Travel Planning

I knew this holiday was going to be different.  We all voted on where we wanted to travel and New York came up unanimously.  But this time we were travelling independently instead of with a tour group.

Times Square, New York

My philosophy for travelling is simple – we pay a crapload to travel halfway around the world, so I’m going to make the most of the time we have there.  I’m all about maximising the experience and I didn’t want to return to Australia to hear people say, “Did you do this? Did you do that?”  No way!

Times Square, New York

But where to start!  I knew that we had 3½ weeks to fill and that we would travel to New York, Washington DC, Boston and Chicago, but how to divide it up?  I decided upon 13 nights in New York, 5 nights in Washington, 3 nights in Boston and 4 nights in Chicago.

New York’s a big place – where do you start??


I had no idea where anything was, but thankfully my 18 year old son had watched enough movies set in New York that he pretty much knew the city from top to bottom.  The only way to start was to purchase a Lonely Planet guide and I read it from cover to cover.

The best way to navigate the city was district by district.  Tribeca one day, Lower Manhattan the next, the Upper East Side and Central Park.

I mapped out the city and worked out where each of the famous sights were – The High Line is in Chelsea, World Trade is in Lower Manhattan, The Empire State Building is in Midtown etc, and from there I created 13 days filled with the most important sights, and some interesting ones only the locals know about.

I settled on a logical route through each of those areas to make the most of our time and save our feet.

We are foodies and using the Lonely Planet guidebook and TripAdvisor I selected (and sometimes avoided) restaurants that would suit our budget and taste buds.  Some of the restaurants I picked were quirky, some were the type that you just must do whilst in New York.

I researched the subway and Google’s Street View extensively to determine the best way to navigate the city.  My instructions were detailed down to the walking route to take, and like a tour guide, I could tell the family some interesting facts about a particular landmark.

Showing some of the detail in my itinerary Information courtesy of The Lonely Planet ePocket New York City

Once I completed the New York planning component I moved on to Washington DC, then Boston, then Chicago.

The planning took me forever, consuming my evenings and weekends for about 4 months, but I loved every minute of it.

Next was accommodation.  We decided that we needed room.  The idea of my husband and I sharing a hotel room with an 18 and 19 year old was not appealing.  We also needed 2 bathrooms!  We didn’t want a hotel experience, but rather we wanted to live alongside the locals in a local neighbourhood.  Enter AirBNB. 

Our Brooklyn townhouse (New York)

I had never tried AirBNB but had heard heaps about it from others.  The cost of hotel accommodation, especially 13 nights of it, in New York is painful to say the least, so AirBNB was a great alternative. 

The rooftop pool at our Washington DC apartment

Now AirBNB is not for the faint-hearted.  I spent hours and hours scouring every possible property, often getting really excited about what I had found only to discover that they were not available or reading through the myriad of reviews and finding something unsavoury.

Our house in South Boston

But when you find AirBNB gold you snatch it quickly and hold on tight.  And boy did we strike some gold!!

Our apartment in Chicago

A couple of weeks before the trip was due to start I printed out my itinerary and had it bound.  It had reached the size of…wait for it...78 pages!  Yikes!

My itinerary was very detailed with transport information, a walking guide, information on each attraction and sight, I also included pictures I found on the internet to make it more interesting to peruse.  Accompanying the itinerary was a set of maps for each city.  They contained marked up Google Maps with each day’s journey.  There were also pre-purchased tickets, bus, train and subway timetables and maps.

The day the itinerary and maps were wire bound was a special day for me.  I was so excited for what I had created and what we were about to experience.

But the proof was in the pudding, would I actually use them?

Well we did.  Every single day.  There was just one day of the 41 that we didn’t achieve what was planned and that was due to a rental car malfunction $%&*@!!!.

It’s now great to see that the itinerary has been put to new use by many of my family and friends, with some of them already having used it to guide them on their travels.

If only I could make these for a living…

Brooklyn looking towards Manhattan

The book has now become a treasured memento of our trip.  We wrote lots of notes along the journey of all that we did and whether we would recommend it to others.  It was also a great way to remember what we did each day.

Now to plan the next trip…  My daughter wants me to plan her next adventure.  Right!

So what do you think of this amount of planning?

Until next time

xx