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Cash Flowing a Family Vacation


I’ve been spending a lot of time this past month thinking about the future. And I’ve been working on plans for 2020 both financial and otherwise. But I’ve also been thinking beyond that…to Princess 2021 high school graduation and what that will mean overall.

And I’ve decided that I want to plan a family vacation for that summer, the summer of 2021. And by vacation, I do not mean a trip to my parents. I mean a trip that will create a lifetime of memories. I’ve always been someone that has loved the idea of a vacation. Just the feeling of being able to relax on the beach under the sun, or to explore an unknown city has always provided a sense of excitement to me. My only wish is that I could hire a private jet, with the help of a company like Jettly, to make the trip even better. This is something that I want to experience and I know it will come with time.

However, for now, my idea of a real vacation is a cruise. That’s what I’ve been thinking about doing, and it will be a celebration of the kids who live at home all graduating and saying goodbye to that phase of my life.

I figure if I plan it now, I can 1) cash flow it over the next year and half and 2) all the kids can plan accordingly. The twins will have to take off work and will most likely want their girlfriends to come. We will all have to get passports. (Sea Cadet has his, but History Buff has never had one and the littles and I will need to renew ours.)

I realize that chances of me being completely debt free at that point are slim to none with the car debt and student loan. But I think it would be worth it. Before Princess heads to college and who knows when we will all be together again.

Searching for a Cruise

So I figure the first step is to come up with a budget for the trip and then a monthly savings goal, right? We haven’t really had a real vacation in forever and the trips we have taken have been mostly bootstrapped. But this one, I want to be able to relax a bit.

I laid in bed the other night a did a random cruise search…and found one in February for $389, 8 nights. Crazy! I can’t wait until I am in a financial place to be able to just get up and go like that. Definitely a life after kid goal! But I don’t think we will find those kind of prices in the summer…

Any cruising experts here that want to give me tips for getting a good deal on summer cruises? Any other thoughts about good family vacations? (And yes, I am doing this now, so I can incorporate it into my 2020 budget starting immediately.)


  • Reply Cwaltz |

    Do you realize how all over the place you are in regards to finances? You still have not even offered numbers on cash flowing Princess’ senior year, your retirement and you are now planning on adding another cash flow item and asking for help in figuring out how to pay for it? We have no idea what your emergency fund\ income replacement is? Our only knowledge is you are committing $100 a month +10%. As far as I can tell you really have not done much in terms of number crunching here so that anyone could advise you in any helpful way other than to tell us you are doing well enough at the moment to pay more than your IBR on the student loan ($400 a month)and that you are committing a hefty chunk of change each month to pay off A $20,000 car in 2 years.

  • Reply anonymous |

    Cruises are a lot more expensive than just the advertised cost. There’s port fees and taxes (usually between $100-$200/person), extra costs for soda and alcohol, shore excursion costs, transportation to and from wherever the cruise leaves from (if you drive you’ll have to pay a daily fee to park your car there), and since you’re self employed you’ll have to consider the lost income for the days you’re gone.

  • Reply Jen |

    In addition to what others have said……you should not be paying for the boys to bring their girlfriends. You are talking about something that’s 12+ months in advance. You have no idea if the boys will still be with their girlfriends. If they feel that strongly about bringing them, they, as couples, should finance that portion.

    • Reply Jen |

      And I’m not saying that to be mean to the twins, or imply that they will break up. There’s a lot of time between now and then, anything could happen. They could get engaged, they could break up, or anything in between. You could end up paying for these girls to go, and then suddenly they’re not going to go. If they’re welcome, they’re welcome, but they (the girlfriends and/or twins) should assume that risk.

        • Reply Jen |

          She shouldn’t, but I’ve learned Hopes gonna do whatever the hell Hope wants to do. If something at least makes her think about many mitigating the damage…:

          • Hope |

            That is certainly the nice thing about personal finances…it’s personal and I am allowed to make my own decisions.

