The Complete Guide to the Caribbean Hopper (with United Miles)

Screen Shot 2014-05-08 at 11.04.53 PMThe Caribbean Hopper is a ticket I came up with that touches two Caribbean Islands for the price of one. The idea is that you use your United stopovers to stop in one island, and use your destination in the other… seeing both for as long as you want.

So for 35,000 miles, you could do something like: Home – Aruba (stopover) – Panama City (layover) – Puerto Rico (destination) – Home.

Previously, this was a complicated route, as valid routings were largely unknown. But all the hard work of the amazing Caribbean Hopper ticket has been reduced to a chart I’ve made. Here’s everything you need to know for booking and more. Thank me later… like after you’ve taken the flight!

1) Find Connectable Islands

Panama City is essentially our only routing option for a ticket that includes two Caribbean islands. See, the thing is that United will charge more if it goes back to mainland US. So you can’t stopover in Puerto Rico and then destination in Aruba if you connect in Houston… but you can if you connect in Panama City. Similarly it would be a higher price if it connects in South America. This has to be the Caribbean and Central America/Mexico.

Again, there is really only one workable hub – Panama City.

Screen Shot 2014-05-08 at 4.06.32 PM

What islands connect to Panama City?

  • St Maarten
  • Aruba
  • Port of Spain, Trinidad and Tobago
  • San Juan, Puerto Rico
  • Punta Cana, Dominican Republic
  • Santo Domingo, Dominican Republic
  • Santiago, Dominican Republic
  • Port-au-Prince, Haiti
  • Kingston, Jamaica
  • Montego Bay, Jamaica
  • Nassau,  Bahamas
  • San Andres Island

Central America

  • San Jose, Costa Rica
  • Liberia, Costa Rica
  • Managua, Nicaragua
  • San Salvador, El Salvador
  • Guatemala City, Guatemala
  • Tegucigalpa,  Honduras
  • San Pedro Sula, Honduras
  • Guadalajara, Mexico
  • Mexico City, Mexico
  • Cancun, Mexico

Unfortunately, flights change. But I did the best I could and made the list based on the scheduled flights for this summer.


2) Find Valid Connections

This isn’t so obvious as you need to connect in Panama City, but make it under 24 hours.  Keeping it under 24 hours is essential to keep it simply a layover, since a second stopover is not allowed.

Copa (the Star Alliance airline based out of Panama City) may not have daily flights to/from the islands of your choice, which makes finding a 24 hour layover a little tougher.

However, I’ve gone through every single one of the Caribbean options to tell you which routes are possible. It doesn’t mean there will be availability, but they are certainly possible. There are actually even more possibilities if you include Central America.

The first Column is where you are leaving fromThe first row is where you are going to. (The chart scrolls left to right, btw).

As you may notice, there may be more availability if you try your flight in reverse.


3) Availability

The next thing, which may seem obvious, is to find availability. While these routes are all technically possible… some of them are much more scarce than others. Some have very little availability at any time. Others are daily most of the year.

Go to –> Click “Award Travel” –> Then click “Oneway”

You need to check availability one leg at a time. You need to check wherever “home” is to the first island. Then you need to check first island to second island. Then you need to check second island home. It’s important to know the availability situation before going into booking.


4) Booking is terribly buggy, but that’s where I would start. –> Award Travel –> Multiple Destination

Now there is a large chance that United will give an error.

If it gives an error on the very first search, without ever showing the first leg: It MAY or may NOT be an illegal routing.

Or in this case or at any point in the process you get an error, it could also mean that there is no availability, OR that just sucks.

And by sucks, I mean that the computer only searches for a limited amount of time before giving up.

If it will not book, just try calling. It’s an odd ticket, I know… but the agents can get it to work, if they aren’t stubborn.


* Bonus: 5) Points Hotels

St Maarten

  • Radisson Blu = 50,000 Club Carlson points


  • Ritz Carlton Aruba = 60,000 Marriott points
  • Renaissance Aruba = 35,000 Marriott points
  • Marriott Resort & Stellaris Casinos = 45,000 Marriott points
  • Marriott’s Aruba Surf Club = 45,000 Marriott points
  • Radisson Blu = 50,000 Club Carlson points

Trinidad and Tobago

  • Hyatt Regency Trinidad = 15,000 Hyatt points (or category 4 cert)
  • Courtyard Port of Spain = 25,000 Marriott points (or category 5 cert).
  • Hilton Trinidad = 30,000 Hilton points
  • Radisson Hotel Trinidad = 44,000 Club Carlson points

San Juan, Puerto Rico

  • W Retreat & Spa – Vieques Island = 20,000 Starwood points
  • The St. Regis Bahia Beach Resort, Puerto Rico = 30,000 Starwood points
  • Sheraton Old San Juan Hotel & Casino = 7,000 Starwood points
  • El Conquistador, A Waldorf Astoria Resort = 50,000 Hilton points
  • InterContinental = 50,000 IHG points
  • Holiday Inn = 15,000 IHG points
  • The Ritz Carlton = 60,000 Marriott points
  • La Concha Renaissance San Juan Resort = 40,000 Marriott points

Punta Cana, Dominican Republic

  • The Westin Puntacana Resort & Club = 12,000 Starwood points
  • Four Points = 3,000 Starwood points (2,000 points on the weekends)

Santo Domingo, Dominican Republic

  • Sheraton = 7,000 Starwood points
  • Crowne Plaza = 25,000 IHG points
  • Holiday Inn = 20,000 IHG points
  • Courtyard = 10,000 Marriott points

Montego Bay, Jamaica

  • Holiday Inn = 35,000 IHG points

Panama City, Panama

  • InterContinental Miramar Panama = 30,000 IHG points
  • Radisson = 28,000 Club Carlson points
  • Le Méridien Panama = 10,000 Starwood points
  • Panama Marriott = 20,000 Marriott points (or Category 4 cert)
  • Hyatt Place Panama = 5,000 Hyatt points



Not all of these islands appeal to me. When I did this trip, I could have easily done Trinidad… but it kind of looks like a junkie city, not a tropical paradise. That being said, most of the islands on the list are super appealing. St. Maarten might be at the top. Would love to get over to Vieques next time we go to Puerto Rico, and I wouldn’t mind a trip to the Dominican Republic.

