Trip Planning

A lot of people ask me, “how did you find that place?” or “how do you know where to go?” Well, I have a LONG list of places I want to go and explore. Working in education, I have lots of opportunities to take vacations. Unfortunately, the timing of those breaks usually makes the trips more expensive. So I use apps such as Hopper and Skyscanner to look at cheaper flights. Both of these sites can track flight prices for me over time. So I may have 15-20 flights being tracked at all times. Every once in awhile I’ll get an alert for a ridiculous deal and that’s how I’ll make my decision of where to go. Once I book the flight, that’s when the fun (planning) begins.

Planning a trip can be overwhelming, solo or group–mainly for different reasons.

Take it step by step. In my opinion, the first step is making a skeleton map/itinerary. What do you HAVE to see or go to? Make a rough sketch of where you want to go and what you want to do and see at these places. Then you can start to get more detailed at each stop/city. Then start at the first stop, and work stop by stop. Hotels are generally the last thing I book. Although, I usually use Booking because (check first) most are refundable unless you’re a few days before your actual trip. That way if you make a mistake or realize you need more or less time at a stop you can easily change your accommodation.

If you’re looking to do a tour that you couldn’t or shouldn’t do on your own, I highly recommend Viator. I have used this company numerous times and recommend them to all my friends and family. It’s basically a company that sets you up with local guides. It has reviews, prices, and details of the tour. It’s very easy and reasonably priced and can be as short as a few hours or as long as a few days.

I’ll use my upcoming trip to Texas as an example. I bought round-trip flights from Tampa to Austin, TX after a great deal popped up on my Hopper App. Then I started with what I wanted to see and do. I know I wanted to spend some time in Austin and a see a few things right outside of the city as well as spend time in Big Bend National Park. So I began researching Austin; what to see, what to do, and what to eat. I visited all my online travel groups, yelp, trip advisor, and talked to friends/family that have been and make lists. That’s how I figure out how long I need in each place and can make reservations (if needed) or book a tour. I figured out I need 4 days in Austin and the surrounding area with a short drive that 4th day. The 5th day was a drive day in the morning and then exploring the town near Big Bend National Park that evening. Then two full days to hike and explore in Big Bend National Park. I use apps like REI as well as my travel groups to find the best hikes, and to make sure they’re manageable–no one wants to schedule two 10 mile hikes in one day in the Texas summer heat!

It took some time but I’ve come to realize I can’t do it all in one trip. So I schedule as much as I think is possible and when it’s time do as much as possible. I’ve had to make adjustments on trips due to weather or blisters on my feet from too much hiking-but it happens. Sometimes those ‘fails’ end up being the most spontaneous fun.

Additional Road Trip Tips