Fashionably Nerdy Adventures: Trip Planning Apps

Though I have been an avid traveler for pretty much my entire life, I have always been more of a “getaway” traveler. My vacations usually consist of a few days away for an extended weekend, or maybe five days. Heck, when my husband and I got married in Las Vegas, we only stayed three extra days for our “honeymoon.”

I think these travel patterns have more to do with the types of jobs I have held, but also just the fact that I couldn’t afford to take an extend amount of time away from work to do any extended travelling.

Well friends, I am pleased to inform you that I am currently in the process of planning my first ever extended (overseas) vacation. My husband and I are really excited to be taking 15 days in the fall to go explore the United Kingdom and Ireland. This is a big deal, and a major bucket list item for us.

For someone who is used to planning trips that only last a few days, I was pretty intimidated on where to even start. I did a lot of googling to find the perfect travel planning apps. Some of them, I find via recommendations on the web, others were recommended by friends, and yet another was actually found through my preferred airline for domestic flights, Southwest. All of these apps work well for me to fill a unique set of needs.

  • Tripit: Tripit is basically an app that allows you to organize all of your travel itineraries. It came highly recommend from reviews online, but I couldn’t believe how amazing it was once I finally started using it. Once I made reservations, I can just forward all my hotel, flight, car rental, and restaurant confirmation emails to, and the app creates a master itinerary that I can access anywhere (even when I am offline). I immediately forwarded all my travel plans for my upcoming trips to Pittsburgh, Chicago, and the UK and suddenly felt super organized. My Pittsburgh plans even include a car rental. We have booked our flights from the US to England (and back), as well as a flight from Scotland to Ireland, but not to Scotland from England. Since I have already booked my hotels in Scotland, the app has been reminding me that I need to add a flight to get there. This is a really helpful feature when planning such a long trip, and it should help us avoid making any mistakes while booking the rest of our excursions.
  • Skyscanner: Skyscanner is a a mobile app and website that helps you find deals on hotels, flights, and rental cars. It was actually recommended to me via a friend on Facebook. They don’t charge booking fees like most other travel search engines, and you can save flights, set price alerts,  and read reviews on hotels. My favorite feature is that the app gives you recommendations on where your next adventure should be. I get lost looking at all the cities I could run off to for my next long weekend, and I’m already planning that next European vacation (hopefully in another year or so). This app was absolutely essential in helping me find the best prices for my flights.
  • I actually only discovered because of an upcoming trip to Pennsylvania. We had already booked our flights through Southwest, and a month later I got an email from Southwest reminding me to book a hotel. Until receiving this email, I had no idea that you could book with partner hotels through Southwest to earn flight rewards. This feature is powered by Not only did I find amazing hotels, they were also for amazing prices. The app gives you detailed maps, as well as reviews of the hotels and surrounding area. In every single location that I used Booking, I found hotels using their amazing “location score,” to make sure that I was staying in a favorable place in the city. With most reservations, you don’t even pay until you check in, which is a huge bonus. If you book through the main site, there are even perks to unlock for frequent reservations, but since I would rather earn flyer miles, I booked through Southwest. Once you have your plans, you can add all your reservations into the app, to keep track of all your hotel details. With most of the bookings, I was even sent a travel guide for the city. Score!

These are three main apps I have been using to book my upcoming travel.

What other travel apps are essential for planning a long vacation? Which travel sites can you not live without?

  • Stephanie Pressman

    not an app but a website : travel pirates is super great for deals
    also I used to love priceline’s name your own price and
    air b&b is great for oversees housing
    we could not live without google maps in japan though google translate left a lot to be desired.