The Power of American Upgrades to the Caribbean, Plus Surprising Availability

November 2018
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Elite, non-elite, business, and leisure travelers can now save big on Caribbean routes—up to 57%.

Ah, the Caribbean. Who can resist its blissful beaches, crystalline waters, and alluring tropical vibes? There’s no better place to relax, re-charge, and renew. Happily, American Airlines serves more than 20 islands throughout the region—with more opportunities to upgrade than you can shake a pineapple at.

Why Use Miles to the Caribbean?

Beaches: Shimmering sandy strands that seem to go on forever.

Water sports: Few places can compare to the Caribbean for its bathtub warm water, bountiful marine life and colorful reefs, swimming, snorkeling, and diving.

Scenery: From lush parrot-laden jungles to palm-fringed beaches, the Caribbean’s natural beauty is legendary, along with the fiery sunsets.

Luxury accommodations: Choose your perfect lodging—everything from a stylish all-inclusive resort with private plunge pools to a luxury beachfront villa with personal staff.

Ready to go? Here’s how to do it using American upgrades.

American’s Upgrade Program

To the Caribbean, American requires 15,000 miles plus a $75 co-pay each way on the lowest upgradeable economy fares (H, K, M, L, V, G, Q, N, O, S classes) to Business Class.

Low Economy Route Saves 52%

Charlotte to Nassau is one of American’s lowest economy fare routes, currently starting at $333 round-trip, while Business Class starts at $1,019. Even with the $150 co-pay you can save $536 (52%) off the published fare by using 30,000 miles to upgrade. (See chart below for a survey of upgrade-award availability.)

When NOT to Use Miles for an Upgrade

Miami to Nassau is one of American’s lowest Business Class fare routes, currently starting as low as $466 round-trip, while coach starts at $202. Add in the $150 co-pay and you are looking at $352 plus 30,000 miles to upgrade. This gives you a savings of only $114 and a return on your miles of next to zero. So always check published Business Class for travel to the Caribbean because it is a region that, at times, offers very low Business Class fares, making the use of miles for an upgrade not a good deal.

Connections Can Save Up To 57%

Savvy travelers use the longer-haul Business Class flight as a “bridge.” All they have to do is get to and from the U.S. bridge gateway.

That means you might even buy an economy through-fare ticket, which gets you to and from the U.S. gateway on one ticket rather than requiring two separate ones. Upgrade all the flight segments if space is available.

Example: Los Angeles-Punta Cana. The through-fare ticket, via Charlotte or Miami in coach is $487 versus $1,479 in Business Class. Even with the $150 co-pay, you can save $842 (57%) off the published fare by using miles.

Use our cheat sheet, below, to know when you can easily upgrade the long-haul segments; fly the short connecting flight/s in coach if you must—although it doesn’t cost any more to upgrade those flights either. All you need is for them to be available for the miles upgrade.

How to Book Mileage Upgrades with American

Before buying your economy ticket, call American at 1-800-433-7300 (upgrades cannot be booked online) to find out if the specific flights/dates you want are available for a mileage upgrade. Book the economy ticket online—keep the American rep on the phone—then have the reservationist book the upgrade. You can also book the ticket and the upgrade by phone, but there’s a booking fee of $35 for international flights.

If the upgrade on the flights/dates you want is not available, have the agent check dates/flights on the days before and after.

Use our survey below to get an idea of months with great upgrade space to get off to a flying start.

How Anyone Can Play This Upgrade Game
and When to Buy Miles

Don’t have enough American miles and need to top off your account? No problem. Just buy AA miles when they go on sale (recent opportunity here).

Don’t have any American miles but do have Starwood/Marriott points? Then transfer Starwood/Marriott points.

Other Recent Upgrade Reports

Just look at these similar examples with American and United (Delta’s upgrade award program is worthless). In the past 11 months, FCF has written 10 special reports for oneworld (American) and Star Alliance (United) members looking to deploy miles to achieve or maintain elite status while flying up front.

In December we focused on American to Europe, in January to Asia on American, in February to South America on American, in March on American’s Transcon, in April to Hawaii on American, in May to Asia on United, in June to South America on United, in July to Europe on United, in August to the South Pacific on United, and this month to Peru on United.

