09 March 2016

How I Plan Vacations

I come from a family that took regular vacations--probably at least once a year--when I was growing up, and I think that definitely influenced my attitude towards vacations as an adult. I don't consider myself much of a traveler, and I don't think travel and seeing the world makes for an especially awesome life goal, but I do look forward to a good vacation periodically. Once or twice a year, with maybe an extra weekend or two of fun, feels like a comfortable ratio to me.

(Hawaii 2014)

Angel did not take many vacations growing up, and doesn't tend to see them as a normal part of life. Hence, in our family, I tend to be the one who originates vacation destination ideas, convinces him that it'll be fun, and then plans everything. One notable exception is our Hawaii layover vacation, which was totally Angel's idea. I still planned it and worked out all the details, but it was his idea to add in a cool destination while we were en route to China in order to get a vacation without additional flight costs. It was an awesome idea.

When it comes to planning vacations, there's a huge range of strategies, from ultra-spur-of-the-moment vacationers to the years-in-advance planners. My parents tends to err on the side of being spur of the moment kinda folks. Usually, my mom is the person with the ideas and my dad is the one who does the booking and research and logistics. When I was 5, it was almost Christmas and Mom happened to have a dream one night that our family went on vacation to Florida. She asked Dad in the morning if they could go to Florida for Christmas--he initially said no, but by afternoon had changed his mind, decided it could work, and if I'm not mistaken, we left on the road trip (from Michigan) the next morning. We spent Christmas in Florida that year.

(Epcot, 2014) 

More recently, they decided to take a family trip to Singapore less than a week before they left (see posts from our trip with them over New Years). Also, in 2014, they spontaneously tacked on two extra nights to our Florida trip to visit Weeki Wachee Springs State Park to see the mermaids--all because Mom had fond memories of seeing the mermaids during a childhood vacation.

I don't have experience with it in real life, but I've heard in passing other people mentioning being in the beginning stages of planning trips that will take place in 2017 or 2018. I feel like I hardly even know what country I'll be living in in a few years, let alone what vacations I'll be wanting to take by then, so that's hard for me to imagine doing. I tend to always be setting aside savings for some trip, because I know we'll be going somewhere someday, but I rarely know where we'll go a long time in advance

(ShenZhen, China, 2014)

For me, a few months ahead of time is my comfort zone for planning a significant trip. A weekend or local getaway is fine for me to do last-minute, but for something bigger, I like some time ahead--it helps me figure out how to get the best deals and understand how to get around and what I want to see. That's where we're at right now, because last week, we committed and booked a trip to Tokyo to celebrate our birthdays this summer. It's a milestone for me (the freakishly mature-sounding 25), and Angel's 32nd, which we'll just have to claim is a milestone too (problems of being almost exactly 7 years apart instead of 5 years). We found a good flight deal and some affordable Airbnb rooms (we're talking $35-50 a night--in Tokyo!), so we're doing it!

Here's my vacation planning process:

Step 1: The Dreaming

I first heard of Tokyo Disney Resort around the time we moved to China. I went to DisneyWorld in 2014 and absolutely loved the experience, so having another Disney park relatively close by made it seem like we ought to visit someday (we did visit Hong Kong Disneyland for our 4th anniversary, but I knew Tokyo would have to be a bigger undertaking than a quick Saturday trip). 2015 was a big and busy year, with an expensive move and a big job change and getting new visas, but I thought we might be able to work the trip in sometime into the next couple of years.

Step 2: Sudden Revelation

I started looking at Fall 2016, but our work/responsibilities schedule for fall is already filling up so much that there was only one week in October we could conceivably get away for a vacation. However, according to my research, Tokyo Disney Resort is especially busy the last week of October, and has lots of special Halloween entertainment, and I don't even like Halloween, so the timing seemed like it wouldn't work. I put all thoughts of the trip aside. Sometime later, I was thinking that I wanted to do something special for my 25th birthday, and suddenly the idea clicked that maybe a Tokyo trip would work then. I did some quick checking--School will be out for the last day or two of our trip, but that shouldn't be the biggest deal. Plane tickets aren't astronomical right now. No can't-miss family or work responsibilities scheduled. Maybe this could work. I approach Angel with the idea.

Step 3: Strategic Booking

Angel agreed that it sounded like a great idea. We finalized the days off with his work, bought plane tickets first, and then made AirBnb reservations (p.s. hit me up if you want to sign up for Airbnb. You can get $20 off your first stay if you use my referral link, and I'll also get $20 off my next stay, which would be great, because we've used Airbnb a lot, and unlike with hotels, $20 actually goes pretty far!). I always say I don't believe anything until the plane tickets are bought. Now is when I give myself license to start believing it'll happen. I handle everything except the actual bookings, that we do together, because we figure it's best to have two sets of eyes so that we don't make any mistakes and choose the wrong date or destination of something of that sort.

Step 4: Making the Itinerary and Budget

We'll have a few days to see the city of Tokyo and a few days to see Tokyo Disney Resort. The trip is pretty much evenly split, with one extra day on the Tokyo side. Yes, there's lots of things to see outside of Tokyo, but with only 7 days on a first trip to the country, I didn't want to put too much on our plate, or overwhelm us with figuring out public transportation to other parts of the country.

