On October 8, 2025, we decided to go on a family vacation I was decidedly unexcited about. That entire week was supposed to be my time to attend the Fairfield Challenger tennis tournament every day with my buddy Richard. September and October are tennis paradise months in the Bay Area, with multiple tournaments and ideal weather. This year was especially exciting with the Laver Cup in town.
However, October 9 and 10 happened to be school holidays for my kids, followed by Columbus Day on October 13. My wife and children really wanted to visit San Diego to see Legoland and SeaWorld for the first time.
I, on the other hand, was perfectly happy to stay home, save ~$5,000, and enjoy watching professional tennis, one of my absolute favorite activities, for $45 or less per ticket. But as frugal tennis fanatics, we actually volunteer as ball boys to get in free and get free lunch. However, the biggest joy is having the absolute best seats in the house – right on the court!
Before having kids, I used to fly to New York City to visit my sister and watch the US Open in Flushing. I could go from 10 a.m. to 10 p.m. without missing a beat. But after becoming a parent, I could no longer justify that kind of indulgence.
My Great Dislike Of Flying
I dislike flying due to the lines, the delays, the costs, seat hogs, and sometimes unruly passengers. After taking around 200 work flights over 13 years, I’ve experienced every kind of travel misery imaginable. And if I’m being honest, I still think about death every time I board. The trauma from 9/11 never fully fades. I lived just a couple blocks away and had attended a conference at the top of the North Tower earlier that year.
If I’m going to fly, I’d rather it be to visit my parents in Honolulu, not to stand in endless amusement park lines. But I also know these trips aren’t really for me, they’re for the kids. So off we went, me internally reluctant but outwardly enthusiastic.
Oh, how I envy those parents who genuinely love Legos, roller coasters, and Disney characters. They look like they’re having the time of their lives! Life really is better when you have more interests.
So here I am – the reluctant, slightly grumpy dad – sharing my thoughts before takeoff on why you should take as many vacations as you can while you’re still working. Vacations are not only more enjoyable while you’re still in the grind, but they’re also therapeutic, helping you recharge and extend your career longevity.
Over the long term, the more vacations you take, the more money you very well make!
Why Vacations Aren’t As Great Once You Retire Early
In a previous post, I discussed how being truly FIRE is terrible for entrepreneurship. Now here are three reasons why vacations lose their magic after early retirement.
1) You Take Your Freedom for Granted
The “problem” with FIRE is having endless freedom and choices. On paper, that sounds incredible with no boss, no meetings, no deadlines. But in reality, too much freedom can start to feel like a burden. When every option is available, deciding what to do with your time can feel oddly heavy.
Every weekday after dropping my kids off at school, I have total discretion over my day. I can play tennis, write, nap, go on a hike, or do absolutely nothing. There’s nobody to tell me what to do or how to do it. Yet, when every day can feel like a vacation, the novelty eventually wears off.
After 13+ years of freedom, I don’t wake up excited by the idea of being able to do whatever I want. Autonomy has become my default setting, not a luxury. What once felt liberating now simply is. That’s the paradox of early retirement: the more freedom you have, the less you notice it.
To counteract this complacency, I’ve found it’s essential to maintain a sense of structure and challenge. That’s one reason why I’ve kept up a consistent 3–4X per week writing schedule since July 2009, even after leaving my job in 2012. Writing gives me a sense of purpose and accountability that pure leisure can’t provide.
Without some form of productive struggle, the days can blur together, and even paradise starts to lose its shine.
2) It’s Hard to Spend Money on Fun When You’re Already Happy
FIRE can make you reluctant to spend money on leisure. It’s like paying extra for tap water, you already have access to what you need.
Since retiring from a traditional day job in 2012, I’ve discovered plenty of inexpensive activities that bring me joy: playing tennis, playing pickleball, writing, hiking, and watching tennis.
