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 – This website allows you to search destinations from a particular airport and filter by price.  It’s a great way to generate ideas if you’re on a budget.  
  2. Discount Airlines – Think RyanAir in Europe or AirAsia in SE Asia – These airlines are often bare-bones and you have to pay for luggage and everything else.  Often these airlines do not show up on sites like expedia or google flights, as they do not pay commissions to third party websites in an effort to keep airfare prices low.  Keep this in mind when booking fares.  If you’re flying to, say Penang Malaysia, for example.  Book a round trip to Kuala Lumpur on your favorite airline.  Then, book a separate ticket with AirAsia to Penang.  This trick has saved me a lot of money on flights over the years.

Rental Cars

  1. Insurance – Obtain through a credit card if at all possible.  Foreign countries however have different variables to keep in mind.  Some cards offer insurance as secondary, meaning your personal insurance deductible will still apply, but the card will cover any overages.  A few cards, like the Chase Sapphire Cards, offer primary insurance.  This means that they will pay out first and cover all costs, regardless of fault, without any need to go through your personal insurance.  Check out Rental Car Mistakes, for a personal story on the matter.
  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.
  3. Off-Airport Rentals – Airport taxes are often quite high.  Off-site locations often provide a free shuttle to their location, so if you don’t mind the shuttle time and time to get to the location, you can save money.


  1. Fees – 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 foam pillows.  Ask questions about these topics before you check into the room.


  1. Lounges – Priority Pass lounges or Amex Centurion lounges can be obtained with a credit card even if you have not otherwise purchased access.


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

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. Social Media – 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. Visa – The 72 hour visa-free policy is in effect.  However – under this policy, you can enter/leave only 1 location in China.  An airline may allow you to buy a ticket without consideration of this rule.  This happened to me, leaving me nearly stranded in Kathmandu, Nepal.  The official would not allow me to board the plane into China without proof of an exit ticket out of the same city.


  1. Expiration Date – Ensure 6 months remain until your passport expires.  Otherwise, you risk being denied entry as many countries require 6 months left on your passport to be considered valid.
  2. Don’t Lose it – If you do or you need a replacement, it’s going to complicate your trip.  This likely means applying for a new one like you did the first time, at an Embassy or Department of State (USA).  To apply for a new one, if you don’t have the old one, you need a birth certificate or other means of identification. 
  3. Get a backup passport – something to consider if you are worried about losing the primary.


  1. Crowdsource Advice – Discussing travel plans with people who have ‘been there, done that’ is a sure fire way to find good advice.  The locals know best!  
  2. Double Check Travel Regulations – New travel regulations are making travel more complicated per the WSJ.  The following tips were mentioned in this article on travel paperwork.                                                                                                                


  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 a Charles Schwab bank checking account with debit card.  You get an ATM fee rebate for all transactions with this card.
  2. Currency Exchange – Obtain currency whenever possible from ATMs – you should obtain a current exchange rate.  Savings, even if paying fees, can be substantial.


  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.  I like to book an entry and exit ticket, and give myself time to wander along the way to the extraction point at the new destination when touring.  At a minimum, build a day or two extra into your plan to allow for unexpected changes.  
  2. Starting Point – Establishing a good base from which to explore a city is normally the most efficient.  For example – take Cusco, Peru.  Tours leave from here up the Sacred Valley and you can do a lot of day trips from this city.  My advice, find a hostel/hotel by the central square.  Then, go talk to a few tour operators which are everywhere and figure out a few trips to go on.  They have companies all over the place that will schedule you for a trip the next day or couple days ahead.  
  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 – jumping on a 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 check in during a rental 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.
  2. Size – Every airline is different with their enforcement of stated baggage size limits.  Dimensions are generally 22 inches by 18 inches by 10 inches for a carry on.  The airlines can charge you more for a bigger bag, but it depends.  I’ve had mixed success.  
  3. Garment Bag – These things have larger size limits than a carry on and can be brought on the plane.  Check with your airline’s website before attempting to bring one on the plane.  However, a garment bag is NOT a garment bag unless it can be carried on your shoulder.  I have a garment bag with wheels and a strap and my one time trying to bring it on the plane resulted in a forced check-in by an attendant who was pretty firm on the topic.
  • 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:


  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!


  1. 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.”