How To Always Feel At Home While On Vacation – Never Feel Homesick Again!

Deep Tahoe Powder

If you're like most people, you love going on vacation! After taking 5 weeks off from 2007 to 2009, and 6 weeks off in 2010 and 2011, followed by 10 weeks off in 2012, 2013, and 2014, I fancy myself as a “certified vacation expert”!  Now, I'm on permanent vacation as an early retiree.

You see, vacation is not just all about relaxing and chilling at the beach.  Not at all.  A vacation is about relaxing, while doing something productive that doesn't feel like work!

Remember during summer vacation in high school how bored you would get after a couple of months twiddling your thumbs?  By the time the third month of vacation rolled around, you were itching to just go back to school!  

I know most people felt this way, and if you didn't, you probably had a nice summer job, or family vacation abroad to kill the time and keep your mind and body active!

Vacation Truisms

1) Vacation becomes more fun when you've worked hard for an extended period of time.  If all you did was go on vacation, you would soon bore and long for something productive to do.

2) Everybody misses home after a while, no matter how fun the vacation.  To sleep in your own bed, to pet your bunny rabbit, to eat at your favorite diner… all these things start pulling at you after a certain amount of time you travel.

3) Vacations are seldom ever a bad thing for the mind.  Vacations allow us to recharge and revitalize.  However, if poorly planned, you might return more tired than energized if you aren't careful!

4) Vacations can be very bad for the body if we are not careful.  I once gained 10 pounds on one of my first two-week cruises with my parents because I ate 5 big meals a day!  There's a tendency to say, “We're on vacation, gorge and spend away!”

5) If you have enough money, you will be able to always feel at home while on vacation!

Related: Vacation Property Buying Rule To Follow

How To Always Feel At Home While On Vacation

After a couple weeks, I used to start longing for home.  The longing period is different for everyone.  I venture to guess that almost everyone misses home after the first month away.  Would you agree?

The beginner's strategy for always feeling at home while on vacation:

1) Bring pictures and things you feel most at home with eg your pillow.  When my head hits my own pillow, it makes me feel that much more comfortable.  Besides, do you know how many bed bugs and fungus are in public pillows?  A lot!  Might as well have your own bed bugs and fungus.

2) Stay connected with friends over e-mail, social media, and Skype.  It's unbelievable that just 15 years ago, we could hardly do any of this. Thank goodness for technology!

3) Know your limits, and vacation only to the point where the marginal utility is still positive.  If you know you start feeling homesick after 10 days, then take a 9 day vacation.

4) Invite all your friends to vacation with you.

The advanced samurai strategy of feeling at home while on vacation:

1) Identify your favorite spots in the whole wide world.

2) Dig deeper into where you want to live in your favorite places in the whole wide world.  It might be the place where you went on your first date, your first hike, etc.  You're looking forward to recreating the nostalgia and memories.

3) Procure property at your favorite spots in the whole wide world!

A Vacation Property Is Not A Great Investment

Waianae Hawaii Mountain RangeOther favorite places include: Rio de Janeiro, Barcelona, Paris, and Kuala Lumpur I would enjoy living.  That said, Lake Tahoe, Honolulu, and SF are the places where it makes most economical sense for me to live, play, and work.  They are all within 5 hours away from each other like a triangle, if you will.

Three of my favorite places are: Lake Tahoe, Honolulu, and San Francisco.  I have traveled to around 50 different countries, and visited over a hundred cities, and I can honestly say these three places rank right up there.

Lake Tahoe: I love to snowboard and chase storms all the time.  If you've ever seen the movie “Point Break” with Patrick Swayze, I'm kind of like Bodi, but the snow version. When a big storm hits the Lake, I'm right in the thick of it and will drop everything, especially work!  Lake Tahoe is about 3-4 hours away from San Francisco, and has world-class mountains.  Squaw Valley hosted the 1960's Olympic Games and has 11,000 foot high peaks.

During the summer, Lake Tahoe is even more beautiful with its endless hikes, mountain biking trails, and deep blue waters.  I could hike and then lay by the Lake all afternoon long!  I also enjoy playing golf about once or twice a week and Lake Tahoe sports at least 10 different golf courses in the area.

