How Do You Prepare Before Taking A Trip?

Filed Under: Travel

As I’ve written about previously, my wife and I are celebrating our 10th anniversary in the Maldives next month.

And with the trip getting closer, I’ve become obsessive about reading reviews and anticipating all the little details.

TripAdvisor, BoardingArea blogs, FlyerTalk trip reports, YouTube videos and Instagram have all started to fill those little breaks in my workday.

From the food porn posted by the resort’s chef…


…to news that the new Etihad first class lounge in Abu Dhabi might finally open.


I’m very much enjoying our trip before it begins.

In fact, I am a firm believer in the school of thought that the anticipation of a trip adds to the experience.

My wife, however, thinks I’m nuts. She ignores most of the things I show her. She thinks knowing too much in advance spoils the surprise. And she very much prefers her “point me in the right direction” approach to our travel.

I’m not sure that she’d ever go for the complete surprise trip like Ben’s adventure with his dad. But, that might have more to do with the fact if she doesn’t ask questions, she could end up on a trip with a routing like this.


My wife has taken on Tiffany’s husband’s mantra of “trust but verify” when it comes to big picture stuff.

The nice thing for us is the balance between our styles works out well and we both ultimately enjoy our trips in our own way. I get the satisfaction of planning with her input on the big picture details. And she gets to not worry about spending too much time

But, I’m curious how you all plan and prepare for your trips. Would you prefer to go in mostly blind? Or, can you not get enough of all the little details?

What’s your travel prep style?

View Results

  1. I voted for knowing all the little details; I like to be spontaneous sometimes, but when you’re visiting a destination that is costing a lot (either in money, points, or vacation time), I think it’s important that you have at least some idea of what you want to do, so that you don’t get home at the end of the trip and say “Oh, I wish I had done that.”

    So, I think it’s important to leave some time for “surprises”, as long as you make sure you’ve done your research to know what is and is not available at your location, based on time of year etc. etc.

    Have a fun trip!

  2. How easy for her to not sweat the details, because you do all the work. If neither of you did any research, you could well end up in a hotel from hell, eating meals you immediately regret, and missing out on cool things to see/do when you are there. She only gets to be “above it all” by depending on you to do it all.

    Maybe sometime, {when it’s not going to be your 10th anniversary of course}, do a trip her way, sans any real research. When that turns out to be less than memorable, perhaps she’ll begin to appreciate how much your planning adds to her enjoyment of the trips. 😉

  3. I hate to say this, but one thing to pack is medications you might need, and (sorry) lots of Imodium. Having made the same trip with a very sick husband(didn’t start until after take off) I now know that business/first class on board bathrooms and lounges are worth all the miles. And that you can get all the medications you need in the Dubai airport pharmacies.

  4. When they were growing up, our kids would always ask, “Why do our vacations have to be so planned?” So we went on a trip (not a big trip, mind you) and when we arrived at our destination lodging (everything can’t be left to chance, after all), I asked, “So what would you like to do?” They were dumfounded. So I pointed them to the display of travel brochures in the lobby and said, “You wanted a trip that wasn’t planned in advance. Here we are. Pick out what you’d like to do.” When we tried to make reservations for many of the activities they selected, all available appointment times were filled. We wasted hours driving around looking for kid-friendly restaurants. You get the picture. When the long weekend was over, they said, “Promise me one thing; we never go on a vacation like this again.” Happy to oblige. Planning is at least 40% of the fun for me. We waste very little time and experience even fewer disappointments. Traveling on a whim is for the foolhardy; I like to leave as little to chance (which, by definition, is a 50-50 proposition) as possible.

  5. I am definitely planner for the big stuff (transportation and lodging). Might have stemmed from a memorable trip when I was about 10 or 12 years old. We drove out to Victoria on Vancouver Island, arriving in the city about 8 in the evening and proceeded to look for a place to stay. Checked all through the city, nothing available. Began driving back toward the ferry terminal, checking each hotel/motel along the way. It was about 11 pm and well north of the ferry, with us thinking that we were going to spend the night sleeping in the car, before we found a motel to stay in. The lesson I learned; always book somewhere to stay, especially if you are going to an island whose ferry service stops early in the evening.

