Thoughts on Travel Planning Details

I have always been an organized person. As a kid, I arranged my books by spine color, reading level or publisher. In middle school, I lived by my school assignment book. My addiction to to-do lists was solidified by highschool. And by college, I had mastered organization to the point where I was always a couple weeks ahead on reading and assignments and I never, ever pulled an all-nighter. You read that right: I had my papers done weeks in advance and got eight hours of sleep every night.

Lest you think I’m bragging, let me take you to the present day. My life has gotten so chaotic and disorganized that I frequently carry to-do lists over for weeks and don’t get around to changing out of my pajamas until 3:00 in the afternoon. It’s not uncommon for me to have a dozen half-started emails, three or four blog posts in progress, a Skype conversation open, an editorial calendar open, my Twitter feed scrolling along and articles in various stages open on my laptop, not to mention water boiling on the stove and kittens that need wrangling in the other room … all while on the phone.

So when it comes to planning the details for my travels, I downright suck, and I’m not even sure it’s because I’m a busy person. Booking flights and hostels are among those things that roll over from week to week until my husband puts his foot down and insists I do something about my procrastination if for no other reason than to ensure I don’t end up sleeping on the sidewalk in a busy city.

The truth, though, is that, even though I love to travel, I hate to plan the details. I don’t mean I can’t let things just happen once I arrive somewhere, because, for the most part, that’s not a big deal. But flights need to be booked, visas need to be secured and vaccinations need to be gotten before I can wonder any streets without a plan. Some places require advance planning for events and festivals, and several tours need reservations several months in advance. But I don’t want to research which hostel I should stay at or wade through all my options for flights. I don’t like to pour over travel guides for details like other people do either. Quite frankly, I just wish the details would fall into place and I didn’t have to deal with them.

I’m lucky to be married to someone who doesn’t mind dealing with the travel details, even when he’s not traveling with me. I pass along the URLs of the websites I know he should use to find the right hostel or I give him my opinions on what I want in a tour operator, but beyond that, I let him work out the nitty-gritty details.

I think part of my dislike of planning travel details comes from the incredible amount of information available. Finding a flight isn’t as simple as just plugging in dates and booking a ticket. For my upcoming trip to New York City, for example, I had to cross reference a variety of dates and arrival and departure times across more than a dozen search engines to find the best deal. Morning or night? Aisle seat or window? Connecting flights are not? Laguardia or JFK?

It’s your turn to sound off: How do you handle planning the details of your travels? Do you like to plan or do you dread managing the visa application, plane tickets and advanced bookings as much as I do?

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29 Responses to “Thoughts on Travel Planning Details”

  1. Gray

    I can definitely relate to some of this, JoAnna. I used to be THE most organized person I knew…until I started blogging. Now I’m constantly multi-tasking from morning to night and I still feel like I’m not accomplishing anything. So much of my time is focused on my blog, everything else in my life suffers, including travel planning. Unlike you, though, I used to LOVE to plan my travel, down to the last detail–it was half the fun of a trip for me. Now, I can barely find time to do it. You’re very fortunate to have a trip planner right on your premises (and free, too!). 🙂

    Reply
    • JoAnna

      I wish I could find the love to plan, Gray, but it just seems like such a drag. Besides, Cory does an awesome job picking out places to stay, etc. I just get so frustrated when I spend hours (okay, 40 minutes) on the phone with travel vendors just to clear up mistakes they made. As if it’s not stressful enough!!

      Reply
  2. Audrey

    Oh, I am so with you on this. I hate planning details for a trip and usually put things off until the very last minute. Dan is the same way, so it’s a miracle that anything gets done at times. For me, I use airline tickets as my anchor. I figure that everything else that happens in between can be made up as we go along 🙂

    Look forward to seeing you in a few days at TBEX! Safe travels!

    Reply
    • JoAnna

      I am fascinated that neither you nor Dan likes to plan … a funny thing to hear coming from a very widely traveled couple! Can’t wait to meet you at TBEX!

      Reply
  3. Cory

    Hey! You’re welcome… oh and Gregg says he can vouch for the authenticity of that photo as he was there and saw the devastation first-hand.

    Reply
  4. Alouise

    In my day to day life I’m completely disorganized and usually don’t plan for anything. But when it comes to traveling I’m organized, I plan months in advance (usually) and I love every minute of it. I think part of it is knowing the reward that comes with making travel plans. I like to research everything, where to go, which hotel to book, which flight to take, even if just to weigh the options. But I can see what you mean by too many choices. I leave for NY tomorrow and haven’t planned much aside from booking my flight, hotel and seeing a show. There’s so much I want to do, to try and schedule everything in would be impossible.

    Reply
    • JoAnna

      If my husband ever retires from making my travel plans, I promise to hire you Alouise! 🙂

      Reply
  5. Candice

    Hahaha, I can sympathize, considering last week I went to you in a panic over not having my tickets. Let’s make it a pact to not stress out over the details of sightseeing at least, yes?

    Reply
    • JoAnna

      Sounds like a deal, Candice. No stress. Only fun!

