Do You Vacation with Friends?

I’m always jealous when I see that other people are vacationing with friends!  For example, Holly from Club Thrifty recently went to Jamaica with a group of friends and Michelle from Making Sense of Cents is planning a Las Vegas bachelorette party with her bridal partyI would really love to vacation with friends but it’s not something we’ve done very much.


Pike's PlaceOur experience with vacationing with friends in the past is limited but very positive (listed in descending legitimate-vacation-ness):

  • We went on a cruise with two of our friends from college.
  • We rented a beach house for a few days with a bunch of friends just before our college graduation.
  • We road-tripped from L.A. to Seattle and back with college friends right after graduation.
  • For several years post-college, we spent a couple days around New Year’s with a group of friends at the family mountain cabin of one of the friends.
  • We attended a wedding in Chicago that several friends also attended – we didn’t stay at the same places, but we met up for some activities over a couple days.


Even though there is sometimes conflict over what activities to do and such when traveling with others (spouse, family, or friends) I think it’s worth it to bond and make the memories together.


I’m jealous of these friend-vacations for a few reasons:

1) They are taking vacations to begin with!  Aside from visiting family for Christmas and taking an occasional day off to travel to a wedding, Kyle and I haven’t taken a proper vacation in over a year and a half.

2) They get to choose where they go (along with their group, presumably).  We haven’t chosen a vacation destination since our honeymoon in 2010.

3) I think they must have really close friends or friend-groups to be prioritizing vacationing together, given the time and money costs.


I don’t mean to be so complain-y about my reasons for my jealousy!  Kyle and I actually do have flexible vacation time officially available to us, we just never take it because we’re so focused on graduating.  We travel for weddings and see our families over holidays but that’s about it, at least in the past few years.


I guess I am also feeling a little strange about the current status of my friendships.  We have great mutual friends from college who we almost never see, and more and more time is passing.  We have good local friends, too, but as we’ll be moving away soon I find myself unsure how much energy I want to invest in the relationships. So many of our good friends have already moved away and we haven’t kept in contact.  Articulating that makes me feel terrible!  I should be better at living in my present.


I can think of several friends, some from college and some local, who we “click” with well enough that I think vacationing together would be fun.  But since 2008 (a year after we graduated from college), I have never suggested that we travel to vacation with any friends, and we haven’t really been asked, either.  I guess it’s just something that I don’t see done very much in my friend circles.  Since so many of our friends are also in grad school and/or live far away from their families, they probably also have limited time and money for vacations and have a lot of obligation travel.  At least, I’m assuming that on their behalf!  Probably if we were asked by the right people at the right time for the right destination, we would say “yes” and be able to make it happen time- and money-wise, but I’m not brave enough to suggest it myself.  Maybe I’m also a little afraid of rejection – of thinking we’re better friends than we are.


Later in life our vacation time will probably be better-defined by our workplaces and we should have more disposable income, but we’ll also probably have kids and I don’t know how that would complicate vacationing with friends.


I think my conclusion is that if I really want to vacation with friends, I should put myself out there and just broach the subject!  It doesn’t have to be anything long or expensive, especially if we are looking forward to a big trip for just the two of us in the late summer or fall.  Perhaps we could plan something for after Kyle defends.


P.S.  I asked Kyle if he is interested in vacationing with friends and he flatly said no.  He doesn’t even like compromising with me in terms of how to spend his vacation time!


Have you ever vacationed with friends and how was it?  Do you see your peers going on vacation with friends and at what life stage?


Written by

Filed under: travel · Tags: ,

35 Responses to "Do You Vacation with Friends?"

  1. Michelle says:

    Thanks for the mention. We usually do one to two vacations with friends each year, and it’s always a lot of fun. They are usually budget vacations, so I would love to be able to one day do a fun Jamaica or another beach vacation with friends like Holly went on!
    Michelle recently posted..7 Considerations When Determining Utility Costs

    1. Emily says:

      Do you always vacation with the same friends?

