Visiting Orlando is one of the most exciting spots to visit in the world, with tons and tons of things to do and so many things to so. Yet it can also be a challenge – especially when you’re traveling with 50 friends. Is it really possible? Check out this article on How to Successfully Vacation with 50 of Your Closest Friends, or just check out our favorite tips below.

orlandovacation_group-vacation-home-rentalGood leaders are essential

The key to group travel is to pick people to be in charge and make sure their roles are clear. One great idea is to rent several Orlando vacation homes and then elect a “captain” of each house. Those staying in each house can make decisions about their own home without having to get the entire group to agree on everything.

Make rules and guidelines

You don’t want things to be too structured, but you do want to set down some rules and guidelines. These may be simple rules like, “Everyone cleans up after themselves every night,” or they may be more serious ones, “No one gets in the caravan pool without bringing their health insurance card and emergency numbers.” The clearer your boundaries are, the easier it will be to get the group to respect them.

Be clear on what group expenses are

Money is one of the biggest issues in group trips, but issues with financials can be avoided by clear communication. For example, if you rent vacation homes then you’ll need to consider what the group expenses are and who’s paying for them. Is one person in charge of the coffee or will all of you split the cost? What about those who don’t drink the coffee? Will they be expected to pick up their share? These are all issues that can be dealt with, assuming you do so ahead of time.

Request payment in advance – with no refunds!

Don’t fall into the trap of allowing payments on the day of your trip. This will lead to serious issues if even one person elects not to come. Set the due date with plenty of time to make adjustments if money you were counting on doesn’t come through. Likewise, make it clear that there are no refunds. The last thing you want is for several people to cancel and expect they’ll get their money back, even though the houses have already been rented, the discount park tickets have been purchased, and all the arrangements have been made.


Group travel can be a ton of fun but there’s no question it takes a little more planning. These simple tips will help make sure everyone’s expectations are in line and give you the best chance at a magical trip!