Pinterest and Google have been helpful friends as I jot down notes of things to see and do. It's worth noting that other than ticket fees for places I really want to see, I tend to be largely a budget traveler (hence the Airbnb stays rather than hotels!), so most of the free sightseeing is what appeals to me. I don't want to do too much train travel in one day, so I'm hoping to put us in one area with a bunch of things to see and do each day, so that we don't spend tons of time on the metro (I spent lots of time on crowded metros in's a little boring). I don't plan strict itineraries, but I've got a word document with a suggested area to visit each day and possible places to see in that area, along with opening hours, ticket prices, and information for the metro lines and stops so that we will hopefully avoid getting lost. The theme park days are easy because we'll just spend the entire day inside the park. I've read lots of warnings that July is hot and humid, but I'll admit I'm not very scared of those warnings, because I'm sure it won't be as hot or as humid as Malaysia (which has been 95 degrees or hotter throughout the dry season this year). When things get closer I'll start thinking about how to strategically pack. As you know, we're cheapskates, which means that we're doing this one-week trip with only carry-ons...I figured the extra cost of a check-in was especially not worth it when I thought about having to lug it all over the place on public transportation...

I am admittedly intimidated by the prospect of visiting a country where I don't speak the language (Since most of my travels have been in the USA, China, Hong Kong, or Malaysia, I've never experienced much of that before), so I'm brushing up on my 1 year of college Japanese classes (uhhh...from 7 years ago...) by relearning hiragana and katakana and some generally practical Japanese. I found that being able to read characters in China was immensely helpful for feeling comfortable navigating, and so I expect that it will also be helpful and provide extra peace of mind during our time in China. Thanks to that previous class, it's all vaguely familiar.

What's your style when it comes to vacations? Are they a regular part of life for you, or do you prefer sticking closer to home? Do you plan everything down to the last detail? Are you up for a spur of the moment trip or are you one of those mysterious beings that can plan vacations years in advance? In your family, do you do all the dreaming and planning, or do you leave that up to someone else and just tag along for the adventure?


  1. I would like to plan a bigger upcoming trip, thanks for the tips!

  2. I have a very similar style of vacation planning. We rarely plan so far in advance just because of life. It's too hard to know what's going to happen so far down the road.

    Weekend trips can be spur of the moment but having a dog also means we need to plan a bit more so she can be taken somewhere.

    When we plan big trips and have made itineraries we have always been very pleased with them since we often manage to see and do more than we would otherwise.

    That said, we both missed our normal trip to a resort this year which was a drag. One sick dog and a car accident was all it took to ensure we didn't have enough money to go away this year. Lucky for us the winter was unusually mild so I didn't mind so much.


  3. Strategic booking can be so huge!! It can save you tons, or cost so much more, depending on how it's done! I still haven't tried Airbnb, but am looking forward to giving it a try sometime! Thanks for linking up!

  4. This sounds like it'll be such a fun trip!! I would love to go to Japan someday-over the past few years, I've had a handful of friends here from the States visit Japan, and it sounds like such a neat place. My family didn't really do vacations much when I was growing up; there were a couple times when we'd do a weekend or partial-week vacation to an out-of-state place, but most of our "vacations" would be day trips to theme parks or other places. In the past couple years of marriage, our vacations have typically involved visiting relatives in our hometowns, so we haven't really had a "destination" vacation since we studied in Europe. When it comes to planning, I'm definitely the dreamer, and I enjoy searching the internet and books for all sorts of fun, less-famous attractions in an area to do. Then, I bring all of my ideas to Jacob, and he works with me in planning out the logistics of travelling.

  5. I love dreaming and planning about vacations, as soon as we get home from one I like to plan the next one! the budget is my least favorite part ;)

  6. How fun! There are so many places I want to visit and travel to. Sounds like your mom and dad are quite spontaneous when it comes to trips. :)

  7. I love this process! I definitely do a lot of big-picture dreaming and research before narrowing in on the actual destination(s), timing and budget. I love travel because you not only learn during the trip, but also beforehand in the planning!

  8. Sometimes the process is almost as exciting as the vacation itself (almost)! I do a TON of research before we go somewhere, but I like to plan a few activities (not too many) and then spend the rest of the time getting immersed in where we are and letting things happen as they will.

