Last-Minute Award Travel Success: $8.7K St. Thomas Vacation PAID on POINTS

P2 and I made a spontaneous decision to take a trip to St. Thomas, US Virgin Islands, just 24 hours before our flight. And, of course, it was paid on points! During our trip, we had an amazing experience and had the opportunity to visit some of the most beautiful beaches in the world, including Trunk Bay in St. John. If you plan to visit the area, I highly recommend taking a short ferry ride from St. Thomas (Red Hook) for only $6 per person each way.

Now, on to how I was able to travel hack on such short notice:

Flight: 49,000 points roundtrip total for two:
Although it was very last minute, I managed to find award availability for the following flights:

• A one-way flight from ORD to St. Thomas via American Airlines for 12,000 points + $5.60 per person. The cash price for this flight was $1,044 in total, which gives a value of over 4 cents per point.
• A return flight from St. Thomas to ORD via United Airlines for 12,500 points + $60.64 taxes and fees per person. This flight was booked on Air Canada for 15,000 fewer points. The cash price for these flights were $972.26.

As an AA Executive Platinum member, my companion and I were eligible for complimentary upgrades (subject to availability) and free bags. Fortunately, we were both at the top of the upgrade list and I was able to secure an upgrade. Unfortunately, there was only one available seat, so we decided to give up the upgrade and instead opted for the comfort of the exit row where we had the entire row to ourselves.

In order to get complimentary bags, seat selection, CLEAR membership, and other benefits for our return flight, I matched my American Airlines Executive Platinum status to United’s 1K Premier status. This also allowed us to add an additional family member to our CLEAR membership, which is already covered by our AMEX Business Platinum. I’ll explain more about airline status matching later on.

In total, we used 49,000 points + $132.48 for two people for our flights. If we had booked with cash, the total cost would have been $2,016.26.

The Westin Beach Resort & Spa at Frenchman Reef

We were able to find availability at the Westin for an average of 82,500 Marriott Bonvoy points per night. Since we stayed for five nights, the fifth night was free, which brought the total to 331,000 points. Although it was a lot of points, this is unfortunately typical for Marriott. During the non-peak season, you have the opportunity to book this property for as low as 62,000 points per night. This is an excellent chance for those who have received or are interested in the limited-time offer for the AMEX Marriott Bonvoy Business Card, which includes five Free Night Certificates. To book, you will only need to add 12,000 points per night.

The cash price for our stay was $6,750. However, we were still able to get over 2 cents per point (cpp) in value, as Marriott is typically valued at around 0.07 cpp. This made me feel a little better about using so many points, especially since we had just received our Rakuten Q1 earnings #EarnAndBurn – but it was absolutely worth it!

The property underwent a $425 million renovation and reopened in September 2023 after being damaged during the 2017 hurricanes. It now sits atop a coveted cliff with breathtaking views. Guests at the Westin have access to the restaurants and amenities of all three Marriott properties, including Bouy Haus and Morningstar, via a free shuttle between the properties. However, we enjoyed the short walk along the beach. We even did nighttime kayaking right on the resort, which was super convenient and fun.

If you’re familiar with the Marriott Bonvoy rewards program, you know that even on award stays, you’re required to pay resort fees. In our case, these were $75 per day, which included access to complimentary snorkeling equipment, non-motorized water sports, sunrise yoga, welcome drinks, free wifi, and more.

To save money, I split up our bill with $300 on my American Express BBP (which has an AMEX offer for 20% off Marriott up to $60), and I also used my CIP, which has a 10% offer on Marriott (and earns 3x points on travel). This way, we got an additional 10% off the remaining cost, including all our dining charges.

While it wasn’t the best redemption for hotel accommodations (we could have used a fraction of these points at Margaritaville with our Wyndham points, but unfortunately, there was no award availability), including our flight, our total cost would have been $8,766.26 if we had used cash for our stay, instead we only paid $439.98 total. The experiences we had during our first trip to USVI were priceless!

If you want to apply for the limited time Marriott Bonvoy Business Card offer and get 5 Free Night Certificates and more, apply using my link here: