How to Plan a Group Trip (Without Losing Your Mind)

A peek into our process, plus a few tips you’ll thank us for later

by Tiffany Figueiredo

There’s a particular kind of magic that happens on a great group trip. The kind where meals stretch long into the night, funny old stories resurface, new memories are made, and a quiet rhythm sets in among the people you love (or work with). It’s connection, distilled. But behind that ease is one undeniable truth: group trips take work. Thoughtful, strategic, behind-the-scenes work.

At Fig Travel Co., we’ve planned every kind of group gathering — milestone birthdays in Italy, Christmas safari buyouts for entire families, company retreats in the mountains, fishing expeditions on the Zambezi, and weddings in Mexico. And while each one is completely different, they all begin with the same idea: this should feel effortless for everyone — especially the person planning it.

Here’s a peek into our process, along with a few field-tested tips you can borrow for your own gathering, big or small.

01. Start with the why

Before anyone says “Greece?” or “Amangiri?” — start with purpose. Why are you going?

Is it a celebration? A reconnection? A creative strat session? The answer will shape everything from the destination to the tone to the pace of the trip. A 40th birthday with a dozen friends calls for a different rhythm than a team retreat or a multigenerational family vacation. We always begin here.

02. Designate a point person

Every group needs one, and not everyone needs to weigh in on every detail. We always work directly with a group lead (or a small decision-making core) to shape the itinerary, handle the logistics, and move things forward without bogging things down.

Tip: If you’re the point person and you’d like to stay friends with everyone involved, hire a travel advisor. Truly.

03. Choose the right destination

It has to be more than just beautiful; it needs to work. That means direct(ish) flights, accommodations that suit the structure and personality of your group, and a location with both shared experiences and space to breathe.

Some of our favorite group-friendly destinations:

The USA, for flexibility and variety

Mexico, for sun, soul, and simplicity

Italy, for when joy is the main objective

France, for artful living, long lunches, and countryside charm

South Africa, for safari, culture, and meaningful shared experiences

Costa Rica, for shared adventure and wellness journeys

04. Book early (really early)

We cannot stress this enough: the best villas, guides, and private experiences are claimed months — sometimes a full year — in advance. For international trips, we start planning 9–12 months out. For domestic, 6–9 months is the sweet spot. If you had a fantastic summer trip with friends or family and want to do it again, get in touch now for next summer.

05. Talk about money early (and clearly)

Not the most glamorous part of the process, but essential. We help our clients establish a comfortable per-person range upfront and clarify what’s included and what’s not. This avoids awkward conversations later and helps guests feel confident from the start.

Tip: Offering guests a few optional upgrades, such as a premium room, a spa day, or a private add-on, is a great way to accommodate different budgets without fracturing the group experience.

06. Plan just enough

Over-planning a group trip is just as risky as under-planning it. Our approach is to design a flexible framework: a few beautifully curated shared moments, like a vineyard lunch, a sunset sail, a private cooking class, paired with unstructured time to rest, explore, or do nothing at all.

A group trip shouldn’t feel like a school field trip. It should feel like freedom, with a soft, almost imperceptible structure underneath it.

07. Nail the details

This is where things get elevated. From seamless airport transfers and celebration dinners to welcome notes, printed itineraries, and thoughtful touches (a custom playlist, a local treat left in each room), we handle the details that make the experience feel not just smooth, but special.

08. And finally, hire someone (like us)

Because when you hire a travel professional, you’re not just booking hotels. You’re getting time back. You’re avoiding the unhinged group texts. You’re gaining access to places and experiences you wouldn’t find on your own, and you’re free to be present, instead of stuck in the weeds.

We’ve done this many times. We know the villa owner, the chef, the boat captain. We know how to solve problems before they surface and create space for joy.

You bring the people. We’ll bring the rest. Let’s talk.