Vacationing with friends – yay or nay?

We’re headed to Palm Springs later this month. We can hardly wait! Last time I checked (five minutes ago) the weather was forecast to be in the nineties! Woo hoo!

We’re meeting two sets of friends there. We had a moment when we were all going to rent a house together, but I decided that maybe it wasn’t the best idea. I mean, I love my friends. Love them. But I kind of want to keep it that way.

Between our three families, we’ve got six adults and six kids. That’s a lot of people for one house, right? Also – the kids range in age from kindergarten to middle school. There’s a lot that happens between kindergarten and middle school.

So we compromised by all staying at the same hotel. I just think that is a much better plan. I got trained by family camp, where we all had our own cabins but shared common spaces. We’ll meet up – all three families – at the pool, or take day trips together, but then we can also have the space for our family to just chill and watch Modern Family episodes if we want and make all of our stupid inside jokes without having to explain them to anyone.

Do you go on vacation with friends? How does it work out for you? Anyone have any tried and true advice for making sure things stay fun?




  1. It’s just Hubs and I, but we love to travel with others (usually making 3-4 trips a year with friends and family). I think the key is to make sure everyone gets to do something they want to do (and that goes for every person on the trip – kids or adults). It’s also important to travel with friends who are comfortable spending about the same (and have similar drinking habits).

    It’s okay to fall back on tried and true methods to be entertained – music, movies and card games. Have a great time!

  2. Stay in separate houses!!!!!!!!
    We had three families(and 7 kids under 10) in one large house at the beach. It took about 3 hours to see it was a huge mistake. and these were our closest friends.
    Just too many personalities in a closed space.

    • Points Pixie says

      Geoff – Kinda my thought. Also – it’s just really hard to be “on” all the time. Sometimes I just don’t want to talk to anyone, and when you are with a large group, that seems weird.

  3. For vacations that are cruises or bus tours, definite YES! Doing so forces each and everyone to be on schedule with everyone else. There wouldn’t be arguments on “I want to see this site today” because there’s already a schedule in place. However, for backpack trips or road trips, I tend to go with 2-3 close friends at most.
    If it’s a family reunion, even if it’s 3 families, I’d prefer for us to all stay in the same house. It will help develop friendships more amongst the cousins even if they range in age from kindergarten to middle school.

    • Points Pixie says

      Joey – I think if we were going with family, I would stay in the same house. But with family, you are stuck with them forever anyway, so even if things get strained/weird, you have to work it out eventually. With friends, it’s a little different. I definitely have ex-friends!

  4. Denise L says

    Most of our shared vacations have been with family. My extended family stayed in a villa in Tuscany – there were 9 adults and 9 kids, ages 2-18. There were 8 or 9 bedrooms on 2 floors and also 2 separate family rooms so we had plenty of space to spread out. Each family had a car and did their own sightseeing during the day and then we’d meet up back at the villa in the evenings to share stories and hang out. A few days were also just spent hanging out at the pool. I think it worked so well because we didn’t do things en masse. We did go to a few restaurants together (reservations were a must!) and had a chef come in and prepare an al fresco meal for us, which was great. But we certainly were not together at all times.

    • Points Pixie says

      Denise L – That actually sounds great. I think having enough space is key. I also think doing your own thing for big chunks of the day works really well. Your vacation sounds incredible!!

  5. I have vacationed with friends, and i think it really depends on the person.

    I have some friends I LOVE to travel with. Usually those who I have similar taste in dining & activities. I genuinely enjoy our time together and am totally fine sharing a house. Mind you I don’t have kids, so it’s not like it’s 10 adults and 10 kids. Much smaller group.

    BUT i also have friends who I won’t travel with. One such friend that i traveled with (exactly once), I learned much about her on that trip. I didn’t realize how rude and picky she was at restaurants. I was completely embarrassed. And how loud and chattery she was in the evenings, and slept in until noon EVERY day (i’m up at 6). It was just awful. Needless to say, we haven’t traveled together since.

    • Points Pixie says

      Rebecca – Yikes, your friend’s travel style sounds challenging to me as well. I wonder if she felt the same way about you??

