What is the Caribbean Hopper?
This is a route I came up with to go from the US to a Caribbean island, either for a layover or stopover and then head to a different Caribbean island for the final destination. When going from one island to the other you’ll have to route through Panama City and will most likely be offered a 17 hour layover in Panama City.
For 17,500 United miles you can go from your home city to a Caribbean island for <24 hours and then to Panama for <24 hours and then to your final Caribbean island for as long as you want.
For 35,000 United miles you can spend as long as you want on the first island as you can add a stopover to a roundtrip. Thus making two islands your destination and still having the option to layover in Panama City.
This post will go over some of your island options, how to find and book this online and some Central American options.
First we’ll go over a bit of the rules included. But I’ll also go over the scenario of finding and booking tickets for one-way and roundtrips. Why would you want a one-way to a Caribbean island? Because you won’t want to leave! No, just kidding. I decided to book this trip as a one-way to Puerto Rico because I had two accounts that had 18,000 United Miles and this was the best way I could come up for spending them.
The other reason is that Southwest now has taken over flights to Puerto Rico and I also had some Southwest points left over. So I wanted to get to Puerto Rico but when using United Miles it’s a crime to only see one place. 
So the goal is to route through another island and Panama on the way to Puerto Rico and the rules are just different doing this instead of a roundtrip, so I’ll go over both. A roundtrip costs twice as many United Miles (and no Southwest points) and you get two destinations essentially and the layover in Panama, for whatever that’s worth.
We’ll do both but first…
The Rules
Let’s back up and explain that roundtrip tickets and one-way tickets have different routing rules and restrictions. There is a very in-depth post about United’s Routing Rules that goes over this already, but here’s the skinny of it. This is information beyond the fact that stopovers are only allowed on roundtrip tickets, there are more strict rules in regards to where you can route through on one-ways.
I’m not saying these are hard written rules but if the rules are simply what you can and can not do… these are the rules for one-ways and how they are different than roundtrip tickets.
One-way rules
If it is an award that touches more than two regions you are only allowed one connection in the transit region.
For example, you are not allowed to layover in San Jose, Costa Rica on the way to the Caribbean as you’re going to have to connect in Panama thus making two connects in that region (which as far as routing rules go, seems to include Mexico?). This is why I made a layover in Aruba instead of Cancun or something.
Roundtrip
On a roundtrip not only is a stopover allowed, but you can make multiple connections in the transit region. Furthermore you can backtrack… a lot.
EWR – NAS – EWR – SJU – EWR
How to find Roundtrip Tickets
I’ll do this first as there is more overlap and I assume more people would rather do this as you get to actually see two islands. Booking this is in many ways much easier. Again, with this route you will pay 35,000 United Miles (in economy) and have two islands (or somewhere in Central America) on which you can spend as long as you want – one the stopover and one the destination. Plus you can have layovers under 24 hours.
If you want a layover in Panama City then you need to go to an island that is reached by Copa Airlines. Locations are listed below, but the difference is that you can route through there from the US and get your layover on the way to the Caribbean. Heck, it may be possible to get two layovers there… if you so desire.
If you don’t really care about a layover in Panama City, then just pick a Star Alliance location in the Caribbean and it’s that simple. As oddly enough, you’ll be able to back track to the US on your way to the next island. O_o
Simply pick two Star Alliance available islands/locations in the Caribbean/Central American region and try to find and book them. How do you know which places are served by Star Alliance partners? Just use the Star Alliance route map.
Rubber meets the road.
Let’s pick two islands and get started. Two islands that I have yet to go to but would like to go: Grand Cayman (my parents love it) and St. Maarten (looks awesome and there’s a Radisson Blu).
The first thing I’m going to do is put in the dates I want and the islands I want in the Multiple Destination search and check Award Travel.
I’m finding right away that availability sucks. The first date works fine – plenty of options. The second date (the 11th) does not work but the calendar shows the 9th available and otherwise terrible availability.
