How to Plan a Trip with Your Friends

Planning a long weekend with your friends? Poll everyone to set a date, agree on a budget, choose your destination, and use Splid to split costs.

Have you tried to coordinate a trip with your friends? It feels near-impossible to find a date and agree on a location… yet, I’ve met up with the same group of women nearly every year for 30 years. We all have our own careers, families, and I swear it gets harder, not easier, to find a date on the calendar for each trip. But we love seeing each other and continue to make it a priority. Here’s the secret sauce:

If some in your group want to stay longer, they can add on days, but to get a group to commit, it has to be a reasonable amount of time away from the demands of their regular life. Make it easy. A long weekend is easy to say yes to.

Securing a date is probably the trickiest part of the planning – anniversaries, birthdays, work deadlines, kids’ sports, etc. Finding a date is what stops trips from getting on the calendar. Here’s how to secure your date:

• Talk about what time of year might work best. Look far out on the calendar, like a year in advance.
• Once you have a timeframe, set up a poll with 3-5 date choices using Rallly, and send it to your friends. Note: only the person setting up the poll will need a free account – your friends will be able to respond without an account.
• After all your friends weigh in, select the date that works best for everyone. If there are no dates that work for everyone, try a different time of year. If that still doesn’t work, select the date that works for almost everyone, and lock it in.

The destination doesn’t matter as much as everyone being there. If there is a split in how much your friends can afford, lean toward the less expensive destination ideas – think a city get-away instead of an all-inclusive resort, or choose free activities like hiking instead of a spa day.

Keep in mind:

• Choosing a destination goes hand in hand with the budget discussion.
• Prioritize destinations with well-connected airports. If you fly into a major city, it will be easiest and cheapest for most.
• Keep in mind the amount of time and money it takes for each person to get to a place. If your friends live all over the country, a quick and inexpensive trip for one person might be expensive and time consuming for another.
• Are you all aligned on what you want in a destination? If so, start there.

My friends have a lot of big opinions, but after 30 years we can agree that we want to be in a place that is fairly easy to get to (i.e. no driving for 4 hours after landing) and in a location that has a good selection of restaurants. Your group might have their own top-line goals – maybe a spa, or a water view, or a dude ranch – whatever it is, if you can agree at this stage, it will be easier to finalize your destination.

Once you have a destination, someone in your group searches for accommodations, and sends the top few contenders that look like the best options for your group to everyone for feedback. Budget/value will likely be on the table for discussion again, and then you all will agree on a specific property.

Choose a rental house if being together matters more than privacy. Consider individual hotel rooms if you have introverted friends who need to close a door at the end of the day to recharge.

Someone books the property everyone has agreed on. Divide the cost among the number of friends traveling, and everyone Venmo’s their share to the person who booked it.

Congratulations, you just got the trip with your friends out of the group chat and onto the calendar!!! But wait! There’s more!

Splid is an amazing, free app. Everyone in the group can keep track of what they’ve paid for and who was there for that specific activity, and then at the end of the trip, Splid tells you who owes who.

Examples:

• If everyone gets there a day before you and has dinner and goes to a concert, you wouldn’t split that cost – it gets divided among only the people who were there, not the whole group.
• If you don’t drink wine, and your friends spend $400 on wine, they would leave you off that receipt.
• If two of you have lunch while the others are hiking for free, you just enter your two names on that entry. You get the idea.

At the end of the trip, Splid tallies up exactly how much each person owes, then takes into account how much they paid for, and then does some accounting magic and tells you how much (if anything) you owe each of your friends. Splid for the win.

Make sure to reserve a lot of time for just hanging out. For a three-day weekend, maybe book one experience ahead of time, and identify a few restaurants that match your group’s budget and expectations. Check out GetYourGuide to see what there is to do at your destination.

Give people permission to skip a group excursion and take a nap, or split into two smaller groups for an afternoon and meet back up for dinner. You will have more fun if everyone has agency over their own schedule.

Final thoughts

If you are determined to plan a trip with your friends to multiple locations or for a longer duration, say, a week or more, I recommend considering a small group tour. Girls trip to France? Walking the Highlands? Cycling through wine country? Hand that trip off to someone else who will coordinate all the flights, the transfers, the reservations, and the logistics, and your group just shows up and does the trip together.