So spending ~$5,000 on a trip I’m not excited about doesn’t feel great. I’d rather have used the kids’ school holidays for giving them tennis and soccer lessons (free), followed by a pool day with a big swirly slide (utilizing my underutilized sports club membership that costs $180/month). Daddy day camp to the max!
In addition, I had recently spent three weeks dealing with tenant turnover, which is always unpleasant. I had to list the property for rent again, clean up what I could for showings, evaluate prospective tenants, draft a new lease, help with onboarding, and coordinate with the departing tenants on their move-out and cleanup. After all that effort, to then spend more than half of one month's rent on a trip felt uncomfortable.
If you're the person responsible for your household finances, you can't help think about cost-benefit analysis. But it's important to think about the other members in your family and what they want to do. Since I turned 45 in 2022, I've being trying my best to spend more money.
3) Your Vacation Property Likely Won’t Be as Nice as Your Home
Another post-FIRE downer: the vacation property usually isn’t as nice as your primary residence. This pertains to most workers who vacation too.
You could spend a small fortune renting a luxury spot, but you probably won’t because that’s not how most FIRE practitioners think. We spent years saving aggressively and avoiding excess. The idea of dropping thousands to rent a house for a week, let alone a day, goes against that conditioning.
Instead, you’ll likely settle for a modest Airbnb or hotel room, cramming everyone in. Only the truly wealthy, the top 0.1%, would rent a vacation home as nice as their own. When you've got lots of active income coming in, it's much easier to spend.
If you’ve recently bought a house you love, you’ll also be more reluctant to leave it. I love our home – the Toto Washlets, the view, the space inside and out. Every day already feels like living in a luxurious vacation property. So paying money to downgrade feels off while our existing home sits empty while we're away.
Remember, the true cost of your vacation is the cost of your vacation plus the daily cost of maintaining your existing home. Here's my vacation spending guide to help you spend more responsibly while away. It is very easy to go nuts while in vacation mode.
When Vacations Are Better Post-Early Retirement
Vacations are most exciting post-FIRE if you’ve never traveled before. If your parents never took you anywhere, your job never sent you on trips, and you never studied abroad, by all means travel! You’ll finally have the freedom and means to explore.
Hopefully, you’ll visit multiple continents, immerse yourself in new cultures, and realize how fortunate we are in the U.S. The world would be a better place if more people traveled and shared meals with those from completely different backgrounds.
It’s hard to hate someone once you’ve broken bread with them.
Vacations are also better if you retire closer to the traditional age of 60-65. After a lifetime of trading time for money, you will appreciate your freedom and the time you have left more than the early retiree.
Sadly, the thrill of travel has faded for me because I grew up living abroad for 13 years. As a foreign service officer’s kid, I lived in six countries, studied abroad my junior year, traveled throughout Asia and the U.S. for work for 13 years, and checked off bucket-list sites like Angkor Wat, the Taj Mahal, the Blue Mosque, the Colosseum, and the Winter Palace.
Sure, I'd still love to visit Cairo and Petra, but they can wait until our kids get older.
The Best Vacations Are When You’re Still Working
If you’re still working toward financial independence, enjoy the incredible privilege of getting paid while on vacation. It’s the same joy as receiving paid parental leave. What wonderful work benefits that should not be taken for granted.
So take all your vacation days. Don’t hoard them out of fear you’ll lose your job or miss a promotion. The only exception is your final year before FIRE. Bank those days since your employer has to pay them out in cash when you leave.
The more you’re micromanaged and undermined at work, the more you’ll enjoy your vacations. Paid time off feels like sweet revenge for all the nonsense you put up with. But once nobody’s telling you what to do, vacations lose that contrast. You’re not escaping anything anymore.
You’ll Still Have Fun While Away
Even though vacations aren’t quite as thrilling after early retirement, I still appreciate the freedom to travel whenever I want. I’m revisiting this post after returning from LegoLand and SeaWorld, and you know what? I had a blast!
