By Joanne Cleaver | April 2, 2025 | The Living Quarter

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Congratulations … or condolences: you've agreed to organize a splurge trip with family or friends. This is a task that plunges you into multiple overlapping and interlocking systems: transport via air and ground; accommodations; activities; and accounting. Fortunately, a raft of new tools and platforms can ease the pain and maybe even preserve some of the cherished benefits of arranging travel on your own behalf.

If you're hoping to dodge the responsibility, good luck. Group tour agency Timbuktu reports a 40% increase in inquiries the past 12 months from friends planning trips together.

You'd think that the first big decision you face is whether you want to be just another guest on the trip or the go-to person, troubleshooting before, during and after.

If it's all about cousins and grandchildren at the beach for days on end, the plan falls together around location and then, season.

And that is a huge decision that you can only tackle after your sort out two other big-picture considerations, neither of them about money.

Travel advisors agree that the place to start is what you hope will last long after it's all over: the type of shared memories and experiences that you hope will become the legend about the time together.

"What is your moment?" asks Rob Murray John, head of special projects for British bespoke travel agency Black Tomato. "Is it a challenge? An event? The grandkids?"

If you want to center the trip around a one-day highlight — say, attending a Broadway show or taking a hot-air balloon flight — the budget and key dates fall into line accordingly. If it's all about cousins and grandchildren at the beach for days on end, the plan falls together around location and then, season. But as this is a group trip, agreeing on the marquee memories requires a consensus, John says.

Next, you'll need to sort out the moving parts of the complicated equation that adds up to a successful trip: season and potential dates; budget; activity level and key activities; number of people in the group; and destination. It's a lot of variables.

Schedules will probably narrow the season and potential dates, which then shapes considerations for destinations. The number of people, activity level and types of activities, and type of accommodation at the destination are flexible factors that you can work with to settle on budget parameters. For instance, for a reunion of your wedding party, you might realise that if you shift to a shoulder season, the cost might drop enough to include a few additional longtime friends, too.

With the variables defined, it's time to decide if you'll plow into the thicket that is trip planning, forfeiting your own leisure in the process, or hand the project over to a travel agent or service.

The more complicated the trip, the more you might need a professional operator.

"It's complicated to marry all those things and get it right," says John. If you are the hands-on planner, you will be troubleshooting and might never get to relax while you're actually on the trip. And you'll have to set and maintain strict rules about collecting deposits and fees — a chore that an agency can handle directly with each member of the group. On the other hand, travel planning platforms and tools can potentially save you money and hassle, but once you're committed, your group is locked into the vendor relationships that a service or agency has and is willing to make on your behalf.

Here's a rundown of helpful tools and tactics, running the gamut from multi-destination overseas journeys to more straightforward options.

Delegate vs. DIY

The more complicated the trip, the more you might need a professional operator. Traditionally, travel agencies negotiate rates on your group's behalf and are paid by vendors, who essentially subsidise your plan when it includes them. If you are booking an all-inclusive cruise or resort stay, you might not get a better deal through an agent.

Complicated itineraries demand professional guidance. A new breed of hybrid agencies combines online tools with virtual collaboration so you can map the level of onsite help as you need — right up to assigning a guide to meet you at the airport when you land at your first destination; ferry you to and through cities, countries, connections and destinations; and see you off at the end. They expect to collaborate with clients, mixing and matching priorities within the time frame and budget.

Johnny Prince, co-founder and CEO of agency Timbuktu, recommends plugging variables into its online planning tool, which lets you whittle an overwhelming range of options to a manageable short list. At that point, you can pick up the conversation with a Timbuktu agent and fine-tune the itinerary based on staff knowledge of nuances such as seasonal animal migration patterns. After all, if you're going to Africa once, you want to be there when the animals are on the move.

Because she co-owns a travel agency – Onward Travel – Valerie Tkaczyk is usually drafted to plan her own family's excursions — most recently, booking a Caribbean cruise for 30. Agents know to ask about special needs, like securing infant car seats, Tkaczyk points out, and can arrange itineraries with a range of activities, from exciting and expensive to lower-key and lower-cost so that each family or individual has choices that meet their interests and budget.

"People underestimate that it's exponentially more complicated with the group. It's so much harder. A group of 8 or more, you have to plan in advance for everything."

And when the inevitable glitches erupt, professionals have more industry weight to throw around to get a fix, says Paul Bertram, the head of London-based Group Tour Shop. If a hotel loses a reservation, it's the agency's responsibility — not yours — to rustle up alternative lodging. Local guides and destinations want to stay in the good graces of agencies that bring them steady traffic so often are eager to extend hours, offer additional experiences and otherwise spice up their usual offerings, he adds.

DIY Collaboration

If the trip is fairly straightforward, you probably can manage it by negotiating directly, sharing details with an iron hand on a shared spreadsheet.

That's what Angela Berardino does. She is a former travel agent now launching a travel industry marketing firm. Thanks to her professional background and hard-wired organizational capabilities, she typically quarterbacks annual friends' trips — most recently to Mexico.

"People underestimate that it's exponentially more complicated with the group. It's so much harder. A group of 8 or more, you have to plan in advance for everything," says Berardino, citing the necessity of group reservations for transport, restaurants, activities and even rentals, like beach umbrellas.

Her approach starts with the shared vision, then the season and highlight activity — most recently, in Mexico, a daylong ocean cruise — and from there, destination and budget.

"Once you've got your heart set on a big trip, and the highlight of it, the options are endless."

Shared folders and documents that enable people to drop in comments, links potential resources and, eventually, the itinerary and photos, are the way to go, Berardino advises. Tkaczyk offers a free group planning template spreadsheet at her agency's website. Another popular option: create a group-only private board on Pinterest, the social media platform, to share ideas, then itineraries and paperwork, and then, during and after the trip, photos. Berardino also recommends creating a group messaging chat for real-time updates on travel status.

Instead of relying on the dubious wisdom of artificial intelligence tools, Berardino researches destinations by joining location-specific groups on social media. Such groups are easily found on both Reddit and Facebook and usually center around local travel providers and residents who can provide specific recommendations for everything from tour providers to laundry services.

For negotiating group rates for lodging, you can negotiate directly with hotel or resort group marketing managers. Or you can use Engine.com, a new platform that negotiates room rates and amenities for groups, says Ariel Katen, a product manager with the company. With a basket of room nights in the offing, lodging companies are willing to sweeten the pot with amenities like free breakfast for the group or free rooms — usually for the group organizer (that's you!). And, through Engine, you probably can earn hotel loyalty points — a benefit that a property marketing manager might or might not allow.

Berardino relies on the Splitwise app to manage shared expenses before, during and after the trip. With expenses tallied after every grocery run or restaurant meal, it's easy for individuals to decide how to manage their last-minute choices: extra wine or a massage? And the app enables group members to detect patterns and preferences, which provides insight for the next trip, Berardino points out.

With the right tools in hand, you can concentrate on the fun part, says Prince. "Once you've got your heart set on a big trip, and the highlight of it, the options are endless," he says.

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