Planes, Trains and Automobiles 

As I approach my final 2016 trip, I started to reflect on how amazing this year in travel has been and although I’ve run through more airports and chased more luggage in 2016 than I ever have in life, I wouldn’t change a thing. It’s all part of the journey.There are pros and cons to being a solo traveler. You set the price, the place and the plan and as things change you adjust accordingly, but that can prove to be a bit more challenging when you’re traveling with someone else or with a group.

Italy was the first non-solo international trip where I was in complete charge of planning the trip and while, the thought of a travel companion was exciting, it was obviously more work than simply creating an itinerary for myself.

April, But before Italy was booked and paid for, I had already decided that I would chase deals and not destinations this year so my first mistake out the gate was booking a travel deal to Vancouver. Vancouver was nowhere on my top 100 places to visit, but it was the first travel glitch (aka fare error) that I actually caught so I booked it and although I hear it’s a beautiful place, I COULD NOT and I mean COULD NOT get excited about it. I joined a travel group for Vancouver, booked a beautiful apartment and put in my vacation days. But two weeks before the trip the thought of wasting 7 vacation days on a place that I just couldn’t get excited about was haunting me. I couldn’t rest and Costa Rica kept popping in my head. Quiet as kept, I tried to book Costa Rica the weekend I went to San Francisco but I couldn’t justify only spending 3-4 days in Costa Rica so I went to San Francisco instead.

On a whim, I looked to see what the cancelation policy was for the apartment in Vancouver and when I realized it was fully refundable, I canceled with no alternate plan. I had decided I’d rather stay home and eat the flight cost, then to spend 7 days in Vancouver. That was the best decision ever and the beginning of what proved to be my BEST travel year so far. I replaced Vancouver with Costa Rica and Costa Rica did not disappoint.


The ability to quickly switch gears is the BEAUTY of traveling solo.  

May, off to planning for Italy and my next travel lesson.  

On my way to work, Emirates’ flight deal to Italy dropped… JFK to Milan, two people for $850 roundtrip

Considering I paid more than $1,200 for my first flight to Europe, I immediately pulled over to reach out to my travel companion so that we could catch the deal. Only to realize that what looked like a deal from a USD perspective did not appear to be a deal from a CAD (Canadian dollar) perspective. Hindsight it was a deal for both of us but I had only researched the best deals from the US…turns out it still beat the best deals from Canada to Italy when converted to Canadian currency. We let the deal go and waited for the next one.

A few weeks later my travel companion found a deal leaving Canada directly to Rome on Air Transat.

I was in Florida with my family and didn’t have a lot of time to think it through but I know how fast a good travel deal goes, so I did a quick search in my travel group and there was no info on Air Transat but there also wasn’t any negative feedback, so I booked it. At that point, I just wanted to get the flight booking behind me. DONE

Now if you haven’t figured it out from previous blog posts… I’m not one to venture too far from American Airlines and when I do it’s typically to United Airlines or Emirates LOL…so Air Transat was nowhere on my radar. I had never heard of them. It didn’t take me long to figure out that it was a “budget” airline and if I was going to Miami, I may have stuck with it, but when I started factoring in the cost for meals, the cost to pick my seat, the cost to check luggage, the cost to have a drink, etc., even if I broke even on an American Airlines flight it was still not a good deal for me. After reading their google reviews… I took the $200 hit on the cancellation fee and booked a flight with American. I have status with American Airlines, so I check luggage for free, I have priority boarding and free access to priority seating, meals are free and alcohol is unlimited (IMPORTANT) AND I earn miles…so a $479 flight to Milan directly from JFK was a no brainer for me.

WHEW Italy was booked!

Planes, Trains & Automobiles

Chicago to JFK (flight) – JFK to Milan (flight) – Milan to Rome (flight)

Let’s just stop right there…

JFK was on high alert, so having global entry was of no use to me considering they had one line for all international travelers. The line was long, the dogs were out sniffing every passenger and of course I was running out of time to catch my flight. I’ll talk about the smell in their international terminal on another day. But I made it through and ran to my terminal, with a few minutes to spare before they started boarding the flight. By now, I’m sweating bullets but I didn’t care. I actually made the flight and that’s all that mattered.  

Only to sit on the runway for an hour

Catching a flight deal seems like a good idea until you’re chasing luggage or running to catch another flight that’s not connected with your initial itinerary. Missing your second flight could cost you more than what a direct flight would’ve cost.

I had a two hour window between my Milan and Rome flight, which was plenty of time if my flight from JFK left on time. I knew we left late & I knew I didn’t have much time between flights but I decided I was going to relax and not worry about it until I arrived in Italy. Towards the end of the flight I became restless because all I could think about was my friend taking her first long flight and being stranded in the airport if I didn’t make my flight.

The beauty of being a solo traveler is had I missed the flight I would’ve jumped on the next train to Rome for around $30, which is typically how I travel between cities in Europe most of the time. I was only flying because I was trying to arrive shortly after my travel companion arrived.

