There are so many islands in the Caribbean that it would take forever to list them all but I will concentrate on the islands that will appeal to birders. The bad news is that very few islands are served by a member of the main three alliances (Star Alliance, OneWorld, Sky Team) so you would be able to book a ticket with miles. The easiest island with the most connections, especially via the USA is Puerto Rico and I have a separate post with the details. So lets look at the rest of the Caribbean. On the map below, I have highlighted in yellow the islands that are most attractive to birders.
LIST OF ISLANDS WITH AIRLINES BOOKABLE WITH MILES
ARUBA – American & LATAM (OneWorld), Avianca, Copa, United (Star Alliance), Delta, KLM (SkyTeam)
BONAIRE – United (Star Alliance), Delta, KLM (SkyTeam)
CAYMAN ISLANDS – American & British Airways (OneWorld), United (Star Alliance), Delta (SkyTeam)
CUBA – American, Air Berlin, Iberia & LATAM (OneWorld), Avianca, Copa, Air Canada, Swiss, Austrian, United (Star Alliance), Aeromexico, Air France, Delta, KLM (SkyTeam)
CURACAO – American, Air Berlin (OneWorld), Avianca, Air Canada,, Copa, United (Star Alliance), KLM (SkyTeam)
DOMINICA – Seaborne is a partner of American Airlines (OneWorld) but not a member of OneWorld. In my experience they rarely release seats, I tried over several months then had to settle for LIAT.
DOMINCAN REPUBLIC (Punta Cana) – American, British Airways (OneWorld), Avianca, Air Canada, Swiss, Copa, United (Star Alliance), Delta, KLM, Aerolineas Argentinas (SkyTeam)
JAMAICA – American, British Airways (OneWorld), Copa, Air Canada (Star Alliance), Delta (SkyTeam)
ST LUCIA – American, British Airways (OneWorld), Air Canada, United (Star Alliance), Delta (SkyTeam)
ST VINCENT – no alliances
TRINIDAD & TOBAGO – American, British Airways (OneWorld), Copa, United (Star Alliance)
HOW MANY MILES WILL IT COST?
Every airline member of the 3 main alliances has it’s own frequent flier program. They often have alliances with other airlines outside the program. I have made some reference charts for the airline alliances and I strongly recommend that you check out the program of the airline in your country and the USA based partners of each program as the USA airlines tend to have the most lucrative bonuses. Americans can get very generous credit card bonuses. Details of credit card partners (and other partners) will be on each airline’s website, however often there are more lucrative sign up bonuses. Details are usually posted in the Flyer Talk thread so I strongly suggest you read this thread and the Miles Buzz forum before you apply for any cards just in case a better bonus has been offered. I don’t have any affiliate links and I recommend you do extensive research on your own when applying for airline credit cards. I’m going to use Port of Spain (POS), Trinidad for my example airport in OneWorld & Star Alliance and Curacao (CUR) for Sky Team.
USING ONE WORLD
AMERICAN AIRLINES
No matter where you live, frequent flyer programs based in the USA usually offer the best deals but it’s still a good idea to look at other members of the alliance. Try to avoid carriers that charge a fuel surcharge. Looking at AA’s award chart, we can see that the Caribbean has it’s own region. These are the miles you will need when traveling to the Caribbean.
You will notice there are taxes and fees with certain routes and that the awards are prices as one way trips.
We can see that a South Pacific to the Caribbean award will cost 45,000 miles each way (90,000 round trip) in economy, 82,500 (160,000 round trip) in business class and 112,500 each way (225,000 round trip in first class.
If you are based in North America, economy will cost 17.500 each way (35,000 round trip), business class is 27,500 each way (45,000 round trip) and first is 52,500 each way or 105,000 round trip. You would be flying on AA or LATAM.
AVIOS (BA OR IB)
Avios can be a great bargain for shorter flights. The awards are priced by distance flown per segment rather than zone to zone.
