My Favorite Trip-Planning Resources

Whether it’s flight deals or getting from Point A to B, here are five of my favorite trip-planning resources.

As I sit here at jury duty — ugh, jury duty — I have one of few options. I could work, but with overly dramatic HGTV Love it or List it blaring, the ol’ brain’s having trouble focusing. I could sleep, but the wooden waiting area benches are just slightly more comfortable than a church pew. (For those who don’t do church, that’s not cozy.)

Or, I could do something that requires little focus and always awakens my senses: trip planning!

Planning an upcoming adventure — in this case, Cape Town (what, what!) — is one of my top five favorite things to do. For real. It’s ALMOST up there with eating cheese, and that’s saying something. Because I heart cheese.

But, from talking to friends and colleagues, I’ve learned that many either don’t know how — or don’t want — to plan their vacations. And that’s totally cool; it leaves more planning/planning help for the rest of us!

Over the years I’ve been fortunate enough to not only plan a number of amazing trips for myself (cough, Iceland, Italy, Oregon, cough) BUT I’ve also convinced my friends to let me plan their adventures … which takes little convincing because it’s essentially free labor (err, right, I should think about that…).

Anyway, free labor or not, here are 5 of the trip-planning resources I rely on regularly – plus one resource to avoid at all costs!

1. Pinterest
Pinterest is a powerhouse when it comes to trip planning; it’s basically the picture book version of Google. (And I love picture books!) It has an insane amount of articles from tried-and-true sites like Lonely Planet, but my favorite part is you get original, unpolished stories from up-and-coming travel bloggers who give raw accounts of recent trips. While the articles may not be totally professional and are hardly written in Rick Steves prose (like this blog… I mention cheese in the second paragraph. Because #cheeseprobz), the content is significantly more unique and the activities/ sights more off-the-beaten-path.

I’ve scoured the “Cape Town” and “South Africa” Pinterest search results while planning our November trip and found several tidbits I would’ve otherwise missed!

2. Google Maps
This is going to seem so ridiculously elementary, but bear with me. Once you know the area you’re visiting, pull it up on Google Maps, zoom in, then scroll up, down and all around the area (within a perimeter you’re willing to travel).

When we were forced to cancel our Big Sur trip due to wildfires last year, we had to improvise and uncover a new destination. I knew we could hit up Sonoma Valley, and realized we could obviously just stay in San Fran, but I wanted something more. Something unusual. Something off the main drag.
Enter Google Maps. I scoured the California coastline and after 30 minutes scrolling up, down, in and out, I noticed a little area called the Lost Coast some 4 hours from San Fran. After researching, I learned this remote, relatively untouched stretch of Cali coast was home to dozens of seals — and hardly any tourists.

You can probably guess where we ended up…

3. Google “My Maps”
I promise this isn’t a sponsored post for Google BUT one of my absolute favorite tools is Google’s custom/My Maps feature. This tool lets you build customized maps for your trips so you can plot out distance, timing, etc., and plan your day’s routes based on what makes the most sense.

I use it for two reasons:

• One, it’s perhaps the best road trip planned out there because you can set specific routes like day one, day two, and it provides distance, driving duration, etc. Super helpful!
• Second, I have a terrible memory so I like to “pin” every possible thing I may want to see so I don’t forget. This works especially well for less planned trips. If I find myself strolling through a random neighborhood, I can open my map and see if any of my marked destinations are nearby.

4. Next Vacay
I just started using this, and will be honest, I haven’t actually purchased a flight from it (because I’m out of vacation days…) but Next Vacay is an amazing, cheap service ($25/year) that finds and shares great flight deals for everyday working people, like myself. Just about every day I open my inbox to options like $300 NYC to Paris, $400 to Rio or — wait for it $550 to Kilimanjaro Airport (a flight that normally costs $1,500+!).

As I mentioned, the deals are for normal, (sadly) full-time workers like myself who have to leave on popular and usually more expensive travel days like Thursday/Friday. As I plan next year’s adventures, you better believe I’ll be capitalizing on those Next Vacay deals!

Update: A new tool I’m just loving is Skyscanner! Talk about wanderlust, ensue — this site has an “explore” option that gives you all sorts of trip options based on your origin of travel. For me? I’m really leaning toward a return trip to Morocco…

5. Meet Ups
If you want to go beyond travel activities and actually meet people in your new destinations, attend local meet ups that center on your passions and hobbies. I’m involved in the creative and travel communities here in NYC, and moving forward have a goal to attend Travel Massive meet ups in other countries or check out Creative Mornings seminars around the world. Finding people with common interests makes communicating across cultures incredibly interesting and gratifying!

6. BONUS: Use ANYTHING but Instagram (AKA, Avoid Insta Travel Ideas)
For a while, I loved the idea of finding new destinations or sights on Instagram; it’s how I found Seven Magic Mountains and Horseshoe Bend on our Southwest road trip. But here’s the thing (and I’m embarrassed to admit this): The more I visited Instagram locations, the more I realized my photos looked exactly like the shots I found on Instagram (which looked exactly like the shots those people inevitably found on Instagram). The platform has its perks (I love the friends I’ve made through it!) it hinders creativity and drives people to visit places for likes and follows, not authentic, unposed adventures. No thank you.

So there you have it! These are my favorite tools & tricks for planning the perfect (or if we’re talking Portugal, imperfectly perfect) adventures! I hope you have as much fun as I do piecing your trip together, and in the meantime, I’ll just sit here at jury duty … alone with my boredom and a cup of crappy coffee…

Disclaimer: This post was created in collaboration with Skyscanner, but all wanderlust obsessions are very much my own!