  6. You have a biased sample. Most everyone who reads blogs like this is an obsessive planner when it comes to travel

  7. Don’t bank on the etihad first class lounge being open for your trip. Their social media folk couldn’t confirm for me if it would be 2016, 2017 or 2018 – I guess a previously reported May 1 opening may have jumped the gun or at least may not be May 1, of this year. That being said the current lounge is fine if a bit crowded at peak times as one would expect. Also just an FYI, immigration at the first class/premium check in area were refusing me entry to departures at AUH until 4 hours before scheduled flight – may be a new rule or an agent having a bad day but poor form when flying first on a380 to jfk – but quickly sorted by station manager with not too much fuss!!! Have a great trip!

  8. The only thing I obsess about on trips is the transportation and lodging….everything else I leave to serendipity. You can easily build up a trip too much….just like anything else. You can anticipate how wonderful a trip is going to be, how excited you will to be there, etc…and when you get there, its great! But its rarely as great as you made it out to be beforehand.

    Also to plan out a trip to the last detail is what tourists do. I travel. What happens if you schedule all day for something and hate it? What happens when you schedule an hour for for Rodins Garden and then the dying gaul entrances you? or you see the gates of hell and melt? Come on…..nobody wants to be around people like that. Now a little preparation is good, you dont want to go to Milan and miss the last supper….you just dont have to plan everything in so much detail you forget to nap, or have fun, or stroll around for more than 6.8 minutes….

  9. I guess I lean more towards the “plan every single detail” method, but not completely. Lodging and ground transportation (if seeing something involves a long drive out of town) is absolutely planned in advance, and I’ll usually map out a “suggested itinerary” in advance. But I also have no qualms about spending more time at a site if we’re really enjoying ourselves, or cutting our losses and doing something else if the lines are too long, it looks lame in person, etc. Too much regimentation – “we have exactly 37 minutes and 24 seconds here to stay on schedule!!!” – is just as annoying as not having a plan at all.

  10. It has worked well for us to reserve the first two nights in a new area . If we like then we stay on or we change after we’ve looked around . I do like to reserve the night before departure close to the airport .
    I like to have an idea of some possibilities but , no rigid schedule .

  11. My husband loves to plan the trip months in advance down to knowing where he is going to park in Florence. I like to just go along for the ride. Our only rule is I can’t complain if I don’t like what he picked.

  12. I agree with Mark-serendipity is the watchword. Our travel philosophy is “if you hear music, follow that sound, something interesting will be going on.”
    As to planning, we book a general refundable stay framework which we then deconstruct. Got back from Barcelona last night. I had booked 21 nights at a suburban HIE-5000 pts/night. He stayed 6 and explored the region north of Barcelona including the Pyrenees. Booked 3 nights in Sitges, a old favorite, and reconnected with friends so we booked another 5 nights. Planned on visiting Tarragona but were having so much fun we stayed another 4 nights in Sitges. Last two nights in Barcelona proper to hit a couple of favorite restaurants using Marriott Visa reward nights which about to expire.
    So we could have stayed at the HIE for a measly 105k points and had a great time, but other doors opened to us and Sitges went from a weekend to 12 nights.

  13. I’m exactly like you, Mike, and my husband sounds pretty much like your wife. I honestly think I enjoy the planning just as much as the travel. For our trip to the U.K. later this month, I’ve even scoped out where we’ll eat our meals and made some reservations … we have spent too much time wandering through unfamiliar streets failing to agree on a restaurant, or finding that there is a 1-2 hour wait for a table, and then ending up back at our hotel defeated, ordering room service. Not this time!

  14. While abroad, my wife and I prefer to have most of our days planned from museums and tours to off-beat and known historical places to visit.
    In the evening, we frequent restaurants mainly serving local cuisine as well as pubs, bars, micro breweries, wine locales and theaters found online and cross-checked with Trip Advisor, TOP 10, Lonely Planet, etc. We also ask the locals where they go to eat.
    While walking we find plenty of spontaneity around town and use the hop on / off buses to get the lay of the land.
    Because we may not return to some locations, we want to have seen as many noteworthy sites as possible.

  15. Did 10 days in the Maldives earlier this year (Angsana and Mirihi) and I do think a bit of pre-planning is needed for the Maldives and all trips honestly…for example our resorts were basically “shoe/sandal free” so there was no need to pack fancy clothes (although I guess some Maldives resorts are different so thus best to know ahead of time).

    And like Liz says getting lost is no fun…

  16. I vote for the planning and preparation but don’t go with the expectation that everything will fall in place. I also enjoy the unexpected. But don’t want to waste time and money by trial and error. Good comment about the biased sample!

