How I Turned a Work Trip to Orlando Into an International Escape Using Points
I had a work trip to Orlando scheduled for the third week of February. Instead of flying in and out and calling it done, I paused and asked myself one simple question:
What else is possible if I’m already there?
That question turned a routine work trip into my international trip of the year — with very little out-of-pocket cost.
Here’s exactly how I layered a Punta Cana getaway onto my Orlando work travel, using points, flexibility, and a little intentional planning.
The Strategy: Layering Personal Travel Onto a Work Trip
Work covered my flights from Sioux Falls, South Dakota to Orlando, and my return flight home after the trip. That part was already set.
Instead of booking a simple round-trip itinerary, I chose to fly from Orlando to Punta Cana after my work commitments, then return to Orlando before heading back home.
This meant:
Work paid for Sioux Falls → Orlando
I added Orlando → Punta Cana → Orlando on my own
Then work covered Orlando → Sioux Falls
By breaking the trip into segments, I created space for an international escape without touching my main travel budget.
Flights: Orlando to Punta Cana Using Points
I booked JetBlue flights from Orlando (MCO) to Punta Cana (PUJ) using points for both directions.
The total out-of-pocket cost ended up being about $127, which covered taxes and fees.
Orlando is a fantastic launch point for the Caribbean:
Strong nonstop and one-stop options
Good award availability
Often lower cash prices if you’re not using points
If you don’t have points, this route is also very affordable when booked with cash — especially compared to flying from smaller regional airports.
Where I’m Staying: Dreams Cap Cana Resort
For this trip, I booked a stay at Dreams Cap Cana Resort.
After a work week, I wanted something simple and restorative:
Beachfront location
All-inclusive ease
No planning once I arrive
Cap Cana is a quieter area of Punta Cana, which made it feel like the right balance of relaxation and comfort. This trip isn’t about packing in activities — it’s about letting the days unfold slowly.
The Last Piece: Airport Transportation (PUJ → Cap Cana)
The final detail I’m still wrapping up is transportation from Punta Cana International Airport to the resort.
There are a few solid options:
Private Airport Transfer (My Usual Choice)
Pre-booked
Door-to-door
No negotiating or waiting after a long flight
Resort-Arranged Transportation
Sometimes offered through the hotel
Can be shared or private
Worth comparing pricing and timing
Taxi
Available at the airport
Fine in a pinch, but I prefer having transportation arranged ahead of time
👉 I typically pre-book airport transportation through Expedia so everything is confirmed before I land.
Once I finalize this, I’ll update this post with what I chose and why.
What This Trip Cost Me (Out of Pocket)
This is the part I always like to see when I read travel blogs — the real numbers.
Domestic flights: Covered by work
International flights: Booked with points
Taxes & fees: ~$127
Hotel: Planned and intentional
Result: My international trip of the year
This wasn’t about luxury or excess. It was about stacking opportunities and making smart choices with travel I already had planned.
Final Thoughts: Travel Doesn’t Have to Be All or Nothing
I’ve learned that some of the best trips come from asking better questions — not from bigger budgets.
If you already have to be somewhere for work, family, or obligations, it’s worth stepping back and looking at the map a little wider. Sometimes a small shift turns a routine trip into something meaningful.
For me, this one simple decision turned Orlando into Punta Cana — and that feels like a pretty good trade.
Affiliate Disclosure
Some links in this post are affiliate links, which means I may earn a small commission at no extra cost to you. I only share tools and booking platforms I personally use when planning my own travel.
