After a few recent dedicated and fairly lengthy planning sessions, I think I have the “big rocks” of our Hawaii trip all set. YAY!!!
My trip planning methods have shifted some over the years. I guess it actually depends on the location, really. I usually use some combination of:
1) Good old-fashioned guidebooks
When I planned our (two) Europe trips, I primarily used actual hard copy travel guides. I really do love a good book complete with nice maps, especially when it’s a “sightseeing heavy” destination. It’s convenient to have easy-to-reference lists of various sights, churches, monuments, etc all spelled out for you.
I generally completely ignore the restaurant/hotel sections of those books and just use books for figuring out things to see and do. And the nice clear MAPS!
Overall, though, I’d say guidebooks are becoming more of a supplemental planning tool for me and less of a primary tool.
2) Trip Advisor
For years I have historically leaned pretty hard into Tripadvisor as one of my main travel planning tools.
I especially love the (very active) community forums + search bar. Many people will post their proposed itineraries asking for feedback, so I like to read a bunch of these (plus the responses). It’s especially useful in the early stages of planning when I’m still really unfamiliar with the destination. You quickly start to see trends; if everyone is mentioning places X, Y and Z as being amazing, those are probably worth checking out. I just jot things down willynilly as I skim posts, and there’s also a Save feature which is nice.
Eventually I start to get a “feel” for the place.
Tripadvisor forums are also a favorite way to learn insider tips. When someone posts their itinerary or a trip recap, I can often learn things like, “Aha, the best beach entrance is not actually the main one, but rather down this side trail instead.” Or, “skip snorkeling there; this other place is even better and not as crowded”. Etc.
I also occasionally post questions for feedback. I’d say for each trip we take, I probably post at least 2-3 questions that I’m stumped on. This has been SO helpful, especially with logistical type questions. For example, trying to figure out how much time we really need at a place, or if others would recommend visiting something in morning vs afternoon, etc. Things where you really need a “boots on the ground” type person to clue you in.
Finally, Tripadvisor has great lists of activities/excursions and many, many specific reviews. I’ve found some very cool things to do via Tripadvisor. (Thinking specifically of our cave tour in Costa Rica, which I hadn’t seen mentioned in my guidebook at all/online but was AMAZING.)
3) Facebook Travel groups
This is where things have started shifting for me! Up until last year, I’d say most of my planning was done using a combination of books + Tripadvisor.
Beginning with our 2023 Costa Rica trip, I (finally?) discovered Facebook travel groups. WOW these are a wealth of information!! There are Facebook groups (private or public) for literally every destination in the world. And people are active on there. Questions, reviews, itineraries, photos, very searchable…. I’d say these groups are actually bumping Tripadvisor out of the way for me.
I have been using these mostly to read up on specific things we want to do (e.g. trying to decide between a few specific luaus, I searched the names for the ones I was interested in and then just perused the many posts that will inevitably show up!) VERY helpful. (And easy to save posts, too.)
4) Google Maps
Google Maps has also suddenly and definitively shot way up my list of Major Planning Tools. I never used to use it for general planning (besides just like, directions from Point A to Point B), but I have recently learned it is soooooo useful in discovering things to see and do!
Last weekend I literally sat down and just started working my way around Oahu on the map, zooming way in and clicking on the various beaches, hiking trails, waterfalls, looking at pictures, reading the Google reviews, saving restaurant ideas…. It’s priceless!!
I feel like I also sometimes discover more “off the beaten path” places this way, too (versus just sticking with major sites that guidebooks would recommend). I am very grateful to the many people who write Google reviews!! I need to remember to do more of this myself. Need to give back to the Travel Community!! (After Costa Rica I did go on Tripadvisor and wrote a dozen or more (glowing) reviews of many things we did on that trip.)
I do most of the Google maps planning on my laptop, but obviously it saves to my Google Maps phone app too, which is what I would use when actually on the trip.
This is so helpful to get a good feel too for which things to group together on a given day, by obviously seeing them on the map.
5) Web Search/ Blogs
I feel like many people might start their travel planning by googling “things to do in Oahu” (or wherever they’re going), but I admittedly don’t actually use basic Google searches quite as much. I mean, I do sometimes, especially when looking up specific websites (e.g. need the official info about booking Pearl Harbor).
