🏝 Optimizing a Babymoon with Miles & Points

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Note: I also recorded a full podcast episode on this entire topic that you can listen to here or if you want to see me share share my screen as I do some searching/booking, you can watch the video version below:

🌎 Where do we Go?

If you didn’t already know my wife and I are expecting our second child in June and for the past month we’d been talking about whether it’d be possible to take some type of vacation before it was too late to travel. Thanks to my parents volunteering to watch our daughter last week, we had a week we could go somewhere, but weren’t sure where to go.

Since we only had a week and Amy was just entering her 3rd trimester, we were looking for a place that wasn’t too far away and that we could spend a lot of time relaxing. I like to start searches for a destination off with Google Flights, because I can search for non-stop flights for a one-week trip in the next month from SFO/OAK/SJC that are less than 10hrs and get a map of all the destinations and prices:

Those criteria really narrowed it down, but when we saw flights to Tahiti for < $600, we thought whether it’d be possible to try and recreate the magical trip we took to Bora Bora back in 2018. French Polynesia had always seemed so far away in our minds but when direct flights from SFO-PPT were announced back in 2017 we realized it was actually only an 8 hour flight and it seemed so much more feasible.

For anyone not familiar, Bora Bora is one of the most beautiful places in the world and with a handful of incredible resorts with rooms that sit right on top of the water. It’s also home to some of the most expensive hotels in the world, but fortunately a few of the hotels on the island can be booked with points, so let’s walk through how we made it all happen.

🛫 Getting There

Once I’ve picked a place, I have a bit of a process for how to get there and some tools I use to make it easier to plan, so I thought I’d just walk through that process:

1. Find the Direct Flights. Before looking for fares, I like to get a sense of all the non-stop flights that fly to my destinations, so I can better search for specific flights/airlines. I like doing this search at flightconnections.com. And I do that because they show you all the routes that you can get to a certain airport from. For this trip, that showed me that unless I want to change planes in Hawaii, the main flight would be from SFO or LAX.

   

2. Check Fares on Google Flights. After I know where I’m coming from, I like to use Google flights to get a sense of the fares. While I’d ultimately need to fly from SFO (or OAK/SJC), I know that some airlines don’t always have partners that fly domestically, so you might miss out on their flights if you search from another city. So for this trip, I just searched for non-stop flights from SFO or LAX to PPT and then when you click the dates, you can choose to see prices for 7-day trips. As you’ll see below, it makes it really easy to understand what days are cheapest to fly on. I also like to check Business Class too, because sometimes (though rarely) it’s only a little more expensive. In the case of Bora Bora it was about $4,800 (or 8x the cost of economy).

   

3. Do Points Even Make Sense? Now that I know the $ cost of the trip, I ask myself whether it makes sense to use points. In general, booking most international award tickets in economy will cost at least 50,000 (miles that would be worth ~$600-$1,000), so when I saw these tickets for ~$600, I knew it wouldn’t make sense to use points unless I could fly business class. Also, when you buy your tickets you earn miles from the purchase and the flight, so that makes it a little more attractive too. However, international award tickets in business usually only cost ~2x the number of miles as economy, so when the fares are 9x, there can be a good opportunity if there’s availability.

4. Check Award Availability. So if I’m looking for award availability, there are a few different options:

   • Search the airline websites. In a situation like this, where there are only a few routes on a few airlines, a good option is to just use the airline websites to search for availability. On many airline sites, when you search for miles, you can see a week or month at a time, making it much easier to find days with cheap flights. For example, United shows a month at a time and made it easy to see that most Sunday flights were only 72k miles one-way in business class.

     

   • Use an award search tool. Point.me (first month for $1 with code HACKS) is a good entry level tool that can search a lot of airlines and help you figure out how to transfer your points from different programs like Amex or Chase to make it happen. However, if you want to go further down the rabbit hole you can check out ExpertFlyer, AwardNexus or KVS Tool.

   • Use an Award Booking Service. You can also just pay for a professional to use all the tools above to find the best options for you. While I’ve had a good experience with FlightFox in the past, they seem to be more focused on business travel now, so I’d recommend trying the point.me concierge or BookYourAward.com, both of which don’t charge their full fee unless they’re able to find you something.

