Booked: Alila Ventana de Oportunidad

I’m off to California for Family Day long weekend, having snagged a three-night booking at one of Hyatt’s most aspirational properties thanks to a last-minute window of opportunity – or una ventana de oportunidad, if you will. 

My visit to the highly-rated Alila Ventana Big Sur will be a quick getaway, but I thought I’d share some of the motivation and thought process behind my decision to spontaneously splurge for what promises to be a very memorable hotel stay.

The Hotel

Alila Ventana Big Sur has been widely regarded as one of the best World of Hyatt properties ever since Hyatt acquired the Alila brand a few years ago. 

Certainly, it’s often touted as the single-best Hyatt property within the United States, and an easy way for North Americans to redeem Hyatt points for a spectacular experience at a great value close-by. 

Like Calala Island, another crown jewel in Hyatt’s portfolio, Alila Ventana is an all-inclusive luxury resort. This means that all meals and activities are included with your booking (although unlike Calala, alcoholic drinks aren’t included).

Throw in the natural setting in the middle of remote and beautiful Big Sur, the expansive property with soaring redwood trees, and the rustic-luxury rooms, suites, and villas, and it’s no wonder that cash rates at this property are often in excess of US$2,500 per night. 

Historically, Alila Ventana Big Sur has been designated as a Category 7 World of Hyatt property, meaning that it only takes 30,000 Hyatt points to book a free night at the standard rate. However, it’s one of a handful Category 7 properties that will be rising to Category 8 as part of World of Hyatt’s 2022 category changes on March 22, 2022. 

On the surface, redeeming 30,000 Hyatt points per night for a US$2,500+/night resort is incredible value, and naturally it’d be one of the most popular Hyatt bookings to secure before the upcoming devaluation. 

However, there’s one added challenge: it’s very difficult to locate Standard Room availability at Alila Ventana to book at the rate of 30,000 points per night. 

There’s one or two rooms that get designated as a “Standard Room”, and once those are taken, then the only way to redeem points is to directly book a “Standard Suite” or “Premium Suite”, which are more expensive at 48,000 or 60,000 points per night (and are only set to get more expensive when the property rises to Category 8 in March 2022).

Alila Ventana Big Sur

The story of my own booking, then, begins on Tuesday morning, the day after we had learned about World of Hyatt’s impending devaluation. 

Between a few other recent trips and a busy work schedule, I had somehow forgotten to plan anything for Family Day long weekend. However, I briefly recalled that Alila Ventana Big Sur seemed to be known for releasing last-minute standard awards, so I popped onto the Hyatt website to run a search.

Last-minute availability, sure, but on a long weekend? There’s no chance…

And so I was dumbfounded when there in fact turned out to be a standard room available for a three-night period from Friday to Monday: the King Deluxe Room with Fireplace.

Now, at this stage, I didn’t have the required 90,000 Hyatt points in my account. In fact, I didn’t have anywhere close – it was only back in November 2021 that I had recently dropped 120,000 Hyatt points for a stay at Calala Island, and I was still in the process of building up my balance.

But then, of course, I remembered that I always had the option of buying points to make up the difference, especially since Hyatt was currently offering a 30% bonus on points purchases. 

Alila Ventana Big Sur
Alila Ventana Big Sur

Before splashing the cash, I weighed up the various considerations:

  • This would be the only window of opportunity to book Alila Ventana Big Sur at the standard rate of 30,000 Hyatt points per night. The resort seems to impose a three-night minimum stay requirement at this time, and there were no more long weekends when Jessy and I would be able to make a three-night stay before the category changes on March 22, 2022. 
  • Even if I were to snag a booking now, before March 22, for some time in the future and lock in the Category 7 pricing, there was simply no availability among Standard Rooms, so I was looking at paying a minimum of 48,000 Hyatt points per night (a 60% premium) for a Standard Suite.
  • I definitely wanted to experience some of Hyatt’s best properties during 2022, when I have Hyatt Globalist status from when it was temporarily easy to earn back in 2020–2021. I haven’t decided yet if I want to make a full effort to requalify for Globalist going forward, so I’d like to book the best stays possible while I’m certain of getting top-tier status benefits. 
  • Last-minute travel planning is always a unique thrill, isn’t it? It was about 5:30am Pacific Time at this point, so I ran the idea past a sleeping Jessy, and she mumbled something that wasn’t an exact “no”. 

