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  • Oriana Skylar Mastro

Organizing Adventures - Travel Edition

Updated: Jul 19


My husband and I go on two big trips every year – one around his birthday (July) and one around mine (December). We don’t get each other presents. Instead, the non-birthday spouse plans the trip for the other. Since we both love traveling I think it is a better way to use our funds than buying gifts. This, of course, means vastly different types of travel as well. We go to Tajikistan to drive the famous Pamir Highway for my husband’s birthday, a private island in Borneo when I hang out at a spa all day for mine.


Of course, now with two small kids (and a post-ish COVID world, almost, hopefully?) our vacations are a bit different. But the need to plan them is still there!


I have separate posts on packing, pre and post-traveling admin (like dealing with cell phones). And if I’m going overseas for more than 30 days, there is a whole other list of things to do. Keep an eye out for a post on that. But for now, let’s focus on the actual planning of the trip itself.


Plan and pay the setup costs. Before you start your planning for this specific trip, its useful to review your status with airlines loyalty programs (see how to manage your airline miles). I also have a list of travel related vouchers that I need to use and their expiration dates (esp. given COVID cancellations, I have quite of few of these). I have one Evernote called ‘travel’ which has links to the specifics of the vouchers and perks we have.


If certain vouchers, free nights, miles, whatever are going to expire, I make a note to try to use these in the upcoming trip. We have travel perks through our credit card (I have booked work conference hotels through the chase travel program, and I get funds for the spa and free breakfast, early check in, late check out. Win) and through our USAA membership, so I review those.


I also review my performance notes on my hotel, rental car, and lodging notes (this of course requires that you put these together as you travel). This reminds me that a small SUV does not fit our luggage and stroller (learned that the hard way in France), to make sure the Airbnb has a washing machine (a non-negotiable with babies) and to ask about bathtubs/highchairs/cribs, so we know if we must bring our own. I also have a list of lessons learned when traveling with kids, like don’t take flights before 10am if you can avoid it, and overnight flights are easier than daytime ones if they are more than 10 hours long. Anyways, these past performance notes help me chose between travel options.


There are two levels of travel planning. First, I book flights, accommodation, and rental car/trains/buses between cities. I also make sure I have the needed travel documents (visas, passport not due to expire anytime soon, etc.) Then I book museum and event tickets, restaurant reservations, and anything else that can sell out or take time to book. In some places, a ticket gets you out of hours of waiting to get into a museum (often the case in Italy and France) so it’s worth to booking ahead. Other times you can just walk in and get tickets – you just need to do the research and know which sites are which.


Putting it together. Once I’ve booked everything, I put together a complete travel itinerary for the level one travel stuff (flights, ground transport, accommodation) I like using Tripit to put most of our itinerary together because you just forward emails to plans@tripit.com and it puts together the itinerary for you. I then read through to make sure I got all the dates right for everything (I have booked tickets on the wrong dates in my pre-professor admin awesomeness days). I also double check that I put in our relevant loyalty information for each and make a note to myself if we have already paid for all or part of the reservation.


For the restaurants, tickets, activities for things while we are there, I like a bit of flexibility (especially if I’m traveling with the kids). So, I create a word document and list for each location if there are certain activities that are better in the morning or afternoon (due to opening hours, crowds) and another list for activities that are dependent on certain types of weather. We can usually choose restaurants the day of, but if reservations are required, I make those and note which nights they are. I may also list the types of food I want to try.


Produce reminders. Usually this doesn’t happen all at once, plans are dependent on other plans. So, for example, we are planning to go to New Zealand in September, but the travel bubble is currently closed as we are in lockdown in Sydney. So, I have created an Evernote reminder for myself that I still need to get the plane tickets and visas once the bubble opens (the accommodation and car rental are fully refundable, so I already took care of those). I’m also going for work so I need to confirm my work schedule before I can book the fun activities, so I have reminders set for what I need to get tickets/reservations for. I also create a reminder on my packing Evernote for anything that I need to buy before we leave.


Performance Notes. It’s useful to make notes not only on how you like to travel (I like to travel place to place in the afternoons, not mornings; I like to be able to walk to restaurants from where we are staying because I hate driving), but also on the specific lessons learned from booking things. For example, if I note our baby in my search, AirBnB restricts the properties I can see. It’s better NOT to put that and then contact the owners to ask if they have a problem with me bringing a baby. I know that if I have a leg that is operated by another airline so I can’t choose seats when I book our tickets, I can always call the airline directly to get our seats ahead of time. I always search on big engines like momondo to get a sense of availability and pricing, but always book directly through the airline or else you won’t get the mileage credit (and you are screwed for customer service if something goes wrong). I wouldn’t remember these things unless I wrote them down.


This is just for the travel part – I also research books and activities to get the kids to expose them to where we are going; research and make a list of books to read, movies/shows to watch, music to listen to, museum exhibits and restaurants to go to close to home to get the most out of the trip. But hopefully this gets you started whether you are planning a real trip or just a fantasy one as we wait for the world to return to kind of normal!


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