Sharing some of the pieces involved when I plan trips - some specific to my situation, but some may be more generic.  This is from the experience of my 100+ trips I've taken in the past few years.


What are the goals of the trip?

  • Take advantage of a long weekend
  • Meet up with friends at a certain place in a certain time slot
  • Tack on to a work/personal trip
  • Sitting at home for too long

Picking a place to go:

  • US specific holidays: Go international to avoid full flights
  • Take advantage of the season (eg: Summer to Europe, Winter to Asia)
  • Go somewhere warm
  • Foodie trip, chill trip, explore somewhere new or re-visit an amazing place
  • Optimal flight times or empty flights, or flights with biz/first class availablity

Usually this involves using 2 tools - Google maps, and Google Flights.

Flight Planning

Now that the location(s) are decided, it's time to get started on planning. A couple of things you should have an idea of:

  • When is the earliest I can leave, and the latest I can get back?
  • What is the ideal # days I need in this city, and the minimum? (A quick google search on "things to do" would be sufficient)
  • If I'll have too much time, can I tack on another nearby city? If so, should it be a long daytime layover, or an overnight stay?

Now it's time to research on flights. Google flights is your best friend here, and these are some of the features you should take advantage of:

  • Filter for direct flights only, or up to 1 stop
  • Enter multiple cities as your origin (eg: sfo,oak,sjc) or dest
  • Sort by flight times (to fit your earliest/latest time)
  • Pricing calendar (less relevant to me, but it does tell me which days are popular and I should avoid)
  • Filter by specific airlines
  • You can even leave the dest empty, and let Google suggest what flights are available with the filters above to pick where you want to go or do a layover

The results of this research may lead you to revisit the location of choice, since flight times may not allow the initial plan (eg: I wanted to take a flight after work to HND, but it'll get there late and there's no more flights to FUK, so I should consider staying a night in Tokyo - which I actually did for Thanksgiving).

Related (future posts):
- Research for standby travel
- Tips for booking a Hotel/accomondation

Now that you have the flights figured out, don't quite book them yet! You need to validate that the specific city you're going to can accomondate the flight times you picked..

If arriving at night (after 6pm):

  • Are there transport options to get to your hotel, and how long does it take? You may miss the last train, or they may not have uber, or an additional late night fee on taxis
  • Do you have a good buffer if you have to change trains, or navigate around the airport or connecting station, and potentially a language barrier?
  • Is the area of your hotel relatively safe to walk around with a noise making suitcase at night?
  • Is the currency exchange or ATM open at the time of arrival?
  • Consider finding a hotel at or near the airport for the night to reduce the stress, given that it makes economic sense

If arriving early morning (before 7am):

  • Does your hotel allow luggage storage?
  • Am I going to have stuff to do at 7am when most things are not open yet and I can't check-in to my room early?
  • Will making the trip to my hotel mess up my travel plans?
  • This is usually the best time to spend on a longer train ride outside of town, but be mindful that you were just stuck on a plane for a long time.

If departing early moring (before 9am):

  • Consider transport options to the airport early morning..
  • Consider staying near the airport the night before so you don't have to wake up super early, especially if it's cheaper to do so.

For connecting flights:

  • Is it a transfer that may require going thru customs and bag recheck, or security re-screen?
  • Do you have to change terminals? Does it require re-clearing security?
  • Is it a busy airport that may delay your flight and miss your connection?
  • Are you in the back of the plane that'll take 15 min just to get off?
  • Allow time for the above.. 50 min may be doable for an easy connection, but sometimes even a 2 hour connection can be tight.

For shorter stays, verify that the logistics will not eat up your plans. Some examples:

  • A 6 hour layover in Hong Kong will not get you much if you need some time to get thru customs, 2 hours to get to/from town, and buffer 2 hours to get back to the airport before your flight.
  • It may appear you have most of the day if you're leaving Osaka on a 5pm flight, but a 2 hour buffer plus 1.5 hours train ride (plus buffer for getting lost in Namba station, and if you miss a train) means you need to get back to your hotel to grab your luggage at around 1pm. Plus if you want to grab something to eat before your flight because you're on United, buffer an extra 30-60 minutes.
  • Other things to buffer:
    • The customs line (Europe: both inbound and outbound can be 1+ hour, Asia: usually just inbound takes long)
    • Airport security (Hawaii, East coast, and European airports are more problematic)
    • Checkin and bag drop (Can get long during peak hours)
    • Distance from train station to gate (train within the airport like CDG/SEA/LAS/HKG or the endless walks like NRT T3 or HNL)
    • Rental car shuttle travel time and frequency
    • If you want to grab food, chill at a lounge, or do some shopping

It is now time to book your flights! Be sure to do this as soon as feasible since flight prices change quickly, especially for long weekends.

