My Travel Blogging Journey has been full off twists and turns, and many fun surprises!  What delights me the most is when readers reach out, and ask me to help them plan their travel!  You all know from this post how much I love to create a detailed travel plan, and I relish the challenge of creating a curated itinerary for every type of client.  You didn’t know I help plan travel???  I DO!  And I would love to help you avoid the 5 Travel Planning Challenges and Tips to Overcome Them!


5 Common Travel Planning Challenges and Tips to Overcome Them!


The Curious Cowgirl holding a bag in NYC


Travel Planning Challenges #1:  Where to Begin???!!!

It’s easy to get excited, and maybe a little tense, about the prospect of planning out all the details for a trip, especially a trip overseas, when the environment is not completely familiar.  How to even begin?  Don’t get overwhelmed friend!.  Breathe in through the nose, and out through the mouth, and begin here with these travel tips:

  • Make your plane reservations first.  Seems obvious, but when you are leaving and when you are returning sets the parameter for every other trip planning decision.
  • And keep in mind that the departure day and the return day are NOT typically days you can count on for site-seeing.  So, for example, you want to take a trip to Italy for a week, then 7 days means 2 days of travel and 5 days of site-seeing.  International Travel tips and the best travel itinerary takes travel days into account.


A beach in Hawaii


Travel Planning Challenges #2:  Where to Stay???!!

I can’t tell you how many times I have heard friends say that they booked a place to stay based on the pictures on the website, showcasing breath-taking views.  But in reality, the hotel or apartment was a very long way away from where they were spending the majority of their time.  That’s totally disappointing and frustrating.  Here’s some travel tips:

  • Consider how long you will be in each location, and how easy/challenging transportation will be.  For example:  Travel Tips in Europe: I always want to be as close to the Major Sites as possible, and near Metro or Subway stops whenever possible.  There might be a fabulous hotel or apartment with a view further outside of the main area, but I don’t like to waste time commuting.
  • Utilize the map function before booking anywhere.  Find the EXACT location is of your hotel or apartment, and then identify the location of SEVERAL important sites you will want to see.  If you are far away in almost every case, reconsider your choice.


Map of Rome Italy

PC: RomeMap 360


Travel Planning Challenges #3:  Hotel vs. Apartment???!!!

In this post, I shared with you my preference to rent an apartment vs. a hotel.  This preference applies to Europe, primarily, but I have rented apartments and homes in San Miguel, Mexico, Beaver Creek, Colorado, and Seaside, Florida as well.  When in NYC, I always stay in a hotel, and the same for most domestic travel that spans a long weekend.  Here’s some pros and cons for each:

Hotel Pros and Cons

  • Pro:  Hotels are “one-stop-shopping.”  Your bed, your bathroom, a restaurant or bar, staff who can answer questions…all in one tidy location.
  • Pro:  The cost is well-defined.
  • Con:  You have one room.  Hope you REALLY like your travel companion, ’cause you are not getting away from them!
  • Con:  Typically, hotels prefer for guests to visit the restaurant or bar in their street clothes.  I guess you COULD venture down in your bath robe, hair in a clip on the top of your head….but I would not recommend it.


Apartment Pros and Cons

  • Pro:  Spppprrreeeeaaaddd out!  You will have a bedroom, and bathroom, a living space, a kitchen…sometimes a terrace or balcony.
  • Pro:  Have coffee in your bathrobe.  Pour yourself an afternoon glass of wine, prop your feet up on the coffee table, open up the windows, and enjoy the sounds of the neighborhood.  Easy to do in an apartment.
  • Con:  You must be willing to find a grocery store to purchase paper towels, extra toilet paper, and coffee/wine/snacks.  I consider this an adventure, but you might see this as a task you are not interested in while on vacation.


Kitchen in a private apartment in Rome

The Kitchen in our Private Apartment in Rome


Travel Planning Challenges #4:  How See As Much as Possible???!!

Ahhhh…this is a GREAT question.  And it’s a very personal one, because everyone travels differently.  Here’s my thoughts and travel tips:

  • Hire a private guide whenever possible for the BIG sites…or if you have seen the BIG sites, then to explore a city more like a local.  It’s pricier to use a private guide, but there is absolutely no substitute for the efficiency and knowledge they bring to the table, as well as adjusting the tour to the EXACT needs and interest of you and your travel companions.  In this post, I shared with you the ONLY private guide service I would ever use in Italy.
  • Utilize a travel planner who knows your destination well.  I help clients create custom curated travel plans for Rome, Tuscany, Paris and NYC.  I know these cities very well, and have knowledge and recommendations for restaurants, private guides, etc.


The Curious Cowgirl and daughter making notes in Rome

Even creating a shopping list can be a fun adventure!


Travel Planning Challenges #5:  Know Your Limits!!!

When working with clients, I like to plan one BIG site in the morning, and one BIG site in the afternoon, and then fill in the details around those sites.  This is an especially good travel tip with kids.  No matter how “in shape” you are, being on your feet for 12 hours a day, and walking easily 10-14 miles in one day wears EVERYONE out.  And there’s nothing worse on a vacation than melt-downs.  Pace yourself!  Allow yourself or others to “opt out” if they are too tired.  And keep a good perspective…it’s VACATION!  It’s supposed to be FUN!

Mary Meier-Evans, The Curious Cowgirl, is not only a Travel Blogger, but also designs custom curated travel guides for clients traveling to Rome, Tuscany, Paris, and NYC.  Email her at marythecuriouscowgirl@gmail.com for more information.


Will Evans eating a raspberry pastry in Paris

Look for markets, fruit stands, cheese shops for local treats!


International Travel Planning Guide and Check List