To book seven nights at the Conrad, we needed to come up with 380,000 Hilton Honors points and two weekend night certificates. I had around 50,000 points to start with, so we needed 330,000 more. First, I got the Hilton Honors Surpass Card from American Express, which comes with Gold status and earns 6 points per dollar on groceries and at restaurants. The sign-up bonus (at the time) netted me 50,000 points. I then got the Citi Hilton Honors Visa Signature Card, which netted me a sign-up bonus of 75,000 points
Finally, I got the Hawaiian Airlines MasterCard from Barclaycard, which comes with a bonus of 35,000 miles that transfer to Hilton at a ratio of 1:1.5. Since you have to transfer in increments of 10,000, I transferred 30,000 miles to get 45,000 Hilton points. After a paid Hilton business stay that I put on my Surpass card (earning 12 points per dollar at Hilton properties), and other grocery and restaurant spending we put on that card, I had about 311,000 points in my account.
To make up the balance, I turned to the Membership Rewards points I had amassed from my sign-up bonus for the Platinum Card from American Express. Hilton is an Amex transfer partner at a ratio of 1:1.5, so I was able to transfer 46,000 Membership Rewards points to get the remaining 69,000 Hilton points. Finally, I got the Citi Hilton Honors Reserve Card and earned the sign-up bonus of two weekend night certificates after spending $2,500 on the card in the first four months. Those certificates are stackable with my points awards, and I called ahead of time to make sure they were redeemable at the Conrad Maldives.
To cover our airfare, my wife got the Chase Sapphire Reserve Card and netted the very lucrative 100,000-point bonus. I transferred about 60,000 of my Ultimate Rewards points to her account (which you can do as a couple or family residing at the same residence), and we booked two round-trip, economy tickets on Cathay Pacific through the Chase travel portal. We also used Ultimate Rewards to book a night at the Hotel Jen Malé, since our flight didn't get in until late on our first night in the Maldives. In both cases, we got a redemption rate of 1.5 cents per point.
We paid nothing for our hotels and airfare, and while we couldn't get around the cost of the seaplane transfers ($560 per person), we did save $70 thanks to an Amex Offers discount at Conrad properties.
We spent liberally on food and entertainment, and ultimately spent less than $4,000 for what would have been a $20,000 vacation. The room rates were pretty high during our stay (the first week of January), so we got a great redemption rate for our Hilton points, and booking an award helped us avoid a lot of hotel taxes and service fees.
We loved the Conrad Maldives and found the service to be impeccable. As Gold members and honeymooners, they honored my request (made when booking) and upgraded us to an overwater villa. Champagne and roses awaited us when we walked into our beautiful and spacious room, which came with its own plunge pool on a private deck over the water. Snorkeling all around the island, we saw everything from sea turtles to reef sharks, and even came across an octopus. The house reefs were simply incredible!
Our Gold status also got us complimentary breakfast each day, which at this hotel was quite a spread, complete with one of the most elaborate juice bars I've ever seen and free flowing champagne. We were treated to a complimentary cocktail hour each evening, afternoon tea, and complimentary massage ad-ons at the spa. As honeymooners, the Conrad also gave us a complimentary three-course dinner at their Mandhoo restaurant. We found the food and drink at this resort to be exceptional. This is definitely the best points redemption we've experienced, and we will absolutely return here in the future!
If you're looking for an exclusive beach getaway, the Maldives is the ultimate honeymoon destination. The trade-off for the intimate location is that the islands are far away and expensive (both in terms of getting there and once you arrive). It's difficult to cover an entire trip there with points and miles, but you can get excellent value by booking flight and hotel awards to make your visit more affordable.
Paul and his wife smartly began planning far in advance, which gave them ample time to earn sign-up bonuses and find award availability. That made it easier to schedule their stay so they could redeem their free weekend nights and take advantage of Hilton's fifth night free benefit, which saved them 95,000 points. You can sometimes find award availability at the last minute, but booking early gives you the best chance at the seats and rooms you want.
In order to maximize your rewards, make sure you use the best sign-up offers available. Paul got 50,000 points from the Hilton Surpass card, but you can commonly find much a higher public bonus for that card — for example, the current offer gets you 100,000 points after you spend $3,000 in the first three months, plus a free weekend night after your first anniversary as a cardmember. Amex generally limits bonuses to one per card per lifetime, so don't settle for a smaller one unless you need the points right away.