5. Book it the Best Way. The reason I love points programs like Chase, American Express, Citi or CapitalOne are that you can can transfer your points to so many different airlines, with each one requiring a different # of miles for a specific route. So when an airline has their lower priced award tickets available, like United did above, that doesn’t mean you need to book the flight with United miles. In fact, I ended up booking that same United flight that would have cost ~72k United miles for only 55k Air Canada Aeroplan miles. Now I didn’t have Aeroplan miles, but they’re a transfer partner of Chase, CapitalOne and American Express, so it was easy to move the miles over and book it a few minutes later. This is actually where the Point.me search comes in handy because it shows you the best way to book a flight:

    

   

I know that was a lot, but let’s recap what happened. I ended up booking $4,783 round-trip business class flights to French Polynesia for 110,000 Air Canada miles each (+$37 in taxes), which I got by transferring 220,000 Chase points. That’s a value of 4.3¢ per point, which makes earning 3x points on my Chase Sapphire Reserve® card effectively getting 12.9% cash back, which is awesome. It also means we were both flying to Bora Bora in Business for 220,000 points + $148 in taxes.

🏨 Where to Stay 

Now that we can get to our destination, let's talk where to stay. Here’s the process I follow for hotels:

1. Look at Prices First. I often use Google Hotels, but I’m less particular on the tool here, and more that it has the right filters you need. Depending on your trip it might be filtering by star-rating, hotel chain or having specific amenities like a spa or pool. But I like to make sure I know what the $ cost is before I think about points. For a big trip, it’s also worth checking out some travel packages. For Bora Bora, half the people we met at the St. Regis said they got an incredible deal from Costco Travel, so definitely search around to see if there are any special deals or vacation packages.

2. Find the Award Hotels. There are two options here, depending on where you have your hotel points. If they’re all in one program, then you can just look on the hotel chain’s website (e.g. this Hyatt map of all their hotels). Or if you have points in multiple programs, I like to use awardmapper.com which has aggregated all the different hotels across all the major chains. Now hotel award costs are constantly changing, so I don’t rely on it for that, but it does a good job of helping find all the hotels in a city (though their data in Bora Bora is actually out of date).

   

3. Check Award Availability. Once I have a hotel in mind, I go to the chain’s website and search for availability with points (there’s no award tools like points.me for hotels yet). Hilton and Marriott have a flexible search that shows you the full month and points required, so I like to do a flexible search for 1 night, so I can see all the availability at once. Both chains also offer 5th night free, so you can maximize your points with 5 night stays.

   

4. Are Points Worth It? Other than Hyatt, unless you already have points with a hotel chain, it’s often not worth transferring points from Chase/American Express to a hotel chain because you get a similar transfer rate as airlines but hotel points are worth ~1/3 as much. However, if you do have points from staying at hotels or a hotel credit card, then sometimes it’s a great deal. My general rule of thumb on whether it’s worth it depends on the hotel chain, so I usually reference ThePointsGuy valuations and see if I’m getting a deal. So in the case of Marriott, their value is ~0.8¢/point right now, so if I’m going to spend 85k/night, it should be saving me at least $680. However if you book 5 nights, you save 20%, so you could argue it’s a good deal if it even saves you $544. In the case of Bora Bora, the rooms were over $2k/night, so it was no question. It was an incredible deal.

5. If You’re Paying Cash. When you’re not using points, there are hundreds of sites you can book on, but as I’ve mentioned before, I like to book directly with the hotel, so I can send them a follow-up email to introduce myself and increase my chances at an upgrade. However, many high-end/luxury properties actually offer amazing benefits to guests who book through certain travel agencies. Those perks can include free breakfast, upgrades, late checkout, and resort credits, and sometimes can be very meaningful (e.g., breakfast for 2 at many resorts can be >$100/day). If you have a Platinum Card you can get some of these perks if you book at one of the ~1,100 properties in their Fine Hotels & Resorts collection, but I’m working on getting our newsletter readers free access to these benefits at ~4,000 properties around the world (see more below).

So to recap the savings for our trip, we booked 5 nights at the St Regis Bora Bora for 340,000 Marriott points + $20 in taxes/fees. That same room was going for $2,783, which means we got a value of ~4¢/pt, which is ridiculous for a Marriott point. In fact, it’s so good that despite my advice above about not transferring points to hotel chains other than Hyatt, I would consider it if you can get value like this (or honestly anything >2¢/pt would be worth it).

🏝 Total Bora Bora Trip Costs

So here’s the damage for our trip:

Round Trip (SFO-PPT) in Business: 220,000 points + $148 (vs. $9,566)
Round Trip (PPT-BOB) on Air Tahiti: $884 (no deal here)
5 Nights at St Regis Bora Bora: 340,000 points + $20 (vs. $13,915)

Total: $1,052 + 560,000 points vs. $24,365

Editor’s Note: We also spent $1,315 on hotel food/activities, but there wasn’t really a way to avoid it.

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