  2. Cash Rebel says:

    It’s so crazy how your vacation possibilities open up once you can take actual vacation time, and you have enough money not to worry about it so much. Since I’ve been single most of my life, I always have taken vacations with friends. It’s a little easier to organize since it’s every man/woman for him/herself, but it’s always a blast. Most of the time I’ll make sure my buddy can go with me and then we invite everyone else. I hope you get to go somewhere fun soon with cool people!
    Cash Rebel recently posted..The frugal Colorado adventure

    1. Emily says:

      Maybe it is different when you’re coupled up. We were dating when we went on all those trips with college friends, but now I think I would prefer to travel with other married couples. And it’s more expensive when you don’t sleep 6 to a room!

  3. I went through a move last year and lost most of my hang-out friends. There are three that I still keep in touch with, but they live very far away, and so our planned trips are just to hang out at their homes rather than another destination.

    Honestly, my fiancé and I don’t have a lot of couple friends, so there’s not a lot of people we’d plan to go away with – perhaps my brother-in-law and his girlfriend. I haven’t been on a true vacation (not business-trip extended, or visiting family over a holiday) since I went to my cousin’s wedding in San Diego in 2011.

    I want a vacation so badly, but I am about to hit a new roadblock… my new employer makes you work for a year before you can take vacation (rather than accruing it throughout the year and using it at the same time). So I am about to start a job where I know I won’t get a vacation until nearly summer 2015. Lame!
    Alicia @ Financial Diffraction recently posted..Newbie Salary Negotiations.

    1. Emily says:

      We have often visited friends where they live, usually when we’re in town for a wedding, and we do enjoy having the time together. But I think it’s different than traveling somewhere new together when you’re both taking off of work and such.

      That really stinks about not being able to vacation in the next year! Do you still have some paid holidays or personal days?

  4. Thanks for the mention, Emily =) I do like vacationing with friends but I like getting our own room and doing our own thing sometimes. All of our friends are bigger spenders than we are so I always tell them upfront not to try to pressure me into $150 dinners or anything =) We’re going to Las Vegas with friends in May and I paid for all four of our plane tickets with Southwest Rapid Rewards points! So we’re flying together but staying in different hotels because I didn’t want to very much. We’re staying at the Travelodge on the strip for $87 per night, and they’re staying somewhere nicer. (I find this slightly maddening since I paid for their plane tickets with points to save them money!)

    Now that I think about it, that’s probably the most stressful thing about traveling with friends. We travel a lot and need to keep it as cheap as possible, while our friends don’t travel much and like to go “all out” when they do. We’re used to it though. They always make fun of us for being cheap but I think that being cheap is awesome =)
    Holly@ClubThrifty recently posted..Your Child Will Need Student Loans

    1. Emily says:

      That’s interesting that your friends like to spend more than you. Do you travel with different groups of friends, since you mentioned traveling more frequently than your companions? Or do you just to more trips on your own?

      That sorta stinks that you got your friends free flights and you don’t get the benefit of staying the same place. Do they compensate you in any way for part of the money you saved them by paying for food or entertainment or anything? I would think you could make it a mutually beneficial experience.

  5. Leigh says:

    I’ve been on a few trips with friends. While single, that’s really the only way to travel! My now-boyfriend and I actually went on a trip together with some friends from college a couple years ago and the four of us all shared a hotel room to keep costs down and it was awesome!

    I went to Japan with a friend in September and that was pretty cool. Her boyfriend isn’t that into traveling and we met up with a mutual friend, so it would have been weird to invite my boyfriend (and I was single at the time that we booked the tickets).

    A few years ago, a friend called me up and said “My boyfriend just broke up with me and I want to go to Mexico – do you want to come with?” and we went! It was amazing. It was also really nice that we did an all-inclusive because we have very different cash flows, so all-inclusive meant 95% of the spending was done upfront and agreed upon together.

    I also traveled all over Europe with some friends many years ago now. I’m not really a huge fan of traveling solo – it’s so much more fun with other people. In fact, in that group, we had so many people that we could book up an entire dorm room for 20 euros a night!

