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Home  >  Family Travel  >  Vacation Roulette: Life Is Better Without Plans
Family Travel

Vacation Roulette: Life Is Better Without Plans

Carly Stewart Posted onDecember 31, 2017January 14, 2021 4 Comments
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We decided to play Vacation Roulette 2017 and didn’t plan a trip until a week prior to departure. We decided to try a new country, Panama, a new hotel chain, Waldorf-Astoria, and a new airline home for myself and my daughter, United. We love our planned trips but perhaps life is (and vacations are) better without plans. 


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Having a Great Time In Panama

I had minimal expectations for Panama and that has nothing to do with anything other than the fact that I did almost zero research for this trip (other than reaching out to our wonderful readers here at LALF.)  With reader recommendations and our time considered we knew we wanted to first make it to Casco Viejo (The old city) and wander about. It is a beautiful area that transports you back into old Panama with bright colored buildings, some under renovations/some dilapidated – all filled with charm. As we wondered about we found good, quick bites and a wonderful cup of coffee. Stopping along the way to take many touristy shots of Lucy, we loved our time in Casco Viejo.

Wandering Casco Viejo
Wandering Casco Viejo

In an effort to find local food in a very casual setting, our concierge, Lille at the Waldorf-Astoria recommended we try El Trapiche. She described it as a place that was meant to be touristy, but the locals love and assured us the food was good. She was right. We enjoyed a few local dishes, but the star of this show was dessert, a “Caribbean Sundae.”

The Caribbean Sundae from El Trapiche.
The Caribbean Sundae from El Trapiche.

The hotel has been quite good as well. I know that Kyle will write a full review soon, but so far our time at the Waldorf has been pleasant and convenient. Speaking of convenience, the local currency in Panama is USD which has meant an equal exchange rate and no need to worry about currency exchange upon departure nor return.

When Things Are Going Great, Extend Them

It might have been the photos of snow-filled roads that family and friends sent from Pittsburgh that prompted us to extend our time in Panama. It may have been that we just weren’t quite ready to go, regardless we are excited to spend an extra day in the warm temperatures. The forecast has shown rain and storms every day, but we have only seen a little bit of rain. Overcast skies at times are welcome given the fiercely intense sun. To this point, we have encountered just a few sprinkles and maybe one downpour so far. All-in-all, the weather has been wonderful for a tropical getaway so who wouldn’t want to hold on to a little more of that?

Taking in the scenery from our room at the Waldorf Astoria - Panama
Taking in the scenery from our room at the Waldorf-Astoria, Panama

Our daughter has been enjoying her time in the very unique pool. Rectangle-shaped and modern, the pool is long and narrow hung high in the sky among the skyscrapers. Each day we’ve managed to snag a wonderful cabana-style bed under a covered portion at the edge of the water. Lucy has become braver with every visit and has been learning to swim without the aid of her “swimmies” (puddle jumper). After about four hours of pool time today, she begged to stay longer and we were excited to tell her that she would be able to enjoy another day at the pool tomorrow thanks to United award space opening up and the flexibility of this trip.

In addition to learning to swim she is learning to speak more Spanish. We both heavily rely on Kyle’s ability to speak the language and she will respond with “Dad, I’m not sure how to say this in Spanish.” At first she would hide as if she was shy, but now she is feeling a bit more brave with her responses and I could really learn a lot from her. When we are back home in Pittsburgh Lucy takes lessons to learn Chinese, but there is so much value in being able to immerse her into a culture and language and watch her start to pick it up.

I am also grateful that Kyle will have more time to relax. His work schedule has been busier than ever before and while I am happy for whatever time we are able to spend on holiday, giving him this much needed extra day away feels almost priceless. Even better is that this change gives us an extra day in paradise without taking an extra day off work (we had a very long route home planned).

Flexibility Has Been Key

The key to “Vacation Roulette” has been flexibility. We had no destination picked out in advance, flexible dates to a certain degree, plus access to a sufficient amount of miles and points. When things started falling in line and pointed to Panama, we took what we could get for flights.

After Christmas we flew one-way to Miami (with a 21 hour layover at the beach) and then to Panama City, Panama around $1000 for 3 passengers.  We then found return award space for 17.5k miles each on United in coach but would have an inconvenient overnight layover on New Years Eve.  The way down to PTY was great, but with the flights home we were taking whatever we could get and hoping that more might open up the closer we got. And it did…

vacation roulette 2017
A view of the city

We have never done a trip like this before. It’s not that we are big planners, in fact, I’d say we are big procrastinators, but this holiday was booked just days prior to leaving and it was both exciting and unexpected. Having status with multiple airlines and hotels has really helped us to adjust our plans on a whim.

Unexpected Surprises

With our extra time in Panama City, Lucy will have an extra day to work on her backstroke, we will be able to try a restaurant we were eyeing, and have an easier flight back home. All of these fall into the win category for us.

The biggest unexpected surprise is definitely the last minute Business Class tickets found in saver level on Star Alliance carriers. The route we found will take us on Copa Airlines, a first for all of us and UA First which will be the first time for Lucy and myself.

The best part?

We are now routing through Tegucigalpa, Honduras where we will get to see the Toncontin approach. This is something I have heard about for years. I have endured many YouTube videos and InfiniteFlight demos of the approach and departure from Toncontin airport.  I am happy that my AvGeek husband will now get to experience and I will try to be excited about it as well.

Pilot in training?
Pilot in training?

Will We Do It Next Year?

As much fun as this trip has been, we probably won’t play Vacation Roulette again net year. But like Lucy, learning to trust the unknown and leap from the side of the pool into the water, we too learned that with the tools we have at our disposal we aren’t going to drown out there. Thinking about next year already (and we will be booking as soon as space opens up 330 days out) we think it might be a return to Asia but are open to suggestions.

Take a leap!
Take a leap!

Have you played Vacation Roulette before? Were we crazy, lucky, or good for this to have all gone so right?

See Carly’s bio for other work she has written that has appeared on MapHappy.org, the Huffington Post, and many other outlets.

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About Author

Carly Stewart

Carly is a freelance travel writer that takes her daughter Lucy along on her journeys, stamping passports and making memories. She has contributed to Huffington Post, MapHappy, Travel Codex and PenandPassport.com. You can also find her over-sharing photos of Lucy on Instagram by following @LucyGoesTo and @AnotherBabyMaybe.

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4 Comments

  1. MeanMeosh Reply
    December 31, 2017 at 12:59 pm

    I’m WAY too Type A/anal to go on a vacation without at least some advance planning, so I can’t ever see myself truly playing vacation roulette. I have to know how we’re getting there, where we’re staying, and how we’re getting back at least a few weeks in advance. We’ll occasionally do an unplanned day trip in the car, usually in search of food, but that’s about as far as I’m willing to take it. That being said, I know Matthew swears by unplanned vacations, so glad to see y’all enjoyed yourselves.

    • Carly Stewart Reply
      January 1, 2018 at 7:49 pm

      It was a fun experiment and I could see us trying it again in future sometime but I think Kyle likes to have a plan a little more in advance too. Unplanned road trips in search of food sounds good to me too!

  2. Ana T. Reply
    December 31, 2017 at 1:57 pm

    I enjoyed this read,
    Thanks for sharing it.
    Me and my Son were just there in Oct.
    5 days.. was not enough.
    Casco Viejo was very nice,
    Went to Porto Bello” also fell in love with the place.

    • Carly Stewart Reply
      January 1, 2018 at 7:51 pm

      Thanks for reading and taking the time to comment. I’m glad to hear you had a good experience in Panama also. We loved it and hope to get back again with a little more time for exploring and venturing further afield.

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