  17. I overplan for a trip, but it is deliberate. If something interests me and I want to stay longer at a spot or doing something different, I will drop a planned activity in a heartbeat and with no regrets. That way, I am never hunting for something to do or wasting time figuring how transportation works in a foreign location, and I have the flexibility to do what I want to do and not what I planned to do if something better comes along.

  18. @Robert Hanson
    I agree completely. I work in Europe, most of the time in France and Italy and I constantly run into Americans who are wasting precious time trying to find hotels and sights – tasks that could have been accomplished from their computers at home, resulting in bad outcomes with higher prices and forfeit of a quality experience.

    I plan my work travel (around 5 to 6 trips to the EU from SAN each year) and my two vacations each year down to the level of a military OP Order! And I enjoy the process. Getting ready to leave for France Tuesday for a month of work and I just spent the day reviewing all seven hotels, loading my GPS for the rental car, researching restaurants and even looking at Google Earth at places I’ll be passing through.

  19. It’s a good idea to have a single course of PEP (Post-Exposure Prophylaxis) in your bag. Gals might also want a morning after pill in addition to the PEP. You’ll need a prescription for it, so it’s a good thing to plan in advance before you go. No one wants to think about this, but trust me, it’s absolutely no fun to lose an entire day of your vacation panicking at a clinic in a country where you don’t speak the language trying to explain what PEP is and then trying to obtain an emergency prescription for it. The pills are good for at least a year, hopefully you’ll never need them.

  20. +1 for if you don’t plan, you miss a lot. You also wait in the long lines with the other “free spirits” who didn’t get their advanced tickets. I’m willing to leave a few meal slots open for serendipity, and maybe 1 day of a long trip, but planning is my strongly preferred method. (I have to admit that my lack of travel sponteneity was very high on the list of reasons my husband left, though. So, do listen to those complaining partners-they may be more annoyed than they are admitting. )

  21. How do you all come up with the routing? I looked into making several stops for the miles and segments but everything that I find that’s not direct costs a bit more.

  22. Half of the fun is planning the trip! Well not half, maybe a quarter. I get such a kick out of dreaming about the next vacation and learning about the history, doing research – if I was forced NOT to plan, I would feel like I lost out on the “vacation” experience I’m paying for. I never stick to a strict schedule; usually aim to see/do two things a day, and everything else I leave up to what interests me that day.

    I can’t imagine going on a Europe trip and not planning where and when to go to certain tourist hot spots. So much time wasted standing in line if tickets aren’t purchased in advance, knowing about discounts, etc.

  23. I am a compulsive planner. Especially because my wife leaves everything on me :p We dont care much of the flights as long as they are within bearable distance of economy (around 6 hours) otherwise business, but accomodation and what we will do at the destination need to be planned. Maybe not every minute but at least each day. If I can prebook some activities I do that too. I love the unexpected too but some amount of planning is needed for me. Both of us do not drive at our destination (I am not comfortable driving in other countries) so planning helps us to know how we will get around to each activities 🙂

  24. I am the planner! We have a ‘rule of 3’ where I ask Hubs three things he wants to do, then I have my three and I make sure all of the elements are included in the trip. I’m also a big fan of booking something in the far distance, practically forgetting all the amazing things I planned and being surprised (case in point, a Bali trip I’m planning for September).

  25. Hi Mike,

    Never posted anything before but read all your articles. I’m traveling 250 days per year mostly in Asia and Europe. I did one trip to Alabama last month I totally screwed up the expense report as I’m not used traveling in USA.

    I’m Star Alliance and I typically do 300k on Star and about 100+k on other airlines per year. Mostly United, SQ, Cathay and Lufthansa.

    Gold/Platinum/Spiral member at Hyatt, Hilton, Marriott and InterCon so I know all the perks you mentions.

    I do recognize many thing you talk about, but there is one difference. I always try to get home as soon as possible as I’ve been doing this for 25 years, I still enjoy traveling and I know the restaurants/bars in Tokyo, Singapore, Hong Kong, Shanghai, Perth, Sydney, Paris and London better than my small home town, but I still want to go home.

    When planning for a trip I never really unpack, as I just got back home. So my bag is always laying close to my bed , I just do laundry and trow everything back into it. Have at least three bags for 1 week, 2 weeks and 4+ weeks travels.