  • Reply Bluezette |

    Don’t forget that Princess will likely have mandatory college orientation obligations that summer that may complicate scheduling. That, plus her summer job to cover college expenses, will not leave her much free time.

    • Reply Hope |

      I don’t think a week long vacation will hamper her college plans or summer job. I believe most children take some sort of break.

  • Reply Angie |

    I don’t think this is a great idea. I agree that any girlfriends should pay for themselves or have their boyfriends pay for them. Also, don’t you have animals? Someone will have to care for them. Cruises are cheap until all the additional fees add up. I agree with the other posters. You are all over the place and I understand your want to give everything to your family but you don’t even have a good base for retirement yet.

    But as much as we squawk you’re going to do it anyway.

    • Reply Lizzy |

      A cruise sounds great! You might look at Vacationstogo.com and search their 90 day ticker. They have deeply discounted cruises disembarking in 90 days or less.

      • Reply Hope |

        Now this is the type of resource I need! I may not can use it yet…but someday. Thanks for sharing!

  • Reply SMS |

    I get that you want to have a special vacation with your children (and maybe girlfriends), but I cannot imagine how you can cashflow it. You are making no discernible progress on the student loan, you have a large car loan and you are facing possible large expenses for Princess’ last high school year. You have no retirement funds…Princess will have college-related costs, even if she gets scholarships or borrows money.
    How about if you save up to take all the kids out for a special dinner or something similar? Your kids know that you love them. You don’t need to give them an extravagant gift to prove it.

  • Reply Jenna |

    I struggle with what to say that might have the opportunity to be constructive. Hope, at this point, it is as though you have lived with debit so long that there is disbelief that you will ever get out of it – so adding a new car, or school fees, or a family cruise [whatever the current justification] seems reasonable.
    It is not reasonable. Total all the expenses that this trip would cost – all of them – you’ll go on excursions, buy souvenirs, eat beyond the designated restaurants, have a drink or two – and then figure out how many months worth of payments that will tally. How much interest those payments will generate by not being paid. How much longer you will be in debit because of it.

  • Reply Jennifer |

    Every penny you spend on that cruise is a penny that could have paid off debt that has interest building everyday. I’ll say it….ridiculous….absolutely ridiculous. Put that cruise amount on the backside of your debt and see how much interest has built up by the time you get to that last payment. Also please remember that every child will loose wages while on vacation. That ups the amount the vacation costs.
    Go on a cruise with your children when they are adults who can pay their own way and perhaps buy your ticket. What your kids will be most grateful for down the line is a mom who does not burden them financially. Pay off your debt and prepare for retirement.

  • Reply Laura |

    If you had a solid plan to save for this, while paying off your debt, I would say research frugal options and keep planning. But let’s face it, you won’t consistently save for this. You may put aside money for a few months then stop saving for it when the next big financial plan comes along and come 2021 the trip will go on a credit card. Right now your best bet is to put all extra money towards debt payment and retirement savings. The logistics get harder as kids get older but you can have a family vacation with adult children after you are in a more secure financial place

  • Reply Jillian |

    I think you should do it! Personal finance is personal and your last baby graduates only once. Other people commenting seem to have lost track of the fact that this is YOUR life and while you’re gracious to share it with us you don’t actually need our blessing.

    • Reply Angie |

      Except Princess isn’t the baby, Gymnast is. So this crave for a big shindig may happen again when Gymnast is prepared to graduate.

      I agree with your desire to for having a big family get together while everyone is starting to spread their wings, but don’t think a cruise is warranted at this time. From the pictures you’ve shared you have a ton of fun as a family no matter what you do! Why not rent a cabin on a lake or an airbnb in a new place for a get together weekend. Splurge on junk food, make everyone’s family favorite meals, stay in, play games, explore a new place together on the cheap. This would be much cheaper than a cruise and just as memorable. What you really crave is TIME together with all your family. In a few years when everyone is out of college and working you can have you dream family cruise.

