5 Group Trip Tips

I’m an introvert. My friends often argue with me about this label, but I KNOW MYSELF! There’s a common misconception that all introverts are socially awkward or shy, which could not be further from the truth, but I digress.

In March, one of my close friends invited me on a trip to Negril,Jamaica. Never being one to pass up an opportunity to travel, I agreed to go. I had been to Ocho Rios before on a family vacation, but my love for Jamaican food and all things Caribbean kept me from being reluctant about repeating a destination.

The price was a reasonable $500 and I learned we would be staying in a castle (no, literally, we stayed in a castle). The trip was being coordinated by two of her childhood friends for their birthdays and the itinerary looked solid. I requested the time off of work and then realized two major things: 1.)the start date for this trip was 3 days after I returned from Colombia and 2.) 20 other people would be going on this trip.

Number one, though stressful, was easy to prepare for. While packing for Colombia I simply set aside clothes for Jamaica. However, I could not do anything to adequately prepare my introverted self for number two.

Prior to the trip the only one I knew in the castle was my friend. There were so many factors that could go wrong. Luckily, every single person on the trip was amazing and I left with 19 new friends.

I believe 5 key factors contributed to the trip going smoothly and today I’ll be sharing them with you to make future group trip planning a breeze.

Collect payment in advance and setup a payment plan. This is the most effective way to mitigate issues on the trip. While it’s impossible to calculate the cost of everything, major costs, such as accommodations, excursions, and airport transfers should be collected in advance. Creating a payment plan may be tricky if you’re not using a travel agent, however, Airbnb now has a feature that allows you to split payments. Also, by providing people with advance notice of major trip costs and breaking the total amount down into smaller payments, even your most budget adverse friend can get it together.
Distribute an itinerary. Keep in mind that everyone will not read this! However, your Type A friends will appreciate this gesture. You don’t have to detail the daily plans down to the minute, but providing a loose schedule of activities will help everything run smoothly. This will also help you with planning, as it is forces you to think about what you want to do.
Consider the personality types of those that you’re inviting. BlackAndWellTraveled.com published an article in May entitled, “Everyone Cannot Go: Why You Cannot Vacation With Everyone“. I could not agree with the opinions stated in that piece more. Everyone isn’t meant to go everywhere. Think long and hard about who you invite on a group trip. That friend that always gets sloppy drunk and loses their stuff? They can stay home. That friend that recites the lyrics to “Knuck If You Buck” as a daily mantra? Leave them home. That friend that stills owe you $50 from freshman year of college? You already know. The group dynamics can make or break a trip. Be real with your friends and yourself about the energy you want surrounding you.
Try to have meals catered. I refuse to attend group meals where the check can’t be split or payment can’t be sent individually. There’s nothing more frustrating than having to put in more money to cover the check for someone that ordered beyond their means. Having some, if not all, meals catered helps avoid these problems. This also helps make tip number one easier to follow. You can still give everyone on the trip the opportunity to taste local cuisine, however, you can collect payment in advance and ensure there’s no post check foolery.
Look on Airbnb for unique accommodations. As previously mentioned, we stayed in a castle on this trip. It was truly gorgeous and had ample space for everyone. I personally love Airbnb for group trips because you can typically find a place that cost less than a hotel and everyone can stay in one place.