Check out My Lake Tahoe Vacation Condo if you want to rent it!

San Francisco: What can I say about San Francisco that hasn't been said before?  With a temperate climate averaging 67 degrees all year long, beautiful scenery, a booming tech industry, wine country one hour north, a thriving entreprenurial culture, tons of diversity, the arts and all the good eats one can find, San Francisco is my favorite city in all of America.

The people in San Francisco are different from the people in New York City, another marvelous city.  We are here mainly for the lifestyle, and then our jobs second.  Whereas in New York City, people are there because of their jobs first.  This is the main difference when people ask, besides the cheaper rent and better outdoor lifestyle.  I love NYC, but I love SF more.

Hawaii: If you've ever been to any island in Hawaii, you will know its beauty is hard to beat.  Winters average 78 degrees, and summers average 83 degrees.  Hawaii is consistently ranked as the happiest state in America, and for good reason!  If you work 20 hours a week, you get universal healthcare.  The beaches, parks, and hiking are all free.  Meanwhile, there is a true sense of family (Ohana) on the island, where everybody looks out for one another.

Hawaii is paradise.  And if you move to Hawaii from San Francisco, you'll find that housing is actually about 30% cheaper!  Food and gas are equally expensive since everything is imported. If you become a local (Kama'aina), golf and many other activities become extremely affordable. We're talking $20 for a round of golf folks!  Hawaii is the best place for an online entrepreneur to work as well.

Slow And Steady With No Excuses

Over the past 13 years, I have systematically purchased or involved myself in properties in my three favorite places.  Some have been very profitable, and one has not.  I didn't buy any of these properties with the intention to sell.  I've always bought property with the intention to enjoy them for as long as my life situation will allow.  Having wonderful experiences while owning property is what it's all about!

Before you buy, just make sure your finances can support the properties based on your cash flow and follow my 30/30/3 rule for home buying.  When you are retired, just think how awesome it is to have all your properties mortgage free and available for you to enjoy whenever you want.  Meanwhile, when you're not there you can collect rental income as well!

Of course, the trader in me is always open to selling if I get the right bid.  With the influx of millionaires due to the IPOs of LinkedIn, Facebook, Zynga, and so forth, I'm thinking of testing the market for my primary home, and at least learning about how the market is right now.

Every time I go to Hawaii or Lake Tahoe for vacation, I feel right at home because I am at home.  I've got my shoes, clothes, bed, golf clubs, snowboard, tennis rackets, hiking shoes, boogie board, flip-flops and everything I want waiting in the respective closets .  I could stay at each place for months on end and never feel homesick.  Every time I return to San Francisco from a trip abroad I feel like I'm on vacation as well. How many cities can you say that about?

Focus On Getting Your Finances In Order

Getting our personal finances right by saving aggressively and investing is so important if you want to solve simple problems such as feeling homesick while on vacation. With strong personal finances, you develop the optionality to do whatever you want. To gain optionality, stop messing around, work hard, and stay disciplined with your finances!  Eventually, the spoils will come.  You've got to get rid of your, “I want it, and I want it now” type of mentality because you will never get it if you continue with this train of thought.

If ever you need motivation to start saving and investing wisely, think about your next vacation and know that: 1) You'll be able to comfortably afford your vacation anywhere in the world, and 2) You'll never have to feel homesick again because you can just buy the place and call it your own!

Related: The Best Way To Travel For Free And Lower Your Taxable Income

Recommendations To Build Wealth And Save

Invest In Real Estate Wisely

If you don't have the downpayment to buy a property, don't want to deal with the hassle of managing real estate, or don't want to tie up your liquidity in physical real estate, take a look at Fundrise, one of the largest real estate crowdsourcing companies today.

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Sign up and take a look at all the residential and commercial investment opportunities around the country Fundrise has to offer. It's free to look.

Instead of buying a vacation property, you could invest with Fundrise and earn income passively. If you earn enough income, you could go on a permanent vacation like I did at age 34!