    Not everyone wants to organize trips and everyone has different budgets, but you can compromise and it can be really rewarding. My trip to Japan was the opposite of the Mexico trip with that friend because we had SO many financial decisions to make. It went pretty smoothly though and I would totally travel with that friend again! (The only catch is that traveling with my boyfriend is pretty awesome too…)
    Leigh recently posted..February 2014 net worth update (+3.2%)

    1. Emily says:

      Wow, you have done a lot of traveling with friends! That is sweet that you were able to go to Mexico with your friend at the drop of a hat. I definitely wouldn’t want to travel alone so it was always with family or friends before I got married. I like the idea of doing something all-inclusive so you don’t have so many negotiations while actually on the trip – that’s hard enough to do with Kyle!

  6. We only vacation with family. DH gets antsy if he doesn’t see his extended family at least a couple of times a year so with that and having my parents visit us, that’s where all our vacation time goes.
    nicoleandmaggie recently posted..Ask the grumpies: Next stage financial advice

    1. Emily says:

      I think that might be our situation once we have kids because our parents live on opposite coasts. :/

  7. Of course, I do see a LOT of my friends at conferences, which is sort of like a vacation, if you’re a nerd.
    nicoleandmaggie recently posted..Ask the grumpies: Next stage financial advice

    1. Emily says:

      That is pretty cool, actually. I’ve been to conferences with established PIs and they seem like they’re having an awesome time with their colleagues. 🙂

  8. Money Beagle says:

    It’s been a long time, probably over 10 years ago when two buddies and I went out to Myrtle Beach for a few days.
    Money Beagle recently posted..I Wasted $11 By Not Following A Simple Routine

    1. Emily says:

      Do you wish you would take a similar vacation now?

  9. moneystepper says:

    We usually take vacations with friends – its always more fun when there is a big bunch of you!
    moneystepper recently posted..Becoming debt free: How I paid off over £100k in consumer debt

    1. Emily says:

      How do you make it work? Who suggests and plans it? Details please!

  10. NZ Muse says:

    Hmm. We’ve done domestic trips with friends (2-3 hours drive away) but never overseas. I don’t think I would want to, either.
    NZ Muse recently posted..How to deal with a layoff gracefully: Advice for couples

    1. Emily says:

      What do you think is the difference? I would say to me it’s a matter of cost – for a vacation that’s mostly about spending time with friends I wouldn’t want to spend as much and wouldn’t go as far afield.

  11. I like vacationing with friends – have been on a weekend getaway with a girlfriend and planning on a Puerto Rico trip with another girlfriend. I probably wouldn’t do really extended travel with a friend (i.e. over a week) because I’m too afraid of having a bad experience on the trip that might somehow jeopardize the friendship.
    Well Heeled Blig recently posted..Using Dropbox shared folder to track our joint finances

    1. Emily says:

      Yes, that is a legitimate concern. I think maybe it would be alright if you were able to have somewhat independent schedules if you couldn’t agree or needed a break from one another.

      Have you and CB ever vacationed with another couple or a group?

  12. Sarahn says:

    Interestingly, my parents are vehemently against travelling with their friends – but will travel to meet friends in far off places. I think that has influenced me.

    I have met some close friends in NYC (from Sydney, Australia) for a few nights, as part of both our greater holidays. It was nice to see them, and to share a hotel room etc. BUt there’s only a few people I would be game to try a holiday with!! I need lots of naps when I’m not working, and some people are go-go-go holiday people whereas I’m more slow-slow-slow, and like to rest no matter where in the world I am.

    I certainly wouldn’t rule out the possibility, that’s for sure. I agree, once you earn more and perhaps have a little more time (or need the time off more, sometimes being student has enough flexibility in it to ‘need’ the holiday less, as least my student years did), it might work for you. But seeing you got a no from Hubby, maybe it’s a no go :s
    Sarahn recently posted..Weight loss update

    1. Emily says:

      When your parents meet their friends, is that where their friends live or a neutral location? Did they have a bad experience or something? Seems odd to me without more explanation!