With the thinking out of the way, it was time to act. I transferred over my remaining Chase Ultimate Rewards points, completed my Buy Points transaction to top-up my Hyatt account to 90,000 points, and snagged the rare Standard Room for long weekend before anyone else could. 

As I write this, I’m enjoying my first sunrise at Alila Ventana, and I can’t wait to explore the property, embark on on a few scenic hikes, and dig into the all-inclusive food offerings over the course of the next few days. 

The Flights

After securing the booking, it was time to plan the rest of the trip, which was only a simple set of flights down to California.

If you’re headed to Big Sur, you can choose from a variety of airports to fly into: Monterey (MRY), San Jose (SJC), and San Francisco (SFO) are all viable options, in order of increasing distance.

While I would’ve loved to fly into Monterey and only have to drive 45 minutes to the resort, unfortunately the earliest arrival when departing Vancouver after work hours would get us into Monterey at 11:30pm, when all the car rental agencies were closed. 

With no direct flights to San Jose either due to Air Canada’s pandemic-restricted flight schedules, our only option was to fly into SFO, land at 9pm, and make the 2.5-hour drive down the Pacific Coast Highway to the remote idleness of Alila Ventana Big Sur. 

I went ahead and took a look at options to book through Aeroplan. Having booked the Vancouver–San Francisco flight quite a few times recently, I knew that these flights tended to get pretty full, especially when booking on a last-minute. 

Indeed, I was fortunate enough to find “R” space for two on the outbound flight, allowing me to apply my eUpgrades to upgrade from Economy Latitude into business class, paying only 18,500 Aeroplan points + 2 eUpgrade credits per person. 

However, there’s no “R” space on the return flight at the moment, and a direct business class booking is pricing dynamically at 60,000+ points per person.

I’ve therefore locked in two concurrent bookings: one in Economy Standard for 9,200 points, and one in Economy Flex for 14,700 points, with the intention of using eUpgrades on the latter booking if “R” space were to open up.


Some of the best experiences booked on Miles & Points are the result of months or years of careful planning, while others are all about taking advantage of a short-lived window of opportunity.

I’m delighted to have snagged some rare Standard Room availability at the beautiful Alila Ventana Big Sur, thanks to some fortuitous timing and the ever-reliable option of strategically buying points when it delivers outsized value.

I look forward to following up my amazing stays at Al Maha Desert Resort and Calala Island with another all-inclusive luxury experience, all in the spectacular scenery of California’s Big Sur region. 

With Marriott and Hyatt all implementing changes as of March 2022, now’s the time to be locking in some aspirational bookings while the value remains strong. If Alila Ventana Big Sur is on your radar, make sure to take a peek at last-minute award availability before the devaluation hits next month.

  1. Jason

    Can you elaborate on your comment about locking in two concurrent bookings and e-ups? I don’t understand.

    1. Ricky YVR

      I’ve made two bookings, one in Standard and one in Flex. If eUpgrade space opens up, I’ll use the Flex booking to upgrade into business class (as the Standard booking would require a co-pay). If it doesn’t open up, I’ll use the Standard booking and fly in economy (as the Flex booking would be unnecessarily more expensive).

      1. Neil

        How long can you wait until pulling the trigger to cancel the unused flight option?

        1. Ricky YVR

          If we’re going by the T&Cs, until two hours before departure.

      2. Chris W YCD

        this is genius. I tried this with flights to Mexico and Hawai’i, but when I called in to adjust another booking, the agent on the phone told me I can’t have 2 concurrent bookings to different destinations, but I’m not sure if this is true or not. I guess concurrent bookings to the same destination is treated differently than different destinations, can you confirm this Ricky?

        1. Ricky YVR

          Looks like my concurrent bookings are fine. However, I have gotten one of two concurrent bookings to the same destination in the same fare category unilaterally cancelled before.

      3. Jason

        If you use the flex booking, what happens to the standard one? Forfeit as it is non-refundable?

        1. Ricky YVR

          It gets changed to a Latitude booking, and then cancelled for free.

          1. Jason

            Of course 😉 thanks!

  2. Tom

    I should mention – a tip – I was there about two years ago – not sure if you’re a big wine guy – but it’s tough to get a decent bottle of red in Big Sur (no idea why)…. If you’re going to drink some wine in the room – pick it up in San Fran.

  3. Tom

    There’s no getting around the cancellation fee on aeroplan when you cancel one of the return flights?

    1. Ricky YVR

      You can change to Latitude for free, and then cancel for free.

Your email address will not be published. Required fields are marked *

Have an Account? Click here to Login