But I feel like browsing through travel blogs/web searches can be a little overwhelming, and I have found many blogs have so.many.ads that it drives me nuts (and/or are completely intertwined with ginormous photos which tend to make me dizzy/ are hard to scroll and look at).
I do like to use Google searches sometimes though when looking for more details about a specific hike or experience. It’s generally easy to find a blog post on almost any subject these days, lol! Typically complete with some nice photos or insider tips!
I’d say I tend to Google stuff more at the end of my planning, once I have the basic blueprint of the trip figured out and I’m just looking to fill in specific gaps.
6) Google Docs
As I plan, I often start by jotting things in a notebook, but eventually I move it all into a Google Doc!
It’s not particularly organized- just a dumping ground for lists, ideas, notes. I like that I can drop a link (to a blog or website, for example) if I want. I try to make important notes here, like “closed on Tuesdays!” or the operating hours, fees, etc. I also copy any important reservation numbers/ details here as well.
Eventually, once I have a good feel for the main things I want to see and do, I’ll start sketching out a loose itinerary (at the bottom of the document; like M, T, W, etc.).
We typically don’t actually maintain a strict itinerary on our vacations; we prefer to be as relaxed schedule-wise as possible. I try to leave plenty of white space also. You never know what we’ll find or will come up!
But we usually have at least one or two scheduled activities/ reservations (this seems to be increasingly unavoidable, unfortunately, especially in highly popular tourist destinations). So these become our “anchor” events, and then I’ll toy around with how the other open days could look. (Again, not etched in stone, just a loose idea, and always subject to change. But I do like having a general idea going in.)
Over the years I’ve gotten better and better at knowing “us”; if I know we’ll have an early morning one day, I’ll make the next day a slower morning. If we have a full day with a scheduled excursion one day, then maybe the next day is a good lazy beach day. Etc.
Generally we’re very happy with the cadence of our trips, but it’s definitely not without some deliberate thought having gone into it on my part in advance! I do spend time just sitting and pondering, trying to envision what a day might “feel” like and finding the right balance.
I think that’s mostly it! Not counting, of course, the all-important WORD OF MOUTH! If anyone I even remotely know has been to a destination we’re going to, I have zero shame in reaching out and asking for recommendations or asking specific questions.
(Obviously I have to take things with a grain of salt/ run it through the filter of how I know we travel versus another family, our preferences, etc, but I’ll always take whatever info I can get. 🙂 )
Oh, and re: the order of booking things, it’s typically:
1) Figure out destination (based on time off, seasons, etc.)
2) Do preliminary research (try to get a feel for how much time I need in a place. Whatever the masses “say” you need, we probably aim for a few more days, because I find many people seriously underestimate this! 😉
3) Book lodging (sometimes 9-10 months in advance, if I can! Not always though)
4) Start figuring out what we’ll do. At least 6 months out (if able) try to pinpoint if there’s any serious “must dos” that definitely require advance tickets. (e.g. When we went to NYC the tickets to the crown of Statue of Liberty sold out months in advance.) I try to get these on my radar, at least, so I can decide.
5) Book flights/cars- timing depends. I’d say usually we book these maybe 4 months or so in advance? Sometimes more, sometimes much less….
6) 1-2 months before travel: Do the rest of planning/ read up/ make my lists of stuff to see and do/sketch out loose itinerary! Mostly just want to be “familiar” with names of places, etc. so that I’m not wasting time on my trip feeling confused or having to research much. (I prefer to just glance at my Google doc for ideas of things to do at that point.) Book any other reservations for activities.
Of note, we never book restaurant reservations as we dislike being tied down to eating at a certain time. What if it’s a gorgeous afternoon and I want to linger on the beach?!? But I will book excursions that are likely sell out, if I have to.
Is all of this “necessary” for every trip? NO. Could we just wing it? Yep!
But I think our trips are usually pretty seamless as a result of some pre-planning, and while it does seem like a lot, we usually have very little actually etched in stone.
For me though, as the “trip leader”, it makes the trip much smoother to be fairly educated in advance of at least what our options are, where things are located, etc. I feel like travel already inherently comes with enough unknowns and potential hiccups!!
