How to Travel with Friends & Come Back with Your Friendship Intact


I spent 10 amazing days in beautiful Grenada with two of my most amazing friends and not once did I want to tip toe into the kitchen to grab something sharp and “accidentally” drop it on one of their pillows as they slept…lol. Grenada was one of my most favorite places I’ve traveled to so far and I had an unbelievably great time but what made it even better was the people I went with. But traveling with friends doesn’t always have a happy ending. I’ve had some moments in my lifetime where I wanted to stick my companions in checked luggage zipped tightly so not a stitch of air came through…lol. Ugh. Bad traveling experiences can make you feel like you wasted your hard-earned money and make you feel super uncomfortable—who wants that when you’re so many miles away from home? Not me! So I decided to write a post on how I manage to keep my cool and my friendships while traveling. Because while it’s cool to do some things by yourself (I love doing tons of things solo) sometimes it’s so much better to travel with friends and be with your homies.

celine shadow sunglasses denim on denim outfit danielle gray the style and beauty doctor ChicagoGSZ-90
Taken in Chicago by Nas

1. The most important part of traveling successfully with friends is….


Yes, you. It’s all in the attitude YOU bring to the table. You need to go on that trip with an open mind and prepare to be flexible. Be willing to compromise. Be willing to calm the eff down before things escalate—why would things need to escalate—you’re on vacation! You’re traveling somewhere fun—why are you so angry anyway? LOL

No really, how YOU react to a situation is what affects the outcome. Trust me. I went on a trip where people were driving me crazy but I decided I didn’t want to mess up my trip nor theirs so when I reached my boiling point, I went to another room to decompress and vent to a third party. After that I was okay and back to having fun.

In LA last April with The Baby Shopaholic and Mama Fashion Files

2. Yeah, it’s you but it’s also who you travel with, too.

We all have heard at some point that you have friends you can travel with and those you can’t. This is true. For instance if financial situations differ, this can cause certain situations to escalate. But as I’m getting older I have fewer people I genuinely call friends and as one person pointed out to me “I don’t worry about friends I can or can’t travel with—I’m not friends with people I can’t travel with.” That’s SO true. If you can’t spend three days or more sharing a space with someone, how on earth can you share your most intimate details of your life with that same person? (I’m talking friendships here—relationships are a whole other thing and as I’m single as the day is long, I don’t feel I have enough experience to talk on relationships…lol).

So what I’m saying here is not only deeply evaluate whether or not a friend travels well, but also deeply evaluate why that person is in your life in the first place. But even still, it all goes back to YOU and what energy YOU bring. I can honestly see myself going on a trip with someone I’m not that close with and still having a great time because I know how I am.

lake placid owl mountain hike
Hiking in Lake Placid with Nas

3. Keep finances separate when you can.

Girl, the quickest way to a fight is over some coins. I personally do not care how many people say it’s the right thing to do, but I DO NOT LIKE if I’m only ordering something small in a group setting and everyone else is ordering a gazillion drinks and when the bill comes talmbout splitting it evenly. That grinds my gears like you wouldn’t even know…lol. Luckily amongst my friends everyone is on the “every woman for herself” line of thinking when it comes to the bill. Or if it’s pretty close (I’m not going to complain over a few bucks) then I’m totally cool with splitting it evenly.

But when you’re traveling internationally, there’s things like currency conversion, VAT, and of course gratuity if it’s not already included and if you’re in a country that accepts gratuity. Try to get separate bills or carry cash on you so you can pay exactly what you owe and be done. I’m cool with paying for one meal and then having my friend/s take care of the next one. Drinks in Grenada were SO cheap I threw down my card like I was a baller and paid for everyone’s drinks one night without blinking…lol. More on that in my Grenada recap. And I’m also good about taking the bill myself every now and then if I can, but don’t order 5 drinks and all I had was a salad and talmbout let’s just split

When it comes to paying for things like hotel and other stuff, I say if there’s more than two of you, have the most responsible person be in charge of collecting money. I’ve had situations where people went silent the second it was time to pay for big ticket items and it can be super frustrating (those are the types whose role in your life you question…lol). But what would be most ideal is to have everyone pay individually and directly. This last trip everyone was coming from different places at different times so we of course paid individually and directly to the airline, etc. We stayed at Nas’ grandmother’s house so what we paid towards utilities and such was again paid directly and individually. I personally feel the less you have to mix funds, the better.

