1) Know When to Go
I don't spin a globe and book a flight. I get inspired to travel to a certain destination by watching Anthony Bordain's Parts Unknown (currently running on Netflix) or the travel channel. A destination may peak my interest after reading a section in a travel magazine. I follow dozens of instagramers and digital nomads who document their vacations...and so on. Once I've chosen, I do research on the attractions and activities as well as the history. One of the most important aspects I recently started paying attention to is the holiday/festivals. Look up when and where they take place. I imagine it would be dreadful to depart a day or two after Brazil's Carnival. If only you had known that Spain's La Tomatina (throwing of tomatoes) started two weeks ago, your itinerary would have let you take that experience home. But it's okay. Next time.
2) Make a List (Give Yourself Time)
Once I have found out the best time to go, I will make a list of all the things I need to accomplish. What museums, which landmarks, who's restaurant, which temple, how many trains to get there...yes, it's homework. I love and hate this step so much because I get super anxious and excited at all there is to do and see and taste and learn that it's difficult for me to stay focused and make sure I don't make any booking mistakes that could potentially cost me a non-refundable $400 plane ticket, or oops!... I got the dates wrong, or overlapped hotel stays or failed to calculate in the time it takes to get from the hotel to the airport. When I'm trying to figure all of this out it's truly a mission to just sit still. But I want to book right away. I don't want to research anymore, I just know I'm ready to go. Like tonight! Book now, CLICK IT!!...Breathe. Lightning strike on whoever said ADD isn't real.
One important thing to remember when creating a list is to give yourself time. Beside the activity, I'll write the cost, how long I predict I will want to spend based on other peoples' reviews and advice, and how long it takes to get to and from. More time is better than rushing to get to everything. It's simply not worth the stress of running from temple to mountain if you cannot take it in. If you have overestimated your time then that means more free time to explore or do something you didn't anticipate.
The number of vacation days, or amount of time away from family may need to be considered when figuring the duration of your trip. So the duration of your trip is in your own discretion.
3) Book Transit First
Book that flight that you've been monitoring for how ever many weeks or months (refer to Hopper; also the tips tab). Once you have found the plane ticket price that best resonates with you and your time window, Book it. That train to the next country, or that day trip bus, Book it. I say book your transit first because as long as you're at your destination, you can figure out your tours, stay and everything else out later or even once you're there. Don't pay for all of your excursions and accommodations without having a way to get to them. That just simply isn't recommendable. It is better to arrive and figure it out than to be stuck at home with some tour company reselling your seat to someone else.
4) NOW You Can Make the Reservation (Call Around)
Now you can go ahead with filling up your schedule. When making my schedule I use Trip Advisor, and Google. Google is the world's greatest invention. Trip Advisor is a bit over commercialized when it comes to activities and tours. It caters to the cookie cutter tourist. I try to find private tours in the nooks and crannies of the web to get that real personal level experience. Email to make sure their site or tours are still running. When communicating with whomever is hosting/guiding, inquire about the reservation times (duration, pickup/dropoff). Because you want to ensure that you have gieven yourself time (step 2).
If you haven't already or are looking for the best prices for accommodations, it could benefit you to call around. I don't always do this. I only do this when I'm really in need of a good deal. Sometimes the price on the website isn't listing the actually price of the room (mostly pertaining to apartments). If you need to get ahold of someone with an international number, download the TextMe app. It's friendly toward both iPhone and Android. Once you add credits, you can call or text anyone in the world. Credits are very reasonable. I paid $8 for 500 credits. I used them in Germany, Croatia, Slovenia, and Mexico and still have over 100 credits left. Calls and texts within the US and Canada are free.
5) Print EVERYTHING
I mean just that. Depending on where you are, you'll need to have physical copies of your flight itinerary. Some airlines do not accept smartphone e-tickets. Print out receipts incase they ask for proof payment. This may sound extreme but you never know. I have been asked to provide proof of payment in the past. Fortunately, I had a copy of the receipt in my iPhone. If they didn't take e-tickets like some scenarios I have heard of, I would have been up a creek. Hotels/hostels can screw up your reservation. If you have proof of payment and reservation, they don't have an excuse. It is better to be prepared. This step is easy.
For tips on how to travel lightly...