My all time favorite award redemptions


I’ve been playing the points & miles game for over 10 years now.  Throughout that time, this hobby has led me to many, many incredible experiences.  For this post, I looked back at my past award redemptions and picked out my 10 favorites.  These are the experiences that were truly remarkable.  In each case listed below, points & miles made these experiences possible because I would never have paid the retail price otherwise.

a collage of a man and a pool
Points & miles have unlocked amazing experiences over the years.  I can thank Virgin Atlantic points for the opportunity to get flipped off (jokingly) by Sir Richard Branson.  Sure, others have been choked by him, but who else has been flipped off?

Two things jumped out at me when I made this list.  First, it’s amazing that 4 of my top 10 awards were possible thanks to Hyatt!  If you’ve wondered why I keep picking Chase Ultimate Rewards as my favorite transferable points program, this is it.  Second, only 5 of the top 10 awards can be reproduced today.  This reinforces why it’s so important to jump on amazing opportunities when they happen.  You may not get a second chance.

Here now, in descending order, are my top 10 award redemptions of all time…

#10 Park Hyatt Paris-Vendôme

Still bookable with points today? Yep

In 2014, my family went on a fantastic trip to Paris and Switzerland.  In Paris, we stayed at the Park Hyatt Vendome, in a suite.  The suite cost us 33,000 points per night at the time (most of which were transferred from Chase Ultimate Rewards).  If you were to book the same room today it would cost 48K standard (43K off-peak, 53K peak) points per night.  If you were to pay for the suite outright it would likely cost over $1500 per night.

a white bathrobe on a shower
The shower doubled as a steam room!

The hotel was awesome. We were upgraded to an Executive Suite thanks to my having top tier Hyatt elite status at the time. Unlike the suite we had booked, the Executive Suite had a living room separated from the bedroom, and a second half bath. This was great because it meant that our son had a room and bathroom of his own. The master bath shower also doubled as a steam room. Seriously. Our room had a freakin’ steam room in it! I only used it a few times, but it was great.

a table with plates of food and a rose

My favorite feature of the hotel was the ability for top tier Hyatt elites to order room service breakfast, for free, up to 50 euros per person.  We typically had enough breads and meats left over each morning to also cover a lunch or afternoon snack.  And, the food was excellent.

a table with plates of food and glasses of juice

I posted a bit about the Paris trip here: A novice’s guide to Paris.

#9 Grand Hyatt Santiago Diplomatic Suite

Still bookable with points today? No. The hotel is now a Mandarin Oriental.

a room with a large window and a large table and chairs

At this hotel, we paid the standard award rate at the time (maybe 12K points per night? I don’t remember) and we were upgraded to the Diplomatic Suite thanks to my top tier Hyatt elite status.  We absolutely loved the huge windows overlooking the Andes mountains!  The hotel also featured a club on a high floor with terrific food, and views nearly as good as ours.

a man looking out a window

a city with mountains in the background

#8 Andaz Costa Rica Resort At Peninsula Papagayo

Still bookable with points today? Yep

I wrote about our trip to the Andaz Papagayo here: Huge value from Hyatt – Andaz Peninsula Papagayo Costa Rica.  At the time, the resort cost only 15K points per night, but it’s now up to 20K standard (17K off-peak, 23K peak).  Regardless, compared to the cash rate (at the time of my stay it would have cost nearly $1500 per night!), paying with points can be an awesome deal!  The resort was beautiful, the staff were fantastic, and we loved participating in many activities available at the resort.

a person's feet on a beach
Relaxing in the shade on the beach
a room with a table and chairs and a chair and a table with a chair and a chair and a table with a chair and a chair and a table with a chair and a chair and a
Our room
Andaz Papagayo Sunrise
View from our balcony
a monkey climbing on a chair
Monkey shenanigans
a man sitting at a table
The coffee tasting barista class was my favorite
Andaz Peninsula Papagayo Costa Rica Mixology Class
The Mixology class was awesome too.
a group of people cooking outdoors
Chorreadas cooking class
a table with food on it
Room service breakfast was included for free for top tier Hyatt elites.

#7 Alila Ventana Big Sur

Still bookable with points today? Yep

a pair of feet in slippers by a fireplace

As I said in my Ventana Big Sur review: Wow.  Wow.  Wow.  Did I say “wow”?  Wow!

My wife and I loved everything about Ventana.  The property itself is beautiful.  The surrounding area (Big Sur) is fantastic.  Our suite was awesome.  We hope to return often (and yes we have booked a stay for this coming winter).

This is not the place to go if you want to play golf or tennis.  You won’t find those options here.  This is not a place to bring kids — it’s adults only.  This is a place to relax, to enjoy nature at its most beautiful, and to bring your dog — dogs are welcome here.

