I now maintain my travel checklist in a Notion Document (follow this link). A copy of it from Notion is pasted below.

Related: I also created a checklist of tips specific to visiting Walt Disney World in Orlando with children.

Big Backpack or Suitcase

💡 Whether on personal or business trips, I always end up acquiring and bringing back things. Be sure to keep some space in my briefcase empty for them.

Clothes

💡 For a trip longer than 1 week, carry 1 weeks’ worth of clothes and plan on using laundry and dry-cleaning services.

Activity, casual, and workout clothes

• Casual pants or jeans, 1 pair per 1-2 days
• T-shirts, 1 per day for workouts
• fitness pants or shorts, 1 per day for workouts
• Cloth laundry bag. Cloth bags are preferable as they are better for the environment and less noisy than plastic bags.
• Workout and outdoor shoes (Vivobarefoot Ultra III Bloom). I prefer barefoot-style shoes. They have a minimalist sole, zero heel drop, and wide toe box. They are lightweight and take less space.
  • If hiking in cold weather, then also pack a pair of cold weather hiking shoes, barefoot-style except for extremely cold conditions that require specialized shoes.
• 1 pair of merino wool socks for every 3 days
• shoe bag(s)
• spare shoelaces (I’ve had shoelaces break during trips before.)

Formal clothes

• 1 suit (2 suits for 3 or more days’ trip): If carrying more than one suit, it should be of a color that the same shoes and belt can go with it.
• 1 tie (2 ties for 3 or more days’ trip)
• 1 leather belt. I now use Grip6 belts.
• 1 shirt (+1 shirt for every additional day)
• 1 set of cuff links (I like to wear shirts with cuff links.)
• 1 set of undergarments for each day
• 1 pair of formal shoes (Vivobarefoot Ra III). I’ll wear one pair of shoes during travel, so pack the other in the suitcase.

Bathroom kit

• comb or hairbrush
• hair product
• toothbrush
• toothpaste
• razor handle with 2 blade cartridges. I use a Leaf Razor. Dollar Shave Club’s “Humble Twin” blades.
• shaving cream or shaving soap. Solid shaving soap bars are more economical than shaving creams: http://www.rajiv.com/blog/2010/04/17/cleaning-soap/
• bath soap bar. Solid soap bars are more economical and easier to carry: http://www.rajiv.com/blog/2010/04/17/cleaning-soap/
• deodorant
• nail clipper
• First-aid kit
• Empty space to bring back things acquired during trip

💡 As of the most recent update (2022 October 22)to this checklist, I have been exercising daily for 1 hour for 937 consecutive days. To do intense workouts while I am traveling, I carry fitness equipment with me. The following are items that I carry by default. When traveling by car, I carry addition items including a kettlebell and a pair of dumbbells. To learn more, read my blog post about the importance of exercising daily on my site.

• Portable Suspension Trainer (Pocket Monkii and Outdoor Anchor 2 by wild gym)
• Portable and door-frame sage pull up handles (Duonamic Eliviia)
• Jump rope
• Workout gloves (Barehand – Minimalist gloves by rawwgear)
• Knee pads (S9000 kneeling knee pad by Lepfun)
Daily Carry Backpack or Briefcase
• MacBook Pro – I’ve found that my iPhone and iPad (even with physical keyboards) are not yet satisfactory for my content authoring and editing needs on business trips.
• iPad (optional, only if I plan to take handwritten notes)
• Kindle (optional) – If I am planning to read books in sunlight, then the iPhone and iPad are not suitable.
• Audio headphones. I use Motorola S-11 HD Bluetooth headphones Apple Airpods Pro.
Power Adapters Kit
• MacBook Pro Power Adapter
• iPad/iPhone/USB Wall Charger
• iPad/iPhone/USB Car Charger
• iPad/iPhone/USB Portable Battery Charger
• iPad/iPhone Lightning Charger Cable
• Micro USB Charging Cable for Kindle, Android Phone and Motorola S-11 HD Wireless Headset
• Power strip with surge protector. Useful when only 1 power outlet is available or convenient to me, which is often the case during travel.
Documents & Information

These could be all in digital form on my smartphone, but if so, should be quick and easy to find on my iPhone.

• airline tickets and schedules
• hotel reservation info
• car rental reservation info
• addresses and directions to and from key places
• to do lists
• complete contacts info / address book
• contact info of people in the area grouped together
• tourism info for the area. Carry a physical tourist guide book only when traveling internationally. For domestic travel within the U.S., use my smartphone.
• Backup eyeglasses
• Eyeglasses cleaning cloth and liquid
• Paper tissues
Additional Wallet for Travel
• 100 business cards to give out
• Passport, if traveling internationally
• Global Entry card, if traveling internationally
• Foreign currencies, if traveling internationally
• Keep cash in a separate wallet in the unfortunate event of being pick-pocketed or robbed.
Pockets
• iPhone
• Wallet
• Keys. Even though I don’t need my keys during the trip, I do need them upon return. Keep them in my briefcase upon commencement of travel.
Do Not Carry
• More than one physical printed book to read unless necessary. I haven’t gotten time to read all the books I carry on trips in the past. Too many printed books are a burden to carry. Examples of unless necessary include textbooks for classes, book gifts for someone
• Bulky audio headphones. I’ve personally not experienced a need for bulky noise isolation or noise canceling headphones. To me, they are not worth the bulk of carrying.
• Digital Camera, unless required for an event. These days smartphone cameras are good enough for many types of casual photography. Carry a digital camera only if I need it for taking high quality or low light photos at and event or when visiting family or friends. If carrying my digital camera, also pack my camera accessories pouch.
• Portable GPS unit, unless traveling internationally. If traveling internationally (even to Canada), consider carrying my Garmin nuvi with international maps loaded. Using data on my smartphone internationally is expensive. I should also research a navigation app that pre-downloads maps and can work without using data internationally.
• Food to eat on the plane or train. On a business trip, meals are reimbursable and carrying food is an unnecessary hassle, especially considering the risk of food leaking in my bag.
• Towel. While sometimes needed on personal trips visiting family or friends, a towel is not needed on business trips since hotels provide them.
• Handkerchiefs. I have switched to paper tissues as they are more hygienic.
• Anything else of value that is not necessary for this trip. Avoiding carrying things that are not necessary for the trip keeps the weight and space manageable and reduces chances of loss or damage.
Before leaving, do the following

• Change voicemail message at work. provide alternate contact person and number.
• Enable email out-of-office auto-response at work. provide alternate contact person.
  • Do the same on Slack
• Ensure that any tasks one-time or recurring that I had scheduled for the duration I’m away are assigned to alternates.
• Download maps including the surrounding area(s) of places I plan to travel,
• Plan itinerary, including confirming meetings including personal visits.
• Reach out to some family and friends in the places I’ll be visiting.
• Back up and secure portable computer I’ll be carrying with me in case it is lost or stolen.
• Back up and secure smartphone I’ll be carrying with me in case it is lost or stolen.
• Allocate a pocket or pouch in my briefcase dedicated solely to storing receipts required for reimbursement of business related expenses.
• Ensure that will, insurance and emergency plans are in place and communicated to immediate family.
After returning, do the following
• Change voicemail back to usual message.
• Disable email out-of-office auto-response.
• File for reimbursement of business related expenses.

Significants updates to the checklist:

• 2022 October: Moved to Notion. Added portable fitness/workout equipment category.
• 2014 February 9: Revision 4. Updated to keep up with the times.
• 2010 January 24: Revision 3. Updated to reflect changes due to popularity of products like smartphones.
• 2001 July 20: Revision 2.2.