But more importantly, our kids had the time of their lives. They told their mom and me, “It was the best time ever.” That kind of feedback is truly priceless and motivating to go on more vacations for them.
As a FIRE parent, it’s also nice never having to ask for time off when your kids are on break. That’s a privilege I didn’t fully appreciate until I realized how many working parents scramble to find childcare during random school in-service days.
If you want to retire early, but are afraid kids will spoil your ideal post-work lifestyle, don't worry! Kids nowadays have so many days off from school, between local holidays, federal holidays, and in-service days, that you'll have plenty of days off to travel. We're talking 3.5 – 4.5 months off a year, which is more than enough vacation time.
Do Hard Things in Retirement To Better Appreciate Vacations
If you want to get excited about vacations again in retirement, do something challenging in retirement. It's helpful to juxtapose the hard with the easy to better appreciate the good life.
For me, that’s been writing books because writing articles is no longer hard. Each book takes about two years to complete, and when I published Millionaire Milestones: Simple Steps to Seven Figures in May 2025, I felt a tremendous sense of relief and accomplishment. It even made the USA TODAY national bestseller list. Not easy when there are only 100 spots across all genres while more than 300,000 books are traditionally published a year.
That achievement made me more motivated to vacation in Honolulu for five weeks because I felt like I deserved it. Of course, it wasn’t a completely relaxing trip. I was remodeling my parents’ in-law unit, confronting difficult childhood memories, and trying to prove my Hawaiian roots. But this time, the vacation felt more meaningful because it followed a period of hard, creative work.
Don’t assume early retirement will create a life full of thrilling vacations. You might go travel-crazy at first, but eventually the novelty fades, and you’ll start craving productivity and purpose again. Enjoy a nice balance!
Reader Questions
Fellow retirees, have you found vacations to be less exciting now that every day can feel like one? Did you travel less than you originally planned, or burn out after going too hard early on? Do you struggle to spend money on new adventures once you’ve found plenty of inexpensive ways to enjoy life at home?
And what do you think – are vacations really that fun once you no longer need an escape from work?
If You Want To Go On Permanent Vacation
If your goal is to one day live like you’re on a permanent vacation, you need to save and invest diligently while keeping close track of your finances. Freedom without financial clarity can easily turn into hidden stress.
Since 2012, I’ve used Empower’s free wealth management tools to monitor my net worth, manage cash flow, and reduce investment fees. The platform has helped me stay disciplined and organized long after leaving my day job.
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A fresh set of eyes can reveal hidden fees, inefficient allocations, or opportunities to optimize your plan. The clearer your financial picture, the greater your confidence in your path to financial independence. And confidence is what allows you to fully enjoy the freedom you’ve worked so hard to earn.
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I’ve always wondered why you don’t use a property management company for your rental properties. I’ve read several of your articles where you complain about dealing with the hassle of tenants. PMs usually charge about 10% of the monthly rent, but in my personal experience its worth every penny. Not having to deal with all the nonsense of tenants takes away so much stress
Retired about 2 years ago at 37 with spouse and 2 kids under 3. I wouldn’t say that we’ve found vacations less exciting now that we no longer work, but that the type of vacations we take now that we have kids and are no longer limited by time have changed.
We’re a lot more intentional about the type of travel we do with our kids; and don’t feel the urge to travel just because it’s a holiday (which is typically when it’s most crowded & overpriced).
In the past 2 years we’ve spent about 4-5 months each year traveling with our kids. This year we spent spring in Italy (3 months), summer in UK (1 month), a few days on an island to introduce our kids to snorkelling and planning 2 weeks in Japan in winter so that our kids get to experience snow (and Japan) for the first time. The experiences our kids have are priceless – as they get to learn in a different country (we send them to school in Italy whilst we’re there); and are exposed to different cultures and worldviews. Most folks tell me it’s pointless traveling so much when they’re young as they won’t remember, but my 5 & 2 year old still retain some Portuguese and Italian from their travels, as well as a smattering of other languages. And they still talk about things that happened and the friends they made. In fact, we still do video calls occasionally with the friends they made from their travels and they keep talking about how when they’re older, they will go visit their friends in Mexico / Miami / UK / Portugal, etc.
