Traveling With Friends, Part 2

This is (kind of) a part two to my original post about traveling with friends. Traveling can stress me out, but when there are friends involved, you really can’t go wrong. Well, actually, I take that back. Traveling with friends CAN go wrong, but it doesn’t have to!!!

Read up on the first post because those are the main big tips that are tried and true. (I go into detail, but they’re: get excited, pick some place no one has been before, be on the same page and set expectations, eat often, and smile.)

I cannot emphasize the importance of eating though. Make sure that everyone is well fed at all times. Trust me; it’s not pretty. And on that note, don’t forget the coffee.

Since I wrote that post, I’ve had some additional trips with friends. I just got back from one with a group of six, including me, and I hadn’t traveled with two of the girls before. We had SO much fun, and it reminded me how important it is to travel with friends. If you haven’t done it yet– you need to! It’s the best experience and a quick way to deepen friendships in a short period.

Matching pajamas

Matching in our pajamas c/o LAKE Pajamas (they fit true to size, but I recommend going up a size for an extra comfortable fit)

This was the first trip with friends that I’ve done where we stayed in one place, so I have some additional tips:

ONE // Be on the same page for wake up (and bedtime) times

I don’t think everyone needs to set a uniform alarm every morning and I don’t think everyone has to march to bed at the same time… but I do think it’s helpful to give a general timing for mornings and nights. Even just saying, we want to be at the beach at 11 am, so we need to be out the door at 10:30 am. Let everyone figure out when they need to be up with enough time to get ready from there. AND, for bedtime, I think a simple “let’s have an early night tonight because we have big plans tomorrow” or “tonight we can be a little more flexible and stay up later.”

The key is that you don’t want someone in the group to not get the memo about the plan.


If you’re traveling with friends for the first time, I cannot recommend game nights enough. It. Is. So. Much. Fun. You can play board games, but I find that the fewer rules and the more flexibility you have within the game, the better. Pick something that people can duck in and out of and something that won’t make people want to kill each other (like Monopoly 🙅🏻). If you have it, Cards Against Humanity or Apples to Apples are both great options. I also love Catch Phrase, Mad Gab, and Speak Out (where you have the dentist guard thing that keeps your mouth open!).

If you don’t have access to any games, classic charades is always a good option as well. You only need scraps of paper, a bowl, a pencil, and some creative thinking to make that one work.

BUT, if you have a phone, I highly recommend downloading Ellen Degeneres’ “Heads Up!” game on your phone. It is SO much fun. We played every night while on Nantucket together. It was the best way to bond a group that had never traveled as a collective whole, and we all got to know each other a bit more. One night, the girls and I played until after 2 am because we just kept having to do “one more round.” So. Many. Laughs.

THREE // Budgeting

I have to say that next to personalities, the one thing everyone should be somewhat on the same page about is budgeting. I think everyone has to be somewhat within the same budgeting mindset. Will your group be okay keeping meticulous notes on what has been paid and who owes what? Or is every one of the mindset of “it all comes out in the wash”? Will there be big fancy dinners out with lots of drinks or will you be cooking budget-friendly meals at home? There’s no right or wrong way to travel, but everyone in the group should feel the same way… one way or another. With Venmo and Paypal, it is pretty easy to keep track of big ticket items and paying people back for dinner bills. (Dividing dinner bills is one of my biggest pet peeves, to be honest!)

Any other tips to add?

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Great tips Carly. I just took a trip with my three best friends and the app Splitwise was THE BEST. It allows you to keep track of all of your expenses and who paid what during your trip, so you only have to settle up with Venmo/PayPal at the end instead of throughout. It made the whole issue of paying for things really easy and without tension.


Great tips! One more to add– if you have certain needs, don’t be afraid to be assertive about them for fear of not “going with the flow.” I need to eat constantly (haha) and have to be vocal about stopping to grab a snack when we are out, or needing to get to sleep early, and no one ever minds. I used to be so afraid of being “difficult” by turning in early that I’d stay up past my limit and was a more miserable travel companion. Don’t be afraid of speaking up!


I know people LOVE venmo, but a lot of the major banks have bought into a new app called Zelle, there is no fee, no maximum, and the money is sent instantly instead of being held in vemno’s “holding account” I know Bank of America, chase, US bank, wells fargo, city, pnc, usaa, tonnes of banks have bought into it, so I’d think twice before using venmo and check out if your bank has zelle

Alex C

Do you have any tips for how to delicately handle budget differences? Or do you think thorough communication ahead of time is enough to prevent any potential conflicts? I’m excited to travel with friends once I graduate college but I’m sort of nervous about budget conflicts– I’m very blessed to have an almost guaranteed (and very well paying) job offer already and most of my friends won’t be in the same situation but I don’t want that to stop us from going on trips together. Thanks for another great post!
Alex //


HAVE THE CONVERSATION BEFORE YOU GO!!! Be open and upfront about everyone’s budget expectations before you even plan the trip.

Caitlin Menzel

Great tips! One thing I’d add is the APP Splitwise! you can make a group and add up expenses and it does all the math for you… so say you pay for lunch Monday, and someone pays for lunch Tuesday, it’ll just automatically deduct what she owes you from what she paid… if that’s making any sense!
I’ve used it on my trip to Greece and Thailand with friends and it works perfect because at the end of the trip you can just venmo what’s leftover!

Sara Miltenberger

I also use Splitwise for trips – I start it at the beginning of the trip and add everyone and then people can go in and add the expenses and it makes it SO much easier at the end.

Audrey | Brunch at Audrey's

haha that first tip is very helpful! I never really thought about it, butI kinda just have always done that whilst traveling. But I never do that for sleepovers. There’s always that awkward period in the morning when nobody knows if anyone else is awake yet so they all just lie silently on the ground until it seems like someone else is up and finally everyone gets the day started 😛 -Audrey | Brunch at Audrey’s


I’m catching up on all the posts I’ve missed and I can’t tell you how great it is that you wrote this one!
These top issues you mentioned can be huge in whether a girl’s weekend is a hit or a flop.
I know I’m planning on sending a link to this post to each of my friends before we head out on our weekends.
Great job! Thanks for taking the time to write this post! 😉