Ventana Big Sur costs 30K points per night standard.  That’s a great deal for a resort that usually charges over $1,500 per night!  Even better: all meals are now included (this wasn’t true when we visited).

a patio with chairs and a fence
We were upgraded to the Vista Hot Tub Suite. This is a photo of our “backyard”.
a deer standing on a rock
This deer visited our Vista Hot Tub Suite.
a bathtub in a bathroom
Vista Hot Tub Suite: Bath and shower
a room with a bed and a fireplace
Vista Hot Tub Suite Living Room & Bedroom Combo
a pool with chairs and umbrellas
The main pool
a path with a sign on it
Path to restaurant
a restaurant with tables and chairs on a deck overlooking the ocean
Restaurant view
Ventana Big Sur Alila Hyatt California Big Sur House Breakfast
Breakfast and view
a forest with trees and mountains in the background
View from path near our room
looking up a group of tall trees
Glorious redwood trees

#6 Brenners Park-Hotel & Spa, Baden-Baden, Germany

Still bookable with points today? No (unless you get bumped like we did)

a large white building with a lawn and trees
Brenners is part of the Leading Hotels of the World

For our one night stay in Baden-Baden, Germany, we had booked a Marriott hotel with points: Roomers Baden-Baden, Autograph Collection.  Before our stay, the hotel reached out to say that they were overbooked and would return our points and put us up in another hotel.  The hotel they proposed didn’t look nice at all, so I wrote back and suggested instead the top rated hotel in Baden-Baden: Brenners Park Hotel.  To my surprise and delight, they said yes.  I wish we had been kicked out of a multi-night stay instead!

I’ve stayed in many very nice luxury hotels, but this was probably my favorite of them all.  Service included a personal greeting as we drove up the hotel, a line of personnel inside to greet us, and a personal tour of the hotel and room.  The hotel offers a connected, and amazing, full service spa (yes, I took full advantage of it!).

a patio with a fence and trees
Backyard view
a bridge over a river
The backyard leads to this public walking path.
a indoor swimming pool with a large glass wall
Indoor pool

We got a kick out of their pillow and blanket menus:

a menu on a black surface a menu on a table

#5 Singapore Suites

Still bookable with points today? Yep

In 2013 I flew international first class for the first time.  I had flown business class before then, but not first class.  On this trip, I flew around the world: from the U.S. to Frankfurt on Lufthansa First; from Frankfurt to Bangkok on Thai First; from Bangkok to Hong Kong on Thai First; and finally from Hong Kong to San Francisco on Singapore Suites.

Until flying Singapore Suites, I thought that first class was a nice incremental enhancement over flying business class.  But then… Singapore Suites.  It was in a class of its own.  The suite itself was roomy and beautifully appointed.  And the service was beyond incredible.  The flight attendants seemed to know what I wanted before I did.  You can read my original review here.

Currently, Singapore isn’t flying many routes with suites, but hopefully that will change when travel to and from Asia opens up more widely.  The only way to book Singapore Suites is with Singapore’s own Krisflyer miles.  Luckily they’re miles are easy to get since you can transfer 1 to 1 from Amex, Chase, Citi, Capital One, or Brex:

Rewards ProgramAmex Transfer Ratio
(and transfer time)
Chase Transfer Ratio
(and transfer time)
Citi Transfer Ratio
(and transfer time)
Marriott Transfer Ratio
(and transfer time)
Capital One Transfer Ratio
(and transfer time)
Brex Transfer Ratio
(and transfer time)
Bilt Transfer Ratio
(and transfer time)
Singapore Airlines KrisFlyer1 to 1 (Instant)1 to 1 (~17 hours)1 to 1 (~1 day)60K to 25K (~1 day)1 to 1 (~7 hours)1,670 to 1K (Instant)
a man sitting at a table with food on it
About to dig into my evening meal
a tv on the wall
View from my seat when my suite’s door and windows were open.
a bed in a room
The flight attendant asked if it was OK if she made up the suite across the hall as my bed.  Why yes!  I then had a separate bedroom and living room!  And the bed was incredibly comfortable!
a man and woman standing together in an airplane
Sure, we appear to be all smiles, but the flight attendant practically had to drag me off the plane kicking and screaming when we got to San Francisco.  I didn’t want the experience to end!

#4 8 bedroom Manor House

Still bookable with points today? No

In February 2017, we reported an absurd Wyndham deal: Book any property for only 15,000 Wyndham points per night.  The deal was only available for a few days, and was limited to 50 bookings, but it seemed that relatively few people jumped on the deal because I had no problem booking my 8 bedroom English “cottage” the day after the deal was announced.  You can read about our trip here: Seeking value, finding adventure for 15K Wyndham points per night.

a stone building with a walkway and trees
We paid only 15,000 points per night for the 8 bedroom Newton Manor House, shown above. The house is in Swanage Dorset, England, which we discovered was an awesome place to visit.
a group of people sitting at a table
Manor House dinner for 12
a white cliffs with a hole in the middle of the water
Old Harry Rocks, in Swanage Dorset England. It was possible to hike to here from the Manor House.
a path on a hill with a lighthouse on the top
Lighthouse view on another hike from our “cottage”.