Sweet Redeem Survey: American Mileage Upgrades to the Caribbean

[table_opt id="6008" style="black-header" width="default" alignment="thcenter" heading="thcenter" rows="tdcenter" responsive="no" /]

[["Routes","Depart","#colspan#","#colspan#","Return","#colspan#","#colspan#"],["#rowspan#","4 to 8 Days Per Month","9 to 12 Days Per Month","13+ Days Per Month","4 to 8 Days Per Month","9 to 12 Days Per Month","13+ Days Per Month"],["Charlotte - Montego Bay","Jan., <span style=\"color: #6699cc;\">Feb., March, May, June,<\/span> July, <span style=\"color: #009966;\">Dec.<\/span>","May, June, <span style=\"color: #6699cc;\">Aug.<\/span>","March, April, Aug.","<span style=\"color: #6699cc;\">Jan.,<\/span> <span style=\"color: #009966;\">March.,<\/span> <span style=\"color: #6699cc;\">April, May,<\/span> July, <span style=\"color: #009966;\">Nov., Dec.<\/span>","March, May, June","April"],["Charlotte - Nassau","<span style=\"color: #6699cc;\">Jan. through March,<\/span> May","Feb., <span style=\"color: #6699cc;\">April<\/span>","March, June, <span style=\"color: #6699cc;\">July, Aug.<\/span>","<span style=\"color: #009966;\">Jan.,<\/span><span style=\"color: #6699cc;\"> Feb.,<\/span> March, <span style=\"color: #6699cc;\">April,<\/span> June, <span style=\"color: #6699cc;\">July, Aug.,<\/span> Nov., Dec.","Jan., Feb.","<span style=\"color: #6699cc;\">March, June,<\/span> July"],["Charlotte - Punta Cana","<span style=\"color: #6699cc;\">Jan., March,<\/span> <span style=\"color: #009966;\">April, July,<\/span> <span style=\"color: #6699cc;\">Aug.,<\/span> <span style=\"color: #009966;\">Dec.<\/span>","<span style=\"color: #6699cc;\">April, May<\/span>","June, July, <span style=\"color: #009966;\">Aug.<\/span>","March, <span style=\"color: #6699cc;\">April,<\/span> May, <span style=\"color: #6699cc;\">June through Aug.<\/span>","<span style=\"color: #009966;\">May, June<\/span>","<span style=\"color: #009966;\">April, July, Aug.<\/span>"],["Chicago - Montego Bay","<span style=\"color: #6699cc;\">Jan.,<\/span> Feb., <span style=\"color: #009966;\">March,<\/span> <span style=\"color: #6699cc;\">April,<\/span> <span style=\"color: #009966;\">Dec.<\/span>","<span style=\"color: #009966;\">April<\/span>","","<span style=\"color: #6699cc;\">Jan.,<\/span> <span style=\"color: #009966;\">Feb., April<\/span>","<span style=\"color: #009966;\">March<\/span>",""],["Dallas - Montego Bay","<span style=\"color: #6699cc;\">Jan., March, Aug.,<\/span> <span style=\"color: #009966;\">Nov.<\/span>","","","Jan., March, <span style=\"color: #6699cc;\">May.,<\/span> Aug., <span style=\"color: #009966;\">Nov.<\/span>","",""],["Miami - Grand Cayman","Jan., Nov., Dec.","","","<span style=\"color: #6699cc;\">Jan.,<\/span> <span style=\"color: #009966;\">Nov.<\/span>","",""],["Miami - Havana","Jan., Feb., <span style=\"color: #6699cc;\">June, Dec.<\/span>","<span style=\"color: #6699cc;\">Jan.,<\/span> March, April, <span style=\"color: #6699cc;\">May., Nov.<\/span>","<span style=\"color: #009966;\">Jan. through Dec.<\/span>","May, June, <span style=\"color: #6699cc;\">July,<\/span> Aug., <span style=\"color: #6699cc;\">Nov., Dec.<\/span>","Feb., March, <span style=\"color: #6699cc;\">June,<\/span> July, <span style=\"color: #6699cc;\">Aug.<\/span>","<span style=\"color: #009966;\">Jan. through Dec.<\/span>"],["Miami - Montego Bay","<span style=\"color: #6699cc;\">Jan.,<\/span> <span style=\"color: #009966;\">Feb.,<\/span> <span style=\"color: #6699cc;\">April,<\/span> <span style=\"color: #009966;\">June,<\/span> Aug., <span style=\"color: #6699cc;\">Nov.,<\/span> <span style=\"color: #009966;\">Dec.<\/span>","<span style=\"color: #6699cc;\">March,<\/span> May, <span style=\"color: #009966;\">July, Nov.,<\/span> <span style=\"color: #6699cc;\">Dec.<\/span>","<span style=\"color: #009966;\">Jan., March though May,<\/span> <span style=\"color: #6699cc;\">June, July,<\/span> <span style=\"color: #009966;\">Aug.<\/span>","<span style=\"color: #009966;\">Jan., Feb.,<\/span> <span style=\"color: #6699cc;\">April,<\/span> May, <span style=\"color: #6699cc;\">July, Aug., Nov.