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How to Plan a Trip in 2 Hours or Less 


*Complete title of this post should really be: How to Plan a Trip in 2 Hours or Less While using Free Wifi in the Airport an Hour Before Your Flight Takes off Before your Final Destination

I’m not a procrastinator, but since I travel so much (no, really I spend 90% of my days on the road) I tend to not give much thought to my upcoming trips until they’re basically in my lap. When a trip to Amsterdam, Berlin, Tokyo, Hong Kong, [insert city name here] is on the horizon, here’s what I do when planning trips on the fly…

1. Pin to your hearts delight. I’m a recent convert to the Pinterest world, but boy has it been a life changer. When planning a trip, I search for everything I might want to see. Sure there’s the obvious “24 Hours in [insert city name post]” itineraries (we create a lot of those ourselves–follow here) but I also like to search for city landmarks (for inspo on the best photo angle), cool restaurants, running routes, clutch photo spots etc. Pretty quickly, you’ll start to get a sense of the city and see trends for the “must-see” places. That’s why searching for more specific items will find you unique spots to discover–like pizza cooked in a disco ball. In general, if I see a cool pic on Instagram or a fun article on the web, I def try to pin and save it for later! Those unique activities are what make a trip memorable! Follow my many, many travel boards on Pinterest here.

Watch this hilarious video about Pinterest and white women. 

2. Reach out to local bloggers! As a blogger myself, I love when people reach out to me for recommendations! I always make an effort to respond timely and provide unique, off-the-beaten-track ideas. People tend to respond quickly on Instagram and Twitter, and typically have an email written on their site, as well. While I was in Vienna, I went to the most adorable cafe (Motte am Fluss) thanks to Tina at Tinera and received fantastic insider tip from Bianca at Elephantastic Vegan to get ice cream at Veganista Ice Cream. In Hamburg, I actually got dinner with a local blogger, Julia from Ms Brightside, at the fashionable Atelier F and made a new friend in the city!

3. Organize your ideas. Now that you have a zillion items on your to-do list, organize them on your phone (I like to use the iPhone Notes app) so that no matter what your cell service is like you’ve got your master plan handy. I like to organize my ideas by categories like food, landmarks (aka quick photo ops), museums (aka stuff with entrance fees and time commitments). I also break the list down into must-see places, versus nice-to-have. Typically, I color code priorities with emojis, checking activities off as I go.

4. Book your hotel/hostel/Airbnb/whatever in center of the city. Regardless of when you book (months v hours before), wherever you stay should be in the center of the city. Sure, it might be more expensive, but ultimately you’ll end up saving time and money (between taxis and public transit) and the confidence will 100% pay off. If you only have a weekend in a city, you def want to make every second count and don’t want to be worrying about logistics of where to leave your luggage when you’re touring before going to the airport. For a comparison of hostels, hotels, and Airbnbs click here.

5. Map out your day. I love a good paper map. It’s very satisfying to mark something up with a pen and carefully fold and unfold it along your journey. However, since technology has progressed and I don’t like being a conspicuous tourist, I’ve taken to creating itineraries based on location in Google Maps. I find all the locations I want to visit and “favorite” them which is designated by a star. The map provides a great visual for what activities are nearby and can get grouped together. GPS doesn’t require a cell signal, so as long as you have a basic sense of direction it’s pretty easy to navigate the city and get between all of your places of interest. This convenience is especially key when you’re hungry because you can quickly scope out the nearest restaurant that you’ve favorited and head directly there.

Trip Planning Tips

Being an exaggerated tourist with backpack, tacky sandals, and huge map in Spain, cerca 2009

6. Create your itinerary. Looking at your map and your list of must see places decide where you want to go and when. Note when things open and close, if you can do certain activities in the dark, and take into account if you’ll be tired at the end of the day, and so on. I also like to check the weather and have a contingency indoor plan (museums, etc.) if it starts to rain. Note if you have to get tickets ahead of time, need a reservation, or have to print something out, etc. Make sure that logistical stuff can get done ahead of time so you don’t show up expecting to get in and get rejected. Ain’t nobody got time for that.

7. Screenshot the important stuff. While I have wifi, I like to enter in important destinations and routes and save the directions. GPS always knows where you are, so even if you’re on airplane mode you can see your location moving around on the map because it’s preloaded. But just in case space monkeys take over the system, I like to screenshot the directions and zoom up on important areas in case the maps don’t load in my time of need. I especially like to do this when I’m planning my route from the airport to the hotel.

For more travel tips, check out my blog post on How to Travel Alone. As well as our It’s Travel section with many travel guides, tips and itineraries!

How do you prepare when planning a trip?

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