A couple of weeks ago I was assigned to a project out in Los Angeles for the remainder of the summer which means I’ll be flying around 4,000 miles and living in hotels for six of the seven days in the week. During this time I plan on taking advantage of the SPG Triple Up promotion and my AA Platinum status offer to earn as many points as possible.

Betty and I are looking to take a trip to the Caribbean over the New Year’s holiday and I’ve been doing my homework on some great places to check out.

The two knowns here are that I am staying exclusively at Starwood properties (Westin and Sheraton) and flying American, where I hold Platinum status. The unknown is which Caribbean Starwood property is the best value for redemption.

So I set out on a mission to find that out…

When evaluating the best value hotels, I kept the following in mind: reviews, point valuations, and flexibility with AA miles (since I’d be redeeming them to get there!).

I personally do not value miles so I relied upon The Points Guy and Ben over at OMAAT.

I’d be using the points and mile valuations from TPG and OMAAT as my basis and then calculate the the dollar per point outlay of the going rate on SPG.com and compare it.

TPG = 2.5 cents per point
OMAAT = 2.2 cents per point
Average = 2.35 cents per point

Understanding that my travel time frame of NYE may skew the results, I made sure to pick a random period outside of any holidays for this research.


W Retreat & Spa – Vieques Island

w vieques

W Resort – Vieques Island. Photo courtesy of SPG.com.

The W Vieques is a Category 6 hotel and thus costs 20,000 Starpoints per night. But when you factor in the ~$400 per night price tag, this works to around 2.0 cents per point which is a pretty good value, especially for a W.

If you’re not familiar with Vieques Island, it sits about 8 miles from the Puerto Rico mainland and is easily accessible by prop plane (not for me) or ferry. Vieques is probably best known for its Bioluminescent Bay, which is a body of water filled with microrganisms that when disturbed, creates a beautiful blue streak!

Note: Hurricane season for Puerto Rico runs from June – November so be sure to plan accordingly!


Westin Punta Cana Resort & Club

The Westin Punta Cana. Photo courtesy of SPG.com.

The Westin Punta Cana. Photo courtesy of SPG.com.

The Westin Puntacana is a Category 4 hotel which means you’ll be dishing out 10,000 Starpoints per night. At roughly $260 per night, you’ll be getting 2.6 cents per Starpoint of value if you redeem for free nights, which is a great deal!

Puntacana and the Dominican Republic in general is a favorite among many and although I’ve never been, this hotel is definitely one that’s on my short list for my upcoming trip.

An added plus is the the minimal 8 minute drive from the airport to the resort. Can’t beat that!

St. Regis Bahia Beach Puerto Rico


St. Regis Bahia Beach, Puerto Rico. Photo courtesy of SPG.com.

The St. Regis Bahia Beach is a Category 7 property which will set you back a steep 30,000 Starpoints per night. However when you consider that a night costs ~$800, you’re getting around 2.7 cents per Starpoint of value which is a damn good deal.

I’ve never personally visited this property, but after scouring reviews it seems that it is very peaceful and serence. I’m not going to be on my honeymoon so this may be a little too quiet for me, but I’m a sucker for relaxing environments so the St. Regis Bahia Beach looks like a great use of points!

It should be noted that there is a $60 per night resort fee, but if you’re looking for a truly relaxing experience, you may find that this fee is worth it!

Trusted Review: Mommy Points


Westin Dawn Beach, St. Maarten

The Westin Dawn Beach, St. Maarten. Photo courtesy of SPG.com.

The Westin Dawn Beach, St. Maarten. Photo courtesy of SPG.com.

The Westin Dawn Beach in beautiful St. Maarten is a Category 5 property and costs 16,000 Starpoints per night. If you choose to book with points you will receive a value of 2.5 cents per point when compared to the ~$400 per night price tag.

This property and the island of St. Maarten are absolutely stunning. The hotel has 341 rooms with 9 suites. Keep in mind that the Westin Dawn Beach levies a $20 resort fee per room, per night.


The Westin St. John Villas

The Westin St. John Villas. Photo courtesy of SPG.com.

The Westin St. John Villas. Photo courtesy of SPG.com.

The Westin St. John Villas is a Category 6 property costing 20,000 Starpoints per night. Choosing to book with points will yield a value of roughly 3 cents per dollar which is a fantastic value, especially when you realize that even a studio villa costs $600 per night.

Unlike the The Westin St. John Resort, there is no resort fee at the Villas, saving you about $40 per night.


Bottom Line

Make sure you shop around as availability and pricing always changes (Starpoint amount, not so much). Make sure you are dividing the room cost per night by the Starpoints per night to get the cents value. Compare to the averages above for the best deal!

Don’t like hotels or free nights? Click here for a free $25 in AirBnB credit. Most of these islands have AirBnB properties for rent!


Where do you like to stay in the Caribbean?