Plus, we haven’t even gotten into combining this with Central America… which is easy. Although, I’ll go ahead and let you know, I’ve had no luck combining two Central American destinations – it’s going to have to stay the Caribbean hopper.

I tried not to blab on and on, and yet make it thorough. But if there’s something missing (obviously I didn’t include all hotel options), or something you have questions about, please let us know!

Related Posts:


  1. Unfortunately, San Andres Island is part of Colombia, so even though it’s geographically in the Caribbean, it prices as part of the Northern South America region. Also, I have had success pricing multi-city itineraries within Central America at 35k. For example, ORD-RTB on 8/9, RTB-BZE on 8/25, then BZE-ORD on 9/2 prices at 35k. The TACA hub at San Salvador is useful for connections within Central America.

  2. Haven’t even read all the way through yet, but saw that flight schedule and know how much of a pain that had to be, but also that this will be an awesome resource. Thanks again Drew, for a thoroughly researched and valuable post!

  3. I think you could add Roatan (RTB) but would have to go Avianca through San Salvador (SAL) and PTY for a 2-connection flight. But there’s likely many more possibilities if you open it up to 2-conn flights.

  4. Drew this is cool. Thanks for the list.

  5. Thanks for the chart. That will be quite useful.

    Have you done any more research on the one-way version of the Caribbean Hopper? USA -> >24 hours on an island -> >24 hours in Panama City -> another island as a destination?

    I tried to put together a few different itineraries like this, but it kept pricing at 27,500 instead of 17,500.

    Either way, great post.

  6. Copa also flies to Curacao from Panama City on T, Th, Sa, Su.

  7. Trinidad is not my cup of tea either–but Tobago (right next door) is fantastic. Can take a puddle jumper or boat over.
    Thanks for the work you did in putting this list together.

  8. Drew, thanks for putting all this together. It’s very helpful and thanks for sharing.

  9. When is the best time of year to visit the Caribbean?

  10. Crazy job, thanks for all the work! I have “hopper” envy sitting here in Guam (was on the Pacific Island hopper, then couldn’t resist the $1000/free day in Guam). PS- for that route, you may be interested to know that it books as one segment with miles if you pick the right one. Tagged it onto the end of a trip to Japan and China. For those of you that think stopping 5 times on the way to Hawaii is cool, anyhow…

  11. been to vieques, it is awesome, swam in the bio bay, apparently before they stopped allowing it due to a shark attack. looking to book an ANA award flight with stopovers in Costa rica, then home(NYC) then any chance I can book another segment?

  12. I actually use this to visit PTY and MIA from EWR. PTY is a great place for a vacation. Great city, history, shopping, restaurants, countryside and the canal. We then fly on COpa to MIA to visit family and then back to EWR for 35K.

    • Glad you like to visit Panama and have taken the time to see truly all that it has to offer (as opposed to Costa Rica!)
      It is my home country an am amazed by all the new and cool things it develops almost every year.just got back 2 weeks ago and there were so many more foreigners than what I am used to, which is great!
      I look for ANY and EVERY hacking idea out there to stop in Panama for less miles, while going anywhere else afterwards.

  13. Furthermore, you missed the Hyatt Regency in AUA.

  14. Hi, Drew! I’ve been learning so much from your site, and now I’m finally trying out thinking outside the box and seeing if I can book a Caribbean hopper. Hoping you could take a look. The legs would be:

    ORD-Aruba, May 3: destination, with open jaw
    Curacao-Cancun, with the Panama City layover, May 24: stopover
    Cancun-EWR, May 28: return, with open jaw

    The first two dates are flexible; the third is not. I tried looking up the legs individually, and there’s availability that works for me. But when I try to piece them together, it throws an error. I *think* the problem is that, even though there is Curacao-PTY and PTY-Cancun space, for some reason when it looks for Curacao-Cancun, the engine is choosing one of the PTY-Cancun flight times *without* award space.

    But I wanted to see if I’m messing up the rules and there’s a problem with meaning the destination to be Aruba instead of Cancun? Or if there’s something else I’m overlooking? So I don’t make a fool of myself if I call in to book it. XD

  15. Has anyone done this in the reverse?

    I’m on a long-term bicycle tour and will give it a try to come back to the States for a couple months this summer. However, I’ve never booked award travel before, so perhaps I might not be able to get it even if it is possible. I’ll be looking at:

    Mid-June: MEX -> 24 hr PTY -> Some island stopover several days
    Island -> RNO (or SFO if necessary)

    Early Oct: NYC -> 24 hr Some island -> 24 hr PTY -> MEX

    I could switch around the some island stopover/layover dates if needed.

  16. I just attempted to book the following:

    6/29 BJX-LAX-SFO
    9/22 LGA-IAH-POS
    9/29 POS-PTY-GDL

    They declined me on the phone saying that the fare rules indicate that we cannot transfer through Panama, which of course would make a Caribbean stopover impossible. Am I missing something or have they changed the rules to eliminate this possibility?


Submit a Comment

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>

We have spent the majority of our marriage traveling full time, living out of hotels.   All the while, we list our expenses publicly, budgeting $25,000 a year for our nomadic life while still staying in mostly 4 or 5 star hotels across ~20 countries a year.
Go to About Me to learn more.