    • Reply Cwaltz |

      I don’t want to be mean spirited but to put this in perspective, Hope started her debt blogging journey in March 2014. Her student loan debt at the time was $31,687. It had a prospective pay off date of September 2017. Flash forward to 5 and a half years….. Hope’s student loan balance is $33,779. She not only did not pay it off 2 years ago but in 5 years she has managed to add interest to the loan because she wants all the things all the time for her family. She needs to learn to tell her own inner toddler “no.” She bought a beautiful car and she’s sending her daughter to private school. That should be enough of extravagant dream shopping for now. It’s time she set some milestones for payoff and then start meeting them. Maybe after the car is paid off and she has taken a chunk off the student loan she can reward herself with a cruise. As of November she had over $ 50,000 in debt(and yes I acknowledge she started with $78000 in debt) and is working with a budget that is missing significant line items(princess school, retirement, additional payments to IBR for loan) in my opinion this is not the time to add one more thing to the budget and potentially draw out her debt payoff.

  • Reply Concerned |

    I can’t help but feel like this is one more way to spoil your daughter. It seems like you mark every accomplishment of hers with some kind of expensive reward (NEW car, expensive school, etc.) while your boys got none of it. Now her graduation is being rewarded with an expensive family trip? I’d think over this one long and hard. As others have said, cruises are expensive once you factor in all the costs and this may not be the best timing. After all, your boys have been out of high school for awhile now and you seem to think they can still go, so there is no reason you couldn’t wait a few more years when your daughter is also older and still enjoy a family trip.

    • Reply Hope |

      Actually, History Buff just graduated from high school this month, and Sea Cadet a year ago…

  • Reply Jennifer |

    While blogging here we have seen her loose her home, sell off a car, loose her pets, loose her apartment, skip out on her lease, loose jobs, live in a camper, buy universal studio year passes, buy new computers for her kids, have her children participate in very expensive sports training, have her children send her kids to summer camp, send a child to private school, loose major clients, receive government assistance for food and health care, buys a very expensive car for a daughter who doesn’t drive yet, has significant student loan debt, has pretty much zero retirement and savings and I’m guessing here, I think she is in her forties and is a single mom….sure on this blood called Blogging Away Debt my recommendation would be go on a cruise

  • Reply Shanna |

    I think the cruise should be a reward for paying off ALL your debt. Senior year in HS is expensive, as is college. Even applications will cost you hundreds of dollars. If Princess is going somewhere far you have travel expenses for orientation, drop off, holidays etc. what about waiting until G is out if HS and by your own account you should be close to payoff then. Additionally, in regard to the car, many schools do not allow freshman to bring a car to college. Will your daughter be expected to make payments on the car when she will not be able to have it at college? There are so many variables in your life right now planning to spend what will be a minimum of $10-$15,000 on a trip in two years is not the wisest decision. I totally get wanting to save for something fun, so perhaps you set up a travel account and put a little in at each paycheck so it’s at least moving in the right direction and you can heavily funded once you have taken care of you’re more pressing financial responsibilities.

    • Reply Hope |

      I can see how this would be an excellent idea…
      However, as an adult with 4 adults siblings, I definitely recognize how hard life gets to get away from as we get older. We begin to have financial obligations, family obligations, work obligations…I suppose that is why the timing is more important to me. The twins will most likely still be in school (not sure what Sea Cadet is planning to do when he returns from Americorps but he is exploring returning to school,) and Princess will be heading to a 4 year school.
      That’s why I think this would be a good time. But from the financial side…maybe not. Still considering and certainly appreciate all the constructive feedback.

  • Reply Meghan1227 |

    Hope – I have read your journey on this blog from the beginning. I have admired your strength, I have prayed for you in your difficult times, and I have shaken my head at decisions made.

    I am hesitant to agree that a family vacation planned for (even with this much advance notice) is still a good idea. In the initial post it sounded like you were planning to pay for yourself and the four kids, and that is not a financial choice you should get behind in your current financial position. If you are anticipating the twins paying the bulk of their share, you run the risk of them deciding your family vacation is not where they would like to spend their money – they may have their own financial priorities.

