I am an enthusiastic trip planner. At any given moment, I would rather be traveling (seeing new things, trying new foods, meeting new people) than almost anything else in the world. For me, planning the trip is almost as fun as actually taking it. The research leading up to it, the itinerary-building, the puzzle of fitting things together in a way that makes geographic and logistical sense is a hobby of mine that also happens to result in a vacation which makes it even better.
By the time this article comes out, I’ll be in Europe, enjoying the Swiss Alps and right now, I’m deep into planning a trip to Costa Rica for December. I asked my husband what I should write about this week and he suggested talking about how I plan a trip, in the hopes that this might be helpful for those of you in the middle of trip planning. So, let me walk you through how I plan a trip, from the first spark of interest to the last booking.
It Usually Starts With Someone Telling Me They’ve Gone Somewhere Amazing
Almost every trip I’ve taken started the same way: someone told me (either someone I know, or someone on a podcast or in an article) about a place and something in my brain filed it away under “I gotta go there, someday”. The first time I can remember this happening was when a friend came back from Cinque Terre with pictures and I knew I had to hike between those gorgeous cities (it took me 20+ years to do it, but it was always on my mind). I rarely go looking for my next trip, rather, I let it find me through the things I’m already reading and the conversations I’m already having.
When the interest is strong enough, I start paying more attention. And eventually “someday” becomes “let’s actually look at this”.
If I have a specific window of time and I’m not yet committed to a destination, I’ll sometimes plan three or four trips simultaneously, building out rough outlines for each, and then let price and time of year make the final call. That’s just a weird “me” quirk though. Who has time to do that besides weirdos (like me!) who love the planning as much as the travel? Costa Rica in December, for instance, won a spot on my calendar partly because December is dry season in most of the country, which matters a lot when you’re hoping to do outdoor activities.
Getting a Lay of the Land
For a big trip, my first stop isn’t Google. It’s the library. For smaller or closer trips (typically those within the United States), I skip this step and go straight to TripAdvisor.
I’ll check out two or three books on the destination (my favorites are Lonely Planet and Frommer’s) and actually read them. While I’m reading, I keep a running Google Doc where I drop in anything that sounds interesting: a national park, a restaurant that keeps coming up, an experience I haven’t had yet, or a neighborhood that sounds like it has the right energy.
I don’t worry yet about whether everything will fit. I’m just collecting. The document gets long. I include pictures. That’s fine. Sometimes I organize it by region, sometimes the document is a big ball of chaos.
If I know someone who’s been there, I reach out again in this stage and ask directly: what were your must-dos? What would you skip? What do you wish you’d known before you went? People who love a place love to talk about it, and this kind of firsthand intelligence is worth more than any guidebook. The best recommendations I’ve ever gotten came from a single conversation with the right person.
TripAdvisor as a Reality Check
Once I have a solid base of ideas from books and people, I head to TripAdvisor to see what I might have missed and to get a sense of what’s highly rated by people who’ve recently been. This is where I start sorting things into buckets:
- What do I really want to do?
- What might be best to do with a guide or tour group?
- What do I want to do on my own?
- Which experiences are “nice to haves”?
Some things are better with a guide. For example, places where local knowledge makes the difference between a good experience and a great one, or where a tour handles logistics that would otherwise be a headache. The Vatican is a great example. Booking a tour that included the tickets meant I didn’t have to think about timed entry windows, I didn’t wait in a massive line, and someone who actually knew the history was there to make sense of what I was looking at. Worth every penny. I also find food tours to be worth doing with a guide. Having a local bring you to their favorite hole-in-the-wall restaurants and telling you about their home is priceless.
Other things I prefer to do at my own pace, without a schedule. That ratio is different for every trip, and figuring it out is part of the planning process.
Itinerary-Building: Where the Puzzle Gets Fun
This is my favorite part because this is where the trip takes shape. Once I have a solid list of things I want to do, I start building itineraries. I usually create three or four versions based on actual timing, geography, and how long things (like transportation) take. What’s close to what? How much travel time is realistic? If I want to do this on day three, does that mean I need to be in this town on day two? I’m a tech project manager by trade, so maybe some part of this complicated planning process is just intrinsically fun for me?
