How to Plan an Epic Group Trip for Your Birthday (I’m Turning 40!)

Turning 40 is one of those life milestones that feels like it deserves a big celebration. And for me? Well, I’m going all out—no wedding, no giant bash in the past, so it’s time to live it up! To celebrate my 40th birthday, I’ve decided to plan a group trip, and let me tell you—it’s been full of fun, excitement, and challenges. Planning a group trip is like herding cats, but once you see everything come together, it’s totally worth it.

So here’s what I’ve learned along the way while planning my own birthday getaway, especially if you’re a millennial (gay or otherwise) trying to organize a group trip with friends, family, and a whole lot of good vibes.

The Guest List Drama: Who’s Coming?

One of the first challenges I faced when planning this trip was deciding who to invite. I’m single, gay, and turning 40—so naturally, I wanted to spend this milestone birthday with my close circle of gay friends. But I also wanted my family to be there. I mean, I haven’t had a wedding or any major life event where all my loved ones got together to celebrate me, so this birthday is it. And since I’m going big, why not throw my straight friends into the mix, too?

This guest list dilemma meant that I needed to plan a trip that was all-inclusive—a destination where everyone would feel comfortable. It couldn’t be some niche destination that only appeals to one part of the group, and definitely not somewhere that my straight or more reserved family members would be like, “Umm… yeah, I’m not sure this is for me.”

Finding the Perfect Destination

Now, when you’re planning a trip like this, the destination is everything. You want somewhere that speaks to your soul but also works for your group. My friends are flying in from all over the world—some from the US, others from Europe—so the place needed to be accessible, gay-friendly (obviously), and somewhere that wouldn’t break the bank.

Oh, and there’s one more wrinkle to this story: my birthday is just two weeks after the 2024 election. Depending on how things go, I didn’t want to end up in a place that would leave me feeling uncomfortable or unsafe. I refuse to spend my 40th birthday surrounded by weird political energy. Nope.

Enter New Orleans.

NOLA is the perfect destination—it’s easy to reach from both the US and Europe, has that gay-friendly vibe I need (hello, Bourbon Street!), and is loaded with a million different things to do. From food to music to late-night bar crawls, New Orleans offers something for everyone, no matter their tastes. It’s also affordable, so my friends can come without needing to take out a second mortgage just to attend my birthday bash.

Keeping It All Organized

Now, I’d love to say that once you pick the destination, everything falls into place, but no. There’s so much more that goes into planning a group trip. Here are some of the behind-the-scenes details that have kept me glued to my laptop for hours:

• The Spreadsheet Life: I’ve created a master spreadsheet to track everything—arrival and departure times, food preferences (because of course, someone’s going to be vegan), activities people can and can’t join, and who’s bunking with whom. This keeps me sane, and trust me, you’ll need one too.
• Group Airbnb? Yes, Please: Accommodations are a whole beast of their own. I wanted my friends to stay together, so I rented a group Airbnb for the majority of us. This required finding a place that was centrally located, affordable, and had enough rooms (and beds) for everyone. Let’s just say, the number of times I’ve zoomed in on bed configurations is embarrassing.
• The Email Shuffle: From confirmation emails to “Hey, just checking if you’re still coming” reminders, keeping everyone in the loop has been essential. I didn’t realize how much of an admin job this would be, but keeping everyone updated has made things run way smoother.

Balancing Everyone’s Budget

Let’s be real: not everyone has the same budget. And when you’re inviting a big group of friends and family, that means taking different financial situations into account. Some friends can splurge, others are budgeting carefully. It’s important to be sensitive about this and make sure there are options for everyone.

For example, while I’ve booked a big house for most of my friends, I made sure there were hotel options nearby for family members who wanted their own space (or more privacy). I’ve also planned a mix of free or low-cost activities, like wandering the French Quarter and hanging out in the beautiful parks, alongside some splurge-worthy dinners and nightlife. That way, no one feels left out or financially strained.

Planning Activities for a Diverse Group

This has probably been the most exciting part of the trip planning process—there’s so much to do in New Orleans, but I want to make sure the trip reflects me. That means everything from fancy dinners with my family to late-night shenanigans with my friends. New Orleans is the perfect city for this kind of birthday extravaganza because you can hop from a drag brunch to a historical walking tour, hit up a jazz club, and then end the night with an epic round of cocktails in the French Quarter.

I’ve also planned a mix of group activities and time for people to go off and do their own thing. Trust me, when you’re traveling with a group, you need to build in downtime. Not everyone wants to do the same thing every day, and that’s totally okay. Giving people the freedom to explore the city at their own pace will make the trip more enjoyable for everyone.

The Anticipation (and Nerves)

With the planning mostly done, I’m so excited (and nervous!) about how everything will come together. I’m a planner by nature, so seeing my 40th birthday celebration unfold like this is a dream come true. But I’m also embracing the fact that things might go off-script—and that’s fine. Because at the end of the day, the whole point is to celebrate with the people I love, in a city that’s full of life and energy.

So, if you’re thinking of planning a group trip for your birthday (or any special occasion), here’s my advice: start early, stay organized, and be prepared to roll with the punches. Planning this trip has reminded me how much I love traveling, but more importantly, how much I value the people who are coming to celebrate with me.

Here’s to turning 40 and making it fabulous!