    I also think this vacation idea is drawn from some underlying fears that a vacation won’t fix. The transition from one phase of life to another can be difficult. Going from being the sole financial support and sole educator to four children to them leaving the nest must be excruciating!

    As you move toward this new phase of life, I would encourage you to instead consider the options that financial freedom would give you. In this case, I would label financial freedom as being fully debt free, having a 12-month emergency fund, and making good strides on a retirement fund.

    Financial freedom could mean (I pull these from examples I saw among family members that I hope will speak to you):
    -If your son decides to settle down in California, you could spend a month visiting every winter.
    -When your daughter calls in the middle of the night and says ‘the baby is coming’ you could drop everything (put all your clients on hold) to go be with her and help her through those first weeks.
    -When your kids are on their own financial feet, if something causes them to stumble, they will know that you are there as the emergency net to help them put food on their table for a few weeks while they right the ship.

    If we do our jobs as best we can as parents, then kids are going to grow up, and move out, and create their own lives. As much as it hurts to let go, to try to hold onto those fully together years prevents kids from doing what they are supposed to do.

    As your kids are getting ready to fly the nest, it is time to turn the focus on taking care of you.

    CWaltz pointed out that in five years of blogging here, your student loan balance has only grown! What I would really like to see in 2020 is for you to put this as a priority over EVERYTHING else. I know you will think that impossible, but it is really time. There are times when your budget has an excess of $1000 in a month – make a principle payment. When you write the post about how you finally chased down the balance due from the non-paying client, end it with telling us you put the money toward the principle on your student loan. As your children are heading off to college, let them see the agony of student loans. A last, and important, lesson you could teach them is the importance of living within your means and fighting like hell to get rid of debt when it does happen.

    • Reply Hope |


      Thank you so much for your post. I appreciate the place it came from and the logic behind it.

      It is so hard to share all the factors I consider when it comes to financial decisions on this blog, but you hit the nail on the head regarding my struggle within myself as my kids have left the nest so unexpectedly and early…I just thought I had more time. And I recognize that as I think of a family vacation. At this point, that is just a savings goal, not a plan.

      And the twins participation or not, would of course, be their choice. But I guess our family dynamic is very different from others, at least those here on BAD. The twins are excited about the idea experiencing more of the world, even helping to pay for it…there are factors from their childhoold and such that come into play here that don’t affect my younger too.

      I guess I’m just rambling at this point. But thank you. I do hear you, and I agree. I am definitely targeting my student loans this year versus anything else. My “safe” goal that I’ve set it to pay 1/3 of it off. And I will post why I have chosen that path as well.

  • Reply Christy |

    We have also used vacationtogo.com for some great all-inclusive vacation experiences at a very low price. We paid right at $2,000 for three of us for a week at a resort in Mexico twice, and the Dominican Republic once, including airfare out of Atlanta. If you can find any way to go at a time other than summer, spring break, or Christmas, the costs are MUCH less, but that is hard to do with kids in high school/college.

    For a cruise, passports are not required, however if something were to happen that you needed to fly home (illness or accident, or if you miss the ship), you would have to get one expedited from the US embassy of the country you are in… which takes time and extra money. I wouldn’t cruise without them, but many do it all the time without any problems. At most ports, you can just walk off the ship and explore or find a beach for little or no cost. It is very easy to not spend any extra onboard, join the cruise groups on Facebook for all kinds of tips on how to save/what to pack. Be aware that often the super-cheap short getaways are ‘party cruises’, filled with passengers who are drinking heavily.

    The time that the kids will want to participate in a family vacation is limited, and we aren’t guaranteed tomorrow. If you can save and pay cash, or mostly cash even, the rewards of taking the vacation can far outweigh the costs.

    • Reply Hope |

      Thank you for the reference, I will definitely check it out.
      A real vacation is a ways away for us, but I have definitely put getting everyone’s passports on my to do list for this year.

So, what do you think ?