✈️ The winner of our San Juan giveaway is...

✈️ The winner of our San Juan giveaway is...

Estimated read time: 4 minutes and 52 seconds

Guess what… if you don’t win today’s giveaway, keep reading… Let’s just say… that’s not the only exciting news today. 😉

Good morning from the beautiful new New York LaGuardia Terminal B!

I’m chilling in the American Express Centurion Lounge at the moment, and it is pretty pretty sweet…

How did I access it? Well, you’ll have to read our Ultimate Guide to Airport Lounge Access on our Facebook community page to find out. 😉

But I know why you’re REALLY here today… you want to know if you won our giveaway…

  • ✈️ The winner of our San Juan all-inclusive luxury getaway (plus another exciting announcement)

  • 🥂 How to book your own Luxury San Juan getaway using miles and points

✈️ The winner of a luxury all-inclusive trip to San Juan, Puerto Rico

In case you’ve been living under a proverbial rock for the last month, we are about to give away an all-expenses-paid trip to the luxurious Fairmont El San Juan Hotel in beautiful Puerto Rico.

I’m very excited to announce that a winner has been selected… Are you ready?

The winner is…


Alexis G. from Colorado!!!!!

WOOH! Congrats, Alexis. I gotta say, I’m pretty jelly. If you need a plus one for your trip, I will make myself available. 😝

🚨🚨🚨 BUT WAIT!!! 🚨🚨🚨

Before you go throw your computer in the trash out of sheer disappointment, let me soothe your worries.

Tomorrow, we will be launching ANOTHER amazing giveaway to a far-flung corner of the world. 

If you’re a more adventurous type, let’s just say… you might pee your pants when you see where our giveaway could take you…

But I’ve already said enough.

For now, how about I tell you how you can book your own luxury San Juan getaway… for free. 👇

🥂 How to book a luxury hotel stay in San Juan for free

If you think the gorgeous Fairmont El San Juan Hotel is the only luxurious game in town, you’re wrong, amigos.

There are lots of options for booking luxury hotel stays in San Juan, and today I’m going to share three specific ones with you.

As a quick aside, there are TONS of options for hotels in San Juan for the more budget-conscious traveler, many of which use the programs we’ll talk about below.

For now, however, let’s unleash our more bougie inner traveler.

Option #1: St. Regis Bahia Resort, San Juan

This is far and away one of the nicest hotels in the Americas. Due to this high standing, you might regularly find this hotel running for over a thousand dollars per night, which is, to put it mildly, egregious.

Thankfully, you can book the same property for as little as 70,000 Marriott Bonvoy points per night.

That may sound like a lot until you realize that cards like this one offer free night certificates every year worth up to 85,000 points, which can book this place for free.

Toss in the welcome bonus, and you’d be able to book TWO whole nights at this hotel and still have almost 30,000 points left over toward your next stay.

That means that simply by opening the right credit card, you could book a $2,000 hotel stay for the price of an annual fee… Yup. Not too shabby.

Option #2: Caribe Hilton San Juan

Let’s move on to the Hilton portfolio, shall we?

This property will run you a much more reasonable (though still offensive) $430 per night, or over $500 after tax.

Compared to the previous hotel, that’s wonderful…

But you’re no dumb-dumb. You’re going to get this bad boy for FREE.

You see, this cobranded credit card currently has a welcome offer of 100,000 Hilton Honors points, which could book you two whole nights at this beautiful property since it’s priced at roughly 50,000 points per night.

The best part?

That card has no annual fee. So you’re getting over a thousand dollars in value out of a $0 investment. Theoretically, you could sign up for a second Hilton card as well and easily book a week-long vacation for next to no upfront cost.

This is the kind of thing we travel hackers live for. Does it really get any better than that?

Option #3: Olive Boutique Hotel

Maybe you’re more like me and you want to do without all the glitz and glam of the big-boy beach resorts and go for something a little more understated without sacrificing any of that luxury.

Thankfully, I have just the place.

The Olive Boutique Beach Resort in San Juan is a lovely boutique hotel that’s part of the Small Luxury Hotels of the World (SLH) portfolio.

If that brand sounds familiar to you, it’s probably because they recently established a partnership with Hyatt that allows you to book properties with Hyatt points, earn elite nights, and earn points on paid stays.

If we pop open the World of Hyatt website, we’ll see that this luxurious hotel is priced at just 20,000 points per night.

As you can see, this hotel also regularly costs more than $400 per night, making this another way to reap some excellent value on a stay in San Juan.

Hyatt points are hard to come by… with one big exception: 👇

You can transfer Chase points at a 1:1 ratio from this card, which only has a $95 annual fee.

The welcome offer alone on that card is enough to book you three nights, which yields a value of about $1,500. Not too shabby for a $95 card, eh?

To make things even better, Hyatt gives you elite-esque benefits when you book stays at SLH properties - even if you don’t have ANY Hyatt elite status.

It’s a really unique “sweet spot” in the hotel world and gets you even more value out of those hard-earned points.

As you can see, you don’t need to win a giveaway to enjoy a luxurious vacation in San Juan.

Like I said, this is only the tip of the iceberg when it comes to places to stay in Puerto Rico with points. But hopefully, some of you who had your fingers crossed for this giveaway are able to go soak up the sun anyway. 🌞

That’s all for today, y’all.

Now that I’ve spilled the beans about our next giveaway that will be announced tomorrow, it’s time for you to guess:

The true answer is one of the following

Only Email Recipients can participate in polls.

You’ll have to tune in tomorrow to find out what the giveaway destination is and how you can throw your hat into the ring to win.

Until then, have a great day!


Mike Dodge
Head Writer, Daily Drop

40.7128° N, 74.0060° W

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