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About The Author

49 thoughts on “How To Always Feel At Home While On Vacation – Never Feel Homesick Again!”

  1. Jayadeep Purushothaman

    Love the “advanced samurai strategy” – we recently did one investment with the same strategy.

  2. Sean Hopcraft

    I think it is important to have things planned of course and have a general knowledge of what there is to do but have a day or two where you have nothing planned. Go walk around and just vegggg out…I def agree about working ahead so that you don;t dread the work you’re going to have to do when you get back. What was your favorite vacation spot?

  3. Matt @ RamblingFever Money

    I very much enjoyed reading this post. What a great topic, as just about everybody loves a great vacation.

    Our current plan to own our vacation home is that it is on wheels! Just bought a camper last summer. The only downfall with it is that we can only travel as far as we are willing to drive, which is fine for us at this point in our lives with young children. Something to be said though for laying our heads on our own pillows, having our own bathroom and shower, own food and dishes, own closets where we can store all of our own belongings.. all the while traveling around wherever we wish. Not to mention the ability to strap on our own bicycles and any other outdoor gear we plan to enjoy. We love it!

  4. We plan our vacations with a “home base”. We currently own with a timeshare company and join the exchanges when we’re looking at traveling somewhere our company doesn’t have a location. Having a home base and having our own kitchen helps tremendously (also saves on costs since we eat out 50% less). That’s our biggest strategy for not being homesick.
    We haven’t found anyplace we love so much that we would like a permanent vacation house, though- except maybe Vancouver, BC. (Though Victoria is also good.) Luckily, our timeshare has a location in the heart of downtown and it’s easy to head up for a quick visit.

    Having lived in Reno for 12 years, I like Tahoe, but if I’m picking a mountain lake, I’d rather own at Donner. (Pyramid is my favorite, but it’s a desert lake, very different.)

    Love the Bay Area (C is from the East Bay), and we often talk about what it would take to live in Half Moom Bay. Still, Seattle (where we are now) is really one of my favorite places ever. We have the joke that we’ll live anywhere between Vancouver and Vancouver.

  5. Untemplater

    I love to travel so I try to save as much as I can after I contribute to 401k and cover all my expenses for my travel fund. My favorite memories are from trips not from when I purchased material things so I really don’t shop that much. I like to be gone for about 1-2 weeks at a time as there’s always a lot to get caught up on when I get back so I don’t really like being gone longer than that. Plus it can get pretty expensive after two weeks!

  6. Anna @ Good Cents Savings

    Your descriptions make me want to pick up and head to the west coast! Love your tips for feeling at home and especially, “Vacation becomes more fun when you’ve worked hard for an extended period of time.”

    I also find it helps make a vacation more enjoyable when you arrange things so you’re not going to come back to a mountain of work when you get back to the office. This could mean working ahead for a few weeks leading up to the trip, having someone you can count on to take care of things while you’re gone, or taking a few quick trips each year so things don’t pile up too much in your absence. Nothing ruins that post-vacation relaxed vibe quicker than 800 emails and a bunch of fires to put out!

  7. My parents bought a condo in Miami, and it has become the family escape. We also have a place a winter cottage that we rent out during the winter due to its proximity to one of the best ski hills in the province. It pays for itself.

  8. My fiancée has two more years of school left, and we have decided to wait until we have two incomes coming in before we start to travel. Until then we are satisfying our cravings with planning our trips of the future, and trying to remember the tips in articles like this one (that pillow thing is definitely going to stick with me). It also helps that we get to spend all summer at her cabin on the lake. I have been all over North America, and I can honestly say I haven’t seen a more pristine place.

  9. Proximity is o so important. I love that I can get on a plane in Calgary, go to Vancouver in an hour and feel thousands of miles away. I’d like to acquire property in White Fish Montana – a short drive from Calgary, it has some of the best boarding I’ve ever experienced. If you’ve never been Sam, it is highly recommended. It is a relatively small mountain in terms of chairlifts and run length but the snow is incredible.

