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

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

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The 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.

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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
  • 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 from. The 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

  • 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

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!