Airlines will sometimes try to sell you roundabout routings, and I can’t help but share one that gave me a bit of a chuckle. While I won’t be flying it this time around, it’s definitely some inspiration for a future review trip…
In this post:
Miami to Nassau via Port of Spain and Kingston?!
I need to fly between Miami (MIA) and Nassau (NAS) for a quick upcoming trip, which is a short 184-mile flight, even shorter than my typical 204-mile flight to Tampa (TPA). The route is well served by American (among other carriers), so my obvious assumption was that I was going to fly nonstop.

However, when I looked at business class options between Miami and Nassau on Google Flights (I always check, just out of curiosity), I was presented with a surprising routing. Specifically, Google Flights recommended a $553 business class itinerary from Miami to Port of Spain (POS) to Kingston (KIN) to Nassau.

So rather than flying nonstop, I could turn this into a 13-hour adventure. It’s not often you see an airline selling you a 3,264-mile routing for a city pair that’s 184 miles apart. That’s nearly 18x the direct distance! And before anyone asks, yes, Caribbean Airlines actually sell this routing as one ticket — this isn’t a case of Google Flights combining separate tickets and passing them off as one.

Sometimes I’ll intentionally subject myself to wildly roundabout routings by booking separate tickets, but to proactively be offered something like this? Purely in terms of direct distance vs. distance flown, this might be the most roundabout routing I’ve ever been presented.
Honestly, I would’ve booked this, except I hate redeyes and want to be awake and alert for the two days I’m in the Bahamas, so I decided against the routing.
I have to figure out an interesting Caribbean review trip
At some point in the near future when I have a couple of days free to travel (beyond what I’ve already planned), I’d really like to give Caribbean Airlines business class a shot, on the carrier’s Boeing 737 MAX. It seems like one of the better business class products in the Caribbean.
I’m trying to figure out how I can create a logical itinerary with that, though. Even though many Caribbean islands are close to one another, air service is often limited.
For example, it would be fun to fly Air France’s Airbus A320 “island hopper,” which goes from Miami to Pointe-a-Pitre (PTP), to Fort-de-France (FDF), to Cayenne (CAY). However, actually linking that with Caribbean Airlines in the other direction is easier said than done.

For example, at least on Google flights, there’s not a single option to fly between Cayenne and Port of Spain on one ticket. Can anyone think of a fun and creative way to make this work, possibly adding in yet another airline? In a dream world, I’d also check out Cayman Airways’ Boeing 737 MAX business class, to experience that Sir Turtle magic, but maybe I’m just getting greedy. 😉
Bottom line
Airlines will sometimes try to sell you very strange routings, though I never saw anything quite like what I was presented during a recent search on Google Flights. I need to fly from Miami to Nassau, and was presented a Caribbean Airlines routing via Port of Spain and Kingston.
As tempted as I was, the redeye combined with the amount of time didn’t work for me this time around, but it is inspiration for a future review trip.
Anyone have any ideas for a fun Caribbean review trip, and how to knock out these airlines on a single trip?
There are many routes for different origin and destination pairs that are offered and do not make much sense. Surprisingly it is often more expensive than the more direct or non stop routing.
The same route on Caribbean Airlines is $366 on November 7!
WestJet/Delta once offered me a $100 one way from AUS to YYZ, but instead of the $600+ non-stop, routed me from Austin to Seattle to Edmonton to Toronto. I took it! Flew all day and lounge hopped and had a great time.
I haven't seen it for a couple years, but around three years ago there were unusual Delta routings popping up on Delta.com or Google Flights. Like first-class tickets with connections through Dallas, O'Hare and San Diego. I did this a few times. The issue was my bag never made it onwards because Dallas and O'Hare weren't used to handling connections. So the bags always went to baggage claim.
I've flown Caribbean Business Class several times ex POS. They are generally quite good and have nice meals. For a time they were actually pouring Moet in Business but I believe they discontinued that. At least the last flight did not have it available.
Yes - Trinidad is interesting. The Hyatt is top shelf, however I prefer the older "upside" down Hilton.
The airline is not permitted to fly directly to Nassau from Miami nor would it make commercial sense for it to do so. It operates primarily serving the Central Caribbean with excellent international service to such routes as MIA, JFK, LHR, YYZ, for example.
Once on an award ticket for NRT to SFO one of the options presented all on AA was NRT-LAX-JFK-SFO! Going from LAX to SFO vis JFK is quite absurd
AF island hopper is fun. I have flown it many times, including when it used to stop in PAP. Now it goes nonstop MIA to PTP, and as mentioned by others, extends into BEL. From Belem, you could route back to FL on Azul's A320 nonstop BEL-FLL.