And finally, something I have learned over the years after planning many, many trips now, is to not stress too much about trying to see and do it “all”. That is impossible, and will never happen. So I try to do my research, find some cool-looking ideas that seem like a good fit for us, balance it with some of the “must dos”, pick some, and move on. No sense in agonizing over every little thing!
What’s your go-to travel planning resource?
Daily Gratitude:
I am grateful for having our main Hawaii excursions picked and booked. I have a UTV tour, Pearl Harbor reservations and a luau booked on Oahu, and a mountain river tubing tour and small airplane tour booked on Kauai. Will still need a few reservations for a couple hikes (Diamond Head), etc but most anything else can wait.
GRATEFUL KAE 
I haven’t done a TON of planning for a trip in a long time since we are in a different stage of travel. The trips I spent the most time planning were my Paris trips and especially the first Paris trip and I leaned heavily on trip advisor. For Maui since it was our honeymoon we did not do a ton of things. We alternated days on the beach/snorkeling with an activity and a good friend has been there recently so I basically did all the hikes she did and even stayed at the same condo building as she did. So I kind of copied her trip and it was amazing. The biggest change lately is that I use Google maps a lot to save possible restaurants, coffee shops, the grocery store, etc, so it’s easy to figure out where we will grocery shop/dine out/etc. Our first step after figuring out where we will go is usually to book the tickets and then we get a VRBO or Airbnb and then we go from there.
I do look forward to a time when we take bigger, more exciting trips but we are several years from that as I need Taco to be older and, well, easier to take places. Ha.
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Yes, Google maps is a lifesaver for finding all of those things! I don’t recall using it really and saving locations to lists etc until this last year or so though. I also will usually scope out some possible restaurant ideas on there too, even though we don’t make reservations, just to have an idea what’s in the area. Actually I usually check that out a bit when I’m picking lodging, too, just to make sure there’s some good options nearby.
I guess we’re only opposite in that I always tend to book the lodging BEFORE our flights. I think this is because on a few recent trips, thinking specifically about Costa Rica, then Egypt trip I planned but cancelled, and now Hawaii, they are pretty “hot spot” destinations where I felt like good lodging options would fill up more quickly than flights. I guess I figure I can always find a flight of some sort, but not necessarily good lodging? Also, I *usually* have the option to cancel our lodging (except maybe some Airbnbs, but I prefer to book ones that allow cancellation at least until closer to the travel date if I can), so I don’t typically stress too much and just get the hotels booked first!
This CAN make flight shopping a little more complicated though, sometimes, like if I already picked specific dates and booked hotels and then find that it would actually be cheaper to fly the day before or after, for example….it’s not as easy to shift dates around anymore. But I feel like it’s normally not recommended to book flights SO far in advance (like 9-10 months, when I often do like to reserve lodging…), so that’s why I’ll do lodging, then flights. For Hawaii we actually had our trip booked from Saturday to Saturday (2 weeks later), only to find better flight deal on Friday! So we just added an extra night to our hotel and are going a day early- which luckily worked out this time, but maybe wouldn’t always…
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I can see how lodging can be better to book first depending on location. We always stay in AIRBNB/VRBO and find ones that are cancellable, too. But they aren’t so in demand that we can’t find one. We don’t plan trips 9 months out either though. It’s usually 3-4 months because of the destinations we are going, like Florida. That’s kind of as far out as I can get Phil to think, too. But again, we aren’t going anywhere that requires super long range planning. Even our Maui honeymoon wasn’t planned super in advance but it couldn’t be since we got married 5 months after we were engaged! Mostly I like to get the flights booked to nail down Phil on committing to a trip. It’s kind of a – ok are we actually going to take this trip or not because if we are this flight price is good. But these specific to our relationship dynamics because he is not a planner and I am but you can’t go anywhere if you don’t plan…
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We are similar in the process, just not 10 months out for me hehehe… .I usually book flights 2-3 months out, then lodging, and finalize lose details a month before. the only trip I booked 6 months in advance was raja ampat as hotels get booked up quickly (learned the hard way).
I do like reading travel blogs for detailed itinerary and things to do/try but I don’t rely on any particular one, I like to read a few to see a common set of recommedations. and if it’s a blog with family even better.
