Soooo….you and some friends want to go on a trip together. While this sounds super fun and great in theory, oftentimes the mechanics of achieving a successful group can leave your dream getaway just that…a dream.

Well, never fear – I am here to give you a few pointers on how to mobilize your plans into action, complete with actual deposits and everyone boarding a plane together headed for sun, sand and unlimited alcohol!

Don’t Be These People. Please. 

Designate a Group Leader

This part is crucial to the planning process. Someone is going to have to take the lead to initiate the group conversation, act as the liaison with the travel agent (me, hopefully!), and communicate back to the group. Depending on the size of the group, you may want to have 2-3 to share the duties in the form of a committee, but no more. One person really is ideal. Having multiple individuals trying to take the lead in planning a group trip can lead to a lot of confusion; one hand doesn’t know what the other is doing, and it’s pretty much inevitable that your group members will get frustrated and drop out.

I always tell my group leaders that they’ve assumed one of the toughest tasks out there, so make sure whoever is assigned has a strong personality and can be decisive when necessary.

Narrow Down Your Options

I know everyone in the group chat is super excited at the prospect of traveling together, but when you have too ideas in one pot, the entire process can get overwhelming. I suggest through the initial brainstorming process, you take a vote and narrow down your options to two or three destinations. If a consensus about where to go has already been reached, then the same should be said for the resort of choice. Personally, my practice in the quoting process is to limit my recommendations for this very reason; too many options make the decision and reaching a majority vote really difficult.

Keep the Group Together

Listen, I love a great deal as much as the next person (just ask my husband), but once you’ve chosen your travel agent, destination and resort, everyone needs to book the same thing…with the same person. I know that some of our friends have VERY strong personalities and/or are coupon queens, but if you have group members running off to book on Cheap Caribbean because it will save them $50, your group will be disjointed. Many times, travel agents can match or beat what your friend Denise found and – at the very least – will verify that Denise’s “great find” is actually the same trip! (Because, yes, a flight with a 5 hour layover and/or a 6am departure time from Cancun will of course be cheaper…but why put yourself through that for $50 less?)

Furthermore, your travel agent will be able to communicate your group’s needs and requests directly with the tour operator and resort…but only for those who booked through said agent.

Lastly, many resorts will offer special concessions and perks to groups of 5+ rooms, so if someone goes rogue, it may affect the group as a whole. (Sad times)

Everyone Needs to Pay Their OWN DEPOSIT

This one is huge, only because I’ve run into so many issues around this matter.

When the time comes to pay your deposits, make sure everyone submits their own credit card and pays their portion. I realize that in a pinch it’s sometimes easier for Rudy to ask Vanessa to cover her deposit and pay her back behind the scenes. However, if Vanessa cancels her trip and asks for a refund, Rudy’s deposit goes back to Vanessa’s card. (Unless Vanessa feels generous and asks for a partial refund, which almost never happens). Suddenly, Rudy has to cough up the money that Vanessa paid for her deposit, which she’s already paid to Vanessa behind the scenes. And before you know it, Rudy and Vanessa are no longer on speaking terms. You see how messy this can get?

Unfortunately, your travel agent can’t figure this out for you guys. Travel Suppliers and Tour Operators are legally bound to refund the original form of payment. As much as we want to help maintain your friendship by mediating the issue, we can only do so much. Whoever signed the authorization form is the person in power.

Likewise, if Rudy and Vanessa are sharing a room, they both need to realize that their ENTIRE trip is at risk if the other doesn’t pay her trip in full by the final payment date. So choose your roommates wisely.


Set FIRM Deadlines

You know your people. If they’re always late to brunch, are always arriving to concerts as the headliner is taking the stage and have missed multiple flights because they can’t get to the airport on time, you’re going to want to set firm (and perhaps padded) deposit and final payment deadlines for them. Communicate this information to your travel agent so that the deadlines are uniform for your entire group. Otherwise…Rudy and Vanessa will be beefed out and the rest of the group will be wondering if Jamaica is even still happening.


Have you ever planned or facilitated a group trip? If so, what other advice/tips would you add?

silhouette photography of group of people jumping during golden time
Photo by Belle Co on