BA and VS have a number of 5th Freedom hops. In April, it was great to toast champagne on BA's 777 ANU-SKB hop. I was the only...
AF island hopper is fun. I have flown it many times, including when it used to stop in PAP. Now it goes nonstop MIA to PTP, and as mentioned by others, extends into BEL. From Belem, you could route back to FL on Azul's A320 nonstop BEL-FLL.
BA and VS have a number of 5th Freedom hops. In April, it was great to toast champagne on BA's 777 ANU-SKB hop. I was the only passenger in the entire Biz Cabin, as everyone deplaned in Antigua.
Last year I also did a fun routing to explore Guyana, Suriname, French Guiana and threw in Norway:
AA: MIA-GEO
PY: GEO-PBM
KL: PBM-AMS-OSL
AF: OSL-CDG-CAY
AF: CAY-FDF-PTP-MIA
All on miles in J, except for the paid Econ flight on Surinam Airways.
Try to fit in some of BA's fifth freedom flights between the islands (St. Lucia to Tobago, Nassau to Providenciales, etc.) Plus, depending on whether it's a Gatwick or Heathrow aircraft, you might get either a first class seat sold as business, or the old Club World backwards seat for old times sake!
Don't forget that you can punch through CAY onward to Brazil with Air France, either to Belém or Fortaleza. From there, you can take Suriname Airways back to Paramaribo, and pick up the Caribbean Airways 737 Max to Port of Spain. Azul also flies back to FLL from Belém...but it's a 6 hour A320 ride.
One is surprised that the virtue signalling trolls are not all over you Ben, for even thinking such a thing …. :-)
Maybe 15-20 years ago, I was looking for an AKL-SYD flight to fill in yhe open jaw I already booked. Expedia offer the following. AKL-LAX-Something in Asis-SYD and a surpringly low price. Of course, I opted for a sub 4 hours n/s.
You could fly between Cayenne and Port-of-Spain back via Paramaribo, Suriname! I would like to hear about Surinam Airways
I've flown on Caribbean's 737 Max in Business Class with the extra-reclining recliners on FLL-POS (piece of... nah, it's fine), and also on their ATR72 between BVI and SJU. Both flights were reliable, comfortable, and the flight crews were professional.
Generally, Trinidad (and Tobago) is an interesting destination; if you do go, there's a decent Hyatt Regency in Port of Spain; a visit to Maracas Beach for a bake and shark is fun; if...
I've flown on Caribbean's 737 Max in Business Class with the extra-reclining recliners on FLL-POS (piece of... nah, it's fine), and also on their ATR72 between BVI and SJU. Both flights were reliable, comfortable, and the flight crews were professional.
Generally, Trinidad (and Tobago) is an interesting destination; if you do go, there's a decent Hyatt Regency in Port of Spain; a visit to Maracas Beach for a bake and shark is fun; if you're a birder, a visit to the Caroni Swamp is worthwhile (to see the scarlet ibis); supposedly, Tobago is more for tourists (haven't been, but would like to, someday).
Anyway, if I were you, Ben, I'd just take the nonstop to NAS, so you don't get stuck anywhere.
POS/Trinidad is perfectly fine, but Tobago is incredible. Less crowded than many other Caribbean islands and way more Europeans than Americans, which is a nice bonus. Some of the most beautiful water I've ever seen. Plus you get to take the gov't subsidized ATR from island to island (but do a bit of research if connecting, the Tobago flights leave from their own section of the terminal)
Well, recently, if you've been following the news, the USA has been murdering Venezuelan fishermen, (sorry, depending on your news source, I meant, 'drug cartels') in those waters off the coast... so, just saying, the region may be 'heating up.' (Like, flashbacks to Secretary Powell at the UN speaking of WMDs, etc.)
When I lived in the U.S. Virgin Islands, One Caribbean News (broadcast from Erie, Pennsylvania) was both the "local" TV station on the NBC and I think CBS affiliate but was also syndicated to most of the other islands -- British islands, French islands, independent islands. In some cases, it was the only station with real meteorologist, which was obviously huge during hurricane season. The chief meteorologist, Joey Stevens, was a huge celebrity and did...
When I lived in the U.S. Virgin Islands, One Caribbean News (broadcast from Erie, Pennsylvania) was both the "local" TV station on the NBC and I think CBS affiliate but was also syndicated to most of the other islands -- British islands, French islands, independent islands. In some cases, it was the only station with real meteorologist, which was obviously huge during hurricane season. The chief meteorologist, Joey Stevens, was a huge celebrity and did a lot of promos throughout the Caribbean. The Hyatt Regency in Trinidad used to underwrite his weather forecasts and advertised special rates. I always wanted to go there.