      Identifying what you want/need when you are on vacation is probably half the battle to having a nice trip with others.

      Eh, sometimes I can talk him into things. 🙂 The friends we’ve vacationed with in the past were all more from his friend-group from college so he had a good time.

  13. Tarynkay says:

    My best friend actually invited my husband and I to accompany her on her honeymoon to Portugal, Spain, and Morrocco. She and her husband had lived together for a few years prior to getting married, so it was more of a fun vacation than a honeymoon. We all had a great time. We split up at one point in Portugal b.c we wanted to go to a quiet fishing village and they wanted to go to a 24 hour party town. But it was a great trip. She and I had backpacked through Europe together when we were 20, so we knew that we had compatible traveling styles.

    We also vacationed with my husband’s best friend from college- we met him in Seattle, WA and tooled around the Pacific Northwest and crossed into Canada. The Canadian border crossing was actually really difficult- the border agents could not understand how we all knew each other since we lived in LA and our friend lived in NYC.

    We have not gone on any vacations with friends since our son was born two years ago, but then, our only vacations have been to visit family (which is the most relaxing vacation you can take with a baby.) When he is older, we will probably travel with friends again, though I imagine this would be more fun for the friends if they had kids as well.

    1. Emily says:

      That sounds like a great trip! And at least you could split temporarily as you wanted different things instead of having to compromise.

      I like road trips with friends. 🙂 Lots of time to talk!

      It would be great to vacation with friends who also have kids. When I was growing up our parents rented a huge beach house for a week together with my aunts, uncles, and cousins for several summers and that was a blast.

  14. I haven’t vacationed with friends, but lately we’ve all been talking about it. We are all in different areas with our finances so most likely it would only be a long weekend away but I’m looking forward to it.
    Jon @ Money Smart Guides recently posted..How To Make Extra Cash

    1. Emily says:

      That sounds like a good idea for the first time out with people who have different abilities to spend.

  15. We’re going to be doing a trip with a girlfriend to Peru this summer. She’s graduated and has a nice job, so it’s possible for her to do it. It should be lots of fun. Hoping to plan some trips to visit some friends this year.
    SavvyFinancialLatina recently posted..What is Your Next Career Move?

    1. Emily says:

      That sounds amazing!

  16. We took a family trip with my grandparents last month and it was so much fun (really makes me realize how important it is to get away and relax-when it fits in our buget). The last time I went on a trip with friends was spring break in college. We found a steal of a deal and had a really great trip. I’d love to do a vacation with friends now and actually mentioned that to a friend of mine a few weeks ago. What’s hard is a lot of my best friends from home and school already have kiddos, so we’d have to adjust the trip a little bit to accomodate kids (which I’d be fine with).
    KK @ Student Debt Survivor recently posted..7 Stupid Ways I (used to) Waste Money on Groceries

    1. Emily says:

      Aw, that is so sweet. I would like to vacation with family. We have with my family of origin but not yet with Kyle’s and his cousins go on some pretty great trips.

      That’s great that you area already thinking of a vacation with a friend. I think going somewhere with kids wouldn’t be too bad if there is built-in entertainment that you would all enjoy.

  17. […] @ Evolving Personal Finance writes Do You Vacation with Friends? – We have limited experience vacationing with friends but I love the […]

  18. […] Do You Vacation with Friends? was featured in the Financial Carnival for Young Adults. […]

  19. Evan says:

    I think travelling with friends can be really great since you get to enjoy a whole different side of friendships. Some people are really fantastic trip organizers that make the planning aspect that I prefer to avoid a breeze, while others might have a wonderful appreciation for food or art that enhances the experience for me more than had I gone without them.

    Of course you might learn some things you wish you hadn’t but there’s always a chance something can go wrong when you take a risk so it shouldn’t hold you back!
    Evan recently posted..Thrifting For Profit

Leave a Reply


CommentLuv badge