This content is not provided or commissioned by American Express. Opinions expressed here are author's alone, not those of American Express, and have not been reviewed, approved or otherwise endorsed by American Express. This site may be compensated through American Express Affiliate Program.
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.
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(TM) World MasterCard® – Earn 2x on All Purchases 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.
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.
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.
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:
How have you incorporated miles and points into some special trips with your spouse or partner?
Disclosure: I do receive a commission if you are approved for a credit card using one of my affiliate links. As always, thanks for your support.