Planning an Anniversary Trip to Hawaii

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Every year since we got married in 2008 my husband and I have planned a trip of some sort for our anniversary.  I don’t know how it works in your world, but in our world being married is both fantastic, and really hard.  Much more so once children are involved.  There is more to get accomplished, and less time for just the two of you.  Don’t get me wrong, it is amazing having a family, but I don’t live in Candyland where every moment is sugar plums and fairies either.  So, we really like to take the opportunity to celebrate and renew our marriage as often as possible, but especially on our anniversary.  On previous anniversaries we have gone to Vegas (pregnant), New Orleans for a night, to San Antonio, had a failed trip to a local winery last year, and now for our fifth we upped the ante and booked a trip to Hawaii for just the two of us.


On the beach in Maui

Hawaii sounds like a sure-fire hit for an anniversary, honeymoon, etc. but it was actually quite a tough sell in my house since my husband was pretty anti-Hawaii before our trip.  I’m not sure I’ll ever understand fully why he had a somewhat negative attitude toward what I consider paradise, but I think the main reasons were that it is pretty far and there are beautiful beaches in spots like the Caribbean much closer to home, he didn’t think it could live up to the hype everyone gives it, it is pricey, and I think he viewed it as a bit cliche.  You know, you win the Super Bowl and “you’re going to Disney World”.  You get married and you are “going to Hawaii”!  If you don’t quite understand it, that’s okay, neither did I.

While I do think that for the most part you should honor your spouse’s travel preferences, by our fifth year anniversary I knew him well enough to know that he was wrong.  I had been to Hawaii several times, and it was perfect for him.  He just didn’t know it yet.  Since he was going into the trip a bit on the reluctant side, this also meant I kind of had to go a little overboard in making sure he really enjoyed the trip.  In part this was so that he (and we) would have a great time, and in part it was because I wanted him to love it so we could return as a family for many years to come.  When you are married with a family, it is really great when you can share special things and special places, and I really wanted him to understand why I thought Hawaii was so special.


Planning the flights:

We bought our flights to Hawaii in early 2013 during a short-lived United fare attack on American Airline’s DFW hub.  We live a little north of Houston, and prefer to fly out of Houston most of the time, but when offered the chance to get tickets to Hawaii for under $400 round trip on our preferred airline we are willing to travel a little.  If we bought tickets out of Houston, we likely would have paid at least double that amount on United.  We booked $40 positioning flights from Houston to Dallas on United and applied some regional upgrades I had thanks to my elite status to enjoy the flights to and from Hawaii in business class.

We certainly could have used miles for these flights, howeer paying less than $440 round trip each all-in to sit in business class on a Boeing 777, and earn valuable elite qualifying and redeemable miles was a far better deal for us than redeeming miles in this instance.  Heck, thanks to elite bonuses, I earned close to 15,000 redeemable miles just on my ticket that are worth close to $300!  If I had redeemed United miles, those same flights would have cost me 160,000 United miles for the two of us in business class and I wouldn’t have earned elite or redeemable miles.  If you have fixed value points that you essentially use as cash toward travel, such as those from the Barclaycard Arrival Plus™ World Elite MasterCard® or US Bank FlexPerks Travel Rewards Visa Signature, then you could have the best of both worlds and get in on fare wars like this one without having the cost impact your wallet.

Our United flights got us to Honolulu, but our actual intended destination was Maui.  I did have us stay one night in Honolulu because I didn’t want to push our luck and add a third flight on a separate ticket in the same day.  I also wanted us to take some surf lessons, so I thought Waikiki to be as good a place as any for those lessons. Our island flights were booked on Hawaiian Airlines.  I used 7,500 Hawaiian miles for each island hopper ticket on one direction to go from Honolulu to Maui, and purchased the other direction with cash as our desired time was not available on the saver level with miles.

Be aware that you can frequently “buy up” to first on Hawaiian for $50 on these short island hopper flights.  This also gets you lounge access and free checked bags, so it can be worth it in some situations…including the situation where you have a large husband who likes to have as much room as possible while flying. 

Booking the hotels:

I knew Waikiki would not be the highlight of the trip, but I still wanted us to be in a nice hotel as that was our actual anniversary date.  I choose the Westin Moana Surfrider because it was a beautiful and historic hotel located directly on the beach.  It also was a tremendous deal when I booked it before it went up a from a Category 5 to a Category 6, and before the SPG cash and points chart changed.  To keep things simple and save time we didn’t get a rental car on Oahu, but instead took a quick cab to and from the hotel.  It probably cost a tad more than a rental car, but it was worth it for the convenience.