      Reply
  6. Andrea

    Nope – I’m with you. Total. Necessary. Evil. I’m torn between planning and just letting things happen. I’m a worrier and can’t show up somewhere if I even think it might be a busy season without an advance reservation. My fiance, on the other hand, wishes we would plan nothing and just wander out into the world with no agenda in mind. Since we’ve been together, I’ve been trying to fall somewhere in the middle. Though, I must say, I do love sites like TripAdvisor where people let you know if a hostel is really nasty. Nobody likes bedbugs…

    Reply
    • JoAnna

      I’ve been known to get sucked into TripAdvisor just to read the bad reviews. Helpful? Yes. Yet another time suck? Unfortunately, yes.

      Reply
  7. Keith

    I actually enjoy the planning, but I’m trying to cut it back on my future trips. I tend to lock the itinerary in and leave no room for spontaneity. What a wonderful husband you’ve got there!

    Reply
  8. Everywhereist

    I hear you, lady! I usually make a list – this makes my life much, much easier. And as time has passed, I’ve learned a few things about myself: aisle seat (unless we’re upgraded, then, who cares?), slip-on shoes, no red-eyes (if possible), and forget LaGuardia and JFK – go for Newark. 🙂

    Reply
  9. Anil

    The one thing I’m consistent about is booking at the absolute last minute. I always put off pulling the final trigger, even though I find good itinerary after another. Definitely not my favorite part of traveling!

    Reply
    • JoAnna

      Sounds like me, Anil! I’m notorious for putting off what I can do tomorrow. I have a bad tendency of buying plane tickets so late that I definitely pay for my procrastination.

      Reply
  10. ayngelina

    I broke it down into weeks so it seemed a bit more manageable and then decided not to plan everything. While vaccines, flights and visas were on the list, I only booked my first night in the hostel and nothing after that.

    3 months later I see it was the best thing I could have done because no amount of planning would have been enough. My plans have changed a million times and because I had no plans I was more open to things.

    Reply
  11. Jill

    Well, Jo, you know where NOT to stay if you ever go to Gatlinburg again! LOL!

    Reply
  12. Abbie

    I just don’t like long plane rides. Although this one on Virgin isn’t too bad (once we got off the ground) since I decided to pay for the internet – it’s so worth it.

    Reply
    • JoAnna

      I could never plug in online. I guess one thing about me that is certain is that I will always use airplane time to catch up on my reading.

      Reply
  13. Brooke vs. the World

    I would say that before traveling long-term I was pretty adamant about setting out plans. Now, I can’t be bothered! I think there’s a part of me now that’s just like, “Oh, things will work out no matter what.”

    And, I can second the feelings of never getting anything done 😉 I’ve been experimenting with going to the library, or working without Internet enabled, and that has helped me focus a bit better.

    Reply
  14. kerl

    Sometimes, even when you planed things up, it doesn’t happened as you had planed. So, I prefer not to plan and I just go on my trips. On the road, I just see sort out things..this is more fun and adventurous..

    Reply
  15. Nicolas

    I’m totally chaotic in “regular” life, but for travelling I like to plan. That’s because planning makes me think and fantasize about the travels, which is a great way to spend your time. And I also think it’s part of the experience.

    Because too much planning takes away the spontanity I try not to plan very much though, but wherever I go I often have an idea of what’s to do, which way the trains and buses go and what the opportunities for sleeping are.

    When I’m bored, I often look at Google maps and wonder what it would be like to travel to this our that country. I try to find the cheapest way to get there, what the main sights are,… It’s fun 🙂

    So if you need info on a certain country, I’m your man!

    Reply
    • JoAnna

      I agree that there’s definitely a balance between planning just enough and over planning when it comes to travel. I’ll definitely keep you in mind if I need to dig in with some research about a place but don’t really want to dig it up myself!

      Reply
  16. Emily S.

    I have a love/hate relationship with planning… it’s so exciting at first, but then, like you, I get so overwhelmed by all of the options and how much is out there. At some point, I just get fed up with searching and go with the last thing I thought about or saw online. Not the most efficient system, but I haven’t ended up sleeping on a street yet!

    Reply
    • JoAnna

      Yeah … definitely not my strongest suit. I’m sure there are better ways out there for me to save money when I travel, but I just don’t have the interest to pursue them.

      Reply
  17. Carrie

    I actually really enjoy travel planning, but I’m married to someone who likes to take it the nth degree. That means that my husband does most of the travel planning for us (with my input, of course) and I generally look forward to planning my solo trips.

    With that said, lately we’ve focusing on being more spontaneous with our travels. This year, we deliberately booked some of our accommodations ahead of time and left the rest to chance, and what a change it made to the journey! John and I are both planners, but it’s nice to let the chips fall where they may every once in a while.

    Reply
    • JoAnna

      It’s a delicate balance between underplanning and overplanning, isn’t it?

      Reply
  18. Abby

    You are the least disorganized person I know — imagine what the rest of us go through trying to make our flights haha.

    Reply
    • JoAnna

      We should travel together some time … then you’ll see how bad I am at planning my trips!

      Reply

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