Also – we typically rent Airbnb’s that are as nice or nicer than our homes. I don’t see the point of going traveling if you want to skimp on the experience. Especially with a couple of toddlers, having a spacious living space that we can spend time in if the kids don’t feel like going out is important for us. We no longer spend on fancy hotels with Michelin restaurants and bars, as that’s not something toddlers (or us) enjoy. We spend on cosy comfortable kid-friendly places with green spaces, good transportation links and easy access for strollers. As the kids grow older, our needs as a family will change – I’m looking forward to taking them skiing, diving, surfing, safaris and camping across the world!
I’m not even retired and feel the same way, especially about Disney/Legoland experiences. We live in a ski town, so leaving during mud season for a warm spring break trip to Hawaii is something we look forward to every year. But for the most part, I want to ski as many days as I can in the winter. In the summer, I want to mountain bike and hike to alpine lakes. And fall? It’s crazy to leave when the leaves change and the town and mountains are so beautiful they look like a painting! Luck to work remotely.
Just wanted to share my situation. Both my wife and I have been retired for several years. We are older parents and our child just graduated from high school a little more than a year ago and is attending college. We were looking forward to the freedom of taking vacations anywhere we liked. My elderly mother moved to assisted living 2 years ago and has declining health and mental capacities. She sees doctors probably 40 or more times a year, and due to her increasing dementia symptoms, needs us to accompany her to doctor appointments to interact with the physician. We recently took a two week vacation and it was stressful. We feel obligated to be there for my mom, but also long for the freedom to travel when we want.
Retirement does allow a person to book flight departure and arrival times at more sane hrs….well at least for me, 75% of the time. Whereas vacation flights during working years, were crammed into leave and return times, that were slightly insane. To make use of every non-working hr./day before returning to work. Or less worry, when one gets sick towards end of a vacation and needs time to recovery. Like my latest Italy trip last month. One could hear alot of different passengers sniffling, coughing on return flight back home across the ocean.
Retirement also allows way more time spent with family living several thousand km. away. Or friends who live in locations which are an extra few hrs. travel time after plane lands. Or when a family member suddenly dies..like my mother.
It’s a bit easier to do executor work in retirement, not while working.
I spent 26 years in the Foreign Service and I always disliked taking vacations because I never wanted to return to work. I did not love my job and I found after every vacation I had to readapt to the work routine. Quite honestly I think the only reason I stayed was because I loved living overseas.
Now that I am retired and no longer have to deal with the travel restrictions placed on Foreign Service employees, I finally feel free and I can travel to those countries/regions that were restricted. I have taken full advantage of this and have visited more than 100 countries in the past 10 years.
I do rent a place as nice as our own more or less when on vacation. This year we will be in Vietnam. Last year in Thailand. That makes it a lot more affordable! We are travelling to Asia (from Australia) to visit my mother in law etc anyway. Then taking a vacation somewhere warmer (it’s winter in China) and much cheaper than Australia before coming home.
Long-time reader, first-time commenter here. I feel like you’re the male version of myself! Since retiring early, I’ve hit the hedonic treadmill hard. I’ve traveled and done so much that I’ve become one of those awful, entitled people who just can’t be easily entertained. My old passions simply don’t have the same sizzle. Adding insult to injury is the sheer audacity of inflation. I flat-out refuse to pay a premium for diminishing returns! Everywhere you go, it’s more expensive, yet you get more delays, more crowds, and more waiting. Case in point: a ski lift ticket at Telluride this season is $293 during spring break, and that’s with a 10% online discount! I’ve skied there enough times to qualify for tenure, and that price is officially insulting. So, I’m pivoting back to the simple pleasures: hiking, reading, playing the piano, a good cup of coffee, etc, etc.
