How I Plan Trips and Travel Like a Pro

Cindy Caldwell, Vice President of Operations

Article Category: #News & Culture

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I love to travel and I’ve always been fascinated by other countries and cultures.  We moved every year when I was growing up -- and I was always the one lobbying my father to request overseas tours.  Therefore, selecting a college with a strong International Business program (and required foreign language fluency) was a no-brainer for me.  I had dreams of spending my life living and working in countries around the world.

Well, sometimes life doesn’t always unfold the way you envision.  I haven’t (yet) worked outside the U.S.; but, I have managed to visit quite a number of countries.  People who know I travel extensively always ask for tips and recommendations.  I’ve found that the research, communications, budget-tracking, and organizational skills I’ve mastered after decades of project management lend themselves quite nicely to effective trip planning.  In no particular order, here are some of the practices I follow and skills I leverage when planning a trip:

  • Build a cost spreadsheet.  I project all trip costs and identify whether they occur pre-trip, during-trip, or post-trip.  I identify whether they will be paid via credit card or cash -- and, I identify whether those cash requirements are in USD or a foreign currency.  I also go so far as to identify the denominations of the currencies I need (e.g., singles for tips, a $20 bill for a visa at the airport).  I include costs for everything from taxis to/from the airport to daily tips for the chambermaid to my evening bar tab.  I typically use Excel vs. Google spreadsheets simply because some of my friends have not embraced Google to the extent that we have here at Viget.
  • Generate a “cheat sheet” reference card to easily convert currencies back and forth.  I use a large index card to plot out $1, $10, $50, and $100 conversions in both directions, which will fit in my wallet or coat pocket.  I reference for the latest currency exchange rates.  This ensures that I don’t get confused when shopping or exchanging money due to jet lag and either pay some crazy amount for some tchotchke -- or pass up a real deal because I’m not thinking clearly.
  • Head to the bank for “clean money.”  Many of the places I travel have strict foreign exchange rules:  money must be new (with the larger Presidential pictures on them); crisp and clean (no dye marks, handwriting, or torn edges); and generally not larger than a $50 bill.  Hundred-dollar bills are commonly counterfeited in certain regions of the world and money-changers just won’t take them.  I go to the bank at an “off” time in the late afternoon when tellers have more patience to search their tills and their cash supplies for just the types of bills I’m looking for.  Depending on how much cash you’d like to take, this exercise may take a couple trips to the bank, so this is one task I do not leave until the last minute.
  • Call my bank(s) to avoid account freezes.  I appreciate the fraud prevention controls my banks put on ATM and credit cards; but, nothing spoils a vacation like trying to use your card somewhere to discover that the bank has flagged and frozen the account for suspicious charges.  Ever since this happened to me a few years ago, I’ve called my banks ahead of time to let them know when/where I’ll be so they’re less inclined to trigger the “freeze account” feature.
  • Double-check immunization and travel warning status of destination(s). I check the CDC web site and this Visa Guide in the early stages of booking a trip; however, I revisit both sites before departure to verify that there hasn’t been an outbreak or new travel advisory issued for either my destination or any transit point on my itinerary.  Your family doctor doesn’t keep all immunizations on hand -- you will need to visit a travel clinic for protection from things like yellow fever or typhoid.  If you are local to the Northern Virginia area, I recommend Capitol Travel Medicine for your immunization/malaria prevention needs.
  • Always have a Plan B.  Think through options for dealing with any problem that may arise with your itinerary.  How will you deal with a missed connection?  What will you do if your arranged airport pick-up is a no-show?  What happens if you get hurt and need medical attention?  What happens if your wallet or passport is lost or stolen?  What if someone doesn’t take credit cards?  What if there aren’t ATMs available?  How will you communicate if someone doesn’t speak English?  How will not having Internet access affect any of the above plans?
  • Take print-outs with you. Yes, here in the US, we can handle quite a few situations via our mobile phones.  But, you may not want to pay for mobile Internet access overseas.  And, places like airports often require registration and fees for WiFi access.  Don’t rely on having access even if you think you’ve planned ahead by getting the appropriate SIM chip for your phone.  Have something with you that has your hotel information printed on it, as well as your flight information and anything else important.  Ditto any research you’ve done in advance about a cool restaurant to try or the phone number and address of that Segway tour operator you want to contact for reservations.  You can simply pitch the paper as your trip goes along and the information becomes unnecessary.
  • Buy trip insurance for peace of mind.  If you book group tours, they often try to sell you their trip insurance.  Sometimes it’s a good deal and sometimes it’s a rip-off.  I don’t believe in any pricing model where the insurance is a straight percentage of the price of the trip (just like I hate buying anything online that uses a similar shipping model where shipping is priced as a percentage of the cost of the item vs. its weight).  Therefore, I typically use Squaremouth to buy trip insurance.  They’re a trip insurance aggregator that allows you to tweak every element of coverage to obtain competitive quotes for exactly the kind of policy you are comfortable with.  I don’t buy insurance for every trip -- but, I do if the trip is expensive and if something like medical evacuation would empty my savings.  I recently just bought a policy for an upcoming trip for $38.  Knowing I’m covered for worst-case scenarios is worth that amount to me.
  • Line up local tours/guides to get a lay of the land.  You may pride yourself on being an independent traveler.  But, it’s often well worth the investment to join a half-day or whole-day group tour to get a feel for how a city is laid out or what attractions will be worth your time.  I love the hop-on/hop-off double-decker buses in various cities for this reason (plus, they typically narrate in English).  I also love the aforementioned Segway tours.  And, I’ve done advance research and called local tour companies upon arrival to arrange things like winery tours, city tours, and township tours.  I’ve also spontaneously hired friendly and honest cab drivers to be my private driver/guide for the day.  I’ve been wanting to try this organization for awhile, but just haven’t had the chance.  If you’ve used them, I’d love some feedback.
  • Make lists!  I love lists.  And, I love crossing items off lists.  I think fellow PMs would agree that hardly anything is more satisfying.  When planning a trip, I make many lists:  a packing list, a workload-coverage list for the office, a prepare-the-house list, etc.  These usually devolve into multiple sub-lists.

As you can see, research, planning, attention to detail, contingency planning, and budget monitoring are all valuable PM traits that I leverage outside of work to plan vacations for me and my friends.  How do you use your PM skills outside of the office?

Cindy Caldwell

Cindy helped start Viget and now serves as our Vice President of Operations. She remains fascinated and challenged by an industry that never stops evolving.

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