In February and March 2022, Kristyn and I went on our first substantial credit card points YOLO (you only live once!) trip. Although we've benefit from multiple trips over the year with the benefit of points, none have ever reached the expanse or luxury we experienced on this trip. It was the culmination of about 2 years of planning and opening credit cards, with 1 year of pricing and booking. The result was an absolutely unforgettable trip.
Our planning of the trip started by choosing one destination and one specific hotel, then building the rest of the trip around it. We had dreamed of visiting an exotic island and staying in one of the overwater bungalows for years. The Maldives and Tahiti are the biggest destinations for this type of accommodation, and we decided to go to the Maldives, as its farther away from us. I saw news of a resort opening in the Maldives in September 2020 - the Ritz Carlton Maldives Fari Islands - which looked absolutely stunning. Their bookings were already open, and I was even happier when I learned that their “base” award room is an overwater villa. A "base" or "standard" room is the standard room that qualifies to be booked with credit cards points. It can be challenging to find resorts in the Maldives that even have any base or standard rooms at all (yes, hotels can sometimes classify every room as premium, meaning certain free night certificates or other reward benefits don’t apply), and we had to be selective about finding one where the overwater villas were base rooms and not premium rooms. This Ritz Carlton fit the bill. With Marriott’s dynamic award pricing at the time, I knew it would take 400,000 Bonvoy points to book this room for 5 nights, at 100,000 points per night with the 5th reward night free.
The next step was figuring out how to get there with an option to add a stopover on the way there or back (or both), booking only business class tickets for trans-oceanic flights. Of the many airlines that fly to Male MLE in the Maldives, the largest international airport in the island chain, we narrowed it down to airlines that fly with a single stop from LAX, and offered multi-day stopovers. Some of the options we looked at were Emirates, Etihad, Cathay Pacific, Singapore Air, British Airways, Air France and Lufthansa.
Another factor we were considering is that we would be transferring Amex MR points and Chase UR points, so we needed airlines for each direction that had at least one of those points currencies as a partner. These points can be converted to specific airlines, which is incredibly important if you don't have a card that specializes in that airline. For example, we don't fly Emirates airline often and thus don't focus our card planning around earning for that airline. But we can earn Amex MR and Chase UR points that can convert to multiple airlines, based on the strategy for any given trip.
After experimenting with the portals for making award bookings, we were deciding between Emirates, Etihad, Singapore, and British airlines. British has high fees with award bookings, and we were just in London a couple years prior, so we wanted to try a stopover somewhere else. Between Emirates and Etihad, I preferred the booking portal of Emirates, and we decided on a stopover in Dubai with a short visit to Abu Dhabi, rather than the other way around. Dubai is a larger city with more to do, while we wanted to check out Abu Dhabi without committing for 5 days. My main goal for this trip was to circumvent the globe, so Singapore Air would be the other carrier we used. Cross off the bucket list item - going around the world in one trip!
When setting up a trip with multiple stops, consider carriers that allow booking with an extended stopover. This means that your layover can be 5 days, rather than booking one flight from LAX to Dubai and then an additional flight from Dubai to Malee. Instead, your "layover" or stopover lasts 5 days while you enjoy Dubai, and then your trip continues to Male on the same ticket. Both carriers we fly, Emirates and Singapore Air, offer stopovers. These are usually the most cost- or points-effective way to visit multiple locations. The biggest drawback is that you can usually only add a stopover at the airline’s hub, or perhaps 1-2 additional airports. For example, Singapore Air obviously allows stopovers in Singapore, but also offers Tokyo as a stop on an alternate route from SIN to LAX. Otherwise, your stopovers on this airline are limited, meaning to make the most of your trip the stop-over needs to be in Singapore or Tokyo.
Singapore Air and Emirates are both transfer partners of both UR and MR points. At this point, I wasn’t comfortable doing complicated bookings like transferring points to a partner to book a flight on one of their partner airlines. I wanted the simplicity of transferring points to the airline, selecting the flights, and pressing ‘book.’ We decided to go East, so the flights were searched were LAX-MLE with a 5-day stopover in Dubai, and MLE-LAX with a 5-day stopover in Singapore. 5-day stopovers were chosen to take advantage of the 5th night free for staying at Hiltons in both locations using the 600,000+ points I had accumulated over a few years of regular work travel and having the Hilton Honors Aspire card.
There really isn’t a bad time of year to visit the Maldives, with consistently nice weather, but there is a rainy season we wanted to stay clear of. Given the other destinations, we didn’t want to travel in the summer, and we typically spend the November/December holidays with family, so we decided on a timeframe in February-March for our 15 day (really 16, since the flight there adds a day) trip.
And that was the plan! We would start and end at LAX. The first leg would take us to DXB. We would stay somewhere in Dubai for 5 nights, before departing for MLE, also on Emirates. Then we would enjoy the main goal of the trip, 5 nights at the new Ritz-Carlton Maldives. Our return would start with the 4-hour hop from MLE-SIN, where we would spend another 5 nights in Singapore. Finally, we would return to LAX on Singapore Air.
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