One of the Coolest Things You Can Do with Miles: The Island Hopper with a Stopover

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United operates a route from Honolulu to Guam with five stops twice per week on Mondays and Fridays. On Wednesday, it flies the same route but skips Kosrae.

This is an inefficient way to get to Guam, but it’s certainly a cool one with amazing take offs and landings on remote islands. Here are a few trip reports that got me excited to book the Island Hopper one day:

• YouTube Video of all Takeoffs and Landings
• YouTube Stills from the Trip
• Three Year Old milepoint Trip Report
• Continental-operated Trip Report

The Island Hopper is an ideal use of miles because ordinarily this flight is ridiculously expensive with miles, since it is a route on which United has a monopoly and has high operating costs.

I’ve been looking into using the Island Hopper as part of my journey from Hawaii to Southeast Asia around New Year. Award space on the Island Hopper comes and goes. Sometimes I see almost no space on the route for the entire 11 month booking window, but right now I see space on every day I’ve searched for award space on the Island Hopper (admittedly not that many days.)

Searching

Trip reports agree that the westbound route is better because it is all during daylight hours.

Right now there is award space for two passengers in economy every day the Island Hopper operates from December 28 to January 8 and the days I checked in March. I haven’t found any Business Class award space. Search dates that interest you, and I bet there is economy award space for two on the Island Hopper at the moment. Search united.com and look for the Honolulu to Guam flight with 4-5 stops. Saver awards are 25,000 miles one way.

Click “Details” and you’ll see the short stops on each far-flung island.

Turning that Award Space into a Trip

For my purposes, I want to stop at one of the islands along the way of the Island Hopper. First, because I’d like to split up the 14.5 hour trip, and second because when else would I have a chance to spend a few days in Chuuk or Kosrae.

United doesn’t allow a stopover on one way awards, but it does allow one on roundtrips, and as I’ll show, the definition of “roundtrip” is very loose. It basically means any two one way awards joined together.

I also want to go to Palau. Snorkeling with the jellyfish looks so fun.

Then after Palau I want to go to Asia for my planned Southeast Asia trip in January. The total trip would be something like this.

The question is, could I book something like:

• Honolulu to Chuuk (stopover)
• Chuuk to Palau (destination)
• Palau to Tokyo (open jaw “roundtrip” because I started in Honolulu and end in Tokyo)

The answer is that yes I can book that because apparently United’s computer considers starting in Honolulu and ending in Tokyo a roundtrip, which allows a stopover en route on the award. Amazingly this award costs 37,500 miles total and minimal taxes.

The 37,500 is the sum of 25,000 miles for Hawaii to Oceania (Palau) plus 12,500 for Oceania to Japan. I have previously singled out 12,500 miles for Oceania to Japan and 15,000 for Oceania to North Asia as amazing sweetspots on the United chart.

If I wanted to fly to Southeast Asia instead of Japan, the award would be 47,500 miles total. I am deciding which I would prefer and where along the Island Hopper I’d like to make my stop at the moment. But whatever I choose I am going to get a great deal.

I couldn’t get Kayak to show me the same exact itinerary, but the same dates and destinations are about $2,400 as a cash ticket–something I would NEVER pay. Getting all these destinations and flights for only 37,500 miles is a steal and a half.

Your Plan

My plan is idiosyncratic because I want to start in Hawaii and end in Asia. You probably want to start at your home airport and end there.

You can do that easily. You can book one United award like this:

• Home airport to somewhere along Island Hopper (stopover)
• Rest of Island Hopper to Guam, another Pacific Island like Palau, or Asia (destination)
• Return home

This would almost certainly require overnighting in Honolulu for under 24 hours since no mainland flight arrives early enough to connect to the 7:25 AM Island Hopper. You could stay in Hawaii longer than 24 hours, but you’d burn your stopover, meaning you couldn’t take one during the Island Hopper.

See United award rules here.

A modified version that saves the stopover, but allows more time in Hawaii would be two awards:

1. One way award to Honolulu with Avios or Singapore miles depending on where you live
2. • Honolulu to somewhere along Island Hopper (stopover)
   • Rest of Island Hopper to Guam, another Pacific Island like Palau, or Asia (destination)
   • Return home

The prices of these awards vary based on the destination you choose, but no matter what you’ll be getting a once-in-a-lifetime that only miles (or being really rich) can deliver.

Also check out this post laying out options to use the Island Hopper as part of a bigger trip.

Flying Business Class on Island Hopper

If I book the Island Hopper, I will try a Plan B award where I pay the Business Class price upfront and get placed at the top of the Business Class waitlist. I would definitely expect to clear into Business Class, and if I don’t, I’d be refunded the extra miles I paid. More on Plan B awards here.

Will anyone try to book the Island Hopper now that award space is wide open?