    1. I love Montana! Such good memories of horseback riding and fishing there when I was a kid. I just don’t have any roots there. I’ll check out White Fish next time. thx for the rec

  10. After College Money

    You make Hawaii, Lake Tahoe, and San Francisco sound like beautiful places. I’m still young, so I can’t afford extravagant vacations, but I am happy with going to the Jersey Shore or OBX every summer.

    I get jealous every time you write about the snowboarding in Lake Tahoe. I would love to go out west and snowboard there. I could only imagine the fun I would have if I owned a house out there; One can only dream. :) That is why I am trying to get my finances in order, so I can enjoy vacations like that later in life!

    1. Sounds like a plan man! When you have a target to achieve, it makes getting one’s personal finances in order that much more meaningful.

      Definitely try and make it out to one of the three places at least once. They aren’t that expensive if you share a room with friends. I think you’ll love it!

  11. Julie @ Freedom 48

    That’s so true in that vacations are more enjoyable after you’ve done a lot of hard work. It’s so much more rewarding and rejuvinating! My husband, a self-confessed workaholic even admits that regular vacations are crucial for staying sane!

  12. Sam,

    I have coined a new term, “The Law of delayed Gratification.” Have you noticed that if you can control your senses to spend money on anything after the craze fades, you can save ton of money. 3D TV is the latest example. Wait for few years, and you’ll buy it at 1/3 of someone who satisfied his/her instant gratification daemon. Having a home away from home also need careful planning, hard work, persistence and staunch belief in delayed gratification.

  13. I love staying in vacation rentals as opposed to hotels. They are so much cheaper and they have full kitchens, washer/dryer, etc. The more money you spend/people you have, the nicer places you can get.

    I have stayed in a great house(12 people) in Tahoe the past two NYE’s with all the amenities for 250/night! I’m also heading to Hawaii at the end of April and staying in a condo style hotel, ocean front room for half the price of the Hyatt down the road. Try out if you’re interested!

  14. My best vacation is exploring another country and culture. I don’t get home sick while I am vacationing because I know I am coming home soon.

  15. My best vacations were with friends. We go skiing together, travel in Europe or rent a beach house together. It created that home away from home. I particularly like to ski because of the physical activity. When you are doing something physical, it helps push everything out of your mind. The result is a great relaxing vacation.

    I had a chance to buy a condo in Maui in the late 70s for peanuts. Do I have any regrets? No, their economy has had many ups and downs over the years. I used to own a condo with friends in Mamouth. We made a profit, but not enough to say it was worthwhile. Property in resorts or recreational areas can be ify at best because you are at the mercy of the economies and other factors. Local real estate is best.

      1. True, but you still need deep pockets to get through some of the difficult times. There was a time, I think in the 80s when tourism dropped off for a number of years. This is one of the reasons I would avoid properties in tourist or recreational areas because there are factors economic or other factors that can break you. 20/20 hindsight is always clearer!

  16. I can’t say I’ve ever been homesick although I’ve been more than ready to go home. I think that has more to do with the fact that all my vacations are spent visiting my family since we don’t live close together any more. Each vacation reminds me why I moved away lol. I haven’t ever taken a vacation where I went somewhere where I didn’t have family. Might be time to work on that.

      1. Well right now I can’t afford multiple vacations, and I will miss my family too much if I don’t see them at least once a year. I think the next plan is to stay with friends instead of family so I can have more “me time”. Then I’m going to start plotting for a cruise or Hawaii when I can afford more than one vacation. Maybe I should just relocate to the tropics so everyone will come to me.

        1. I live in KC where it was 70 yesterday and snowing like crazy today. It’s not exactly a prime tourist destination, although there are tons of golf courses. I really need to relocate to a tropical beach.

        2. I usually want to move during winter. The rest of the year is fine. I’m not in a financial position to move right now either, but I’m working on it. My long term goal right now is financial independence so that I could work from hawaii year round. I think I could happily work from a hammock on the beach.

  17. As far as vacation being bad for the body, I am happy to say most of mine is spent surfing. Surfers always come back from a vacation a little healthier (assuming they don’t drink and party the whole time too)

  18. Lisa @ Cents To Save

    The older I get, the more homesick I get. Like Michelle, I miss my dogs too. Maybe I should stick to shorter stays :)

  19. I don’t usually find homesickness to be a problem on vacations. I guess that means my vacations just aren’t long enough!

