15th Anniversary Trip (on Points)

Last month we celebrated our 15 year wedding anniversary (26 years together!) and went big! While most point connoisseurs say you need to be ready to book bucket list trips 11-13 months in advance, when airlines and/or hotels release their calendar dates, I did not do that for this trip! Last September (2024), when we theoretically should have been pulling the trigger, I got stage fright. Yep, paralyzed from the vast list of options - we couldn't decide on a trip, so we didn't.

Fast forward to this spring (April/May 2025) and I decided it was go-time. By the grace of extreme flexibility (and probably some lucky), I was able to book the most sought after business flights five months in advance, which set up the trip.

In this post, I'm going to give you an overview of what points I used and how many, in order to make our Singapore/Maldives anniversary trip happen. In in future posts, I will break down each booking in detail (when I booked, the transfer process, upgrades, etc) so that you could mimic that portion of the trip if you wanted!

Singapore, Maldives, and Doha on Points

Below is a cleaned up version of our final trip itinerary. As you'll see, the total cost of the flights and hotels for our trip would have been over $34,000 cash! We spent just around $3,400 for these items, which includes the mandatory seaplane flight from Maldives airport to our resort. I debated whether or not to include this expense in the trip totals and ultimately decided I needed to include because you really can't avoid this cost if going to the Maldives.

If I pull out the costs of the seaplane, we spent just over $2,000 for 11 nights hotels and 6 one-way flights for two people (80% in business class), which would have cost $32,700+ in cash!! Insanity! Points are legit people!

As you can see above, overall I used just about 742,000 points; which I know, it's A LOT of points! But, depending on your spending levels, this amount of points could be earned in less than a year (we average earning around one million points a year as a household from sign up bonuses/strategic spend).

You will also notice that I used a variety of transferable points and NO specific hotel points. I've been booking flights on points for close to 10 years and hotels on points for the past 2.5 years (once our kids were old enough to tolerate a hotel room vacation, ha!) and I still don't have hotel brand specific credit cards. I'm not against them, but I continually find great sign up offers for flexible points, that I haven't had a need to go with co-branded hotel cards yet.

As you'll see when I follow up with break-out posts, I also did not book any of our travel in bank travel portals. All of the travel above was booked by transferring points out of the bank directly to a travel partner to book. This helps maximize point value. If you see the far right "CPP" column, that standard for Cents per Point (calculated based on Cash Price - Cash Paid for Fees/Taxes, divided by Point Price). If you were to redeem your points in a bank travel portal, you generally get a fixed rate of 1 cent per point; sometimes up to 1 cents per point. Note that this trips average CPP is almost 4 cent per point; meaning I got 4 times the value of my points by transferring to travel partners than I would have gotten, had I booked the identical itinerary in book travel portals.

I point these facts out to emphasize the value I point on earning flexible/transferrable points and earning them from multiple banks, to give me maximum options (and also more opportunities to take advantage of various transfer bonuses; which you'll see in the individual post breakouts!)

Follow along as I break down each booking, step by step, so that you could repeat yourself! These are some of the cards and strategies I used to earn ~750,000 points to book this trip. Click on the link to learn more about each card:

• Chase Sapphire Preferred
• Chase Ink Cash and Unlimited
• More on Business Cards and step-by-step application help here
• American Express Gold
• American Express Gold Business
• Capital One Venture

Looking for more information on points/miles? You can find all of my points talk posts linked here

Curious what cards I (and/or my husband) have, and why? Read here!