For our time on Maui we booked the Andaz Maui at Wailea.  It was months away from opening when we booked, but it looked like a very promising place to spend an anniversary.  We locked it in for 22,000 Hyatt points per night instead of the $500 per night rate.  The hotel experienced about and month and a half of delayed openings, which resulted in us being there the week it opened.  I was a little nervous about how that would play out, but it ended up working very much in our favor.


Hotels, especially nice resorts, in Hawaii can be very expensive.  That means it can be a very good destination to consider using some hotel points.  If you are traveling with your whole family, it can also be a good spot to look into renting condos or houses for your stays.

Rental car:

We did book a rental car in Maui via a good rate with Hertz and had very adventurous plans of doing a sunrise trip and driving around.  The reality is we ended up just being a little lazy and spending most of our time in Wailea.  However, we had booked a base rate via Hertz and then negotiated an upgrade to a convertible Corvette for less than a $50 surcharge per day over our Ford Taurus or whatever exciting car we had booked.  This was another example of something I would never do if it were just me, but it is the kind of thing that makes the trip even more special for him…and it was pretty fun to drive around in.



I did some research (and asked for suggestions) on some good spots to eat on Maui and Waikiki.  I made reservations at the major spots ahead of time on OpenTable so that we were ensured a spot, and so that I would earn OpenTable points toward free food on future meals!  Eating out is a huge highlight for both of us while on vacation, so we like to make sure we have some pretty great meals, preferably with local food.


Our anniversary dinner at Hy’s in Honolulu was amazing!

Don’t Over-Schedule:

I have a bad habit of over-stuffing some of our trips.  Because of limited vacation days and limited childcare coverage back home, our trips are always too short.  I’m working on this bad habit of trying to cram too much in to our trips, but it is hard when there is so much to see and do.  I think going into our trip we had tentatively planned to do a little more than was realistic given our desire for some “downtime”, but we adjusted on the fly and made it work.


Use Miles and Points for Hawaii:

If you want more info on using miles and points to get to Hawaii for your own trip, I wrote a series on this topic a little earlier this year that can be found below.

Plan a Hawaiian Vacation Using Miles and Points (Overview)

Strategic Airline Ticket Decisions

Airline Award Options

Intra-Hawaii Flights

Rental Car Deals in Hawaii


Now that you have the rough outline for our trip, stay tuned for many detailed reports of the adventure including many posts on the brand new Andaz Maui at Wailea.  This trip report, including video, is going to be done very quickly as I know lots of folks are excited about that hotel, and I love re-living our Hawaii trip.

Hawaii Trip Report:

Planning an Anniversary Trip to Hawaii

Flying to Hawaii in United Business Class

Westin Moana Surfrider in Waikiki

Flying Hawaiian Airlines from Honolulu to Maui

Review of a Room and a Suite at the Andaz Maui at Wailea

The Pools at the Andaz Maui at Wailea

On-site Restaurants at the Andaz Maui

The ‘Awili Spa at the Andaz Maui at Wailea

Exploring Maui Beyond the Andaz Maui (Little Beach, Monkeypod, and More)

How have you incorporated miles and points into some special trips with your spouse or partner?


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  1. Awwww. You two are just too cute. Thanks for sharing! (P.S. I have not traveled to Hawaii for those reasons you listed — also it’s a long flight from the east coast) so it has not appealed to me yet). I’ll be revisiting hawaii as a vacation destination though.

  2. Glad that you were able to convince your hubby to go to Hawaii and had a great time! My husband has everything against Hawaii as well (which I don’t understand) so my kids and I have been going without him for the past four years. But kids and I have decided that he must come with us next time and eat with us at Mama’s Fish House (our favorite on Maui) and brunch at St Regis in Kauai, and shop for fresh poke at Foodland etc. Hopefully that would do the trick as he is a foodie. We want to show him Hawaii is just as nice as Mexico.

  3. BOShappyflyer, I knew he couldn’t be the only one. 😉 It is far from the East Coast, no doubt. I think it is worth it, but I would not make a quick trip out of it, stay for at least a week and enjoy!
    Sharon, what’s up with these husbands? It was too funny my daughter went to Hawaii before her 39 yo dad! I am thankful he was willing to give it a shot though, and it was a success. Hope it will be for your husband as well!

  4. I’m one of those husbands, after vacationing in the Caribbean for 25 years I finally decided to give in Hawaii. That was three years ago and I’ve been back 6 times.Things I like about Hawaii:
    1.I speak the language fluently
    2.I understand the currency
    3.My car insurance works
    4.My health insurance works
    5.My cell phone works
    6.I can order food in restaurants, and can assume they have been inspected by some type of Health Dept
    Sorry… just trying to be funny,and I still travel the Caribbean, I find both offer something special.

