How-to: Plan a trip + a template

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Flat whites are good fuel for trip planning (The Commons)

Disclaimer: There is no right or wrong way to travel. This is merely a guide of how I plan trips in an organized fashion and I thought it might be useful to others. You mustn’t be surprised at my fastidiousness – the name of this website literally translates to “plan”.

If you’re just looking for the template, it’s here.

Flights

After I have a rough idea of when the trip will begin and end, I start looking at flights – sometimes months in advance, sometimes within a couple days of leaving. If you have the luxury of time, I recommend tracking the most appealing flights with Google Flights (select outbound and return flight, then scroll down and click “Track price”).

Despite normal human preferences, I have left at all hours of the day with layovers between half an hour and 13 hours. The worst layover time is probably between three and six hours. It’s long enough so that your travel time is significantly increased but not long enough to leave the airport. If you find yourself booking these kinds of flights pretty often, it’s very worth it to buy lounge access. Priority Pass is probably the most popular lounge membership – it gets you into over 1000 lounges worldwide with an annual fee of $99 (each visit costs $27 on top of that). They’re typically not the most luxurious lounges but generally beats sitting at the gate for hours on end. You can purchase one-time passes to many airport lounges but some of them require a certain class of ticket.

  • There are also credit cards that offer lounge access – I personally have the American Express Platinum card but I think the best travel credit card overall is Chase Sapphire Reserve
  • The LoungeBuddy app is handy to scope out lounges ahead of time but beware, it may not show all the lounges that you have access to so it’s worth double-checking with whoever you have your membership through

If your travel companions are booked on the same flight but on separate reservations, most airlines offer the option to link your reservations. This means that you will be seated together by default, saving you the mad dash to check in online once the 24-hour window opens hoping to find two/three seats together. All you have to do is call the airline with your booking confirmation numbers. If there are multiple legs and some legs are operated by other airlines, call the airline that the flight is operated by (e.g. if you booked through United but the particular leg of the journey is operated by Lufthansa, call Lufthansa).

  • Which seat should you pick? It depends on the plane so it’s often worthwhile to check out SeatGuru

If you are traveling with other people and they’ve booked different flights, it is highly advisable to share flight numbers. Between unexpected changes (delays, early arrivals) and the possibility that you won’t have wifi/data once you land, knowing which flight your travel companions are on is very helpful. Plus, it’s easier to coordinate transportation between the airport and your accommodations.

Itinerary

Ah, my favorite part. My travel days typically take three formats: (1) full-day excursions, (2) early morning, mid-day, evening or (3) late morning, afternoon, late night.

Full-day excursions are relatively rare. They’re typically a long drive in a rural/natural environment or a booked tour. Early morning starts for me are usually because an activity or point of interest necessitates it or if there’s no nightlife so it makes sense to get the most out of the day. As a nightowl, late morning starts are generally my favorite.

There are three types of items on my itinerary: (a) activities, (b) meals, and (c) travel. Activities could be something like a hike, museum visit, or a walk through a particular neighborhood. Meals are self-explanatory. Travel means flights in/out as well as ground transport to nearby cities. Depending on the trip, I will also differentiate between items that are booked and items that are not booked. For instance, some points of interest and meals require pre-bookings and reservations while others don’t. The same goes for transportation (e.g. you might not need to pre-book a train that leaves every hour).

For activities, I do a lot of googling, often ending up on TripAdvisor or Atlas Obscura. Word of mouth works too, from friends who have gone recently or even better, locals. Reddit is great for that – r/travel can be very helpful, or look for subreddits of your specific destination(s).

Restaurants vary so much between places. Sometimes TripAdvisor is a good resource, sometimes the recommendations are not to my taste at all. I wish review sites would compare your profile to other reviewers’ profiles so that reviews from those who share your taste will be weighed more heavily. In any case, Google is still your friend. As is Chowhound, although digging through posts may take some time.

I’ve also found cool spots through Instagram, just filtering by location.

Bookings & Reservations

The best part of group travel is that you get to hang out with your friends with new and unfamiliar places. The worst part about group travel is that everyone has their own style of traveling and it’s often hard to get everyone on the same page. It will feel like herding cats at some point. This can cause issues with bookings and reservations because you generally need a headcount.

The best you can do with a larger group is circulate a signup sheet ahead of time with a cutoff date to make the booking/reservation. For activities, you can also just indicate that a pre-booking is recommend/required and get people to book their own for the same timeslot.

Misc tips for group trips

  • Expenses: Splitwise will make your life so much easier
  • Communication: Start a Whatsapp/GroupMe/Facebook/etc group chat so you’re not constantly texting four different people “where are you?”

Trip planning template

Do I sound like a nightmare to travel with?

If not, you might find my trip planning template useful. Please make our own copy to edit/distribute (File>Make a copy) for easy group trip planning or download it as an Excel file or .csv (File>Download as) for a solo trip.

How-to: Plan a trip + a template