This was EASILY our best credit card points redemption to date….

Hermitage Bay All Inclusive in Antigua was a literal DREAM…and unbelievably with just a bit of strategy you srsly can vacation at this renowned GEM too (for not $2-3,000+/night).

Now full disclosure: All the very BEST redemptions are likely not easy, but if you have your eye on this specific property (or really any other aspirational SLH hotel for that matter!) – this will give you a solid path forward!

Getting these UNREAL experiences only because we figured out how to pay for them with points instead of our precious dollars – never ever gets old. PINCH ME.

Hermitage Bay All Inclusive

We have stayed at a LOT of hotels, and this one is just standout, one-of-a-kind.

Hermitage Bay is a (true 5 star luxury!!) all inclusive hotel in Antigua, Caribbean. The only 30 villas on the entire property make it feel SO exclusive and just truly special.

This isn’t your standard Mexico all inclusive- the food is outstanding quality. However, it really is the staff and service that bring Hermitage Bay to the next level. Never, ever have we stayed somewhere where the entire staff was so warm and friendly…no exaggeration we left feeling like family.

Anddddd if the glowing review wasn’t enough, it was recently awarded TWO Michelin Keys – the true proof of an outstanding stay.

We’re going to dive into HOW to book this ultimate bucket list stay below, but here’s a few 50,000 ft view highlights:

• EACH AND EVERY of the 30 rooms is an individual, massive villa (personally I’d try to go for a Beachfront villa or Hillside one!)
• Did I mention it’s an all inclusive? And did I mention the food is a 11/10?!??
• Sushi Happy Hour at the Beach Bar at 4:30 every day was our HIGHLIGHT. Carlos there worked at Nobu for 7 years and it SHOWS.
• The staff, the staff, the staff
• Barefoot luxury – This was the nicest place we have ever stayed, without being overly pretentious. LOVE
• Antigua in the Caribbean is a lovelyyyy island – the beach at Hermitage felt private, secluded, and the color of that water needs NO editing
• Only 30-40 minutes from the ANU airport made it really accessible! ( i.e. parents of young kids friendly)
• If you book 3+ nights (even on points!) you get a free roundtrip airport transfer and complimentary Fast Track through customs at the airport (SO valuable!)
• And of course nothing tops that we booked this complete aspirational resort that typically goes for $2-3,000/night for $0 instead. NEVER GETS OLD.

How to book Hermitage Bay on points

Alrightttt what you’re here for 🙂

Hermitage Bay is a part of the SLH Collection (Small Luxury Hotels) – this is group of boutique, luxury hotels around the world, all independently owned.

HOWEVER, in 2024 Hilton announced their exclusive partnership with SLH (i.e. you can book many of these boutique luxury properties with POINTS 👏🏼👏🏼👏🏼)

Now is 230,000 points/night WILD??? Yes, but just wait…

We booked this resort 13 months in advance for PEAK post Christmas week – at the time it was 130,000 points/night (stop waiting on the sidelines, this world is alwayssss changing!!).

Because we hold the Hilton Honors American Express Surpass® Card, we get the 5th night free on award bookings. So we redeemed 520,000 Hilton points for a 5 night stay worth a whopping $17,500 in cash.

We earned these points in 3 ways:

• Welcome bonuses on Hilton card sign ups
• A few referrals on Hilton cards
• Transferring American Express points (1:2) during a transfer bonus!

YOU CAN DO THIS TOO. Let’s get more specific though…

Hermitage Bay on points continued

The other KEY part of booking an SLH hotel like this using Hilton points is Hilton’s Free Night Certifcates.

These are goldddd, because they are essentially UNCAPPED (i.e. you can use them for any standard night at almost ANY hotel…even the top, top tier 230,000 point/night ones).

You’ll want to use Hilton’s wildly valuable Flexible Date Calendar to identify the “standard nights” that are bookable on points at this bottom 230k rate.

When Hilton card welcome offers are elevated (and worth going for) – they come with Free Night Certificates AND bonus points.

Here’s the strategy:

• Partner 1 Applies for the Hilton Honors American Express Surpass® Card (ONLY when it is elevated with a Free Night Certificate!!)
• Partner 1 refers partner 2 for another Hilton card when elevated (my top picks here)!
  • Hilton Honors American Express Card
  • Hilton Honors American Express Surpass® Card
  • The Hilton Honors American Express Business Card
• You now EACH have a Free Night Certificate and a stash of Hilton points to book at least 3 free nights at Hermitage Bay (or any other high value Hilton or SLH property you are eyeing!)

Make sure to keep your eye on my Friday emails and Instagram stories for when these cards increase their welcome offers!

** Hilton DOES allow you pool points with a partner but not Free Night Certificates. I recommend making two separate bookings, and then emailing the resort to merge your reservations so you don’t have to switch rooms!

**You DO have to call into or message Hilton to book a night using your Free Night Certificate (odd I know…it is what it is hah)

Earning additional Free Night Certificates

Both new and existing holders of the Hilton Honors American Express Surpass® Card can earn an additional free night certificate after spending $15,000 on eligible purchases on the card in a calendar year.

If you have a big expense coming up and you have a high value redemption like this in mind- this could be a really smart strategy.

Take Advantage of the 5th Night Free

ALL Hilton card holders get the 5th night free on award bookings (and ZERO resort fees! Rejoice!).

Now sadly this can’t be combined with Free Night Certificates, but if you are booking straight on points- definitely try to take advantage of that perk to stretch your points EVEN further!

Buying Hilton Points

Another strategic way to really save and get aspirational properties like this for so much less.

ONLY buy Hilton points when they are offering a “sale” or promotion to give you a 90-100% bonus (these can be targeted)!

Example: You buy 115,000 points for $1,150. You get 115,000 free bonus points. That’s a night at Hermitage Bay or similar for 1/3rd of the price!

This can also be a great “topping off strategy”!

Transferring points to Hilton from American Express

Lastly, another fantastic option if you are short on points or want to extend your stay!

American Express points transfer to Hilton at a 1:2 ratio. If you can pair that with a juicy transfer bonus– that’s some REALLY solid value there!

My favorite cards are the American Express Gold Family of Cards

• American Express® Gold Card (the BEST card if you spend a lot on groceries and dining!!)
• American Express® Business Gold Card (SUCH a valuable forever keeper for business owners with the 4x points in your top two highest spend categories!)

As with all the very best redemptions, availability can be spotty (but totally NOT impossible!). Book 13 months out, set alerts, try to travel in shoulder season- all strategies to really increase your odds of snagging from free nights at DREAM properties like this!

💳 Learn how to apply for the Hilton Honors American Express Card HERE!

💳 Learn how to apply for the Hilton Honors American Express Surpass® Card HERE!

💳 Learn how to apply for the The Hilton Honors American Express Business Card HERE!

**Thank you SO very much for using my links when you applying for new cards- it really keeps all the free guides like this going!!