Help Me Finish My Hawaii Vacation Planning

I’ve been posting over the last few weeks about my Hawaii Vacation Planning and my goal to spend $3000 or less for 17 nights including airfare.   I will be in Hawaii in December, and one of my primary goals is to go whale watching and relax by the pool.

I will spend 2 nights in Honolulu when I arrive. I have a child-hood friend who lives there, and I’ll take this opportunity to see her.   I will arrive around noon, so I’d like to try to use my “Your 24” SPG benefit. (For those of you who don’t know, the Your 24 benefit is available to SPG members who stay 75 nights or more in year. With Your24, members can request their preferred check-in time, and if approved in advance by the hotel, you check-in at that time and check-out 24 hours later.  So for example, if I wanted to request a 1pm check-in, I’d check out at 1pm.  Most hotels don’t enforce the check-out time and frequently offer late check-out platinum benefits.)

My current plan for 2 days in Honolulu is to use 20,000 Starwood points at the Royal Hawaiian. Taxes and Resort fee will run me $63/per day.

From Honolulu I will fly to Maui. Why Maui? Well, I received a special award from Starwood of 3 free nights that must be used consecutively and can only be used at cat 1-6 properties that have standard rooms (aka, no villa properties.)  So after considering all the options, my dates, and cost (cash or points) for the eligible hotels, I decided the best use was at the The Westin Maui Resort & Spa, Ka’anapali.

For my 3 days in Maui I will use the 3-day reward. Taxes and fees will cost $31/day.

After Maui, I’m not sure what I should do. I’ll have three nights to fill.  I have points with Chase Ultimate Rewards, Marriott and Hilton that I’d prefer to use over cash.  I’m completely open to visiting a different Island, the only thing I won’t do is go back to Oahu.  What do you suggest?

Following those three days I’ll head to Kauai where I’ll spend 3 nights at the St Regis Princeville. For this stay, I’m currently using a combination of cash and points. I would love to switch it to a full points say if I can rebuild enough miles (which is a good possibility).  This will run me 105,000 points and $88/day in taxes.

After Kauai, I’ll meet some friends in Kona. We will be celebrating New Year’s Eve in Kona and will spend 4 nights at the Sheraton Kona Resort & Spa at Keauhou Bay before heading back to Oahu.  This stay is an all points stay.

For my 5 nights in Kona, I will spend 40,000 points and $31/day in taxes and fees.

So, my question for you is, what should I do with my 3 extra days?

14 Comments on "Help Me Finish My Hawaii Vacation Planning"

  1. Have you ever been to Hawaii before? That’s a lot of island hoping. There is so much to see and take in on the islands. I’d suggest adding a day onto each of the islands, or at least staying put at some point to really enjoy everything, versus spending so much time at the airports.

  2. Miles, Points, and Mai Tais | June 19, 2013 at 9:55 am |

    I would spend 3 more days on Maui 🙂

  3. For your open time, I’d add in an extra 2 nights at the Westin Maui. If you want, you can still island hop by ferry from Maui to Molokai or Lanai by ferry. A day trip by water IMO is more relaxing than flying, plus you don’t have to pre-book weeks in advance and would have the flexibility to just explore Maui if you prefer.

    I’d add the last night still in Maui but in Hana for a very different experience. No SPG there, though, so if that’s an absolute necessity, I’d probably still just add the time to one of your existing hotels to keep packing up and moving to a minimum.

  4. adelantando | June 19, 2013 at 12:16 pm |

    What about the new Andaz opening on Maui? It looks pretty swanky to me.

  5. @Becky, great ideas. I was thinking about Molokai and Lanai, but didn’t look yet at how to get there. This helps a lot!

  6. @Adelantando – I actually have thought about the Andaz, I’m waiting until I can see how many points it is 🙂

  7. @Miles, Points & Mai Tais, that seems like the prevailing opinion! Looks like it’s Maui for me.

  8. @InACents, yes, I’ve been to Hawaii 3 times before. Twice on Business, but I added on time for sight-seeing.
    I think I’m taking everyone’s advice and will add 1 more day to each island (except Oahu as I’ve already spent enough time there in the past.)

  9. go to grand hyatt Kauai at Poipu beach. much more sunshine and a different world then princeville

  10. I agree with Becky — stay on Maui, try to spend a night in Hana, but also take a day trip to Lanai. I haven’t been there yet, but iit was one of the missed items on my wish list from last year. There’s a ferry that runs out of Lahaina for ~$30 each way, and you’ll need to rent a 4×4 if you want to see Shipwreck Beach and the temple ruins ($140). That could be a budget-breaker, but there are plenty of other interesting things to do that wouldn’t require the 4×4.

  11. Also, if you stay at the Westin on points for four nights, your fifth night is free. 🙂

  12. @April, thanks! Good ideas.

  13. The Mystery Traveler | June 22, 2013 at 3:10 am |

    When on Maui, go to Tasaka’s Guri Guri. Only place in the country I know of that serves it. It’s like a cross between sherbert and ice cream. Two small scoops for $1. Nothing earth shattering, but brings back memories for Buddaheads and Katonks alike :o)

  14. Agree with Rick. Spend more time on Kauai – for my $, it’s hands down the best island – good reason why so many movies are filmed there.

    SPG Princeville is ok but it’s isolated. The Grand Hyatt in Poipu is nicer and the weather is almost always better, plus you are closer to Waimea Canyon and some great beaches (day trip out to Polihale Beach is amazing – fun getting there on the bumpy road especially after some rains, but the beach itself is stunning – and only a handful of people go there – it’s next to the Pacific Missile Range so you can sometimes see some missiles being launched)

    Consider taking an ultralight flight over the island early in the morning (when winds are lightest) – something you won’t forget – way better than a helicopter tour. Company name is Birds In Paradise and takes off close to Poipu at Port Allen airport.

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