Traveling with Friends? Don’t Make These Mistakes!

Tips for traveling with friends
Updated: Mar 9th, 2017

Not every vacation with friends goes smoothly.

Sometimes, shit goes sour.

Now a perfect vacay for me is just me and my sweet boo, at a romantic all-inclusive resort located on some gorgeous tropical beach.

But occasionally I’ll travel with family or friends (or even work colleagues on our annual retreat), and over the years I’ve learned some very important “DOs” and “DON’Ts” when traveling with other people.

First, the DOs
  • Discuss the trip budget — Not everyone can – or wants to – spend money the same way. Talk about who pays for what and don’t overlook things like when and how much to tip, activities that aren’t included in your all-inclusive vacation (off-site activities and tours, spa treatments, boat rental, etc.) as well as stuff like ordering that a la carte (and expensive!) bottle of wine or champagne……discussing the budget ahead of time means that no one should wind up going home resentful.
  • The bottom line is that a little pre-trip planning with everyone involved should ensure that you STAY friends with everyone after you get back home.

  • Discuss shared/group/individual responsibilities — The larger the group, the more important it is that you designate someone to (at least loosely) coordinate things. When everyone is standing around saying “I though YOU were going to take care of that” then invariably something slips through the cracks, like reconfirming your airport transfers, or making dinner reservations when they’re needed.
  • Recognize and respect personality differences — Sure, we love our family and friends for who they are, even if that’s very different from who we are. You can usually avoid problems if you understand different personality types and how to compromise to make sure everyone has a good time.
  • Schedule some time apart — The extroverts in your group may not need this, but doubtless you’ll have some introverts as well, and they certainly will. An introvert needs to have some ‘down time’ to recharge the batteries and will be much happier during the ‘together’ times if they get it.
Tip: Schedule a group meeting (which is a great excuse for a party!) to handle your pre-trip planning sesh….if your friends/family are far-flung, Skype has free group video calling for up to 25 people. Just be aware that not everyone is comfortable discussing financial matters in a public setting.
Next, the DON’Ts
  • Share a room (the kind with two beds) if you’re ‘coupled’ — this leaves you with virtually no ‘intimacy’ time with your partner. Exceptions: If you’re traveling solo and want to room with a close friend or sibling, OR you’re sharing a double-bedroom suite, where each couple has their own bedroom and bathroom, with a nice big living room in between.
  • Room right next door — it’s amaze-balls how thin the walls are! NO one wants to hear friends or family arguing, discussing a member of the group that they dislike, or (gasp!) actually having great vacation sex. And yes, they can hear you.
  • Expect to do everything together — Sure it will be fun to share some meals and activities, but don’t put the pressure on your friend to go horseback riding or shopping when all she wants to do is relax at the Spa. A little time apart means you’ll have stories to swap over dinner.
  • Over-imbibe — Now I love my evening cocktails more than as much as anyone but sometimes that one-drink-too-many turns into a truth drug that can bite you. Your BFF’s hubby does NOT need to know that you really think he’s a pompous ass with ‘performance’ issues.
  • Make assumptions about activity levels or dining habits — Plan in advance what activities you’ll share and which meals you’ll partake together. Some may like to have every day full of activities and dinner out each night, others won’t.
  • Flirt excessively with your best friend’s wife/sister-in-law/the waitress — This one is just a big no-no unless you’re both single – otherwise those comments or touches that you think are innocent can set off an explosion of hurt feelings (your spouse), discomfort (the object of your flirtation), and anger (your object’s partner). Friendly is okay, flirtatious is not. If you don’t know the difference, discuss it with your partner.

The bottom line is that a little pre-trip planning with everyone involved should ensure that you STAY friends with everyone after you get back home.

What steps do you take to ensure a great trip when traveling with others?

About Trisha Miller 46 Articles
Trisha is the Editor-in-Chief at Travel Writers Exchange, a community for travel writers & bloggers. She's also a member of the Society of Professional Journalists, and a former member of the IFWTWA, serving on their Board of Directors from 2009 through 2015. When not traveling the world, Trisha occasionally guest-blogs for a number of websites, writing mainly about travel and technology, sometimes both at the same time.


  1. I’ve just recently returned from a cruise with friends. Trust me, I am in desperate need of a getaway at an all inclusive resort with a beach where I can find my own private self. Even though the ship was large, we seemed to be on top of one and other. I love my friends but, I value my privacy. Hopefully I will find just that at the all inclusive resort that I have booked for late summer.

    • Hi Kim,
      Thanks for dropping by and sharing your cruise experience – I have the same issue with cruises, just too many people in a confined space, and I hate that I have to retreat to my cabin to find any sense of privacy – what’s the point of a vacation if you have to spend it in your room?

      The key is to find the right all-inclusive resort for you – and if you’re willing to travel in the off-season, then you’ll have many to choose from, as they’ll be far less populated and you’ll not only be able to find a nice secluded spot at the pool or beach, but better service too!

      If you need help finding just the right resort, post a question in our forum and one of the travel experts who hang out there will come along to give you some great advice. :-)

  2. Just read your comment to Kim and I had a thought. My granddaughter will be staying at an all inclusive resort in Mexico in September. She will be there with a college girl friend, not a “partner”.
    Do you think that they will be friends after a week in a close company.

    • Hi Barb,

      Excellent question!

      If they’ve been close friends for a while and have traveled together before, then I doubt they’ll have any trouble…….usually two friends of the same gender can travel together IF they know each other well……..the only time I’ve seen disaster strike is when one of the friends meets a ‘love interest’ and winds up ‘hogging’ the room, leaving the other friend alone and shut out……but a discussion between them before the trip — about that specific possibility and setting some ground rules for handling it — will go a long way to keeping their friendship intact, and ensure a good vacation!

  3. Hi, liked your comment to Barb. I am a single lady and by choice, I prefer to vacation alone rather than with friends. I have never stayed at an all inclusive resort but, I am thinking of doing so in the Fall. Among the all inclusive resorts are there some that cater to singles or a least don’t charge extra because of the single booking?

    • Hi Janice,

      Great question – I’m sure there probably are, but I’ve only ever traveled with my hubs or with girlfriends….I think this is a good question for you to post in our all-inclusive travel forum, where we have a number of travel experts who are better qualified to answer, I’m sure they can make some good recommendations for you.

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