Nick, speaking of hurricanes, what happened this season?! It’s been silent in the Atlantic for the most part. Probably a record low landfall. Like, wow. I mean, thank goodness. Thank all the deities.
This is really bad for the environment and this is why there should be some limit to how much indirect routes can deviate in terms of the miles flown.
If you backtrack to Suriname you can fly GUM air to OGL in Guyana and fly CA from there too. You can also originate at PBM with a CA itinerary to anywhere.
Ken, I think we lost the whole climate debate, at least in the USA; like, China’s probably gonna lead the way on renewables, and, let’s be honest, aviation isn’t the primary contributor, besides, unless we repeat 2020 and halt all flights, or develop a teleported there’s no good alternatives to jet fuel for large-scale intercontinental aviation. (Don’t worry, 20 years ago they said that ‘fusion’ is the solution and it’s only 20 years away.) Sorry,...
Ken, I think we lost the whole climate debate, at least in the USA; like, China’s probably gonna lead the way on renewables, and, let’s be honest, aviation isn’t the primary contributor, besides, unless we repeat 2020 and halt all flights, or develop a teleported there’s no good alternatives to jet fuel for large-scale intercontinental aviation. (Don’t worry, 20 years ago they said that ‘fusion’ is the solution and it’s only 20 years away.) Sorry, bud. Enjoy the corals, rainforests, and large game on the savanna while you still can.
Was it possible to make one or two proper stopovers on the routing? Then the ticket would be interesting to explore various places
Try all of the fifth freedom flights on BA and Virgin (I believe they only have one) within the Caribbean!
If you end up booking a review on Caribbean Airlines.....good luck!
Have friends from Trinidad and Jamaica here in Miami who will spend anything or connect anywhere just to avoid flying Caribbean
Another well known vlogger - whose name rhymes with a baby horse - took multiple flights on CA and tried to make out it was TERRIBLE!! Didn’t seem so bad to everyone else.
You're truly an odd duck for even considering this routing. :) Would be cool to see reviews of the Air France island hopper and BA or KLM's interisland flights. Maybe MIA-PLS then PLS-NAS on BA?
Yes, please review my airline, Ben!
I did the short distance hop between EWR and JFK so many times.
But it's gonna cost you. Going via SIN is way more expensive than taking a cab ride but you can't lieflat and book the cook on a cab, so it's not too bad.
You win… this time.
Re: the AF Island Hopper, you can fly from Cayenne to Belem (also on AF) and it shouldn't be hard to get back to Miami from Northern Brazil. Cayenne hotel review would be fun too.
Two things:
1) The Bahamas is not in the Caribbean.
2) That aside, I suspect this is sold as one ticket because crazy routings like this aren't totally unheard of in the West Indies/Caribbean. I have twice lived in the U.S. Virgin Islands. One on St. Croix and the other time on St. Thomas. When I first moved there I thought I would spend weekends once or twice a month flying around to other...
Two things:
1) The Bahamas is not in the Caribbean.
2) That aside, I suspect this is sold as one ticket because crazy routings like this aren't totally unheard of in the West Indies/Caribbean. I have twice lived in the U.S. Virgin Islands. One on St. Croix and the other time on St. Thomas. When I first moved there I thought I would spend weekends once or twice a month flying around to other islands in the region. Even when you can get nonstop flights, they're not inexpensive and the schedules can be limited. Toss in an IROP and you can get stranded for a day or two. Try flying from San Juan or St. Thomas to Jamaica or Trinidad and Tobago. You're likely going all the way back to Miami or Fort Lauderdale. San Juan has some interesting options, but you might end up going through Panama on Copa or Bogota on Avianca to get to another island.
@ Nick Thomas -- Understood about Bahamas not being in the Caribbean (at least technically), and I don't think I suggested it was. Instead, this routing to the Bahamas through the Caribbean prompted me to want to take a Caribbean review trip (which almost certainly won't include the Bahamas).
Bahamas is, or Bahamas are? Maybe a future post from Ben. By itself, or with his discussion of the difference between direct and nonstop (as in, Miami to Singapore).
The country is the Bahamas. So, correct usage is the Bahamas "is." Just like the United States. But remember, it's also "an historical hotel" and never "a historical hotel."
You do you, but you are going to pay 500+ dollars to fly business class for like 30-45 minutes lol.
@ Andrew -- The $500+ would be for a 13+ hour Caribbean Airlines adventure, not the nonstop.
I'm surprised that AA sold this as a single ticket without some crazy price. I sometimes if flying on a Saturday IN FALL AND SPRING (after thunderstorm season and before winter weather) I'll do a three stop to a west coast city, like MIA/CLT/PHX/TUS if the price isn't much more than a single connection.
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