When you book separate flights you have to re-check your luggage and go through security again. Had I arrived in Milan earlier, their baggage claim service desk would’ve checked my luggage for me….but off I went sprinting through the airport 40 minutes before my flight was scheduled to depart and every airline employee that I encounter telling me to go or I’ll miss it.

Sweating, panting and ears popping I made it and so did my luggage.

4 days Rome (train) 3 days Florence (train) 2 days Venice (train) 1 night Milan (train)

I took the latest train out of Venice that was heading to Milan, which arrived in Milan at 10:30pm. 10:30 doesn’t sound late until you realize you’re in a foreign country with no hotel booked and no arrangements made to get to the airport in time the next morning to catch a 5am flight back to the U.S.

At this point, I was a solo traveler. My travel companion was flying directly from Venice back to Canada the next day. Remember the good thing about being a solo traveler is I can have a solid plan or no plan at all. So while I sat on the train, I started googling hotels and modes of transportation between the Milan train station and the Milan airport. The airport was an hour away from the train station so I definitely needed to get closer to the airport because of my early flight.  

After 20 minutes of back and forth up and down the escalator trying to find my way to buy their local train ticket I finally asked a stranger and when I say stranger…he was strange but turned out to be a lifesaver. He was bouncing through the halls, talking to himself, singing and dancing. Don’t ask me why I chose him, but I did. He took me directly to the kiosk for the train ticket. Imagine arriving at O’Hare for the first time and someone tries to tell you how to go from Terminal 1 to Terminal 3 to catch the city train, but they speak broke English. That’s what it was like getting directions from everyone except this guy. We had a very nice conversation in route to the kiosk and off he went. He left me in the hands of two vagrants and told me to hurry because I only had 5 minutes to catch the last train. Catching the train was worth the $1 that I gave the gentleman (read: begging gentleman) that helped me to quickly buy the ticket and once again with two suitcases in hand, I ran to the train. I made it.

Sheraton scored major points by being attached to the Airport. They proved to be a life saver a few months later when I left Egypt and had an overnight layover in Canada. I arrived there with no plan as well.

I said that was it for me and multiple flights….and then the New Zealand glitch fare fell. There was no way I could travel that far and not go to Australia. Here we GOOOO… A $215 glitch was worth the hassle.

ORD to LAX – LAX to NZ – NZ to AUD – AUD to NZ – NZ to ORD

August, my bags were packed and already in the car ready to go. It had been raining all morning, but rain never stopped any of my flights from departing so I wasn’t even concerned until I received a text message midday telling me that my flight was delayed by two hours.

YIKES!!! Guess who only allowed a two hour window between her ORD and NZ flight?

I immediately called American Airlines and asked them to put me on an earlier flight. I raced out of the office and headed to the airport. As I’m approaching the gate they’re changing the flight panel to say the flight was also delayed. I walked straight to the gate agent and asked if there were any other flights leaving. She said yes, but they’re boarding now and the doors are probably closed. She said if you run you might catch it but I’ll at least call to let them know that you’re heading in that direction.

I took off running and another gentleman who was asking the same thing followed me. The doors were closed but we could still see the plane. We stood there for about five minutes before a passenger walked up and asked if we were trying to catch that flight (pointing at the plane). I said yes. She yelled over to the next desk of agents and asked if they could call down to the other agents to see if they could add two more. Seriously…this was a perfect stranger who was on standby with her husband and children that intervened on our behalf. When the gate agent appeared through those doors and said who needs to board, I almost cried. As I rolled my carryon suitcase down the runway I turned back and looked at her and mouthed thank you!  

We sat on the runway for 20 minutes but we eventually took off.

But where was my luggage?

I didn’t care if my luggage made it in time to catch my NZ flight but I knew there was no way I was going to miss it.

If you’ve ever waited in baggage claim at ORD, LAX or JFK you already know that it’s always slow. But that wasn’t my issue. The flight that I was supposed to be on had my luggage and it was delayed so it was scheduled to arrive in LA an hour after my original flight. Remember the two hour window. At most airports checked luggage has to be checked at least 50 minutes before your flight is scheduled to leave.

It was my lucky day. I ran into two beautiful spirits in the baggage claim service office and they said go ahead and check in for your flight and find out how much time you have to check your luggage. If your luggage doesn’t arrive in time we’ll forward it to you, just come straight to the desk 5 minutes before the window she gives you and will quickly complete the claim.  

The airline attendant was very clear…she said you have until 8:42 to check your luggage, not 8:43…but 8:42. At 8:40 I checked my luggage and ran to my gate.


The limo picked me up at 3:15 this morning for Cuba. I don’t plan on doing any running on this trip.

Happy Holidays!!!

 

 

 

2 thoughts on “Planes, Trains and Automobiles 

  1. Jamie says:

    Omg! What a crazy cool adventures! Still laughing about the stranger that helped you out. Sometimes those people are the biggest helps 😂😂. I wish you more safe and happy travels in the new year!

    Liked by 1 person

Leave a Reply to Jamie Cancel reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s