This is one of my favorite destinations and a really easy trip to plan for many people with scores over 700. Here’s my last post on how to get to Hawaii from earlier this year. In fact the challenge has gotten easier with the advent of several new cards and their exclusive hotel benefits.

Let’s try this scenario and see how Jeremy from Internet Brands does:

Jeremy does not have a business and does not want one. His girlfriend Holly doesn’t either and also is afraid of business cards. Their scores are each 725 and they want their first trip to Hawaii to be a multi-island vacation. The islands they want to visit are at least 3 of the four main ones: Oahu, Kauai, Maui and the Big Island of Hawaii. The couple’s total credit card spend is $4,000 per month.

Using only their good credit, they need to get to three islands for a minimum of two nights each and coach tickets to Hawaii. Don’t forget to try and cover the inter island travel for free as well!

Let’s see how  Jeremy and Holly pull it off for only $327

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JEREMY’S APS: Three cards – US Airways Dividend Miles Premier World MasterCard, Bank of Hawaii Hawaiian Airlines Visa Signature Card, Hyatt Visa from Chase

HOLLY’S APS: The same three cards – US Airways Dividend Miles Premier World MasterCard, Bank of Hawaii Hawaiian Airlines Visa Signature Card, Hyatt Visa from Chase

ITINERARY OVERVIEW: On May 14 we’ll fly United out of LAX to Maui and stay at the Hyatt Regency Maui Resort & Spa. We’ll spend two nights in Maui before flying to Kauai on Hawaiian Airlines on May 16, where we’ll spend two nights at the Grand Hyatt Kauai. On May 18, we’ll fly Hawaiian to our third island, Oahu, where we’ll spend three nights at the Hilton Waikiki Beach. On May 21, we’ll fly out of Honolulu and back to LA.

TOTAL TRIP VALUE: $4,479.20

HERE’S HOW WE DO IT:

May 14, 2013 – Open Jaw Booking: Los Angeles – Maui
Cost: $1,805.60 ($902.80 per person including return from Honolulu)
Method: 80,000 US Airways Miles
Cards:

1. US Airways Dividend Miles Premier World MasterCard– 80,000 US Airways Miles
   1. I receive 40,000 miles after my first purchase
   2. Holly receives 40,000 miles after her first purchase

Explanation: As explained by Howie last week in his trip to Disney World, though the US Air card typically only offers 30,000 miles, the above link will get me 40,000 miles. If I get a card and Holly gets a card we’ve got 80,000 US Airways miles, which happens to be the exact number we need for two round-trip tickets to Hawaii.

As US Airways doesn’t have a direct flight out of LAX to Hawaii – everything is routed through Phoenix – we’ll book through StarAlliance-partner United, who like US Air, allows open jaw award booking.
Out of Pocket Cost: $50 reward ticketing fee

May 14-16, 2013 – Hyatt Regency Maui Resort & Spa
Cost: $658 ($329 per night)
Method: Hyatt Visa Free Nights
Cards:

1. Hyatt Visa from Chase
   1. I receive two free nights after first spend on the card

Explanation: The Hyatt Visa gives us two free nights at any Hyatt in the world upon first spend. There’s a $75 annual fee, however I’m getting a $658 value.
Out of Pocket Cost: $75

May 16, 2013 – One Way: Maui – Kauai
Cost: $178.60 ($89.30 per ticket)
Method: 15,000 HawaiianMiles
Cards:

1. Bank of Hawaii Hawaiian Airlines Visa Signature Card  – 72,000 miles
   1. I’ll receive 20,000 miles after my first purchase
   2. Holly will receive 20,000 miles after her first purchase
   3. I’ll receive 15,000 miles after spending $1,000, which I’ll accomplish in the first month
   4. Holly will receive 15,000 miles after spending $1,000, which she’ll accomplish in the first month
   5. I’ll receive 1,000 miles for spending $1,000 at a rate of one dollar per mile
   6. Holly will receive 1,000 miles for spending $1,000 at a rate of one dollar per mile

Explanation: A one-way interisland ticket costs 7,500 miles. One for me and one for Holly will cost us 15,000 miles. (Note: there’s also a Bank of America Hawaiian Airlines Visa Signature Card with the exact same bonus offers, however Bank of Hawaii allow me and Holly to transfer our miles together to consolidate.)
Cost: Taxes may apply

May 16-18, 2013 – Grand Hyatt Kauai
Cost: $968 ($484 per night)
Method: Hyatt Visa Free Nights
Cards:

1. Hyatt Visa from Chase
   1. Holly receives two free nights after first spend on the card

Explanation: As Rick loves to say, “Double your pleasure, double your fun.” My Hyatt card got us two nights in Maui and Holly’s gets us two nights in Kauai.
Out of Pocket Cost: $75

May 18, 2013 – One Way: Kauai – Honolulu
Cost: $122 ($61 per ticket)
Method: Out of Pocket
Explanation: Though we could use another 15,000 miles to make this trip, at a cost of only $122 we’ll just save the miles and pay out of pocket.
Out of Pocket Cost: $122

May 18-21, 2013 – Hilton Waikiki Beach
Cost: $747 ($249 per night)
Method: Hilton HHonors Points
Cards:

1. Bank of Hawaii Hawaiian Airlines Visa Signature Card – 57,000 miles left

Explanation: HawaiianMiles convert to Hilton HHonors points at a rate of 1:2. Our 57,000 HawaiianMiles are actually 114,000 HHonors points. The Hilton Waikiki is a Category 6 hotel, meaning it costs 40,000 points per night. We’re short 6,000 points, but if Holly and I spend an additional $3,000 on our Hawaiian Air cards (which we can do in the first and second months of our spending), we make up the difference.
Out of Pocket Cost: $0

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Next week’s challenge comes from Terry Moore on Facebook who challenged us to get to St. Thomas in the Virgin Islands. Howie will show you how it’s done.