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Home  >  Family Travel  >  Flying By The Seat Of Our Pants
Family Travel

Flying By The Seat Of Our Pants

Carly Stewart Posted onApril 8, 2018April 8, 2018 10 Comments

The more points and miles we have and the more we travel, the finer we cut our trips. However, the trip we took this last week was booked in part while we were on it, leaving surprises at every turn for ourselves and our daughter. This family travel experience was truly flying by the seat of our pants. 

Plan? Nah

We hadn’t even been home for 24 hours when the poor excuse for spring weather in the northeast was already getting old. My husband was returning from a business trip, Lucy and I returning from a holiday in Florida. We decided to ditch the cold weather and head somewhere warm but where would we go?  A quick scour of google flights, a glance at some mileage balances and we had narrowed it down to a few sun-filled options.

Lucy in a "Big Front Seat"
Lucy in a “Big Front Seat”

Options

We considered hitting the “easy” button and staying with family in Fort Myers, but decided to check for something a bit more exciting. Key West (a place I’ve never been) became a possibility with numerous nonstop flights into Fort Lauderdale and a few hours drive by car. Nicaragua, Grand Caymen and other places in the Caribbean all came into play but which flights would work the best and where would we stay?

After a little deliberation we decided to get to Florida and roll the dice on the rest. We called this the “Choose Your Own Adventure” trip.

The first and only thing we figured out was that we would fly to Florida on Monday but hadn’t booked a flight until day of.  OneJet now offers a nonstop flight from Pittsburgh to West Palm Beach, this would be our flight down but we wouldn’t stay in West Palm for long. Instead our adventure lead us to Miami where we would cash in one free Hyatt night at a favorite of ours, The Confidante.

Once we were settled in Miami, we went back to the search. Would we stay in Miami? Drive to the Keys? Or leave the continent?

With our hotel fully booked the following night we searched for another place to lay our heads on day two. Checking hotels lead to checking flights and just like that we saw our golden ticket. A flight leaving Fort Lauderdale the following day on Spirit Airlines into Cartagena, Colombia for $123/pp. (P.S. We upgraded to the Big Front Seats which was totally worth it.)

It was hard to narrow down the hotel options in Cartagena as many of them appealed to us and we found more than one to be an affordable option. The good news is when you choose your own adventure, you might just end up trying more than one property… and we did.

Dancing in the rainy streets of Cartagena.
Dancing in the rainy streets of Cartagena.

From there we made a rough itinerary for our route home flying from Cartagena to Fort Lauderdale and up to Orlando to fly back home at the end of the week. It was still slightly up in the air, but we knew that by Monday morning we would make our way back to our home snowy home.

Details

For those that are concerned with the details, here is our cost breakdown in both points and cash for this impromptu trip. The most important detail is the total cost on a per person basis. While it may not seem like a steal to some, this trip spanned six days and most of the reservations (flights and hotels) were made inside of 24 hours of arrival.

Total Costs

  • PIT-PBI = Free (details in a following post)
  • PBI-FLL Rental Car = $18.50 (1-2 free certificate)
  • Hyatt Confidante = Free (credit card annual 1-4 category night)
  • FLL-CTG = $544 ($136/per one way + $45 big seat/per)
  • Conrad = Free (48,000 points)
  • Hyatt Regency = Free (12,000 points per night, club floor)
  • CTG-FLL = $280 (taxes for three people plus 30,000 True Blue points)
  • FLL-MCO Rental Car = $18.50 (1-2 free certificate)
  • Marriott Residence Inn MCO = Free (promotional 1-5 category night)
  • MCO-PIT = $11.60 for two passengers (companion pass plus 16,000 Rapid Rewards) and $239 for Kyle

Total cash outlay = $1,111.60

30,000 True Blue points

36,000 Ultimate Rewards points (transferred to Hyatt)

48,000 Hilton Honors points

(4) Promotional certificates

Per person:

  • $370.53
  • 10,000 True Blue points
  • 12,000 Ultimate Rewards points (transferred to Hyatt)
  • 16,000 Hilton Honors points
  • (1.3) Promotional certificates
Patacones every day
Patacones every day

Execution

We don’t usually fly by the seat of our pants, though I can’t say we are typically organized when it comes to trip planning either. With this adventure we booked almost everything the night before, and even the day of. It all worked out great and we had a wonderful week in Cartagena. Did we get lucky? I don’t think so, but I don’t really believe in luck… I would say we just found what worked best and utilized our resources from free stays, free car rentals and affordable flights. We used what we had available – which included sometimes difficult to utilize certificates – and when cash was the right answer, we paid cash. We could have used all points to pay for this trip, but it wouldn’t have been as good of a value.

