. This goes doubly for large groups. Group discounts during off-peak travel can massively discount your final expense bill and can save you thousands if planned well.”

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