This is also, inevitably, where the hard choices happen. There is always more to do than time allows, and some things just don’t fit no matter how you arrange them. I don’t mourn what doesn’t make the itinerary. I put it on a “next time” list.
I don’t mourn what doesn’t make the itinerary. I put it on a “next time” list.
For my Costa Rica trip, for example, I’d love to volunteer with a turtle conservation program, specifically helping protect sea turtle eggs, which is one of those experiences that sounds extraordinary and extraordinarily useful. But December isn’t the right season for it nor do most organizations need your help for a day, they need it for a couple of weeks. So it goes on the next time list, and I’m already thinking of it as a reason to go back rather than a reason to feel like I’m missing out. That reframe keeps the planning energy positive and the trip feeling full rather than lacking.
Booking: All at Once, Then in Waves
Once I have a clear sense of what I want to do, I book the big things, usually one right after the other. Flights first because they set the frame for everything else. Then hotels or other accommodations. Followed by major transport between locations. Then the big experiences that might fill up: tours, diving, anything with limited availability that I really don’t want to miss.
I’m also doing all of this in parallel with confirming who’s actually coming. By the time I’m ready to book, I need to know exactly who’s in the travel group because booking for four people who are all definitely coming is very different from booking for six people two of whom are maybes.
After the major things are locked in, I let the rest breathe. There are almost always secondary experiences like smaller tours, restaurants I want to try, or day trips that sound fun that I don’t need to book months ahead. I leave those deliberately open, partly for flexibility and partly because some of the best additions to a trip come from conversations I haven’t had yet. Someone I meet at a dinner party in November might tell me about a place in Costa Rica I’ve never heard of that becomes the highlight of the trip. I want space for that to happen.
Booking Timed Tickets
One of the more specific things I’ve learned through years of trip planning: a lot of the world’s best experiences require timed tickets that don’t open up until a set window before the visit: sometimes one month ahead, sometimes two weeks, sometimes six months. The Uffizi in Forence , the Anne Frank House in Amsterdam, the Eiffel Tower in Paris, and certain national park permits, I’ve had to book at specific moments.
When I first discover the booking window, I put a reminder on my calendar one or two days before it opens. That gives me time to prepare: have the credit card ready, know exactly which time slot I want, and not be caught off guard when availability disappears in the first twenty minutes.
Alternatively and this is worth mentioning twice, I find a tour that handles the tickets as part of the package. If the ticket window opens up at 3am Central Time, I don’t want to be up for that. This is exactly what I did for the Vatican, and it removed an entire category of stress from that trip. The tickets were suddenly someone else’s problem, and they dealt with it far better than I would have.
The Final Month
I typically start trip research 6-8 months before large trips and 3-4 months before smaller ones. By 3-4 months before the trip, essentially everything major is in place. In the last month, I pick up travel insurance if the trip warrants it and book any remaining last-minute things.
And then I wait, pleasantly, for the trip to actually happen. We’re ready and this trip is going to be GREAT.
Is It a Lot of Work? Yes. Is It Worth It? Absolutely.
I know this sounds like an elaborate process, and it is. But I really enjoy almost every part of it. The research phase is basically exploration and learning. The itinerary-building feels like solving an interesting puzzle. And by the time I actually get on the plane, I know the destination well enough that I feel oriented without being over-scheduled and I have a strong framework and plenty of room to improvise.
The planning is, for me, part of the trip. The anticipation is real. The Google Doc full of possibilities is its own kind of pleasure and I’m able to share it with grateful friends later.
I’ve thought about doing this for other people (i.e., building custom itineraries for trips they’re planning) and I’m just not sure it would be as much fun if I’m not going, but I’m open to trying it. I’ve planned and booked trips for my husband and I loved that just as much because I was able to live them vicariously through him. Either way, if you’re planning something and want a thought partner, reach out. I’m probably already looking at something similar anyway.
Currently deep into Costa Rica planning for December. If you’ve been and have a must-do recommendation, drop it in the comments. Any and all intel is welcome.