I love short trips. Easier to pack for, less tiring, and less expensive. I also start to miss home after about 5 days, so I’ve found 3-4 days is optimal.
Glad you and the fam enjoyed Legoland and SeaWorld. They’re awesome!
The family trips I took as a kid are some of my fondest and most vivid memories. And that was even before digital cameras!
Sam,
First of all, after retirement, they are no longer called “Vacations,” it’s “Travel!” (:> We are on vacation the minute we wake up every day. We also decided to “live” were people vacation. Summers on the lake and winters at a ski area. It’s the best of both worlds. We travel in the off season (April and October), when everyone else is working/going to school. FIRE is how you afford it. It’s up to us to rock retirement!
My father in law use to call Family vacations an oxymoron, and there is some truth in that. I am retired almost 2 years and absolutely love traveling with my spouse or friends around the world. I have plenty of time to plan the trips and the itinerary.
Family vacations are hard especially when the kids get older their school/work schedules don’t all overlap they have different sleep and eating habits. Also they have might have significant others who you suddenly have to pay or heavily subsidize there trips. Enjoy the trips with the little ones now because it only gets harder!
Oh, snap! I didn’t realize family vacations would get harder, not easier. I’ll have to do more research on that.
Their significant other’s parents can pay for them if they want to come. Easy peasy!
We just got back from a week in Scottsdale and enjoyed it as usual.
Our schedule remains jam packed with travel, no change from before I retired ( barring all the kids now.)
The novelty of new locations and activities doesn’t wear off and it’s actually more exciting now to share it as new experiences with children.
While it’s obviously more complicated, no more last min jumping on a plane, it’s still enriching and dare I say, relaxing.
Good to hear it. Did you travel much when y’all were working?
Yep, it was more international travel then now until the kids are older. But travel has always been a passion so we’ll do it until we physically can’t.
100% disagree but maybe it’s because we don’t have kids and your commitments. Vacations when we were working were nice but there was always the stress of being on a fixed timeline and the dread of having to return back to the grind. Now that we are retired early there’s rarely a need to stick to a fixed schedule and no more dread. We don’t enjoy flying which is why we have owned an RV and truck camper giving us more freedom to explore places in the US, Canada, and Mexico with the comforts of our mini-home.
Good to disagree! And I’m glad you’re still enjoying your vacations in retirement. I don’t not enjoy my vacations, I simply don’t enjoy them as much because there is not much to relax from.
Did you take a lot of vacations while working? And did you travel munch for work? Because I found that the more you travel for work and the more vacations you take at work, the less fun vacations are after work.
But yes, vacationing with small children is not an easy task. And maybe that is the biggest variable regarding vacationing post retirement. Vacations with children can turn out amazing or they can be a total disappointment.
I always took more 3-4 weeks of vacation and traveled a good amount for business. We mainly use Airbnb when not in the RV because they are unique and I don’t want to stay in another drab faceless corporate hotel room. Currently in Prague on a European vacation and have a cute inexpensive studio apartment with laundry, a small kitchen, and a good bed. Like you said in another post spending some of the gains on experiences. Cheers.
Cool beans. I loved Prague! The boar sausages and beer are so good there!
Enjoy your gains!
All true, BUT a big caveat I’d add 5 years into retirement is that going “travelling” solo or with your partner is still fun to me – exploring new places, adventures, food, culture etc. Going on ‘vacation’ to a tourist place at peak time with kids…not so much.
Good to hear you are still enjoying your travels. Speaking of which, I want to have my parents get back to cruising. They loved it pre-pandemic.
The funny thing is, October isn’t peak season at LegoLand and SeaWorld. But the parks were packed. I was impressed with how much people were spending, not working, and YOLOing. Makes me confident to buy the dip!
Did you travel a lot or a little before retiring?