      • ha! she probably did feel the same way about me. “gee that Rebecca, she’s on vacation and doesn’t even sleep in.”

        I’m a get up & go kind of person. Doesn’t mean i wont schedule in time to have relaxing mornings,or a stroll on the beach. I like to take full advantage of the SUN light and day.

        I think it’s impt to have some discussions before committing about general plans and how it will work to ensure everyone’s on the same page.

  6. I will be traveling with friends next month, and hope to still be friends when we return. We are sharing a beach villa in St Martin. I think good communication before hand in very important. So whatI have tried to do is talk about activities,expenses,beach time/site seeing and meals. I have told them if there is some thing you want to do or not do please speak up. If you get tired and want to go to bed go, if you want to sleep in then go ahead.
    I would love some comments

    • Points Pixie says

      Jim – It sounds like you did a great job setting expectations. It also sounds like you are a good communicator. I predict you will have a fabulous time!

  7. We have rented houses and condos with family and friends over the years, and MOST of the time it works out just fine, but I do agree that you need to be clear in advance (before booking) with each other about basic things like how you like to eat (out in restaurants mostly, cook as a group , as a family? how much you usually spend etc). The ones that worked well were those we had often had “family” meals with at home on weekends or when we had separate cars to go on different day trips. The kids loved having a new “roommate” usually (we split them up and they shared with the other kids). We also are big into going to local markets and cooking (one of the best times was 3 families in a Gite in the Dordogne region).

    • Points Pixie says

      LauraPDX – I really like the idea of having the kids bunk with new roommates. I LOVE going to local markets as well. 🙂

  8. Stephen Kalman says

    When traveling in a group, you move at the pace of the slowest person. Same for sharing space. Longest shower, slowest eater, etc. All dictate the pace of the trip.

    We’ve met other couples on trips that we know we’re compatible with — in terms of how we like to tour/travel — and we book joint vacations with them.

    We have lots of other friends at home we see for dinner, shows, and other social events, but we made the mistake of taking a joint 3 week vacation and it almost ruined a vacation. Everything from budget for meals to taxi vs bus vs walking sparked disagreements. Friendships are too valuable to risk on an incompatible vacation.

    • Points Pixie says

      Stephen – Yes, good point about moving at the pace of the slowest person. That is one reason I chose not to rent a house with these particular friends. Love them, but they take FOREVER to get out the door. Meanwhile, we are a family that is ready in five minutes. We’re learned to simply meet these friends at our destination. Usually we’ve been there for at least an hour by the time they arrive 😉

  9. never.

  10. We shared a beach house with friends over a long weekend. We each had kids that were close in age so everyone got along. On the 2nd to last day, our friend got a stomach bug. When their daughter got it, too, just a few hours later, we packed up our family and left, figuring we could make it home before it hit us. Fortunately, we escaped the bug, but were still glad we left a day early. Who wants to share a house with two violently sick people?

  11. Totally agree it depends on the people. My husband and I do things quickly and hate slowpokes. Completely agree about the slowest person in the group.

    I travel well with girlfriends. But the more people you add to a group the more people have to be in on the decisions, and nobody wants to feel they are pushing their decisions off on you, so sometimes nobody will MAKE the decisions. And you are so right about alone time.

    I have to say I have had two trips in my entire life that ended the relationship. One was with my husband’s nephew and his wife on a cruise. They almost never traveled and were in their early forties. I carefully spelled out expectations ahead of time. We would each choose our daily activities and if they synced up fine, if not okay, too. But the fun part would be getting together over dinner and sharing the day’s adventures.

    They totally ditched us for the entire week, did not want to eat dinner with us even. We were so hurt that we never socialized with them again.

  12. I have one tried and true friend that I travel everywhere with! We call eachother travel soulmates. We have been all around the world and although sometimes we can get on each others nerves, we have the kind of friendship where I can state “Hey, I’m getting a little annoyed, so I’m going to head off to such and such cafe, I’ll be back in a bit” and she can do the same. We even traveled to Venice and then decided to explore seperately. The reason we travel so well together is because we are both very easy going when it comes to travel. Thats the most important thing when picking a travel companion, which is why I travel with my friend instead of my husband

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