I talk a lot about how traveling alone to new places is one of the best ways to get to know yourself better and challenge yourself. What I learned recently is planning a trip for others can teach you just as much about yourself as traveling alone can and even bring on new unexpected challenges that are even more fulfilling when overcome.
This about the time that I planned a getaway for 20 people who I’ve never met before in real life in a country that I don’t speak the language. Here’s the tips I took away from my first time planning a huge trip like this that you can use if you’re an executive assistant planning the perfect company retreat or even for the planning an extra special bachelor or bachelorette party or getaway with friends.
Choosing the right venue is absolutely key as it sets the tone of the entire trip. I don’t trust anyone who doesn’t do a ton of research prior to booking to determine where there going to stay for a trip – especially if we’re staying there a week. The only guidelines I had for this trip is somewhere warm and I needed to find a venue for twenty people to have their own room and bathroom yet it couldn’t be a hotel. Simple enough right? After weeks of searching and leaning toward just renting out an entire hotel resort, I found this villa in Puerto Vallarta, Casa Azul Profondo and instantly knew this was the right choice.
Casa Azul Profondo is two villas (with an optional third villa) right next to each other, almost every room had an ocean view and the entire villa was mostly outdoors so it was an added bonus that helped with our COVID safe policies. It was located slightly off the beaten path with beautiful nature surrounding it but completely in the middle of nowhere that there wasn’t a Hilton and a public beach nearby. It also came with a private chef for family style dinners every night, a cleaning crew and what I’ll call a house “concierge” who helped with everything from airport transportation to getting us a poker set to taking us an incredible hike nearby the villa.
Also extra trip – book the venue for a day earlier than the trip is planning for so everybody has the option to come in a day before to get settled, etc. This is especially important for whoever’s planning it to get there meet the staff and make sure everything runs smoothly.
With the venue secured I moved onto activities. This is when I had to be more open minded. My ideal trip is yoga on the beach, margaritas, massages, art/culture and maybe a hike if I’m feeling up to it. But I was planning a trip for twenty people so after a quick survey of what they wanted I planned this itinerary (keep in mind half of this was a work trip so anything not listed is work time!):
Monday: Massages/Spa Day
Wednesday: Boat Ride
Thursday: Morning Hike with a “Goodbye” Beach Bonfire at Night
This rough itinerary allowed for free time, socializing, etc. and also the work we needed to do while we were there. A general good rule of thumb is you want set group activities for at least half of the trip but not the whole time, make sure you leave enough time for people to do there own thing and spread out the activities so that they’re not always in the morning or afternoon, etc.Some of the best activities the entire trip won’t be the ones that you planned. My favorite memories is night swimming under the star singing impromptu emo karaoke every night with whoever was still up at the time. (See my post on emo music on why this is a very special way to bond with people you just met.)
- You’re not going to please everybody and by trying to please everybody you’ll fail to please anyone. (Good rule of thumb for life really) I learned very quickly when you have twenty people not everybody was going to agree on everything, your job isn’t to get everybody to agree on the location, the activities, etc, your job is to make the location, activities, etc. so incredible the day of that they regret not going along with what you were thinking in the first place.
- Things are going to go wrong. With so many moving pieces it’s impossible to get everything right. For me, it was completely underestimating the amount of cash on hand we would need for tips/emergencies and forgetting that many ATMs in Mexico have withdrawal limits. It caused a headache end of day running around trying to get all the cash needed to pay or tip certain people. But if you plan the rest well, when the stressful times did come up, we were able to pivot quickly and it didn’t ruin the trip.
- No really things are going to go wrong and it has nothing to do with you. On my trip someone forgot to mention that they got seasick after we mentioned multiple times we’d be going on a boat and had to miss out on some latter activities. I felt so incredibly bad thinking if there was anyway I could’ve predicted that and the answer is no, you couldn’t have – move on and focus on the 90% of the trip you were able to completely nail.
- Ask for help when you need it. As someone who is very independent and stubborn, this doesn’t come easily to me but I also know my strengths and weaknesses. Strengths – finding an incredible venue and amazing activities for all us. Weakness – rallying people when it came to go to those said activities and getting people to put down their margaritas and hop in the shuttle. Find someone with a loud voice who can rally when you need to rally. That’s just one example but if you’re planning a group trip, unless you’re planning it for a bunch of assholes (which like, don’t plan trips for assholes?) then they’re going to be asking you “do you need help?” at multiple stages of the trip before you default to no thanks I got it. Be honest with yourself and take that help!
- Don’t forget to have fun! If you figure out how to do this let me know but I think the one thing I wished I did more was relax. It’s your vacation/corporate retreat/bachelor party too! If you need a few minutes to have a margarita, sit in the pool and just do nothing, don’t be afraid to ask for that. Take naps when you need to recharge your social battery. Trust that you planned things well enough that nothing is going to fall apart the minute you decide to have a little bit of fun.
I’m well aware planning a trip like this for some people sounds like a nightmare. Especially when I mention things like how American Airlines decided to cancel half our flights the night before, someone missed their connecting flight due to an engine failure, our tech equipment was delayed in its arrival and that’s all before I even got to Mexico.
But at the same time, there’s nothing more rewarding of a feeling for me than to see everybody having the best time, relaxing in the pool drinking margaritas or talking about this is the best trip they’ve ever gone on and knowing you made it all happen.