I enjoy doing the planning and “surprise” with the family what we do. For our next international trip (somewhere in china), I’ll probably do the month before as work will be packed until June.
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I have been booking our lodging earlier and earlier in the last few years, I think just because it seems like travel is increasingly popular and everything just seems extra “busy”! So I’ve become a little paranoid. Also, because we often take longer trips, I do try to keep our lodging costs pretty reasonable BUT I still like really nice places. So I have found that if I book earlier, I can often find a better selection to choose from that is in our price range and still very nice. I worry that if I wait until too close to the trip, I will be left with either super expensive places OR cheaper places but not nearly as nice as what I would have found earlier.
I think it depends on the destination, too, of course. Some huge cities etc are not going to run out of lodging options really! But like in Costa Rica, the small town of La Fortuna doesn’t have THAT many places to stay, you know?! The hotel we stayed at I booked 10 months in advance and I watched it online and the “superior” rooms we stayed in definitely did sell out well in advance, so I was so glad I booked it when I did. So, I think it just depends on the place, really.
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I love this post! It’s funny how traveling planning has changed over the years–in my 20s (pre-kids) I would buy/borrow a Lonely Planet guidebook and plan my whole trip from that! But now I rely mainly on travel blogs (I have a good sense of the ones I like now, particularly for national parks), Google searches ( to read about specific hikes/activities like you said), and TripAdvisor. That is a great tip to check out FB groups–I really haven’t done that. I truly love travel planning and it’s almost a hobby in itself for me, so I can definitely spend waaay too much time on it before I actually start booking stuff. For instance, for 2025 I have about 3 different summer trip ideas that I’m researching right now (one of them is roughly modeled on your Costa Rica trip!). But generally I tend to do things in the order you do too–choosing location, then booking lodging, then when it’s closer booking the flights/car and then filling in the remaining activities, etc. I never book restaurant reservations either; I try to look for a few restaurants for each day that look interesting and then when the time comes, either we check one of them out based on our mood, or sometimes we just wander in somewhere. I don’t feel like we’re usually super focused on food on our vacations so it sort of takes a lower priority than the activities/sights that we tend to book things around. We have been doing a lot of national park trips lately and one thing I love about staying in the parks themselves is they usually require a one night deposit at booking but then it’s a free cancellation up until 48-72 hours (sometimes a week?) before you go. I have definitely booked hotels then canceled them when our plans change.
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I feel like we are travel twins. Every time you comment about your trips I feel like we’re just so on the same page about the types of trips, approach, everything! I also usually try to make sure the lodging is cancellable, which makes it low stress to book way in advance. Then you get the more wide open selection, while still knowing if there’s some issue or you can’t work flights out or whatever, you can always cancel! I am more nervous about booking flights far in advance just because there’s generally no way to cancel those. So that always feels very “final”!
And we approach restaurants the exact same way, too. Restaurants/food are not the main focus of our trips (besides making sure we find some fun breweries to try, usually!). We focus more on sightseeing, local experiences, etc. But I will scope out the restaurant scene in advance and bookmark some that look like we’d possibly like to try. Making reservations would stress me out, because we don’t usually follow a super tight itinerary. So having a dinner reservation when I don’t know what the rest of the day will look like exactly is hard. But I can see how that would be useful in certain situations or specific types of trips, I suppose!
I need to scroll back on my site- you gave me some Hawaii recs one time, didn’t you??? I just remembered this now… going to search….
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Thank you for a great post! Yes to all of that! Google maps has been so very helpful in our latest two trips- Paris and Spain/Portugal. Not so much TripAdvisor since I can go down the rabbit hole. For us flights are always first, then lodging then everything else. I really like to have flights and lodging locked in then I can plan at a more relaxed pace. I can’t wait to read all about your trip!
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YES once I have both the lodging and the flights booked, I always breathe a sigh of relief. Because really, I mean, if you did ZERO planning and just showed up with those two things, you could still probably have a perfectly nice trip! It does astound me sometimes though, as more of a “planner”, when I’ll see someone in my Hawaii Facebook group post something like, “Heading to Hawaii next Thursday with our family of 4. What things should we see and do? We don’t know anything about Hawaii!!” And I’ll be like…. whaaaaat?!! Sometimes they won’t even have a hotel or car or anything booked! I mean, I could see traveling that way if I say, suddenly got a week off work unexpectedly and it was like, ok, let’s just go! But if it’s our “big family trip” of the year type thing, then I guess I approach it more systematically and want to make it as complete/ smooth as possible.
