Treasure Island: How AA Pays You to Go to St. Thomas

How to add the Caribbean jewel St.Thomas to a domestic round-trip on American Airlines and pay up to $223 less.

Last month we alerted you to a stopover treat in San Juan, Puerto Rico. As it turned out, we were just getting warmed up. Now we’re staying warm in tropical St. Thomas, which suns itself among the world-famous Leeward Islands.

Yes, get ready for another happy chapter of our Stopover Loophole Strategy.

The SLS Brings the Heat When You Need R&R

A stopover is a planned stop between flight segments on a trip. For international trips, a stop for 24 hours is usually allowed for free, but on domestic flights it’s generally just 4 hours. That said, there are some amazing “exceptions to the rule.”

To offer an example, you could pay $1,145 for a Business Class return trip between San Francisco and New York. But with our stopover loophole strategy, you could sneak in a relaxing few days or longer in the Caribbean on the way home. Imagine adding a paradise like St. Thomas, and paying $223 less on your overall fare. Who wouldn’t be happy as a clam with that?!

Viewed another way, you add a vacation in St. Thomas and only pay a total of $922 for the entire trip in Business Class. Not all of these add-on trips are “less than free” as we like to say (when you end up paying less than your original price, for more).

Note that you can stop in St. Thomas in either direction using the same cities, but the cost may be different. Still good, just different.

For example, Chicago-Dallas-St. Thomas-Chicago is $732 (Chicago-St. Thomas round-trip is $622) while Chicago-St. Thomas-Dallas-Chicago is $782.

You can find the current Covid testing requirements here.

Need a Reason, or Two, to Visit St. Thomas?

St. Thomas is the second-largest and most visited island in the U.S. Virgin Islands, and it shows off its assets with pride. The capital of Charlotte Amalie, one of the prettiest in the Caribbean, frames a gorgeous turquoise harbor dotted with sleek yachts and splashy cruise ships. Its 200-year-old red-roofed buildings climb hillsides and offer jaw-dropping views from the top. In addition to excellent dining, exciting nightlife, duty-free shopping, and even submarine rides, you can still see remnants of the island’s Dutch and Danish heritage in museums, forts, and historic houses around the island.

And we can’t fail to mention the beaches. St. Thomas is blessed with 40 sun-drenched beaches — from intimate pocket coves to long sigh-worthy strands like bleach-white Magens Bay, which is the glorious granddaddy of them all. You can swim, fish, snorkel, sail, windsurf, or just swing on a hammock sipping a fancy umbrella drink. After dark, join the fun at the waterfront bars and taverns in the Red Hook area, which turns into a bustling nightlife scene.