On a per-mile basis, these First Class fares are hard to beat

Dividing the price by the miles flown is a way of leveling the playing field when comparing airfares to different destinations because it tells you how far a buck takes you from your departure city. Caribbean First Class fares, in many markets as low as $700 to $900 round-trip, stack up well compared to lower-48 First Class fares, often $900 to $2,000 or more.

We surveyed dozens of routes and found that the following destinations have First Class fares of $700 to $900 from many US cities: Grand Cayman, Montego Bay (Jamaica), San Juan (Puerto Rico), Santo Domingo, and Nassau (Bahamas). Many other destinations are available for another $100 to $200.

Low First Class fares to the Caribbean began in 2002 when US Airways, trying to avoid bankruptcy, slashed fares to less than $1,000, a level rarely seen ($1,600 to $2,600 had been the norm). At the same time, the carrier launched a slew of new routes to the region, and the two initiatives drove down fares overall as other carriers matched US Airways.

Most routes have stayed relatively inexpensive ever since.

No need to use miles to the Caribbean… With fares this low, it doesn’t make sense.

…Or 2-for-1s… Buying two published fares will usually cost you less than using Continental’s or Delta’s (Amex IAP) 2-for-1 programs because they’re valid only with full fares. These usually cost more than twice the lowest discounted First Class fares, but it never hurts to check both fares as there can be an occasional surprise.

…Or elite upgrades In this case, they’re a lose-lose proposition. If you’re flying American or United, the surcharge could bring your outlay close to that of a paid First Class fare—and you can’t confirm until just before departure. If you’re flying Continental, Delta, Northwest, or US Airways, which all offer “free” upgrades to elites on Caribbean routes, you’ll have a lot of competition, especially in peak season. So, why play elite upgrade roulette when there’s a sure bet?

Last-minute elite status help If you’re just short of reaching your elite status qualifications, now’s the time (and the Caribbean is sure a fine place) to go on a ‘Mileage Run,’ a term used for flying for the sake of earning mileage and/or elite status credit. On a per-mile basis, these are some of the lowest fares you’ll find. Business Class bonuses can yield up to 150% elite and mileage credit.