But when you do have to pool money in the case of hotels and such, I say come up with an agreement upfront. Know exactly how much each person needs to pay and when it needs to be in. Have everyone agree to this (hate to say this but get it in writing if you have to) from the beginning and then use something like PayPal or Chase Quick Pay to pool funds.

seven sisters falls grenada
Hiking Seven Sisters Falls in Grenada with Nas

4. Plan your itinerary in advance.

We all like to do different things and there may be some things someone in your group may not want to participate in and that’s PERFECTLY FINE. Planning your itinerary in advance allows for you to plan activities you can all do together and then plan things you may want to do separately (when safe) and in the case of bigger groups be able to pair off. Planning in advance also helps everyone visualize the trip and plan accordingly.

am bush trinidad 2014
At a fete in Trinidad with Lexi with the Curls and Glamazon Jessica

5. Keep the lines of communication open.

One time I went on a trip where someone was so adamant about not having any quarrels or complaining that they failed to communicate when something was justifiably wrong and that actually made things worse. It’s okay to speak up if something’s wrong but remain respectable. Instead of saying something like “YOU’RE RUINING MY TRIP!!!” say something like “I was looking forward to doing some shopping on this trip and since we spent so much time site-seeing yesterday, I thought we could head to a mall today.” It’s all in HOW you communicate which I feel isn’t something practiced enough in friendships or just regular female interaction.

grand anse beach grenada
On Grande Anse Beach in Grenada

6. Have separate spaces when you can.

I don’t mind sharing but I much prefer to have my own space. When it comes to shorter trips I don’t mind sharing a room—in fact the last bunch of domestic trips I took with friends we shared hotel rooms and it worked but mostly because these were short—no more than 2-3 day trips. For longer trips always try to have your own room if you can afford it or look at alternate accommodations. Four of us went to Barbados earlier this year and stayed in a 2-bedroom condo with a full living room that was less expensive than a hotel and allowed for us to have our own separate living quarters for the time we were there. In Grenada we each had our own rooms as well. I highly suggest having your own space when possible.

poland 22222
In Warsaw, Poland with Pretty Connected

After I came up with these I started to draw a blank so I asked my girls to add their thoughts.

seven sisters grenada
My girl Marie selfie-ing it up as we hiked Seven Sisters Falls in Grenada with the Grenada Tourism Board

Tips from my girls:

(my comments are in brackets)

*Understand that not everyone is going to want to do everything together so it’s okay to pair off or allow some quiet time. [I —meaning me, Danielle…lol—knew in advance of the trip that Nas and Marie LOVE going to the beach and I didn’t as much so I brought along a book so I could pass the time. Turned out I got turned out over the beaches in Grenada and loved it as much as they did—this is why it’s important to keep an open mind–you might find something new about yourself.]

*Travel with friends that have similar vacation goals (i.e. relaxation vs tons of site-seeing) [Yes, SUPER important—I once went on a short trip with a friend who went to bed at like 9:30/10 every night and I wanted to go out—talk about awkward]

*For long trips travel with friends you’ve had a previous trip trial run with—if you cannot work for 3 days, 2 nights then 10 days might be hell [TRUE. Try a road trip first before you go to say a 15-day excursion to Australia]

*Try to come up with a flexible budget beforehand so no unexpected expenses come up [Yep. Like if there’s some really nice but really expensive restaurant you MUST try, keep some extra funds on hand just in case—I’ve gone on press trips when I was DEAD broke but I had expenses paid for me but I could never go on a friends trip without some extra funds on hand]

*Understand everyone has different finances when it comes to choosing restaurants, hotels, etc. [So true—try to compromise or stalk Groupon or Living Social type sites for deals where you all can meet in the middle]

*When traveling in groups try to plan at least a few activities where everyone should attend to keep the trip cohesive. [Yep—otherwise why did you all go to the same place at the same time? lol]

cloud gate bean chicago millennium park danielle gray the style and beauty doctor ChicagoGSZ-9
With Nas in Chicago

Traveling is such a rewarding experience and doesn’t have to get messy when you travel with friends. Did I miss any tips? Tell me in the comments! Also share your travel experiences with your friends (good or bad) in the comments below!



  1. Fola
    January 13, 2015 / 5:42 pm

    This is exactly what I need! Thanks Danielle. I’m planning a getaway trip for my 21st birthday and I’m still struggling to find a great, affordable location for my friends and I. Its going to be 5 or 6 of us and I’ll definitely be using these tips on the trip. Any suggestions on places to go would be helpful.

    • Danielle
      January 13, 2015 / 7:00 pm

      Hey Fola!