If I had to choose our adventure all over again, I would. I look forward to choosing another one soon.

This was a fun adventure.
This was a fun adventure.

Coming Up

Thanks to this unexpected adventure, we will have some great reviews to follow;

  • Our flight OneJet from PIT to PBI
  • Review of Conrad Cartagena and the Hyatt Regency Cartagena
  • Our favorite spot in the walled city.
  • A spa day fit for a princess, and more.

Do you enjoy the last minute “choose your adventure” style of travel? or do you prefer to have everything all planned out?

Previous Article Air New Zealand Unveils New Flat Beds in Economy Class for Infants
Next Article Review: Hilton Orlando Bonnet Creek Resort

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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10 Comments

  1. Ben Reply
    April 8, 2018 at 7:59 am

    Carly,

    Love the recap and the practicality of it. Love the blog and others like it, but a trip like this seems much more “in reach” for the normal folks of the world compared to the crazy stuff that other bloggers write about.

    • Carly Stewart Reply
      April 8, 2018 at 2:46 pm

      They can’t all be over water bungalows in the Maldives, right? 🙂
      To be honest, we’ve stayed in five star resorts, flown in business class all over the world, but this trip gave us so much joy and just as you said, it’s so “attainable” that it just inspires us to do more of them.
      Thanks for reading!

  2. NoVA Rick Reply
    April 8, 2018 at 2:22 pm

    Was there any charge for parking at the Hyatt in Miami?

    • Carly Stewart Reply
      April 8, 2018 at 2:41 pm

      The Valet charge at the Confidante is $44 per day. For our Globalist award stay the parking charge was waived.

  3. MeanMeosh Reply
    April 8, 2018 at 6:21 pm

    I’ m so anal I don’t think I’d find something that seat-of-the-pants even remotely enjoyable. I’d be stressing myself out about not having a flight or hotel in place for the next day. Then again, traveling with a toddler, I’m coming to realize that what we end up doing has nothing to do with daddy’s meticulous planning, and everything about what mini-me decides he wants to do when he wants to do it. Haha.

    • Carly Stewart Reply
      April 8, 2018 at 9:50 pm

      We always knew we had reasonable options and that we could make something work. We just kept reminding ourselves that each day was a surprise! And just like most times traveling with a small child – you expect some of the unexpected.

  4. Jake P Reply
    April 9, 2018 at 8:58 am

    Cool trip, and thanks for the details.

    However, I would caution against using the term ‘free’ to describe all those certificates and hotel stays (perhaps $0 is more accurate?). The Hyatt ‘free’ night, for example, typically requires that you pay the annual fee. For sure, you got a great value on the trip. But those certificates have to be attained, and therefore are not free, in my opinion.

    Also, it seems you left the RR points out of your summary of costs.

    • Carly Stewart Reply
      April 15, 2018 at 12:13 pm

      That’s a fair statement regarding the credit card annual fee and indeed it is not free. However, it is also less than the annual fee for because we earn more Hyatt points by paying with the card than we would normally. You are absolutely correct that there is a cost to the Hyatt night through the annual fee ($75), however, if I were to subtract out the earnings and apply my point valuation, the cost of that night would come under $40, then split per person to $13.33.  I will update this and also the RR points which my husband corrected in his piece on the same topic.

      The Marriott certificate, however, was fully free as it was a promotion running while he was staying in a Marriott property that he would have chosen anyway. In fact, until Award Wallet reminded him that he had it and it was expiring soon, he didn’t realized he had earned it, so the cost there was truly $0.

      Thanks for the comment – great point!

  5. Sajer Guy Reply
    April 15, 2018 at 10:03 am

    For the per-person cost, should it be 4k Hyatt points? Looks like you only used 12k total.

    • Carly Stewart Reply
      April 15, 2018 at 12:17 pm

      To clarify, it was 12,000 points per night for three nights – a total of 36,000 UR points we transferred to Hyatt.

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