Trip Planning 101 – How I Plan My Trips

There are two types of people: people that would happily give their credit card over to a travel agent so they can sit back, and people who look forward to planning trips almost more going on the actual trip. Guess which one I am?! (I do take payment via Venmo, cash, or PayPal if you are interested in my services)

There is, however, an art to planning trips. The internet, of course, makes the process easier than ever, but it’s also an overwhelming resource to have. So where to begin? I’ll tell you my process of how I book trips, stay organized, and make itineraries that I’m (almost) always happy with. Here we go.

  1. Start with flights

    Obviously, lol. One of the most fun ways to book a trip is to give yourself a window of time that you can travel and book a destination based off that and wherever is cheap at the time (instead of just searching for flights to Rome, for example). This way, there’s still some excitement left in where you’re going and what your trip could end up looking like. Something to always keep in mind: If you want a trip in Italy, your flight doesn’t have to land in Rome. Look at surrounding airports, even outside the country/city you truly want to see.

    Google Flights is my top resource for booking, as they show convenient calendars with options to customize the length of the trip, good flight prices highlighted in green, and a new feature now stating whether a bag is included in the price or not.

    Read up on my cheap flight tools and tricks to see more on how I get the best deals.

  2. Befriend Maps

    One of the most disappointing things about planning trips is thinking you can bop over to another city/country just to realize it’s not close at all. I always look at Google Maps to see what’s a) realistic, b) possible, and c) available. For example, if you’re on a short weekend trip and a city you want to see is 6 hours away, you probably shouldn’t squeeze it in– it’s not realistic. If you don’t have a rental car and you want to visit a remote town in the countryside, it may not be even possible. And lastly, what opportunities are out there that you didn’t even think of or know of?

    My friends and I are looking at planning a trip in the spring and there was a good flight deal into Zagreb, Croatia. I initially thought we’d visit Dubrovnik and whatever else was around there, but we realized we could see Slovenia and northern Italy without spending the whole trip in the car. Our beach-hopping Croatia trip turned into a mountain trek! My point is, being familiar with maps can completely change the route and vision of a trip.

  3. Utilize Pinterest

    This is my number one resource for planning the outline of trips. SO many bloggers share their itineraries and ideas on trips, and many times there will be 5 day, 10 day, or weekend trip itineraries that do almost all the work for you. Search keywords like “One week in Portugal” or “Los Angeles weekend trip” and you’re guaranteed to find both popular spots and places worth skipping.

    On this same note, it can be easy to get swept into tourist traps or places that may be cool, but not for you. Know what you enjoy and look for that– even if you don’t think you can find it in that spot. On our next trip, my friends and I are trying to spend more time hiking and visiting cool nature spots, rather than strolling through museums and buildings. Instead of searching for European itineraries, I’m now looking at top European hikes, best nature spots in Europe, etc. Know. Yo. Style. And follow me on Pinterest where I compile MANY itineraries sorted by continent.

  4. Read Reviews

    You know how everyone says social media is a scam and nothing is ever like it is on Instagram? Same goes for websites. A hostel/hotel/Airbnb is ONLY as good as its reviews. This part of trip planning takes time and patience sometimes, but looking through accomodation and transportation reviews is what keeps things going smoothly while traveling.

  5. Find food

    Surprisingly, this is a new addition to my planning services. I was always VERY focused on the towns we would visit and how we would get there that I didn’t spend much time looking for good food. LOOK FOR GOOD FOOD– enjoying every meal made our Central America trip 20 times better.

    Most countries use TripAdvisor as their rating website over Yelp, so start there. One tip from me: sort your food by “most reviewed” instead of “highest ranked” to see the places that a ton of people have visited. Usually those ratings are worth a little more : )

  6. Good ol’ word of mouth

    Because speaking to people is helpful sometimes! In all honesty, though, trust the locals and trust the people who have done it before you. Sometimes I get ideas from people through social media, but asking people about their hometown or trip experience is an awesome way to get some insight on something that may not be public knowledge.

    And there you have it! These methods aren’t for the people who need every spot planned out (I’m not that Type A) but for people who need a rough itinerary with ideas of what to do/eat once you get there. See below for an example of what my “itineraries” look like going into a trip. This way, you don’t waste time searching for restaurants and activities, but you still have the freedom to switch things around if needed.

How do you plan your trips? What am I missing out on?