Using the Great Circle Mapper, we can see that a direct flight from Miami to Port of Spain, Trinidad would cost 10,000 Avios each way, a direct flight from LAX to Port of Spain would cost 20,000 Avios and a direct flight from NYC to Port of Spain would cost 12,500 Avios. If you are using credit card miles, transferring them to Avios rather than UA or AA could save you some points. If you need a connection from elsewhere in the USA to the gateway city, you need to pay for that segment separately with the Avios cost for the distance flown. Example OKC-MIA is 1222 miles so you need to add 10,000 Avios to the total price of the ticket. There are also some attractive 5th freedom routes on British Airways such as Port of Spain to St Lucia for a mere 4500 Avios!
QANTAS FREQUENT FLYER
For Qantas, it is easiest to use their points calculator to see how many points you need, then look for availability. Not all itineraries can be booked online, sometimes you have to call them. Using the example of Sydney to Port of Spain we can see that they route through London or the USA and economy is 75,000 points one way. Be careful with the business class offering, if you hover over it, you will see that the SYD-LHR segment is in economy. On the last screen you see the miles required and the taxes including YQ fuel surcharges you have to pay.
If you are based somewhere else, leave a comment if you don’t understand this part and I will help you out. Meanwhile, here is a reference list for other One World carriers.
USING STAR ALLIANCE
United, Avianca and Singapore are probably the most common Star Alliance programs in use because of good credit card deals and buy miles promos.
UNITED AIRLINES
United Airlines is a USA based carrier that offers one way awards on its own flights and other Star Alliance carriers. Due to the size of their award chart, I can’t paste it here so will link to it and give examples. For example Orlando to Port of Spain has availability on several dates which I picked at random. They are colour coded for economy, business/first or all three classes. Make sure you scroll all the way down to see all the options. Some routes are only 17.5k and others are a whopping 37.5k! And beware of routes where it is cheaper to fly business class than economy!
AVIANCA TACA LIFEMILES
Lifemiles has some very attractive promos to buy and share miles. While this doesn’t give you a free trip, it can greatly reduce the cost of a trip especially if you are after business or first class awards. You need to be an existing member of Lifemiles when they announce a promo so join now if you haven’t already. Use their calculator to get an idea of award costs. This will be a range which depends on class and any promos.
They have a Star Alliance Award chart and you can see that they divide the continent of South America into northern and southern regions and the Caribbean is on it’s own region. Australia and New Zealand are in the “Others” category. The chart shows one-way awards. I prefer to keep my Lifemiles for intra-South/Central America awards which can get pricy but are bargains using awards.
SINGAPORE AIRLINES
SQ miles have become much easier to get in recent years. Americans can use Chase Ultimate Rewards, Citi Thank You, Amex Membership Rewards. Aussies can use the Australian Amex Membership Rewards. Everyone can use SPG. Just beware of the high fuel (carrier) surcharges when you use Krisflyer. Personally, I would be happy to use SQ miles for intra-South America awards where surcharges are low or even non-existant but would use other programs to get from Australia to the Caribbean. The one oddity is that they include Hawaii, Central America & the Caribbean in the same region so you can get really good value if you are making a multi-centre holiday!
SKY TEAM
FLYING BLUE
The only Sky Team program I use and can personally recommend is Air France/KLM. The awards are reasonably priced and fuel surcharges aren’t TOO bad! Let’s use a sample route of Madrid to Curacao. You can do even better than this if Flying Blue is running a promo but these promos are usually only for the next couple months so you can’t book far in advance.
I don’t use all the programs that are out there but these are the most commonly used programs by travel hackers in the USA and Australia so do some research to see which one works for you! Bear in mind that the tickets are not completely free, there is usually a booking fee of $25-50 and various taxes, but you would have to pay the taxes whether you pay cash or miles for the ticket in any case.
The trail gets more challenging as you keep going up. They do have signs to point the way. 
Boarding is generally via stairs on the tarmac through both front & rear doors. Therefore you don’t want a seat in the middle of the plane. Passport control lines are long and move slowly at most islands.