  5. Jim, so true on all accounts! We also have a couple trips booked to the Caribbean, so I think you can love both (I just happen to love one more than the other….) 😉

  6. I somewhat sympathize with your husband about trips like Hawaii. Some of the ultimate aspirational award (or paid travel) destinations like Mauritius, Seychelles, Maldives, Tahiti…no interest at all. Can’t imagine a more boring trip.

    I had gone to Hawaii 8 years ago or so and had never been tempted to return, even on great fares. Until now, but that is more who I am with than where I am going. Leave Saturday. We shall see if it is a place I’ll choose to go more frequently or not.

    But, great trip review.

    • Cory, there is no place for everyone. However, if you are married to someone who likes so much of what Hawaii has to offer and yet says they don’t like Hawaii, well eventually you just need to strap them on a plane and either come out a hero or a loser. 😉 Many of these places are better when you are with someone you want to spend time with than not, so that is very much a factor…though I have loved Hawaii solo and with a kid as well.

      I hope you love Hawaii, or at least have fun with the person accompanying you!

  7. Agree with his Hawaii resistance. To me, it’s just always seemed like one of those places the nonworldly types go to pretend like they are leaving the country without really doing it.

    However, looks like you guys had an awesome time! I’ve only ever been to Waikiki for work and a friend’s birthday, guess I should venture further out some day.

    • Will, Waikiki is only technically Hawaii. Go to Maui or Kauai. I know who you are married to, so I know at least she would have a blast…and you probably would too. Just not on Waikiki. Go to the Andaz on Maui and then on to Kauai.

  8. I live in Miami, FL and have gone with my wife and two children, 9 and 4 twice. Once to Maui and the other in January 2013 to Honolulu. The first time we really felt it, flying to Dallas and then a straight 8 hour shot to Maui from there. I wanted to throw the little one out the window midflight. It was well worth it though. Hawaii is a paradise.

  9. Congrats on the great trip! Your update is perfect timing for me. Hubby and I are going to Maui and staying at the Andaz for our anniversary this Friday! If you have time, would love to hear which restaurants you liked in the area so I can make quick reservations.

  10. While I am not a Hawaii hater, I just find other places so much more interesting. Funny that people call it paradise. I’ve had a few good trips there, but doubt I will return anytime soon. But I am still enjoying reading about your trip!

  11. Before we had kids, some opportunities came up during my business travels where I was able to book last minute award tickets (on DL no less at the low level!) and hotel nights that enabled my wife to meet me for a long weekend or week. As a result, we had some nice little couple trips to London, Amsterdam, Paris, Munich, and Santa Barbara. Now that I think about it, my wife made one of these trips to Munich with my 8 m.o. daughter when my business trip was extended – they hung out with me for a week and we had a nice time visitng Christkindlmarkts when I wasn’t working. Due to last minute award availability, the kicker was that the return flight was in biz class so my daughter was able to ride in style before the age of 1!

  12. I was thinking this weekend about your failed one-day trip. My husband and I had a long weekend in Montreal sans kids, and it was well into the evening (after leaving the house at 7:30am) that I stopped feeling anxious and irritable, and could relax and have fun. It was a four day trip and was the perfect amount of time. We do one nighters without the kids sometimes, too, but it really is hard to switch gears so quickly.

  13. Michelle, in the area MonkeyPod was good and even better at happy hour prices. The food at the Andaz was actually pretty good, though perhaps a bit pricey for what you get. Mama’s Fish House is about 30-40 minutes away, but gets consistently good marks. I would also check out the recommendations on this post in the comments section.
    Jamie, so true and glad you booked enough time for the two of you. We have tried to avoid the one-night trips as they just don’t work for us in terms of “relaxing”. I think 4 nights is a great amount of time as well.

  14. Felt the same way about Hawaii until I actually went there. Now I find myself checking for Maui every once in awhile to see if there are ever any interesting job postings.

    Got the same offer for the Corvette but didn’t end up getting it and after driving on Maui, came to the conclusion that it would have been a waste since there isn’t any roads where you can really let it out.

  15. Well that’s convinced me, that and the $500 AUD return flights, next trip is BNE/SYD to HNL. For under 3k we can do a family trip!!!

  16. So happy to hear you had a great time at the Andaz! I’m going to book 4 nights there next April with my Hyatt CC and Chase UR for our wedding and part of our honeymoon. Any tips on getting an upgrade to a suite? I was thinking of doing a Diamond Challenge. Thanks!

  17. Wonderful tips and a Happy Anniversary to you! Husband and I are EWR to HNL this fall on United points. Just economy, but that’s OK as we are happy to have this “once in a lifetime” opportunity! I look forward to the rest of your reports. I’ve also booked Andaz for a few nights, two free with the Hyatt card offer.

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