Dreaming of sun-drenched beaches and the legendary fish tacos of Baja California, Cabo San Lucas had been on my bucket list for years. But as our travel adventures became more frequent, our focus shifted to unique and luxurious accommodations, leading me to the stunning Waldorf Astoria Los Cabos Pedregal. Intrigued by its reputation as one of Hilton’s most aspirational properties, I embarked on a mission to turn this dream vacation into a reality. Here’s how I managed to make it happen.
Airfare to Cabo San Lucas
With its proximity to the United States and its reputation for exclusivity, finding free reward nights at the Waldorf Astoria Los Cabos Pedregal is tricky. They tend to open up at the last minute, demanding flexible travel plans. Luckily, we found a Thursday through Sunday slot – perfect for minimizing disruptions to our kids’ school schedules. But a Sunday departure meant pricey one-way flights ($500 per person!), way over my $350-per-person total flight budget.
That’s when I turned to my credit card points. Delta offered the best flight times for our getaway, and with their award pricing at 88,000 SkyMiles plus $178.92 in taxes and fees, it looked like a possibility. My Amex Delta Platinum card came in clutch – it offers a 15% savings on award bookings, bringing the total down to 74,800 SkyMiles!
I had just over 20,000 Delta SkyMiles saved up, and since Delta is an Amex Membership Rewards transfer partner, I easily topped off the remaining points with a 1:1 transfer. Mission accomplished!
Hotel – Waldorf Astoria Los Cabos Pedregal
The Waldorf Astoria Los Cabos Pedregal had captivated me from the first time I encountered it online. Reviews on various platforms like forums, Google Maps, and pretty much everywhere else, praised everything from the exceptional guest service to the breathtaking ocean-view rooms with private plunge pools. However, the price tag proved daunting. Starting at $1,636 per night, the cash rate skyrocketed to a staggering $2,229.80 after adding taxes and fees. Knowing I wouldn’t spend that much on a hotel, I started planning a year in advance, determined to find a creative solution.
Earning
The first option was using points. My wife, however, wasn’t keen on a five-night stay, which would have unlocked the “fifth night free” perk on points bookings. This left us with leveraging Free Night Certificates offered by American Express co-branded Hilton cards. I already had the Hilton Surpass card, granting one free night after spending $15,000 annually. My wife, however, didn’t have any Hilton cards, but opening the Surpass card would provide a second free night.
However, American Express enforces a “once-in-a-lifetime” rule for welcome bonuses, making timing crucial. After extensive research, I discovered Amex had offered a welcome bonus of 80,000 Hilton Honors points and a free night certificate in the spring of 2021 and 2022 for spending $4,000 within three months of opening the card. We decided to wait patiently, and in April 2023, the offer resurfaced! I referred my wife to the Hilton Surpass card, securing a referral bonus, and strategically shifted our spending to meet the welcome bonus and surpass the $15,000 threshold for the second free night certificate.
Booking
Equipped with three free night certificates, I embarked on a daily search mission. My objective was to find three consecutive nights at the Waldorf Astoria in Cabo San Lucas, which required 120,000 points per night. After a month and a half of persistence, I finally found three nights, including a coveted Friday and Saturday, at a discounted price in late February.
While booking the stay, I realized reservations using certificates couldn’t be done online. I contacted Hilton’s Guest Service through the app and found the process delightfully smooth. The friendly representative even noted that both mine and my wife’s certificates would be used for a single reservation, eliminating the hassle of switching rooms during our stay.
Conclusion
A dream of visiting Cabo San Lucas for 20 years has finally become a reality, thanks to the power of travel hacking! Leveraging loyalty programs, co-branded credit cards, and strategic timing for maximizing welcome bonuses, I’m not only crossing Cabo off my bucket list, but doing so in style at the renowned Waldorf Astoria Los Cabos Pedregal.
We’d love to hear your thoughts and experiences if you’ve ever stayed at this luxurious property! Share them in the comments below.
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