#3 Etihad First Apartment

Still bookable with points today? No

In late 2019, I flew Etihad First Apartments.  I paid 80,000 American Airlines miles plus $51.40 in taxes and fees to fly from the Seychelles to London, with a very short layover in Abu Dhabi.  The flight from the Seychelles to Abu Dhabi was an unremarkable four hour business-class flight.  The 8 hour flight from Abu Dhabi to London in Etihad’s First Class on board their A380 aircraft, though, was remarkable.  It was awesome.

Not only was the first class suite amazing, but the cabin crew was phenomenal.  Four crew members separately came to introduce themselves and to help plan my time on board.  It was an overnight flight, so I wanted to sleep, but I also wanted to get the most out of my time on board.  We worked out a plan that included a small meal before sleep, then a cold meal at breakfast so that I could sleep a bit longer (a hot meal would require more time), then an on-board shower.  This had to be the best flight of my life, edging out even Singapore Suites.

Sadly, thanks to the pandemic, Etihad has indefinitely parked its A380 aircraft (the ones that featured Apartments).  It is likely that they’ll never return to service.

a leather couch in an airplane
My seat. Along the right is a bench seat that would later be turned into a bed.
a room with windows and a couch
View from my seat toward the aisle. Across the hallway is a second suite. Each suite has doors that close.  I found it interesting that they styled each suite with different hues.  My apartment had dark brown leather whereas the one across the hall is more cream colored. 
a bed with a book and a magazine on it
Bed time! I found the bed to be very comfortable.  This is one place where my Singapore Suites flight was better: it had an insanely comfortable bed. This one was comfortable, but not insanely so.  I still slept very well!
a bagel sandwich on a plate
The original breakfast plan was smoked salmon on bagel. Unfortunately, it wasn’t good. How could they make this tasteless?
a plate of food on a table
A crew member quickly noticed that I hadn’t eaten the bagel sandwich and asked if I’d like something else. Curious what would happen if I went off-menu, I asked for an Eggs Benedict. The chef met the challenge brilliantly. It was awesome.

#2 Le Méridien Maldives Resort & Spa

Still bookable with points today? Yep (but price will jump in March)

Marriott’s Le Meridien Maldives Resort & Spa opened September 1st 2021.  Just 10 days later, Nick and I visited the resort for a brief 3 night stay.  It was fantastic!  For details, see: Le Meridien Maldives Resort & Spa: Guide & Review and Le Meridien Maldives first impressions: Wow!.

Incredibly, this resort is currently only a category 5 Marriott which means that rooms are bookable for 35K points per night standard (30K off-peak, 40K peak).  That’s an incredible deal.  When we booked our stay, overwater bungalows were available at that rate, but now you’ll have to pay $50 or 10K points extra per night for a sunrise overwater villa (totally worth it — I recommend paying cash instead of points for this).  Unfortunately, in March 2022, Marriott is planning to do away with award charts and so the award prices at Le Meridien are likely to spike much, much higher.  Book before March (even for a stay after March) in order to secure this deal.

a pool with chairs and umbrellas on the side
Le Meridien Maldives Riviera Pool & Bar. Doesn’t this look like an artist’s rendering? It’s almost too perfect. But, no, I snapped this photo myself in real life with my iPhone 11 Pro.
a bathtub in a room with a view of the ocean
View from the shower. Here you can see my room’s bathtub and deck.
a group of fish swimming in the water
It was possible to swim from the overwater bungalows to a reef with terrific snorkeling.
a wooden walkway over water with houses on the water
Overwater bungalows
a deck with chairs and a table on the water
Nick’s deck at sunset.  His room was on the sunset side of the west jetty.  The sunset rooms cost more, but we preferred my sunrise room since the surf was calmer on that side and it was closer to the snorkeling reef.

#1 Necker Island

Still bookable with points today? No

Picking my favorite award redemption of all time was easy.  Necker Island wins hands down.  My wife and I had an incredible time, we got to hang out with Richard Branson and a bunch of Lemurs, we enjoyed nearly non-stop included activities, and we made lifelong friends.

To be sure, it wasn’t cheap.  I paid 1.2 million Virgin Atlantic miles.  That award included all meals and activities for two.  Sadly (very sadly!), at this time, Virgin no longer offers the option to use points to book a Necker Island Celebration Week.

For details about our stay, see: Is Necker Island really worth 1.2 million miles?

two men standing next to each other
From left to right: Sir Richard Branson (not yet astronaut at the time), Me
a pool with lights on
Great House pool at night
Necker Island View from Patio
View from our Patio
a man wearing a helmet and harness
Zip lining
Necker Island Breakfast
Breakfast table
two men in white shirts
Richard Branson jokingly gives me the middle finger… At least, I think it was a joke…
a man holding a black and white animal
I loved the Lemurs!
a man in scuba gear underwater
Even scuba diving was included!

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What were your favorite award redemptions?  Please comment below!

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