How To Turn Your Group’s Drunken Promise Of Traveling Into A Reality


The planning of my first group trip came in four stages: the first stage took place at a crowded bar in New York City last winter. My friends and I had mixed cocktails with imagination and were letting our words run wild with promises of traveling together one day. We called out destinations as easily as we ordered drinks and in that moment it felt like planning the trip would be just as effortless. The next stage came the morning after when everyone sobered up and I remembered our cocktail-infused promises from the evening before. Why not take a trip together? Was the idea really so ludicrous that it should fade away with our hangovers? I asked my friends the same question: Why not?

The third stage brought the planning: the joys and woes of turning a drunken idea into a living and breathing reality. When we eventually reached stage four, just three months after we giddily shouted out destinations over spilled drinks, every hurdle of planning was made worthwhile when we stepped off the plane in beautiful Colombia with friends in tow. In the planning of a group vacation the key is patience, persistence and compromise; making sure everyone has a say on timing, flights and accommodations while avoiding getting hung up on meeting each person’s criteria. One friend may want a beachfront apartment while one prefers a cheaper, party hostel and yet another desires a hotel; it can seem like a hurricane of preferences but in the end the desire to take a trip together will reign supreme. All too often I have heard people lament their group of friends for letting their travel plans fall through due to getting “complicated.” I have found that planning a group trip is more manageable when tackled in parts rather than all at once. Consider this your guide:

1. Spin the Globe

Your friend may want to visit Puerto Rico while you have dreamt of exploring Belize; everyone has a list of destinations they are hoping to jet off to but most of your friends can agree they don’t want to set their wallet on fire in the process. In deciding where to go for your group trip, the key is to listen to everyone’s destination ideas and put together a list of all the countries thrown out. Sure, a trip to Argentina sounds fabulous but if the airfare to Panama is a third of the price chances are your group will lean more towards the affordable option. Look up the flight prices to the various destinations your group discussed and share them with your friends; you’ll see that once a price tag is attached the list of places will narrow itself down.

2. When to Fly

Everyone needs time to check their calendars so start planning your trip at least 2-3 months out to allow friends to take time off. Look at long weekends or off-season travel periods (such as Jan-March) when flights tend to be cheaper. Another trick is to try and plan your group trip earlier in the year (when vacation days renew) as taking time off gets trickier closer to the summer and holidays.

3. Booking the Flight

In the planning of a group trip people tend to fall into one of two buckets where either they take a backseat to planning or lead the efforts. Regardless if you are playing travel agent or taking solace in the fact that someone else is handling the planning, when it comes to flights everyone gets involved. Airfare will likely prove the most expensive part of your trip and everyone will have an opinion on timing and price, so rather than tackle the world of travel at once, give your friends a few flight options that stand out and decide as a group. My friends and I tend to take red eye flights as they prove cheaper, allow us not to waste a day traveling and get us to our destination early in the morning, so share the best flight options with your group and give your opinion on which to take. Once everyone decides on a flight, book the ticket!

4. Accommodations

What do you need? Where do you want to stay? How much are you willing to pay? Three questions shape the conversation when choosing where your group will be setting up camp while away. Accommodation options run the gamut from hostels to hotels to apartments so know the neighborhoods you’d like to stay in and share a few options with your friends to choose from. If you manage to find the holy grail of accommodations that meets everyone’s criteria then I salute you but likely the group will need to compromise and ultimately agree on what they absolutely need to feel comfortable and what they can live without.

Planning a group trip can sometimes feel like herding sheep but when the time is taken off, flights are booked and accommodations are reserved there is nothing left but that same giddy excitement that fueled the idea months ago over cocktails.