For my 30th birthday me and 21 of my friends (3 could not make it the day of) descended on Panama CIty and Bocas del Toro for a celebration. This was the second time I had done a big birthday trip, the first being my 25th birthday which I celebrated in Puerto Rico with 18 of my friends. I have also put together trips with smaller groups, including Martha’s Vineyard and the Smoky Mountains.

Weeks after my 30th and years after my 25th, people are still talking about these trips. People are often impressed that I pulled them off, but there are a few key ingredients to ensure success:

The Guest List

The key to a great group trip is the guest list. Some people did not join my 30th birthday celebration because they, “don’t like group trips.” The key is making the group big, but not too big and to put together personalities that work as a whole yet also that work well in smaller groups.

Inevitably, the group will be split into smaller groups at various times and everyone should be able to find themselves among a group of people that they feel comfortable with. I do not think anyone on either of my trips did not enjoy themselves because it was a “group trip”. Even though you are on a group trip, it doesn’t mean that you must constantly be with the group. You are always able to separate. No one should hold anyone hostage on a group trip.

There were two people that came to my 30th who I did not know, but they were friends of friends who were familiar with my personality, and were the type of people that I wanted on the trip: e.g. fun, open-minded, ready to release all inhibitions, nonjudgmental types. It is best that you invite your friends and CLOSE friends of your friends. You know the saying…birds of a feather… As far as numbers go, I would not go above 25.

You also want to pick a few characters with big personalities, the people that you know will be able to keep everyone entertained in case there is a lull in fun. Someone who can keep the jokes flowing and keep everyone in a good mood. You also need a few responsible people who will make sure things do not get too out of control. You need one or two people who can take control of situations without being told to do so. And lastly, everyone should be trustworthy. This is essential!! Who likes theft or someone that shorts a bill?!

Location, Location, Location

So how do you choose the perfect place for group trips? A lot of the choice will depend on personal preferences. I personally like to go places that I have never been and I also prefer staying in houses or small hotels where we can feel like we are the only guests. For the trip to Puerto Rico we stayed in a large hotel which was not bad, but in Panama we stayed in a small aqua lodge which had 9 villas, 6 of which we occupied and I definitely preferred the latter. When you stay in smaller hotels, the staff tends to cater more to you as opposed to a hotel where you are a group among hundreds of other guests.

Negotiate EVERYTHING! 

When booking accommodations, make sure to get a group discount and if meals are not included get them to also give you deals on meals or drinks. If you do not ask you will not receive anything. It is difficult to get group discounts on flights, especially if everyone is flying in from different airports, but if you all are taking a single flight together, like we did in Panama, be sure to ask for a discount.

Be Flexible

This tip refers to the schedule once you arrive in your destination. I find the best way to keep stress levels low and the fun factor high is to have one or two things scheduled and leave all other things to be decided upon once you arrive. People will inevitably be in different moods and have different interests. Some people may want to zip line, while others lay on the beach, while others go hiking. I find it best to give people an idea of activities prior to arrival and once there, they can talk to the locals to decide which activities they want to engage in.

Show Appreciation

It is very important to show appreciation for people who join your trips. People take time off from work and spend money on flights, hotels and more to spend time with you even though it is a vacation for themselves. You can show appreciation by paying for drinks, putting together a gift bag, sending thank you cards, etc.

These are the key ingredients to the trips that I plan. If you have any tips or questions, please leave them in the comments below!