This Couple Booked a Hotel Stay Worth More Than $10,000 All On Points

David Tibbitts, 33, and Eric Naumann, 35, consider Big Sur to be one of their favorite places in the world. Therefore, it’s no surprise that this rugged stretch of California’s central coast was the setting for the couple’s long-awaited proposal.

The San Francisco-based couple, who have been dating since 2015, did something unconventional. While they legally became husbands during the height of the pandemic, Tibbitts and Naumann had skipped all of the traditional norms—like a cute engagement, an actual wedding ceremony, and a honeymoon. 

“We purposefully decided to keep our union unromantic for the time being, file the paperwork in time for tax season, and save the romance for a later date when we could enjoy it properly,” Tibbitts said. Fast forward to 2024, and they decided to finally have their “proposal.” 

Dramatically situated 1,200 feet above the Pacific Ocean in the redwoods, the Alila Ventana Big Sur became the ideal place for such an occasion. In fact, Tibbitts and Naumann had stayed at the all-inclusive luxury property before, using Hyatt points (which the pair now call “Ventana points”). 

This long weekend escape would be different, though. “We had a trip to Ventana coming up, and since we had been before, we both knew we were in for a relaxing and romantic getaway.” Here’s exactly how they booked the stay and how the surprise engagement went. 

How They Booked It 

Tibbitts and Naumann were at the Hotel Chelsea lobby bar in New York, a few martinis in, when they peeked at Hyatt’s website. “We were less than one month out [from the trip], so we were lucky to find the availability,” Naumann recalled. 

To redeem Hyatt points, you need a World of Hyatt account. Conveniently, two of the best loyalty programs in the space—Chase Ultimate Rewards points and Bilt Rewards points—transfer to the Hyatt program instantly, at a one-to-one ratio.

To transfer Chase or Bilt points to travel partners, you need to log into your account, navigate to the respective travel portal, and select the option to transfer to Hyatt. For first-timers, you’ll also need to enter your World of Hyatt account information.

Naumann, who made the points booking, is a World of Hyatt Explorist elite member at the time that they were booking a room. As a result, he received an upgrade to the Big Sur Forest Shower Suite.

The Alila Ventana Big Sur is one of the most sought-after hotels in the world of points and miles. Few properties can provide the level of luxury, tranquility, and overall value on a per-point basis. For instance, at $3,475 per night and 45,000 World of Hyatt points redeemed, that’s the equivalent of getting over 7 cents in value per point.

In addition, the adults-only enclave is all-inclusive: meals, activities, valet parking, tips, and even one alcoholic drink per evening are fully covered. (Yes, even on points.) Because what you get out of it is so great, only a set number of rooms are allocated towards points bookings, which you can book months in advance.

What the Experience Was Like

The upgraded suite at Ventana had everything Tibbitts and Naumann needed for a romantic escape, including a wood-burning fireplace, ocean views in the distance, an open-air shower for two, and even a private hot tub on the patio. 

On the morning of the proposal, Naumann sent Tibbitts off for a massage as a distraction tactic. “As an executive assistant at the time, I was familiar with working with hotels for anything one of my executives might need during their stay, but it was exciting to do it for myself for a change,” Naumann said. 

The plan was to go on a hike, and the property kindly supported the couple in this endeavor: Staff supplied him with a bottle of champagne, recommendations for a hike, and the world's heaviest takeout container full of “enough charcuterie for a small army,” as Naumann put it. 

“We reached a vista at the very end of the hike, and it turns out David had also planned to pop the question, too, but I beat him to it,” Naumann recalled. “That was our first full day at the hotel, so we had a ton of fun basking in the engagement glow for the remainder of the trip.”

That meant ample time to relax in the on-site Japanese baths, share their hopes and dreams for a future wedding, and get used to the feeling of rings around their fingers. 

“Our favorite part of the resort is probably the walking path to the restaurant,” Tibbitts said. “You get to experience the beautiful forest to and from each meal at the Sur House, and it's the perfect time to decompress as you appreciate the beauty of Big Sur.”

A Points and Miles Tip for Travelers

If you're not seeing availability using points for a hotel like Alila Ventana, check that property's cancellation policy. According to Neumann, you might see availability appear in the days or weeks before the cancellation window closes, as was the case for the couple’s stay. 

Another perk of loyalty programs like Hyatt’s is that, once you’re in them, you are more likely to receive upgrades like the one Neumann received if there is availability on the property. It’s often free to sign up for these programs, too.