I just went on a $7,000 vacation for around $100 out of pocket!
It's been a while since our last getaway. Granted, it was only about two months ago, but for us frequent flyers, that feels like forever! 2 weeks ago, Monday was our anniversary, so I wanted to take my family on a special trip.
FlightsAs far as flights, we usually like to fly with Southwest Airlines because I have the Southwest Companion Pass, which I earned by getting 2 Southwest cards at the end of 2023 and accumulating >135,000 points in January. So, for the rest of that year(2024) and the following year(2025), I get to enjoy the benefits of the Companion Pass. This means I can book a Southwest flight for myself, and I can add my wife as a companion, and she will fly for free (besides the $5.60 tax per trip).
On Sunday, we flew from PHL to MCO (14K points) and stayed there for four days. Then, we flew to FLL (11K) and stayed for two nights. For the weekend, I wanted to spend time with my extended family, so we flew to ATL (11K) and then back home to PHL (14K).
In total, that’s 50K points plus $45 in taxes and fees—instead of $1,400 in cash! That comes out to 2.8 cents per point (CPP)!
HotelsOur first stay was at the Hyatt Regency Orlando, where I booked a Presidential Suite for 36K points—already a great deal. Thanks to my Hyatt status, we were upgraded to the Penthouse Suite, plus we got complimentary valet parking. That’s a $2,500 per night room! 🤯 We stayed for one night and really enjoyed it. That came out to almost 7 CPP.
For the rest of our stay in Orlando, we stayed at the Hilton Mystic Dunes. I got a marketing deal—three nights for $150—as long as I attended a timeshare presentation. I agreed, and when I got there, I simply explained how I vacation using points. Even the manager admitted that their program wasn’t a good fit for me! The suite was pretty nice, had a washer/dryer as well. Helped us get our swimwear dry before hitting the road.
In Miami, we stayed at the JW Marriott Turnberry Resort for two nights, using my two free-night certificates (50K points each) from the Amex Business Marriott card as part of my sign-up bonus and a few extra points I transferred from my Chase Sapphire Reserve when there was a bonus to Marriott. I booked the cheapest room and later called to upgrade to a junior suite using my status. That suite would have cost over $1,000 per night! The first night, the fire alarm went off at 2 AM, and everyone had to evacuate to the lawn. As compensation for the inconvenience, the hotel gave us 30K points. Not bad for an unexpected wake-up call! That factored in, it came out to be a 2.86 CPP!!
Finally, we wrapped up our trip in Atlanta, spending a great weekend with my extended family before flying home on Monday.
Extra Expenses? Covered!
Now, you might be wondering—what about food, activities, and other expenses?
Great question! My wife and I both got the Bill (formerly Divvy) business card, which had a sign-up bonus: spend $500, get $500 back through a special link. That was an easy decision. Between the two of us, we earned $1,000 in statement credits, which covered random purchases, dining, activities, rental cars, and more.
Dining OrlandoFor two nights, we had dinner at Kosher Grill and enjoyed lunch at Kosher Eatery (dairy side).
On the third night, we went back to Kosher Eatery (meat side), and all the food was up to par!
Info about Orlando restaurants we went to:
https://www.koshergrillorlando.com/https://koshereateryorlando.com/ MiamiRight after landing, we grabbed a bite at Milano's Pizza near Aventura Mall. Then, we davened Mincha/Arvit next door at the Breslev Learning Center before checking into the hotel.
Later that night, we went to Café Noir, an upscale dairy spot my wife loves. 🧀
The next morning, we had brunch at Grand Café, which held us over until dinner.
For dinner, we went to Soho Asian Grill, easily one of the best meals of the trip. The bartender asked what we were celebrating, and when we mentioned our anniversary, he surprised us with a few rounds of drinks on the house! 🍸🎉
Info about Miami restaurants we went to:
https://milanoskosher.com/https://cafenoirhollywood.com/https://grandcafe.us/https://sohoasiangrill.com/Want to Travel Like This?
Feel free to ask me any questions.