  9. How I plan vacations - I book tickets and figure it out when I get there LOL!!!

  10. Very much a planner- for our next trip, I've even booked 2 tours before we go!! That's a bit over the top but they're both out of town so I didn't know how hard it would be to book, and we only have 2 days in each city to do them, so I didn't want to miss out...probably OTT

  11. I love this! My husband and I DO make a lot of travel goals, but it has just been a priority for a while. :) We tend to try to do a mix of trips. My family now lives across the country, so visiting them has to be built in. We sometimes take a family trip with his family. Then there are short or road trips just the two of us, and if we are lucky bigger trips just the two of us! :) We seriously make the most of our time and travel more than most people would even want to. Now, I have no desire to drive through 9 states to "see them all" in 2 days or anything like that... we just tend to take at least 4 trips of some size each year. :) When we plan we do a mix of research; from travel books, pinterest and blogs, and then from folks who live there or have visited before. We also use trip advisor sometimes. We love it when we are able to combo a trip with visiting friends and family. It makes things cheaper, but we also get to see people we don't get to see so often! :) Tokyo for your birthdays sounds great! Two of our friends did a trip in Japan recently and they got engaged on a rooftop in the city! So cool! Happy planning & travels! :) XO - Alexandra

    Simply Alexandra: My Favorite Things

  12. We are big itinerary people for vacations. I wish I could be a fly by the seat of my pants kind of person but I cant

  13. Great tips. I love the idea of using Pinterest for travel. I never would have thought to do that. We went to Glacier National Park with no plans or reservations once. I thought I'd be super stressed without an itinerary but it was really liberating.

  14. I like how you plan your vacations! When we plan our vacations, we preplan everything besides meals and we're pretty much ready to go!

  15. We went to Tokyo Disneyland when I was a teenager and had a great time! One of my favorite memories was when my sister and I did the Haunted House and everyone in there with us was TERRIFIED because the spooky voice was apparently saying scary things. But we didn't understand any of it so we actually found it pretty comical. ;) It was a fun trip, though!

    We definitely travel a lot. Some of our trips are planned out a couple of years in advance (our first big Italy trip was planned 2 years before) and by "planned" I just mean that we picked the place and the approximate date. We don't actually start planning (sites to see, places to eat, where to stay) until about 6 months out. But most of our trips are planned within a few months. Cruises especially tend to be somewhat spur of the moment decisions for us. We definitely do have a very specific itinerary (usually thanks to Rick Steves if we're traveling overseas or TripAdvisor and Urbanspoon if we're staying Stateside), but we're flexible and occasionally decide to re-order things once we arrive at the destination. But we're definitely planners so we like to be sure we won't miss anything. :)

    Currently our big trip for this year is a Europe trip. We decided last year that it would be fun to go to Europe in 2016 so we set aside $$ for it. And just this past week we have started narrowing down places we might like to go in Europe. Like you, I don't really count on a trip happening until we actually have plane tickets bought. And so far, we don't have tickets for this year. That's on our agenda for this next week. :)

  16. Love the pictures. Planning, I haven't had that many far away vacations to do much of it. Mine are usually weeks now and then. I love the idea of the layover trips to cut down on travel. I will definitely keep that in mind.

  17. My husband and I love to travel and we're definitely on the planning side since we've got a basic idea of the vacations we'll take this year, next year, and the year after--Europe, Mexico, West Coast respectively. We have such a long list of places we want to visit that it just keeps growing. For international trips we book flights up to a year in advance to get the best deals, but otherwise we do it in the months leading up. That's where the hubby and I split. My family always had the hour-by-hour itinerary. His family gets there then spends half the day arguing about what they want to do. So far, we've always vacationed with someone so I haven't really gotten to see what we'll do when left to our own devices.

  18. This looks so so fun! I can't wait to travel this year!!

  19. I have a similar process for planning! While I like to plan ahead, it blows my mind too that people are able to plan and book trips years out! I won't actually pull the trigger until at least a few months ahead of time!

  20. Tokyo sounds like so much fun, you guys are going to have a blast celebrating your birthday's in Japan! When it comes to planning vacation I am exactly like you, I need a few months to as I like to plan ahead. Though I love to plan to the very last detail theres always a lot of things we do n spur of the moment based on how we feel, so its a nice balance. So excited for your upcoming trip!
    xx, Kusum |

  21. We are more spontaneous with weekend trips (though it has to be at least a month out so I can request it off from work). With big trips we'll talk about where we'd like to go year but the specific "planning" period happens a few months in advance. We went to Europe in 2013 but we had decided in 2012 to not take a big trip so we could have a better budget for Europe. We went in April but I purchased the tickets in December. I like the process of planning so for me it's exciting to think about where we'll go the following year.

    I didn't grow up traveling much besides seeing family (which our families were both on the West and East coast so I did see a lot). but I knew when I became an adult I wanted to see more of the world.

  22. I could never do a last minute trip these days. It would stress me out. My father was always the planning type down to where we would stop to use the restroom on each trip. BTW I had more to say and then I got inspired to write an article. So I did and then I went on a tangent and wrote another one. Hours later and I am finally back here.. off topic.. and commenting on what got my brain turing! I will go now because my head is tired! Great post love!

  23. I loveee Japan and Tokyo! I recommend going to see Ueno. You can get there quickly on a train and can easily spend all day looking around. There are museums, a zoo (which I think is free), etc.

  24. If I am going on an international trip, I download maps and make hotel reservations. I usually buy a rail pass if I an traveling in Europe. I like to read travel guides and blogs. For travel in the U.S.A., I make hotel reservations and save articles, blog posts to the Pocket app. When I have some free time, I'll read the articles and make a list of restaurants to visit.