This summer officially kicks off a season of 40th birthdays for my group of friends. After a long travel hiatus, the text messages have been flying around about where to go and when to go. No one has yet taken the leap in making reservations, even our number one organizing friend, and I think that’s in large part because she doesn’t want to be fully responsible for the fun (even though she does a great job at creating it)! I was sharing this with Amina Dearmon, Owner of Perspectives Travel, and like all the experts in my network, she did an excellent job of convincing me why I should hire the expert. I thought you might like to read Amina’s advice to me — including the five important questions to ask before you start planning — because it might just be the push you need to get the fun started. Go ahead and copy and paste it into that group text chain. Here is what Amina shared:

The one common thread in all of the groups that I work with is that the person who reaches out to me is usually the planner. They’re the organized friend, or the one who planned last time, or the most traveled, but they’re also ready to enjoy the trip themselves, be fully present in the adventure, and not have to be the person that everyone asks “what are we doing today?” By the time I get a planning form in my inbox and a call on my calendar, the group leader is typically already frazzled and that’s where I step in to make travel planning the exciting and fun experience that it should be.

When I work with groups, my role includes helping to understand what the goals and priorities of the trip are, so that we can match those with a destination and accommodations that make sense. Then I act as a logistics coordinator and figure out how we can get guests coming from multiple locations to their destination, what transportation, activity, and dining options there are to accommodate a group, and if there are any COVID protocols that we need to plan for. And since absolutely no one wants to be responsible for extracting money from friends or family, I also make sure that invoices are paid, and that components like travel insurance are customized for each guests’ needs. 

In all of the group travels that I’ve planned, there are five key questions that I always ask. These questions are meant to be conversation starters for the group, but they also provide insightful information that help me create a travel experience that is seamless, fun, and most importantly memorable. Ask your group these questions as you begin brainstorming your next trip, and reach out to me when you’re ready to start planning. And while it is quite the honor to be trusted by your friends and family to guide them across the world, the organized friend deserves to enjoy this trip too, and I’m here to help!

5 questions to ask yourself before you start planning a group trip:

Has this group traveled together before? If so, were there any frictions or issues? What was the root of the issues? (too early start times, not enough free time, personality clashes, etc).

What is one thing that everyone in the group enjoys doing?

Does the group prefer a new-to-everyone destination or to revisit an old favorite?

Keeping in mind that private group transfers, tours, and dining can often be more expensive, what is the desired per-person budget for the group? Will exceeding this number by 10-15% for more personalized or private options during the trip cause anyone in the group to be unable to attend? 

What stories do you want to be able to tell when you return from this trip? 

Amina Dearmon is the owner of Perspectives Travel, a SmartFlyer and Virtuoso affiliated luxury travel agency that specializes in travel experiences that are authentic and immersive, allowing you to gain more from each trip.