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I admire people like that. But I’d be scared LOL
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thanks so much for posting this! I enjoy traveling but the planning is overwhelming to me and more so now with the kids. I’m always curious about how people are doing it, the timelines to actually get trips organized and booked, what resources are actually helpful these days when there is so much content out there so this is perfect. Our kids are now at an age where it is more fun to explore so I’m going to use this to get jump started for Thanksgiving break.
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Glad you found it helpful! I too am always interested in how other people approach trip planning. I find it to be a BIG JOB and have just sort of developed my own systems over time, but I’m sure everyone does it differently! Where are you headed for Thanksgiving?!
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Oh brother, 7 days behind in replying, but I’m hoping for some road trip at Thanksgiving We’re doing an Alaska cruise this summer so that is sucking up a lot of the travel budget this year. We’re excited to do it. I haven’t been able to read a lot of blogs this week due to work but recall seeing a “sick day” title. I hope you are feeling better and got some rest this weekend!
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I love this post! My two favorite resources are Trip Advisor and Facebook travel groups. I follow FB groups for places that I want to go to as step one to figure out what the place is like and things to do, and then when I’m ready to plan the trip I usually go to Trip Advisor for more ideas. I keep notes in a Word document in Dropbox that I can access anywhere. If the trip is more complicated, then I might switch over to Excel – for example my summer trip in June has too many moving parts so I needed to map out a time grid in Excel. I also like watching Youtube videos of these places.
I would always rather plan sooner than later. Like you say, I don’t plan every minute of the day, just the “musts” that I want to get done. For my simple solo trips I usually book things about two weeks out. For our big family vacation last summer everyone booked their condos back in December so that we could be sure of being able to stay in the same building.
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I am a recent convert into FB travel groups as well! They have fully replaced Trip Advisor forums for me, I feel like they are much more active. I used them SO MUCH especially when planning our recent trip to Japan and truly found so much value there. I mostly search through, but it really helped to get a feel by following along for probably 9 months before we went.
I also EXTENSIVELY use google maps, both for searching and saving things. I have huge maps for almost everywhere and while I’d never get to go to all the places, it’s so handy to have recommendations I can look at no matter where I am – I’ve been trying to get better at adding notes for WHY I’ve added a spot to the map.
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There’s some great info here. Lately, when I’m going somewhere I just google “best things to do in XXX.” But I will say I haven’t planned a family vacation in a while. For various reasons (ahem) we’ve put off/canceled forever family trips (sigh.Long story.) BUT, I will say this- if you’re traveling with kids, the planning is even more important. I feel like if it’s just me, or just me and my husband going somewhere, it could be more loose. Going on a trip with kids and failing to plan could lead to a lot of disappointments. I wonder if your family appreciates all the thought you put into these trips! They probably have no idea how much work goes on behind the scenes to make it all happen.
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I do things similarly to you. If it’s cancellable, like a hotel, I will often book it early, and set a task a month or a week before the cancel date to review it to see if I still want it.
However, the most important thing you said here is this: For me though, as the “trip leader”, it makes the trip much smoother to be fairly educated in advance of at least what our options are, where things are located, etc.
YES! I always make a list of things and I know that I am not going to do or see them all, but I always have something to pull from if there is down time. I also put them all on https://mymaps.google.com/ and then you can share it with your group members so that everyone has it, and then THEY CAN HELP YOU later! I don’t always want to be the tour guide, do you know what I mean?
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It sounds like you have a pretty solid system down with a few different resources. Nice!
I did not know about Facebook Travel Groups. That’s interesting. Thanks for sharing.
Honestly, I haven’t done a trip in a long time that required planning to the level you’re doing… I’ve been going back home for most of my vacations and then traveled with others, so very little planning fell into my hands… but I usually do use Google Maps quite a bit, I like to look for travel blogs (I follow a few) and then often ask for personal recommendations.
I haven’t used a Lonely Planet in forever 🙂
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