      When is your 21st? And what major cities are within a 4-5 hour or less drive from where you are? (unless you’re the Fola that came to my BECCA event then I know you’re in NYC…lol)

      But New Orleans immediately came to mind as a suggestion. It’s a beautiful city, so many cool things to see and do, and you can walk outside with drinks legally so perfect for turning 21…lol. You can get a pretty decent flight depending on dates and hotels aren’t too bad. I’d also say Vegas—another cool place to turn 21 and flights and hotel there are pretty affordable depending on when you go. I’d suggest not staying anywhere too long since it’s so many of you—maybe two nights max.

      If you want to go international, try looking at places like St. Maarten or Dominican Republic—flights don’t seem to get too expensive there (at least for me since I’m in NYC) and then perhaps you can look into finding non-touristy bars and parties around your birthday.

      Hope this helps! Let me know where you wind up going :)

  2. January 14, 2015 / 4:41 am

    Great tips! I totally agree with “every person for themselves” when it comes to paying restaurant bills. If you’ve been ordering the expensive wine and lobster, don’t count on me to pay for your expensive tastes. :-)
    Looking forward to more Granada Recaps.

    • Danielle
      January 14, 2015 / 8:26 am

      haha! right! Don’t try to have the power of a group finance your lavish tastes…lol.

      Can’t wait to get the Grenada recaps up—hope you guys enjoy them :)

  3. January 14, 2015 / 7:43 am

    Really great advice Danielle! My husband and I had a trip planned and a friend asked to join us, last minute and it got super frustrated because she didn’t want to do things that M and I planned before she joined the trip, and she was “afraid” to go out on her own. We felt like we were babysitting the entire trip and when I finally spoke to her about it (quite nicely I might add) she wasn’t too please :-( I swore off trips with friends after that mess!

    • Danielle
      January 14, 2015 / 8:22 am

      Hey Nesha!

      WHAT. OMG. SO sorry that happened to you and hubby! How dare she be the third wheel and then act the fool. UGH. If I’m latching onto something already planned and I asked to go I’m totally doing everything everyone else is doing. UGH. And the nerve of her to get mad when you confronted her about it. SMH. Are you still friends with her?

      • January 15, 2015 / 10:50 am

        I know huh lol M and I still laugh at it, no more of that nonsense for us. Yes, we’re still friends but as you can imagine not as close as we were before.

  4. Claudette
    January 14, 2015 / 12:21 pm

    Great article, Danielle. Once invited a friend to share my suite at a resort. My friend got bitten on her face by a mosquito (like you, Danielle). She decided she was going to sue the hotel. I said to her, can you prove that you were bitten in the hotel; you could have been bitten while on your way to the hotel and it showed up later. That was the last time I ever invited her on any of my numerous trips to the resort. Another friend used to order the most expensive meal on the menu. Even though the meals were comped (free), I always tried to stay mediocre. And to add insult to injury, she was rude to the servers…UGH!!!

  5. Fola
    January 14, 2015 / 1:36 pm

    I’m turning 21 Feb. 27th and you remembered! It is me from the BECCA event lol. Thanks for the great suggestions, I’ll definitely look into it. You’re the best!

  6. January 15, 2015 / 9:35 am

    I wish I could vent to you about the trip I took this past summer around my birthday. Ruined the whole weekend! UGH. But honestly I knew better. I just didn’t trust my gut like I normally would. Anyway, all of these are so true and I’m glad you wrote this!

    Brittany x

  7. January 25, 2015 / 1:26 pm

    GREAT TIPS!! I hate to argue about money so yea I’m with the every woman for herself because some don’t understand tip is extra lol…trying to get some girls together for EssenceFest this year so thank you for the Chase Quick Pay idea! P.S. I’m sneaking in your carry on for the next trip K!

    • Danielle
      January 27, 2015 / 6:20 pm

      Girl, money can make some people act the damn fool. Thank goodness for Chase Quick Pay!

      Thanks for reading :)

  8. January 25, 2015 / 7:26 pm

    This is so informative. I mostly travel by myself, but want to start traveling with my friends. You definitely presented some things to ponder on. Side Note: I hope you have Warsaw articles/recaps as I am headed there soon to visit friends.

  9. Tara
    November 2, 2017 / 3:25 pm

    Danielle I loved all of your Iceland travel info and came here looking to see if you had any Costa Rica ideas and I think a lot of your Grenada packing advice will transfer! I am traveling with 4 other women–we do an annual girls’ trip and have been doing it since college and I look forward to it every year! This is our first international trip together so it will be a new experience but I’ve never been to Central America so am really excited. I love your site and mix of content!

    • Danielle
      November 5, 2017 / 1:34 pm

      Hi Tara!

      So happy you loved it! I haven’t been to Costa Rica but I want to one day. Hope you and your friends enjoy it! Thanks so much for reading :)

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.