The crappy availability probably has more to do with getting to St. Maarten than it does leaving GCM (since there was great availability there). There are a few fixes to this:
1) United could be lying to you. The Multiple Destination tool already limits results, which is a bummer. But the calendar just is inaccurate. The fix? Open up a separate browser or use incognito mode (which for me is apple (command) + shift + N) and search for oneway award availability. (If you open another tab it will mess with your original search).
Here’s what I show when opening a new browser to search one-way the same leg, GCM-SXM:
So still not great but better. The 10th may work instead.
But don’t stop there! The calendar still may be lying to you! Click other dates if you prefer those. There may a couple economy seats on the 12th and it’s just not showing up. Click and find out. If it has an easy fix that works for you, that’s fine. Otherwise, don’t rely completely on the calendar.
2) Reverse your search. Just try going to SXM first and then GCM. Who knows, it may work better. Unless you have a timeshare or something, why not try and reverse the dates?
3) Try making a long layover somewhere. Listen, part of the reason it’s not showing results could be that there are no open award seats to St. Maarten. Or it could be that there are no flights leaving Grand Cayman and connecting to St. Maarten in a timely fashion.
Unfortunately this is a bad example for that as it’s going to allow us to backtrack but won’t really let us request back tracking to region of origin, it just allows it if it’s necessary to get somewhere… If that makes sense?
4) Change your dates. It’s kind of lame advice for people who aren’t as flexible as us… but ultimately I ended up booking the ticket by making the following changes in dates:
While it seems St. Maarten is a much harder pick, it’s where I’d like to go and thus is realistic.
How to find One-Way tickets
The rest of this article is pretty much just about how to stick multiple layovers in one ticket.
When choosing an island to layover in, two things matter: When the first flight lands and when the Copa flight to Panama leaves the next day. We want to be as close to 24 hours as we can without going over. (Also understand that because of the nature of airline flights, you can’t come in on a Copa flight as that same flight is your exit ticket. Meaning – it will surely leave in an hour or so, and when it leaves the next day for Panama again it will surely be 25 hours+ after landing.)
The end result of this has to be that you get to an island you can leave from. So there needs to be an exit plan… unless you of course live at the final destination or something. Then this is just a more fun way (in my opinion) of routing there.
Exit Plan 1: Southwest Points
Our flight dropped to 8,000 points from SJU – BWI, which is a killer deal. Even though it dropped after I changed the flight online to that price and got 2,000 points refunded. If you have a companion pass, 8,000 points for two people is plain awesome.
While San Juan, Puerto Rico is currently Southwest’s only international destination, they are now taking over Air Tran routes. In fact, this route was an Air Tran route, so hopefully soon they’ll take over their other destinations. Here are the current Air Tran/soon to be Southwest destinations:
San Juan, Puerto Rico
Aruba
Punta Cana, Dominican Republic
Montego Bay, Jamaica
Nassau, Bahamas
Cancun, Mexico
Mexico City, Mexico
San Jose Cabo, Mexico
All but San Jose Cabo overlap with Copa.
Exit Plan 2: This is positioning
The Caribbean sometimes has better award chart options than the US. Or course it depends on what you’re trying to do. If you’re trying to use US Airways Miles for a First Class ticket to Asia, the 17,500 pays itself off and lets you see more places. Look at their award chart:
Whatever your reason is, I won’t judge.
Combinations that work
Due to the rules mentioned above, you pretty much have to pick a destination in the same region as your destination to make your first layover. Then you’ll route through Panama and get a direct flight to another Caribbean.
