Traveling with Your Besties Without Breaking the Bank 👯‍♀️✈️💸

By Molly Benjamin, Founder of Ladies Finance Club

Traveling with friends—aka Friendcations—can be the absolute best. Whether you're exploring a new city, relaxing on a beach, or just enjoying each other’s company, these trips can create some of the best memories full of ‘had to be there moments’. Plus, traveling with friends often means sharing costs, making it more affordable—especially if you're flying solo. Things like splitting Ubers to and from the airport already save you money right off the bat!

However, as wonderful as Friendcations can be, they also come with potential challenges—especially when it comes to money. Different spending habits and financial situations can sometimes lead to tension, but with a little planning and open communication, you can avoid those awkward money moments and ensure everyone has a great time.

Be Upfront About the Budget 💵✨

One of the most important things to do before embarking on a Friendcation is to have an honest conversation about the budget. It might feel a bit uncomfortable at first, but it's crucial to ensure everyone is on the same page. Discuss what each person is willing to spend on accommodation, meals, activities, and other expenses. By setting expectations early on, you can avoid any surprises and make sure everyone feels comfortable with the plan. Plus if someone is on a tiger budget they wont feel pressure to do certain activities. Work out how many meals you want out vs cooking at the pad.

My gfs and I always used to have a kitty we would all put in $100 at the start of the trip and use that for taxes, drinks (when we would all order the same thing) and money for cheese and wine etc.

Decide What Will Be Split—and What Won’t 💡💸

Not everything needs to be split equally, and that’s okay! Some friends might be happy to pay extra for a nicer room or an expensive dinner, while others prefer to keep things more budget-friendly. Talk about what expenses will be shared (like accommodations) and what might be individual (like personal shopping or fancy dinners). Being clear on this upfront can prevent misunderstandings and keep the trip stress-free.

Use Apps to Keep Track of Shared Expenses 📱💰

Managing shared expenses can be tricky, but thankfully there are plenty of apps that can help. Splitwise, for example, is a great tool for tracking who owes what, making it easy to settle up at the end of the trip. Using an app like this can take the guesswork out of splitting costs and ensure everyone pays their fair share. Just make sure to take turns of paying so one person doesn't have to put every meal on their card. Once the trip is over make it a priority to work out the splitwise asap.

Address Differences in Spending Habits 💳💬

It's natural to have different spending habits among friends—some might want to splurge on a five-star dinner, while others are happy with a casual meal. These differences can create tension if not addressed early. Generally, we tend to hang out with people who have a similar financial situation, but when preferences diverge, it’s important to find a middle ground. Discussing how to handle these situations before they arise can help prevent any awkwardness.

For example, you might agree that everyone will have one or two “treat yourself” moments, but for the rest of the trip, you’ll stick to a more agreed-upon budget. Flexibility and understanding go a long way in making sure everyone has a great time without feeling financially pressured.

Be Upfront About the Budget (Appoint a Holiday CFO) 💵🗣️👩‍💼

The Holiday CFO can help set clear expectations for the trip, gather everyone’s input on what they’re willing to spend, and ensure that the financial plans are realistic for all. This role isn’t about controlling the purse strings but about making sure everyone feels comfortable with the plan and that there are no surprises along the way.

For instance, if one person prefers cocktails while the rest are sticking to wine, it’s important to clarify that the wine drinkers aren’t expected to cover the difference. Everyone should pay for what they order, ensuring fairness and preventing any resentment from creeping in. Having these discussions upfront can make the trip more enjoyable for everyone, allowing you to focus on having a great time together.