Things to do

On to the fun part! These are the sources I use:

  • Physical tour guides from the library (preferably the Chinese ones)
  • Google (Search the city name plus things to do.)
  • Travel blogs
  • Food review sites for that location

Tools to keep track:

  • Google maps
    • STAR the places I want to visit
    • HEART the potential food places I want to check out
    • FLAG the potential hotels I'll stay in

Over the years I've tried creating an extensive excel spreadsheet, detailed document, a time slotted list, but ultimately I've found using Google Maps to be sufficient, especially for short trips. It can be supplemented with a Gmail draft if I needed to get the specific timings right (tracking flight times with activities, open hours, etc). Having both of those available on my laptop and offline on mobile also helps with execution.

Once you have everything saved, you can carve out your time slots based on location. Things to consider when carving:

  • Transit options to the places you want to see
  • Consecutive timeslots available
  • Visiting restaurants around meal time, but avoiding peak times
  • Open hours, or optimal time to visit (eg: the viewing deck at night)
  • If you expect to be buying/bringing stuff with you, such as shopping or beach attire
  • Taking breaks for long walks (by chilling at a coffee shop, taking transit, or back to the hotel)

NOTE!! Some places have a sparse transit schedule (eg: 5 trains a day) or trains with reserved seats only - and require more careful planning.

Accommodations Planning

This can be done before your "things to do" list is finalized, but you must have an idea of which area you will visit, as this affects where you want to spend your nights. In general, there are 3 options:

  1. Stay in the tourist area
  2. Stay near the large transit station to the airport
  3. Stay near the airport

How these are picked depend on the city you're visiting. Some selection criteria:

  • Costs (for the hotel and transit options)
  • Timing of flights
  • How far you're willing to drag your luggage vs time spent getting to where you need to go
  • Duration of trip

You may also decide to split in different hotels if you're visiting another city, optimize for flight schedules, or there are pricing variations for weekday vs weekend.

For car rental or uber trips - main considerations are the parking situation in tourist area, parking charges at those hotels, and distance from airport to town. I usually optimize for food.

Here's a quick chart of a handful of cities and my recommended hotel locations (optimizing for 1-2 night stays):

City Optimal Location Reason Time to Airport
YVR Richmond Heart of canto food. 5 (drive)
HNL Waikiki The food central, bus to airport 25-60
OGG Kihei Cheaper accomondations 20-60
KOA Your resort A car is a must ---
LIH South side Car required 30
CTS Sapporo JR 10 min walk to tourist area susukino 40
HKD Yu-no-Kawa Onsen Onsen town! 10 min to airport 10
NRT Shinjuku Tourist central, train to airport 90
HND Ginza Train to airport 40
NGO Sakae Tourist area, 1 stop train 50
KIX Namba Next to tourist area, train to airport 90
FUK Hakata JR 10 min subway to airport or Tenjin 10
OKA Asahi-bashi Monorail to airport, walk to tourist area 10
ICN Myeong-dong Tourist area, 1 connection to airport 60
BUS Haeundae BEACH. 75
TPE Taipei 101/Xinyi Big shopping/food area 50
HKG Jordan/MongKok Bus to airport, subway to others 30-60
BKK Siam Tourist 60
SIN ??? Everywhere is expensive 40
KUL Bukit Bintang Tourist 45
PEN French Quarter Tourist 20 (uber)

Hotels vs Airbnb.. I prefer hotels because:

  • More consistency in service and cleanliness (luggage storage, checkin early/late, shuttle/transit stop to airport)
  • Less coordinations in the check in/out process
  • Knowing the exact locations helps with transit planning
  • Works better with last minute bookings
  • For party of 1 with my own bathroom, prices are usually similiar
  • Works with my hotel/credit card points setup

There's one more thing to consider before booking your accomondations...

How to get around

Transit vs uber vs car rental...

  • How many pockets of places will I visit that are beyond walking distance?
  • Are these places reasonably accessible via public transit?
  • What is the parking situation like at these places?
  • What is the price difference between car rental and average uber costs?