    I think the best thing for me is to bring the people I like spending the most time with along with me on vacations. It’s more fun that way, and I don’t have to miss them!

    Interesting on choosing Hawaii as the best place for online entrepreneurs. I haven’t seen anyone make that claim before.

    1. Yep, that’s right! Go on longer vacations to the point where you start feeling homesick, then revisit this post for the solution!

      Hawaii is the shiznits for a global online entrepreneur as I’ve detailed out in the post. No brainer imo!

  20. How come Detroit wasn’t on your list of favorite places? Did you not want to list 4? :)

    I am not homesick on vacation anymore. We make sure we stay in condos and such so that the 5 of us are not crammed and uncomfortable. As a matter of fact, when we vacationed in Florida this past December, I dreaded coming home like never before. I suppose that should be telling me something too…

    1. You’re right, I forgot Detroit! Sorry about that. For some reason, I never hear about people choosing Detroit as a vacation destination though. Don’t know why.

      If you’ve got 4 of your “belongings” (your family) with you on vacation, then I can see how it will be hard to miss home!

  21. I also go away for 5-6 weeks every year – ussually in South East Asia or India. I use email and also skype people and thus I really never get homesick.

    I love meeting people and really enjoy visiting temples and the like. If you do not like visiting religious sites – I would definately recommend NOT visiting South East Asia and most importantly recommend NOT visiting Southern India. The temples of Southern India are wonderful but for the most part are the only sites of southern india.

    I do gain weight on vacation – I gained about 8 pounds on this years trip to Indonesia, Malaysia and Singapore. I got back on New Years day and am happy to say I dropped the 8 pounds and 2 or 3 more and am now back to were I want to be. Every morning on vacation, while my wife is sleeping, I go for a walk of an hour or more – I still gain weight but this helps keep the number of pounds gained down.

    Also we love to eat when we travel. We eat at the most expensive restaurants and also eat at the least expensive restaurants. We were in India and my wife can read Hindi – thus we went into a restaurant were the sign was written in Hindi – I did not even know it was a restaurant. The food and the people that worked there were WONDERFUL! We ended up eating there 4 times over the next 3 days. It was all you can eat and we had 2 cups of chai each with our meals – the total cost per meal was 66 ruppees or about $2.00!!!!!! The meal was 25 ruppees and each cup of chai 4 ruppees – what great memories I have of this restaurant and our time spent there. Great food and great conversation with the employees!!!!!

  22. I would love to buy a lake house about an hour or so away from my house, but that is a purchase that seems extremely hard to justify. I think I would feel terrible paying for it each month, and almost feel obligated at times to go and use it. On the other hand, having my own getaway to use during weekends, long holiday weekends, and basically whenever I wanted would be awesome, and something I could see myself really enjoying.

    I doubt the vacation property is in my near future, but maybe out in the 5-7 year timeframe. Might be easier to justify once I have kids and they are of the age where they are also able to enjoy the property.

    As it is right now, I enjoy going different places on vacation, so I don’t want to be tied down to one property. But with a couple younger kids, I could see the benefit of having a property. Would probably become cheaper at that point than flying to other locations, plus they could keep their things at the property and it wouldn’t be much of a hassle at all, just drive there and enjoy.

    Might be time to set the goal and start saving.

    1. Definitely don’t buy a vacay property if you don’t absolutely love the area and the property, and if you have to stretch your cash flow. That would be badly ironic to have a vacation property cause you stress!

  23. Money Infant

    I never had a problem with homesickness when vacationing before. 2, 3 4 weeks no problem. It wasn’t until I moved halfway around the world that a type of homesickness struck and that took about 6 weeks. It passed with time as I became more acclimated to my new home and created friends, favorite places and a routine. And now that I’ve mastered the move I am kind of thinking that the phrase “Home is where you hang your hat” may be truer than we realize. I’ll let you know when we make our next big move :)

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