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How to Plan a Group Trip

Boarding the plane to Bocas del Toro, Panama to celebrate my 30th.

For my 30th birthday me and 21 of my friends (3 could not make it the day of) descended on Panama in 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 smaller trips (with less people), including Martha’s Vineyard and the Smoky Mountains.

Weeks after my 30th and years after my 25th, people are still talking about those trips. People are often impressed that I pulled them off, but there are a few key ingredients to planning the perfect group trip.

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 but 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. Even though you are on a group trip, it does not 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 are familiar with my personality as well as 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 activities. 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 key!! Who likes theft or someone that shorts a bill?!

On the beach in San Juan celebrating my 25th

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 at the El San Juan Hotel and Casino, a large four star resort which was very nice, but in Panama we stayed at the Punta Caracol Aqua Lodge, which was a small family run resort with nine villas, six of which we occupied and I thought it was a much better experience. The staff truly catered to our every need, whereas at the larger hotel in Puerto Rico, though it was a four star hotel, they had hundreds of other guests to cater to as well.

For the smaller group trips to Martha’s Vineyard and the Smoky Mountains we rented houses. Websites such as airbnb, VRBO and HomeAway are great for booking houses.

Hanging out with my girlfriends in Martha’s Vineyard. This is the house we rented.


When booking any 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. I have ALWAYS received discounts on every trip that I have planned!

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. I did and we got it! It wasn’t a huge discount but we saved $10 each.

When to Start Planning

Timing is everything, especially when you are trying to book hotels and flights and coordinate a group of people who likely have to put in requests for time off. For international trips I usually give people a one year heads up and book the hotel about nine months in advance. This allows people to pay slowly over time which is less painful for many people. For domestic trips, depending on the cost and whether or not it is during a holiday, I think that four to six months is sufficient for the beginning of the booking process. If it is a holiday period and you are going to a popular destination then it is better to book earlier.

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.

A family vacation to the Smoky Mountains required the rental of a five bedroom house

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.

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