This means we need to pick two islands reached by Copa. There’s pretty much no way around this. So here are the Caribbean destinations served by Copa Airlines:
San Juan, Puerto Rico
St. Maarten
Aruba
Trinidad & Tobago
Curacao
Kingston, Jamaica
Montego Bay, Jamaica
Punta Cana, Dominican Republic
Santo Domingo, Dominican Republic
Santiago, Dominican Republic
Port Au Prince, Haiti
Nassau, Bahamas
And for the info of the roundtrippers, here are the destinations that Copa serves in Central America:
San Jose, Costa Rica
Liberia, Costa Rica
Managua, Nicaragua
Tegucigalpa, Honduras
San Pedro Sula, Honduras
San Salvador, El Salvador
Guatemala City, Guatelama
Cancun, Mexico
Mexico City, Mexico
Guadalajara, Mexico
Searching for flights
My preference for a layover is to get there early and feel like I have the entire day without care of getting back late to the hotel. What I do not want is to get there late and have most of my daylight hours be the day I leave. Then I’m worrying about getting back to the airport on time and end up not doing anything.
Then there are the kind of places that are better for 24 hour layovers. Like St. Maarten. It’s a tiny island and the hotel is near the airport, with a beautiful beach right there. The Renaissance Aruba is an example of a hotel 5 minutes from the airport. Once you’re at the hotel you get a boat shuttle that comes into the lobby of the hotel and takes you away to the Renaissance’s private island. Awesome. The perfect way to spend my evening.
Finding an island to layover in is a matter of searching. Search the inbound and then search the outbound on Copa. That’s it. It at least sounds simple, eh?
Sometimes I break this up and search oneways but I’ll stick to the multiple destination tool for now. But if you get an error try searching whatever part you got the error on in the oneway. I often keep a second browser open searching oneways.
Put in the search like you’d want. You need to add at least a day in between the dates. If you have an overnight layover domestically before you leave (since a lot of these flights are going to be in the morning) you need to allow two days. So I’ll search like this.
Let’s run through an example
How about a layover in St. Maarten on the way to Puerto Rico. I’ll search like this:
Note that we land at 1:29 pm on the 23rd, which means the next flight needs to leave by that time on the 24th.
In all actuality I had to find those dates first. I searched oneway for ORD – MBJ and in a different browser searched oneway for MBJ – SJU. I looked and pieced them together and then brought it to the multiple destination search. Minor details.
Examples & More Examples
To close, some islands just have terrible availability and for some reason things sometimes work going oneway instead of the other. But I recommend trying routes both ways to see what does or doesn’t pop up. For example, you don’t have to just try Aruba and then Puerto Rico; you could also try Puerto Rico then Aruba.
I’ll leave you with examples of islands that have <24 hour layovers. Of course, airlines can change times, even seasonally, but it’s a good start for someone really interested. Perhaps these are notes more than examples…
Aruba is a good location because there are multiple 23 hour options. The best is Newark to Aruba as it lands at 1:49 pm (and was very early when we did it) and the Copa flight leaves at 1:33 pm. There are other flights as well from EWR, PHL and YYZ that land at 2:something.
Copa seems to leave Montego Bay at 12:31 pm and there are many flights in.
IAH – POS (Trinidad) gets in late, like 7:40 pm, but luckily there is an outbound to PTY at 5:44 pm, as well as an early am option.
Punta Cana has the ability to land early and leave even earlier. And you might have the option to route through Toronto or Montreal on the way there.
Santa Domingo is incredibly open. Though it seems to have more options coming in at night.
Why can’t I get a layover to work in SXM when the timing works?
Bahamas did not work as the only ex [Copa] flight is at 4:11 and nothing I saw lands that late.
Same with Kingston.
Only saw route to Santiago, DR via PTY. So doesn’t work for layover.
Can’t get a layover in Port Au Prince to work out in under 24 hours.
Whether it’s seeing more on a oneway (for 17,500 miles) for positioning or just to use your Southwest Points, or whether it’s splitting your vacation between two islands (for 35,000 miles) the Caribbean is awesome. There are some beautiful waters, great snorkeling spots and it’s just right there. For us, it was a 4 hour flight from San Juan to Baltimore (wait, no. We got diverted so someone could get arrested…).