How I Booked an $8,700 St. Thomas Vacation Using Points and Miles

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Planning a tropical getaway to the U.S. Virgin Islands? In this post, I’m breaking down exactly how I booked a luxury five-night trip to St. Thomas on less than 24 hours’ notice—using points from American Airlines, United, and Marriott Bonvoy. This is a prime example of how last-minute award travel can deliver five-star value when you know how to navigate the points and miles game.

If you’re sitting on a mix of transferable points, elite airline status, or hotel certificates, here’s how to maximize them in a high-cost destination like the USVI—without paying thousands out of pocket.

Flights: 49,000 Points Roundtrip for Two People

We booked this entire trip to St. Thomas just 24 hours before departure. Despite the short notice, I found award availability and booked the flights using a combination of points across two major programs:

One-way from ORD to STT via American Airlines: 12,000 miles + $5.60 per person

Cash value: $1,044 total → Over 4 cents per point
As an AA Executive Platinum member, I was eligible for upgrades and received complimentary checked bags

Return from STT to ORD via United Airlines: 12,500 miles + $60.64 per person

Booked through Air Canada Aeroplan for fewer points than booking directly through United
Cash price: $972.26 total

I also status-matched my Executive Platinum to United 1K, which granted added benefits like CLEAR membership, free bags, and preferred seating.

Total: 49,000 miles + $132.48 in taxes and fees for flights worth over $2,000.

Hotel: The Westin Beach Resort & Spa at Frenchman’s Reef (Marriott)

We transferred American Express Membership points to Marriott Bonvoy to stay five nights at the newly renovated Westin Beach Resort & Spa.

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.

Award Rate: 82,500 points per night × 5 nights
Marriott 5th Night Free Perk: Only paid for 4 nights → 331,000 points total
Cash Price: $6,750

Despite Marriott’s dynamic pricing model, we still received over 2 cents per point in value—well above the 0.7 cent average. If you’re holding Free Night Certificates from the Marriott Bonvoy Business Card, this property is eligible. On off-peak dates, it can go as low as 62,000 points per night.

Guests staying at the Westin also have access to amenities at the adjacent Morningstar and Buoy Haus properties via complimentary shuttle or beachfront walk.

Resort Fees & Credit Card Strategy

Even award stays at Marriott properties require resort fees. Ours came out to $75 per night and included:

Complimentary snorkeling gear and kayaks
Non-motorized water sports
Sunrise yoga and beach chairs
Welcome drinks and Wi-Fi

To offset some of the out-of-pocket costs, I split charges across multiple cards:

$300 on my Amex Blue Business Plus to activate a 20% Amex Offer on Marriott
Remainder on my Chase Ink Preferred to earn 3x points on travel and trigger a 10% Marriott offer

We also leveraged Q1 Rakuten earnings to help justify the redemption.

Final Cost:

Total Cash Cost: $439.98 (taxes + resort fees + incidentals)
Total Retail Value: $8,766.26
Points Used: 49,000 airline miles + 331,000 American Express points

While this wasn’t the absolute best redemption value for Marriott, it made sense given the scarcity of award availability elsewhere and the last-minute nature of our trip. We explored Wyndham’s Margaritaville option, but there were no award nights available.

Takeaways: Should You Use Points in the USVI?

Yes—if you’re strategic. St. Thomas and the broader U.S. Virgin Islands can be extremely expensive, especially in peak season. But award availability exists, and when leveraged well, it can make a luxury trip surprisingly affordable.

Unlike international Caribbean islands, U.S. citizens don’t need a passport to visit the USVI, making it an ideal destination for domestic travelers looking for a no-passport-required beach escape.

If you’re planning your own trip to the USVI, consider:

Booking flights early with American or United for better award availability
Leveraging Marriott Free Night Certificates or off-peak points at properties like the Westin
Timing your trip during the shoulder season to avoid inflated redemption rates

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