Consider renting within the city instead of the airport if..

  • It may be expensive to rent/park the car for the entire duration of the trip
  • Can rent near the hotel for only the 1-2 days you need it.
  • Can walk/uber/chill on the other days
  • Cities to consider: HNL, SEA, PDX

If you decide to rent a car...

  • Use expedia or similiar to search for the best price
  • You may want to avoid those with bad reputation so they don't ding you for minor scratches
  • Some airports may have on airport vs off airport facilities - keep that in mind
  • Rent early, if you haven't decided! Many rentals can cancel for free until day of. The closer it gets, the more expensive it usually is, and they may be sold out.
  • Many companies have corporate discounts, and many rental companies have loyalty programs that let you pick up the car skipping the counter. Keep that in mind.

If you decide to uber..

  • Make sure uber is available in your city (some cities are banned, many have their local companies)
  • Make sure you have data on your phone in that city
  • Get some uber estimates.. city and airport fees vary by region
  • In some cities uber can take a long time to come (eg: 30 minutes in Dallas). Always buffer.

If you decide to take transit..
Weee.. This is my preferred method (when feasible) since I'm usually a party of 1. Things to consider here..

  • Frequency: If it comes every 30 minutes for a 15 min ride and may not be on time, I might opt for uber, or use it as a backup.
  • How much longer does transit take vs uber? Does it justify the cost?
  • Are there day passes or round trip passes available that make sense to get?
    • Am I going to take that many rides? If not, I may opt for a transit card with cash loaded
    • Is the day pass 24 hour days or calendar days?
    • Which transit systems do they work with, and would that restrict me from going to certain places? eg: Tokyo metro has 2 different metro systems, plus JR and others. For Kyoto you need the bus and train to get around - JR and metro are not as helpful. If you wanted to mix and keep it simple, paying per ride would make more sense.
    • Does it cover airport trips? If you have late arrival and early departure with a day in between, it would make sense to stay near the airport and do a day trip to town. It can also mix and match with - perhaps coming back to the airport the night before to stay nearby. This was my strategy for a couple European cities.
    • If the cost of day pass and per ride are similiar, I tend to get the day pass so that I'm more willing to take a 1-2 stop ride to not burn myself off too quickly.
  • Is it a complicated process? Do I need exact change? Am I able to purchase a ticket on a complicated machine where it lists all the station names in a foreign language? Do they travel thru zones that I would have trouble identifying? How do transfers work?

Pro-tip: Always take a screenshot of Google map directions from the airport to your hotel, in case your data doesn't work for whatever reason and you're scrambling at the airport, or the search directions don't turn out as expected because you're in a different part of the airport or offered a suboptimal route. That way you can peacefully figure out the rest in the comfort of your hotel room, usually with better wifi.

Once you have an idea of how you'll get around, you should be ready to book your accomondations. The search process for that will be in a future post.

Day of Travel

Now that everything is sweetly planned, it's all about execution. I'll go thru packing in a separate post, but basic things to keep handy:

  • Bring your passport!! And make sure it has enough space left, and has at least 6 months before expiring from your return date
  • If visas are needed, bring them PRINTED!
  • For Canada, if you have global entry, bring the global entry card!! It also gets you thru "priority" checkpoints
  • Take note of your flight number, ticket number/PNR (the 6 alphanumeric letters), and double check the flight date and time. 8:45am is not the same as 9am and you'll end up at the airport rushing!
  • Note the terminal you should go to check in/go thru security
  • If you can check in online, do that and get a mobile boarding pass. Make sure your phone won't die at boarding though...
  • For connecting flights, note the connecting airport (that's what you'll search for on the airport monitors). Familiarize yourself with the connecting procedures (do I need to re-check bags, go thru customs, take a shuttle to a different terminal, dump my water, etc)
  • For long flights (>5 hours), wear something comfy, but still keep you warm with the plane AC. Also, keep a jacket in case your plane is at a remote stand or your checked bag is lost.
  • Remember to eat! For domestic flights with no food, especially the longer ones crossing timezones, always bring some food in case your seatmate is eating chick-fil-A and making you hungry. Plus a water bottle to fill up at the airport.

Happy travelzz! I didn't realize this is a real hobby until it can no longer be executed - it can't even be planned due to the uncertainty. Hope the world gets back to normal soon..