    NOTE: A warning, I’ve been a big fan of RIMOWA, German Rolls Royce of luggage for many years. Last month my purple RIMOWA was totally destroyed by United (Shit happens). However, I was called up by United agent in Texas, and they said that I would of course get a new RIMOWA bag but it was 18-24 months delivery time!!! The United agent was very helpful and after a couple of days he called me again and offered other solutions. So I ended up with a Haliburton $1300 replacement for my $800 RIMOWA. This is nothing to do with United. United have replaced my RIMOWA bags at least 4 times before without any questions, so this is not a United issue.

    So if you travel frequently. Make sure you use a well know brand name, but do not buy RIMOWA.


  26. For my wife and I, compulsive planning usually is involved on the plane/hotel/transport end. Knowing how to get to/from the airport/train station to the hotel with minimal fuss is a requirement of our trips. Past that, we usually have a few things we want to go and do in an area, a few things we’d like to do if we get time, and anything past that is a bonus. Wherever we’re going will be heavily researched, and we’ll have a rough idea of what we’ll be doing. This is done as much for giving us options if XYZ is closed, or weather doesnt permit something getting done as it is for giving us an idea of the area we’re going to. Some of our best trips have been when we had a plan, couldnt execute it because of circumstances, called an audible, and loved it. Major attractions (Eiffel Tower, Uffizi gallery, Leaning Tower of Pisa, etc), however, will always be booked in advance if possible – even if its from a laptop/tablet in the hotel room the day before – for no other reason than to avoid the queues.

  27. We are firmly in the plan every detail camp. But we do take the “deal a meal” approach. If we are spending 5 days, we will plan 6 or 7 days worth of activities/walks/options and then decide once we are there which we want to pursue. If there are popular restaurants, we will book in advance. We also take a list of restaurants that are nearby sites we might visit. So we have a planned schedule but we go with the idea that in all travel, flexibility is the key to enjoyment. Nothing worse than finding yourself in a foreign city with no idea of where to go and what you want to see. Too much wasted time trying to figure things out on site. Plus, planning is almost as fun as the trip. You get excited about what you will see and you arrive with some appreciation of what the city has to offer.

  28. I make a list of all the things we want to do on our vacation trips and put them all in an Excel spreadsheet, organized geographically in order to reduce travel time between each target. Then I print it on 11 x 17 paper, fold it and put it in the travel guide (I only use DK Travel Guide books), and use a pen to tick each item off the list as it’s completed.

  29. This is a bit more complicated than three choices… I definitely don’t micromanage the trip in advance, but wish I had more time to do some advance planning and dreaming. I tend to be too busy wrapping up things at home. However, I really identify with the comments from people who have a travel prep routine. Since we have lived overseas, either full-time or part-time for many of the past years, I have a checklist that covers everything needed to leave home, down to resetting the time in my camera when we arrive in our new destination. I also have lists of steps to accomplish the tasks, some of which have become obsolete over the years, thanks to advances in technology. I keep them all in Dropbox, so I can access them anywhere.

  30. We combine the two: a hotel to land in for the first night, and a “something” planned for each day. Then we let serendipity happen, augmented by our Lonely Planet guidebooks. They have greatly spiced up our travel, particularly in China, where English speakers cannot be expected once you get off the beaten path! It’s helpful to know what’s there to be found!

  31. We split up the tasks. My husband takes care of the “bones” – airfare, lodging, general structure of how many days to be spent where (with my input). I take care of the “what we’re doing when we get there” part. We both know we’re the type of people who can’t 100% wing it, it’s just the way we are.

    I don’t plan down to what we are going to do on which day unless there’s a particular thing that we need reservations for (like an awesome restaurant I read about) or where it would be wise to have a timed ticket instead of waiting for hours in a line. I try to read enough about a city to have an appreciation for the sites and local culture, get an idea of where the good food spots are, and to have an idea about what I want to see versus what I can pass on. Then we figure it out when we get there based on weather, what we feel like doing, etc. It usually ends up being a mix of hitting big sites and wandering around.

  32. I’m a researcher. Without hours of time browsing Trip Adviser, we would have spent an extra $500 on food during our recent trip to Phuket as we would have eaten four additional meals at the resort (JW Marriot Phuket Resort and Spa). We found several amazing and cheap joints in the neighboring areas thanks to the research.

  33. @mike
    Hi Mike, slightly off topic but massive favor needed please.

    Booked Etihad first Syd – Dub via AAdvantage last year. Now need to add an infant and they are saying they can’t and that I have to go to Etihad who are showing 20% of fare ($3000+)

    Any ideas on how to get the 10% of fare or how to get this cheaper?


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