I have been planning trips on my own since I was 17. After doing something consistently for eight years, having a system for it is inevitable. Nowadays, I can plan a four day trip in just a few hours. To be fair, I’m a relatively flexible traveler, but I like things pretty planned out at the same time. I’m not the type of person who just picks a place, goes and waits to see what happens. I make lists, and spreadsheets, and have most boxes checked before I leave. Above all, I like to travel without breaking the bank. I’ve already gone through my tips to afford travel, but here’s how I figure out everything else.
Step 1: Pick the dates (sort of)
The best place to start is to decide when you are going on this trip. You don’t have to know exact dates because adjusting by a couple of days can get you the best deals. But have a window of when you’ll be traveling. For me, the first thing I check is my work schedule. Is there an event I can’t miss or a holiday that I already have off? Then I go from there. Remember that holiday weekends are more popular travel times as are certain months of the year (mainly summer) so knowing that before you begin to plan will save you from any surprises (like the insane price of flights in July).
Step 2: Pick the location
Now that you know when you’re going, it’s time to pick where. The reason I plan the details this way is mainly because of weather. If you’re going in the summer, Florida may not be awesome because it will be a million degrees. If you go in winter, picking somewhere cold with a lot of snow can make travel very difficult. Even for milder climates, some places are a must see in fall, while others are rainy many months out of the year. So it’s good to be prepared for that. Choosing the dates first can also help you avoid peak travel times as well if you want to steer clear of them (i.e. New York on New Years or New Orleans during Mardi Gras). However, you can always make this your step one if there’s somewhere you really want to go, then pick when.
Step 3: Book transportation
Booking transportation is where the flexibility comes in. In this stage of the plan you can decide to fly, drive, or anything in between. This is also where you can save yourself some cash by being flexible on dates and location. Especially for short trips, Tuesday and Wednesday are typically the cheapest days to fly and Sunday is the most expensive. So, try to shift your trip around a day or two to see if the price changes. Some of my best deals have been on Thursdays and Tuesdays. You can also be flexible with your location. Flying in and out of major airports is usually more cost effective because they have a higher volume of flights which drives the price down (like flying from Chicago to Boston instead of to Providence on my Rhode Island trip). If it isn’t too far from your final destination it may be worth checking out. Recently, I’ve been booking transportation separately. Splitting up one-way airfare between different airlines and services is a bit more time consuming, but without fail it has cost less every time.
Step 4: Find Accommodations
I’m the queen of booking lots of places to make sure I get the best deal (but only if there’s free cancellation of course). Sometimes, I rebook the same hotel two, three, or four times if the price changes. Many services will also price match, which can save you the time and hassle of rebooking. Either way, once you figure out how and when you’re getting somewhere, you have time to figure out where you’re staying. First, I like to check comparison sites like Trivago as well as Airbnb to see just where I want to stay. Then, as I mentioned in another post, I go for the most cost effective option.
Step 5: Organize the “must-sees”
Once I know when and where, it’s time to plan out the what. I usually start this process on Pinterest because that is where lots of people post city guides for weekend trips. From there I have an idea of some of the must see things. Then, I look for food, because I don’t like to waste time searching for good eats while I’m there. TripAdvisor and Thrillist are my go-to’s for this. Then I book any tickets, tours, or reservations if necessary. Occasionally, I’ll take this list of things to do and lay them out by day or location so I have an itinerary. More often than not, I wait until I get where I’m going and play it from there.
Now all you have left to do is pack and go! Feel free to also download our Travel Planner to plan all the details.