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Five days in Los Cabos

Waves against rocks Hilton Los Cabos Beach & Golf Resort

There was pretty much only one way I ever considered spending my 30th birthday, and that was in Los Cabos, Mexico. I adore Mexican food, which puts Mexico above all other tropical getaway spots for me. Plus, my birthday falls in December, making it the perfect time to go.

Well, almost. It actually falls between Christmas and New Year’s, making it one of the most popular—and expensive—times to go. And as someone who likes to book her own travel rather than going through a third-party company, when it came to sifting through deal websites and packages, I had no idea where to start.

After months of fruitless browsing, I was almost ready to throw in the towel on my beach dreams (no pun intended, seriously). Hotel and flight prices were already heading through the roof. 

But on the last night of September—well past the ideal booking window for a holiday-season trip—I checked points redemption rates at the Hilton Los Cabos Beach & Golf Resort just one more time, hoping for some magic. And I got it!

Los Cabos, Mexico
December 2016-January 2017


My boyfriend, Jake, and I came from Chicago, where we celebrated the end of my 20’s with my family. We got a direct flight on United, and since taxis can run well over $100, we arranged a pickup in an advance through our hotel for about $60 round trip.


We stayed at the Hilton Los Cabos Beach & Golf Resort, which could barely have been more ideal. The staff was friendly, the food was amazing (yes, really—amazing chain hotel food), and the property was beautiful. Plus, it had a beach, which are hard to come by in the area thanks to Cabo’s rocky coastline. Only slightly negative thing I can come up with: the pool was warm. Like, really warm. But that’s what the beach is for, no?

Room at the Hilton Los Cabos Beach & Golf Resort
Pool chairs at the Hilton Los Cabos Beach & Golf Resort
Infinity pool at the Hilton Los Cabos Beach & Golf Resort
Beach at the Hilton Los Cabos Beach & Golf Resort
Shore at the Hilton Los Cabos Beach & Golf Resort


By far, the best Mexican food we ate was at Los Tres Gallos, where we had my birthday dinner. They had a beautiful outdoor space and unreal guacamole, sopes and enchiladas, making it our favorite Los Cabos restaurant. Other spots we tried—such as Edith’s in Cabo San Lucas and Don Sanchez in San Jose del Cabo—felt touristy and overrated.

In the non-Mexican division, Flora’s Field Kitchen at Flora Farms was phenomenal (think chilled cucumber soup, pizza with house lemon ricotta and thyme, and a hibiscus margarita). And we really enjoyed El Merkado, a hip, new food hall that you can easily (and cheaply!) reach by public bus from the Hilton Los Cabos.

Edith's restaurant Cabo
Flora's Farm Bar Los Cabos
Flowers at Flora Farms Los Cabos


We grabbed cocktails (…and wine) at Sunset Point, one of three restaurants that make up Sunset Monalisa. As the name implies, it’s a great place to catch the sun setting behind Cabo’s famous arch and other rock formations. Closer to home, we liked the drinks at Lateral, a bar on the second floor of El Merkado.

Sunset Monalisa Cabo restaurantCabo San Lucas arch 


We spent most of our time at the pool, with a couple trips down to the beach as well. The beach was beautiful, but it was cold and got very deep very quickly. No complaints, of course, but it wasn’t the best activity post-quesadilla(s).

We also made one trip into San Jose del Cabo on the night of the city’s art fair, which was lively with lots of colorful dance performances. Another day, we attended a real estate presentation at Flora Farms, which, I admit, we did just to get into the booked-solid Field Kitchen. It was actually really fun to see and learn about the property, but be warned—it did make me want to shell out every last cent in my bank account on an ownership stake.

Easily the highlight of our activities, though, was a whale-watching trip. We saw lots of wildlife, as well as Cabo’s famous arch up close!

Whale watching Cabo San Lucas 


We didn’t do a glass-bottomed boat tour, which I’ve done on a previous trip. We also didn’t get a chance to snorkel, which I really wanted to do in the day-trippable Cabo Pulmo National Marine Park. But leaving the pool is just…so…hard….

Street in San Jose del Cabo 


At the time, I was a Hilton Honors gold member thanks to the Hilton Honors Surpass credit card from American Express (now retired). One perk of the status: For every four nights you book with points, you get a fifth night for free, which came in very handy for this five-night stay. The total cost was 256,000 points, and the insane December cash rates definitely made this redemption worth it. And the icing on the cake: Hilton doesn’t charge resort fees when you book using points!

The majority of what we spent was at the hotel (as I said, amazing food). But while I normally would put Hilton charges on the aforementioned Surpass thanks to its 12x multiple, doing so would have incurred foreign transaction fees. Instead, I used the no-foreign-fee Chase Sapphire Reserve. It offers 3x on all travel purchases, including those made at the hotel.

All outside-the-Hilton dinners went on the Sapphire Reserve, too, thanks to its 3x on dining. And I paid for the whale watching with the Citi ThankYou Premier, a card that gets me 2x on entertainment purchases.

For more on earning and using points and miles to travel for free, visit the 52 Cities free resource library or register to join me on my next live masterclass!

Have you been to Los Cabos? What were your favorite parts? Let me know in the comments! >>

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Five days in Los Cabos






1 Comment

  1. Reply

    Nadalie Bardo

    February 11, 2019

    Oh my, Los Cabos is simply gorgeous! What a beautiful place to watch the sunset and sip on something yummy.


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