5 Ways Planning a Trip is Almost as Fun as Going On It

Over the last few years, I have begun to realize that going on a trip is only about 20% of the thrill. I honestly believe that planning a trip can be the other 80% of satisfaction you get from the vacation. Is it just me? Am I a super-nerd? Maybe. But I’m going to share with you the ways in which you, too, can make planning a vacation all part of the wonderful experience of travel.


I believe whole-heartedly that the earlier you start planning your trip, the better it will turn out. Find out all of the things you want to accomplish while you are there. It is likely that you have a limited amount of time to spend, so you have to figure out how to order these priorities so that you’re able to experience everything. It’s like a puzzle—how can you fit these excursions and must-sees together in a way that is the most time efficient?

Otherwise, you show up in a destination and you’re simply wandering around looking for things to do. When you have a plan—I would even go so far as to say when you have a day-by-day itinerary, you’ll see and experience so much more than you ever could without one.
But don’t plan out every minute—leave a day or two here and there for improvisation if you have time for it. Wandering can be the highlight of your trip. My point here is that you don’t want to come home from that destination halfway across the world and wish you’d have done something you didn’t. Many times that will be the first and only opportunity you have to see that place.


My absolute favorite planning tool. So many times people sit down at my desk and ask me “When is the best time to fly?” or “Isn’t it cheapest to fly on a Tuesday or buy your flights on a Wednesday?”
If I knew the answers to these questions, I would surely be a millionaire. There seems to be no rhyme or reason to the pricing of flights and no pattern to how they fluctuate. I’m the most wishy-washy person in the world when people ask me those questions because my reply is always something like, “Not necessarily,” or “There’s really no way to tell.”
Google Flights is my solution to this. It’s a tool that allows you to view a month, enter your origin and destination, and search through (most) all of the airlines at once to show you what is the cheapest day to depart. You can filter the results by non-stop flights, times, airlines, and even add multiple airports to see which would be the cheapest to fly into. This makes planning not only easier for the flexible traveler but a bit of a fun challenge. Save itineraries and watch them over the course of a couple weeks, then when you see a price you’re comfortable with, jump on it.

GOOGLE FLIGHTSI’m giving away all my secrets here but that is your advantage to following my blog. 🙂


My personal favorite is Lonely Planet, but try out a few at first to figure out your travel style. Lonely Planet is my style because it’s geared more toward backpackers than vacationers and has out-of-the-way attractions as well as tips for exotic destinations. The accommodations are often B&B style recommendations and the restaurants are usually local favorites and tourist spots alike. I first tried a Fodor’s guidebook and it just wasn’t for me—I couldn’t relate to it or get excited about what I was reading. I think it catered more toward luxury travel and travelers that are more timid than I, but that doesn’t mean it’s not the perfect guide for someone.

A guidebook is perfect to get your mind jogging–to really put you in that place before you’re actually there. You can highlight restaurants and put attractions on your must-see list that you never would have known about otherwise. There are maps, safety tips, health advice, and so much more—and although I think they could be a bit too bulky to lug with you on the trip, I would definitely recommend leafing through one before you get to your destination. They help with planning but they really get you pumped up for what you’re going to see and do while on your trip.
You can get used guidebooks on Amazon for cheap. They’re always coming out with new editions that are more expensive and updated but I’ve never had a problem using the prior year edition as of yet.


If there is a Bible for travel consultants, TripAdvisor is it—at least for me anyway. There’s no way for one person to know about every destination, every hotel, and every attraction in the far corners of the globe. TripAdvisor helps to make the world a bit more manageable.

We’re in a time where glossy magazine ads and Photoshopped pictures and commercials just don’t convince us anymore. Anyone can say their hotel is the best.
Did you know that there is not actually a universally accepted star rating scale for hotels? In the US, there is a system for rating hotels based on the amenities they offer, the quality of the facilities and so forth. But in foreign countries, anyone can say they operate a 5 star hotel. Don’t base your decision of where to stay on a star rating, as you could end up in a 5 star cockroach-ridden cardboard box of a room.
We want to hear from our peers what they thought of a place. Getting lost in the stories and reviews of others who’ve actually been there is a huge chunk of the fun of planning. I’ve actually pulled up TripAdvisor with clients at my desk and showed them hotel pictures from real travelers. I want full disclosure with my customers—I’m not going to show them the pictures from the hotel’s website. If it looks nice in pictures from real people then chances are it will look nice for them when they get there.

But don’t get overwhelmed by reviews or let them hinder you. Even the nicest of hotels can’t please everyone. And make sure there is a large pool of reviews to choose from. A hotel with a 100% rating and only 2 reviews may actually be horrible and those two reviews could be one from the owner and one from the owner’s cousin.



Message boards are also an invaluable resource. If you don’t know anyone who has been to a certain place, what better way than to ask a bunch of fellow travelers for their opinions and personal experiences.
I’m currently planning a trip to Peru. Peru is a very large and mountainous country. I posted a question on a forum on TripAdvisor asking basically “What is the best way to get from Puno (Lake Titikaka) to Cusco (Macchu Picchu)?” There are many options, but I’m trying to find out the best for me—fly, train, bus? I got nearly 20 replies from people who’ve actually made the journey themselves. “If you have a lot of time, take the bus.” “If you’re in a rush, fly.” “The train is very expensive but scenic.”
Not only was it helpful in planning the logistics of my trip, but I had some pretty nice conversations with these people. Many of the responses came from people who live or work in Peru. Who knows, maybe you could even make a friend who could be called upon for help in case of an emergency while you’re there!
If you’re going on a group guided trip, many tour companies also have message boards where travelers can meet and chat before their trip. For example, G Adventures has what’s called the Watering Hole. You can talk to others who will be in your group or people who have done the same tour you’re about to do. It’s a great way to see different ways of traveling for others and to get a head start on friendships that could last a lifetime.

Take these tips and start planning your next trip. The ideal time to start is about 10-11 months before you’re adventure. The anticipation of a trip will give you almost as much satisfaction as going on it. There are actual studies that prove this! Don’t wait—just put it in motion.

When the time finally comes to travel, you know that it is truly your own creation. When I come back from a trip where everything went like clockwork, I really do attribute it to my meticulous research and time spent on making sure I was knowledgeable about the area and what to expect. The trip is the gift to yourself for all of your planning and it is the best way to wrap up the year—by turning your vision into a reality.

Until Next Week,