<\/span>","Jan., <span style=\"color: #6699cc;\">Feb., June,<\/span> <span style=\"color: #009966;\">Aug.,<\/span> <span style=\"color: #6699cc;\">Dec.<\/span>","<span style=\"color: #009966;\">March through July,<\/span> Aug., <span style=\"color: #009966;\">Nov., Dec.<\/span>"],["Miami - Nassau","<span style=\"color: #009966;\">Jan.,<\/span> Feb., <span style=\"color: #6699cc;\">June, July,<\/span> Aug.","","March","<span style=\"color: #6699cc;\">Jan.,<\/span> Feb., <span style=\"color: #6699cc;\">March,<\/span> June, <span style=\"color: #6699cc;\">July, Aug.<\/span>","","<span style=\"color: #6699cc;\">June<\/span>"],["Miami - San Juan","Jan., March, <span style=\"color: #6699cc;\">April, June,<\/span> July, <span style=\"color: #6699cc;\">Aug.,<\/span> Nov.","Feb., <span style=\"color: #009966;\">May,<\/span> Aug.","<span style=\"color: #009966;\">May, June<\/span>","<span style=\"color: #009966;\">Jan., Feb.,<\/span> <span style=\"color: #6699cc;\">March, Aug., Nov.,<\/span> Dec.","Jan., <span style=\"color: #6699cc;\">April, May,<\/span> Nov.","Feb., April, May, <span style=\"color: #6699cc;\">June., July,<\/span> Aug."],["Miami - Santo Domingo","<span style=\"color: #009966;\">Feb.,<\/span> <span style=\"color: #6699cc;\">March,<\/span> <span style=\"color: #009966;\">April, May,<\/span> <span style=\"color: #6699cc;\">June through Aug.,<\/span> <span style=\"color: #009966;\">Nov.,<\/span> <span style=\"color: #6699cc;\">Dec.<\/span>","April, <span style=\"color: #6699cc;\">May,<\/span> Dec.","","Jan., <span style=\"color: #009966;\">March, April,<\/span> <span style=\"color: #6699cc;\">May,<\/span> <span style=\"color: #009966;\">July,<\/span> Aug., <span style=\"color: #6699cc;\">Nov.<\/span>","Feb., <span style=\"color: #6699cc;\">March, April,<\/span> <span style=\"color: #009966;\">June,<\/span> Nov.","April, <span style=\"color: #009966;\">May,<\/span> June, <span style=\"color: #6699cc;\">July, Aug., Dec.<\/span>"],["Miami - Sint Maarten","<span style=\"color: #6699cc;\">June,<\/span> <span style=\"color: #009966;\">July<\/span>","<span style=\"color: #6699cc;\">July<\/span>","<span style=\"color: #009966;\">Aug.<\/span>","<span style=\"color: #6699cc;\">July, Aug.<\/span>","July",""],["New York - Antigua","March","Aug.","","June, July","",""],["New York - Punta Cana","","","<span style=\"color: #009966;\">July through Aug.<\/span>","","","<span style=\"color: #009966;\">July through Aug.<\/span>"],["Philadelphia - Montego Bay","Jan., <span style=\"color: #009966;\">March,<\/span> April, <span style=\"color: #6699cc;\">Aug.<\/span>","<span style=\"color: #009966;\">April,<\/span> May, <span style=\"color: #6699cc;\">June, July,<\/span> <span style=\"color: #009966;\">Aug.<\/span>","<span style=\"color: #009966;\">May through July<\/span>","Jan., <span style=\"color: #009966;\">March through May,<\/span> June, <span style=\"color: #6699cc;\">July,<\/span> <span style=\"color: #009966;\">Nov.<\/span>","July, Aug., <span style=\"color: #009966;\">Dec.<\/span>","<span style=\"color: #6699cc;\">May,<\/span> <span style=\"color: #009966;\">June through Aug.<\/span>"],["Philadelphia - Nassau","<span style=\"color: #6699cc;\">Jan., March<\/span>","","","March, April, June","",""],["Philadelphia - Punta Cana","<span style=\"color: #6699cc;\">Jan.,<\/span> <span style=\"color: #009966;\">March,<\/span> <span style=\"color: #6699cc;\">April, May,<\/span> Aug., <span style=\"color: #6699cc;\">Nov., Dec.<\/span>","<span style=\"color: #6699cc;\">June,<\/span> July","May, June, <span style=\"color: #6699cc;\">July, Aug.<\/span>","<span style=\"color: #6699cc;\">Jan.,<\/span> Feb., March","<span style=\"color: #6699cc;\">May, June,<\/span> July, Aug.","June, <span style=\"color: #6699cc;\">July, Aug.<\/span>"]]
<small>Months in black at least one seat available; <span style="color: #6699cc;">in <u>blue</u> at least two seats</span>; <span style="color: #009966;">in <u>green</u> at least four seats</span>.</small>