Travel Tips

In the broadest possible strokes, here are a few high-level travel tips that have significantly reduced costs/hassle associated with my travels.

Air Transportation

  1.  Skyscanner – pick the flexibility option and explore the possibilities.
  2.  Discount Airlines – just get over to europe anywhere and figure it out from there with a discount airline.

Rental Cars

  1.  Insurance – obtain through credit card.  Obtain primary insurance through the chase sapphire reserve card insurance.
  2. Parking Fees – Remember, the price to rent a car does not include parking fees.  Like the cost to eat candy does not include the cost of a dentist visit.  Factor in anticipated parking costs before renting the car.


  1.  Beware of extra Resort fees, parking fees, and misc. fees in addition to the room rate.
  2. Ventilation, Light, and Pillows – Waking up to the sunrise through the window is much different that trying to sleep with a noisy fan in a room with no windows and stiff pillows.  Ask questions about these topics before you check into the room.


  1. Priority Pass lounges or Amex Centurion lounges work well and can be obtained with a credit card even if you don’t have any airline status.


  1. Not all international airports have reliable wi-fi.  Such as Cairo (as of 12/16) – which makes calling an uber rather impossible if one lands at the airport without any cell phone plan as well.

Phone Coverage

  1. T-Mobile International Data Pass – For short trips T-Mobile has an international pass that is $20 for 10 days, max 1 GB (As of May, 2018).  For long-trips, they have a $15 a month add on for select countries.  Check out the T-Mobile Website for more information.


  1. Google, Facebook, Twitter and other western technology firms are banned in China – Neither is offline map software always the most reliable.  Download apple maps before you arrive or find a way to get a private VPN.
  2. Private VPN – Best recommendations I’ve found here are via Gary Leff at View From The Wing.  He recommends HeExpressVPN and Astrill.
  3. The 72 hour visa-free policy is in effect.  However – remember this means you can stay enter/leave only 1 location in China on this visa.  An airline may allow you to buy a ticket without consideration of this rule.


  1. Ensure 6 months at least until expiration dates.  Multiple countries require passport not be close to expiration in order to travel.
  2. Don’t Lose it – If you do or you need a replacement, it’s going to complicate your trip.  Likely means applying for a new one like you did the first time.  The old one will get cancelled.  Which means you need a birth certificate or other means of identification.  A list of locations to go to can be found on the Dept. of State website.
  3. Get a backup passport.


  1. Ask people on the ground – discuss travel plans with people who have ‘been there, done that’ for advice is a sure fire way to find answers.  Such as crossing the border of Costa Rica and Nicaragua by TicaBus.  Just ask a fellow traveler.


  1. ATM Fees – Cash is necessary in the local currency, often if traveling abroad, depending on the destination.  Avoid ATM surcharge fees from your bank ($3+) and the ATM ($3+) for every transaction by obtaining the Charles Schwab debt card.  You get an ATM fee rebate for all transactions with this card.
  2. Currency Exchange – Obtain currency whenever possible from ATMs – you obtain a better exchange rate and limited fees.


  1. Flexibility is key!  Some days the rain might pour.  Perhaps you’ll be feeling sick or just tired.  Maybe you’ll enjoy a moment here or there and want to enjoy it again.  Maybe you’ll meet a special someone.  Whatever the case – be flexible with your itinerary.
  2. Base – Establishing a good base from which to explore a city is always the most efficient.  For example – Cusco, Peru.  Find a hostel/hotel by the central square.  Then, go talk to a few tour operators which are everywhere and figure out what to do
  3. Day Tours – Free walking tours or half-day/full-day trips are often a great way to get orientated to a new culture.  For example – Day tours of Wickow and the countryside around Dublin with a local historian as a tour guide presents a tremendous cultural experience.
  4. Hostel Tours – Even if you stay at a hotel, check out the hostel tours.  For example – Abraham Hostel in Tel Aviv has connections with multiple tour operators and can easily get you signed up for a dead sea or northern Israel tour.

Bicycle Rentals

  1. Check the time bicycle rentals open in Amsterdam before you rent.  Also, don’t rent a 1 speed in San Francisco if you’re going to go all the way to Muir Woods to hug a Redwood.  And, don’t assume that just because you can return a bike to the point-to-point stations that it will just work no problem (Tel-Aviv).  Finally, remember those bicycle stations typically require you to return the bike every 15 minutes or be charged a fee.  Like the $500 fee I nearly incurred in New York City for failing to do so for an entire day.

Travel Suitcase

  1. Carry-On Only – If you want to avoid the possibility of the airline losing your bag or want to quickly change plans, don’t check in a bag under that plane.

Some Advice from Mr. Grayson – Ultimate Travel Strategist:  His main piece of luggage is a reinforced aluminum suitcase by Rimowa that goes in checked baggage.  In his carry-on, by Italian leather-goods maker Serapian, he always has a mini-pharmacy of antibiotics, a sewing kit and extra collar stays. A small roll of duct tape has come in handy to fix everything from a broken bag handle to a ripped inseam. “I used it on the inside. It worked great. You couldn’t even see it,” he says.

At home, he keeps about 20 clear plastic envelopes, labeled by country, each containing a few hundred dollars in foreign currency and a local transit pass. He carries two passports—his regular one, which is pushing 200 pages, and a backup, just in case.

Mr. Grayson admits it might be overkill, but he carries about a dozen electronics chargers and converters:

Miscellaneous Replacements

  1.  Phone – Identify your mission critical items like your phone.  Then think about what happens if you lose it or something happens to it, like the battery dying.  Figure out a solution, which means back up battery in this case and writing down a couple key things on physical paper somewhere.  And backing up your phone to the cloud of course too (Don’t lose your photos like I did in Bali after my computer was stolen!)
  2. Wallet – If you lose your wallet or key or purse, what would you do?  If you’re traveling with someone, establish a dual-control procedure whereby, for example your friend always has something of yours like a key.  And photo-copy all items in your wallet and store that in the cloud – it makes it a lot easier to remember what you lost if you can just look at a picture.  Make sure of course your passwords to that cloud are secure!


Some good advice from an executive that travels frequently:  One of the first things I do in a city is go for a run. It’s a great way to orient yourself—even if it’s just for a mile or two. And I usually listen to NPR podcasts. Those tend to keep me company, although for the most part, I have a no-earphones approach to travel. I think when you wear earphones you’re not able to see as much of a place.