I'm a little crazy and like to plan my trips a year in advance because I'll know how I'm tracking in terms of my travel goals. This also helps me keep an early eye out for cheap flights if I know where I want to be when.
Is it off your Bucket LisT?
Hopefully you have a bucket list of places you want to visit sometime in your life. Look to that list as a starting point for possible options. Depending on what you have on your list, and how much time you have, you might be able to do 3 weeks hitting 5 cities (ie European cities) or spend a whole week in just one city (ie NYC).
Don't be so concerned about checking all of these places off, but put patient and strategic of which you want to check off first, and when. It's not about how many you can visit and check off, but about experiencing different places, opening yourself up to new cultures, and enjoying great food.
have good company
I ask myself out of these places, where is good for what occasion. I'll just real life examples for myself:
Depending on the location and the specific people you go with, your trip is bound to be different! You don't need to be that specific and picky with every single location, but I think it's good to be mindful of who'd you want to share experiences with based on the different locations. Easy example: going to Vegas with your crew vs. going to Vegas with your family...
Another thing to consider is if you are traveling with family or children, does the destination have family-friendly activities and accommodations?
If you're traveling, make sure it's safe! Check the Travel Advisory website to check the safety level of your destination. I also enroll myself in STEP: Smart Traveler Enrollment Program, which will basically alert you of emergencies happening around you. See my blog about traveling smart for additional tips! Otherwise, here is a list of the best countries for solo travelers!
Timing is everything
Once I've decided where I want to go, I look at my calendar to see when the best time to go is.
What time of the year does it make sense to visit this place? AKA What time of the year is the best weather? I generally save my #1 draft pick for October since you can make a safe bet anywhere will have amazing weather in October, and it's generally cheaper since it's off peak.
I'd also consider peak events and seasons of your destination: you probably don't want to go to Miami in April when every college student will be there for Spring Break, or Austin in March when everyone will be there for SxSW. Or maybe you do, who I am to assume?
I try to avoid peak seasons and cities when I know there will be an increase in population density. They also tend to be more expensive in flights and accommodations, and airports tend to be more crowded that usual.
I've finally decided...
So once you have an idea of the place(s) you want to go at a certain time of the year, go ahead and look up flights to get a gist of how much it would cost. Then, track your flights and subscribe to alerts for any fare drops so you can sense fare patterns and trends to help you purchase flights at the best time.
How to find the cheapest flights, is a separate post... to come soon.