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Islands… they are just so wonderful. Nothing like an island getaway to relax and refresh! With this in mind, I decided to book our very first round-the-world award trip, which I am calling Islands Around the World. After spending much of 2015 earning millions of miles/points, I vowed to put them to good use over the next couple years. So far, we’ve booked awesome trips to Hawaii, Ireland/Scotland/London/Paris, and Australia/New Zealand (coming Dec 2016).
This trip, however, is definitely the most ambitious itinerary yet… with visits to islands in Hawaii, Thailand, the Maldives, and Greece! In total, we will fly 25,809 miles to visit 12 locations over the course of 30 days… Total cash price: $259 for two people!! Follow along to see how we did it…
Leg 1 – United Airlines: MCI to KOA – 22,500 United miles + $5.60 each
The first leg of our journey will take us from Kansas City to the big island of Hawaii, with connections in Denver and San Francisco. We will spend 4 nights on the big island, to complete our sweep of the Hawaiian islands. We visited Kauai, Oahu, and Maui back in 2015.
We booked this leg, together with legs 2 and 7, using United Airlines miles. I will explain more about the reason for this in the next leg.
Leg 2 – Hawaiian Airlines: KOA to HNL – 0 United miles + $0 each
Yes, you read that correctly. This short island hopper flight will literally cost nothing… zero dollars and zero miles. Usually, this would be 6,000 UA miles or 7,500 AA miles. We got this flight for free using United’s new “Excursionist Perk.” See this article for more information on this perk.
In short, we booked legs 1, 2, and 7 together. United’s system sees the routing like this: MCI-KOA-HNL; ATH-MCI. Since the itinerary begins and ends in the “North America” region, and the KOA-HNL leg is fully within the “Hawaii” region, the flight qualifies for the Excursionist Perk. This makes it FREE!
Leg 3 – 35,000 United miles + $24.60 each
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Asiana Airlines: HNL to ICN (18hr layover)
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Thai Airlines: ICN to HKG (8hr layover)
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Thai Airlines: HKG to BKK
Leg 3 takes advantage of some long layovers to let us see a few more cities. Since neither layover is more than 24 hours, we are only charged for the HNL-BKK segment at 35,000 UA miles. We will get to spend the night in Seoul, South Korea, and take a city tour. We will also be able to get out and see a bit of Hong Kong, before continuing on to Bangkok.
Unfortunately, with the change in United’s routing rules, these types of segments are more difficult to book. The United search engine must find the itinerary when you search the original city pair (HNL-BKK). In this case, the search found this routing. Long layovers are a GREAT deal to add a few more cities for free.
Leg 4 – BKK to HKT to USM – Chase Ultimate Rewards @ 1.5 Cents Per Point
We will be spending nine nights in Thailand. At this point, we have not decided exactly how we will allocate time between Bangkok, Phuket/Phi Phi Islands, and Ko Samui. Also, Google flights show that the cash price for tickets between BKK and HKT decrease as the trip gets closer. We will wait until the price bottoms out and book using our Chase Ultimate Rewards points. My wife has the Chase Sapphire Reserve, so our points are worth 1.5 cents per point toward travel.
Leg 5 – 16,000 Amex Membership Rewards + 17,000 Barclay Arrival + miles each
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Singapore Airlines: USM to SIN (22hr layover)
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Singapore Airlines: SIN to MLE
Leg 5 includes a 22-hour layover in Singapore, en route to the Maldives!!! First, we will spend a day touring around Singapore and visiting Changi Airport, the #1 rated airport in the world. Then, we will head to the middle of the Indian Ocean for five nights at the Sheraton Maldives. Five nights in the Maldives will cost 80,000 SPG points, using the 5th night free offer. We have dreamed of visiting the Maldives for years, so we are VERY excited!
We booked this leg by transferring Amex Membership Rewards points to Singapore Airlines. Unfortunately, the fuel surcharges are high on these award tickets, so we paid with the Barclay Arrival+ card. This allows us to cover the surcharge with our Arrival+ miles!
Leg 6 – 25,000 United miles + $18.60 each
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Turkish Airlines: MLE to IST (14hr layover)
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Egyptair: IST to CAI (19hr layover)
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Egyptair: CAI to ATH
Leg 6 takes us from the Maldives to the Greek Isles, with a couple more long layovers along the way. We will spend 14 hours in Istanbul, where we plan to take the free city tour offered by Turkish Airlines. They take you to see the major sites around Istanbul, complete with free meals.
Next we will fly to Cairo, Egypt, for a 19-hour layover. We booked a night at the Le Meridien resort next to the pyramids for only 3,000 Starpoints!! You can literally see the Great Pyramid out your window, and this is only a category 1 Starwood property! After riding camels and touring the pyramids, we will board a flight to Athens, Greece.
We booked this incredible leg of the trip for only 25,000 United miles each. Similar to Leg 3, the system sees this as a flight from MLE-ATH. We had a bit of trouble booking this one, however, because the search did not show this as a possible itinerary. I had to call and speak with an agent to get this segment to work. For more information, see this article.
Leg 7 – ATH to JTR Roundtrip – Chase Ultimate Rewards @ 1.5 Cents Per Point
We plan to spend seven nights in the Greek isles, between Athens and Santorini. Like with Thailand, we have not decided exactly how to allocate our time. Flights between ATH and JTR are inexpensive, and we will use our Chase UR points to book them at 1.5 cents per point.
Like the Maldives, the Greek isles have been a dream destination of ours for years. We can’t wait to see the major historical sites, chill out on the pristine beaches, and enjoy the tastes of Greece!
Leg 8 – Lufthansa/United Airlines: ATH to MCI – 30,000 United miles + $80.80 each
Our final leg will take us home from Athens to Kansas City via Munich and New Jersey. I would have loved to build in long layovers in a couple European cities, but we simply ran out of time for our trip. As I mentioned above, we booked this leg in tandem with Legs 1 and 2 to qualify for the Excursionist Perk.
Final Thoughts
To recap, we used the following award programs and airlines for this trip:
- United Airlines Miles
- Singapore Airlines Miles
- American Express Membership Rewards
- Chase Ultimate Rewards
- Barclay Arrival+ Miles
- Hawaiian Airlines
- Asiana Airlines
- Thai Airlines
- Turkish Airlines
- Egyptair
- Lufthansa
- Starwood Preferred Guest
- Chase Sapphire Preferred (Lounge Access)
- Amex Platinum Card (Global Entry Credit)
We will be traveling to twelve cities around the globe, including four island paradise destinations! The total cash cost for these flights was only $129.60 per person!! See the table below for the total breakdown of points/miles/cash.
This award booking experience shows how you can save cash and miles if you know how to identify sweet spots, utilize partner bookings, and recognize synergies between award programs. Hopefully this inspires you to think creatively when booking your next big trip! If you need help putting this complex puzzle together, check out our Travel Coaching services. Cheers!
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