Taking on the SPG Holiday Challenge

Every traveler I know who has the Starwood American Express Card loves it! I’m one of them, which is probably why I was invited to be part of their SPG AMEX Stars program to help communicate the benefits of the Starwood American Express Card to travelers.

I’ve been a part of this team for the past two years and have been invited to so some really cool exclusive cardmembers-only, behind-the-scenes events like attending the past two U.S. Opens and having a meet-and-greet with tennis legends Monica Seles and Lindsay Davenport.

One of my favorite parts of this program is that they allow me to bring a guest along so I get to show a loved one the card benefits as well. FYI: I don’t get paid to be part of the program but they do give me 70,000 Starwood points and part of the deal is that I need to use them just like regular cardmembers would. My job is to book a room without any special help and then write about the experience.

This year, I had the choice to go anywhere in the U.S. that has a Starwood Hotel (St. Regis, The Luxury Collection, W, Westin, Le Méridien, Sheraton, Four Points by Sheraton, Aloft and Element) before December 31, 2013. This holiday challenge really put my SPG points to the test. Would I be able to book a great vacation during the busiest travel time of the year? I was about to find out.

Naturally, I chose my wife @NatalieDiScala to accompany me and she wanted to go to the St. Regis New York. New York?! Over Christmas week? It will be freezing, I said … and besides, we had stayed at that amazing, historic hotel last year during our honeymoon. I suggested we go someplace warm that we hadn’t yet visited as a couple.

When I mentioned the island of Kauai, Natalie’s eyes almost popped out of her head! Fortunately, SPG AMEX was paying for the flights because traveling over Christmas week, practically at the last minute, is about triple the normal fares. I then picked up the phone and called the number on the back of my SPG card and prayed that there would be a vacancy. One of the best things about SPG points is that there aren’t any blackout dates so using them over the holidays is a great way to offset your costs during this high-priced period.

Unfortunately, our first choice, The St. Regis Princeville Resort, was completely sold out – again not just for points but for cash, too. The friendly agent informed us that there is another Starwood hotel, The Westin Princeville Ocean Resort, right next door and that a couple of suites were still available.

I asked how many points that would cost me and was told it would be 40,000 points a night. I wasn’t planning on using that many points but Kauai during Christmas week is pretty special. So instead of booking three nights, I cut it back to two. Tip: The agent suggested I call back every couple of weeks to see if any regular rooms opened up but none did.

I wasn’t upset about paying double the points because we were in a gorgeous suite and loyalty points are meant to be burned. To even be able to use my points during the busiest time of the year in Hawaii is amazing in and of itself. And if I had booked way in advance instead of just six weeks out, I would have been able to stay at any of the hotels for the regular amount. Lesson learned: Plan ahead.

Natalie and I arrived in Kauai after a five-hour, 44-minute flight from Los Angeles. We rented a car and drove 28 miles to The Westin Princeville Ocean Resort. There are no signs for the Westin from the main road so we ended up going too far but it turned out to be a blessing in disguise since we came across the Wishing Well Shave Ice truck. Shave Ice is my favorite treat in Hawaii and it was so good, we ended up going back the next day.

I quickly realized that this hotel is perfect for families and so was our room. It was basically a one-bedroom apartment with a full-size and fully loaded kitchen, two flat screen TVs (one with a DVD player) Bose  stereo, pullout couch, dining room table for six, Jacuzzi tub, balcony and, the best part, a washer and dryer! They even supply detergent and dryer sheets for the first few rounds of washing.

Since The Westin Princeville Ocean Resort and The St. Regis Princeville Resort are sister properties and are situated so close to each other, they have a free shuttle between the two every hour on the hour. It’s about 10-minute drive. I doubt any of the guests from the St. Regis are coming up to the Westin because the St. Regis has beach access but Westin guests are welcome to use the St. Regis beach, but not the pools – the Westin has its own great pools. Just remember to bring your own towel if you head over to the St. Regis beach.

Natalie and I did go down to the St. Regis to get an incredible couples massage at the Halele’a Spa and then had dinner at their world-class Kauai Grill by celebrity chef Jean-Georges.

Good to know:

• The Westin charges $13 a day for valet or self-parking and it’s valid for parking at the St. Regis too.
• WiFi is included and is good for up to four devices.
• There are a bunch of barbecue grills around the property and are available on a first-come first-serve basis.
• The Westin has a popular on-site marketplace that sells all kinds of food for breakfast, lunch and grilling. It’s only okay and is a bit overpriced so you might want to hit the grocery store on your way over. There’s a Foodland located right near the entrance to Princeville.

As you can see from the pictures, these two hotels and this part of the world are beautiful. For this holiday challenge, I really pushed my SPG Starpoints to work hard for me by choosing to travel to Hawaii during the year’s peak travel season … and I came out on top. I guess that makes me most likely to ring in 2014 in style from one of the most beautiful places on earth … Hawaii. Hau’oli Makahiki Hou or Happy New Year!

Disclaimer: I was provided SPG Starpoints by Starwood to book this stay at The Westin Princeville Ocean Resort. I was also provided flights for me and my wife. All other expenses were not paid by SPG.