We had our flights lined up with our first 4 day stop on the Big Island which we had never visited before. We’d then head to Maui for 10 days which we were definitely looking forward to returning to.

Big Island Hotel

Since we were flying into Kona, we concentrated our search on hotels in that area since the Big Island is… well, big!

We were searching for Marriott hotels due to my wife’s Titanium Elite status. Based on the cash prices there was one option that stood out when searching for AAA rates. We could get an ocean view room with two double beds for $170 per night at the Kona Sheraton Resort. There were some other options around Kona and some on the northern part of the island, but they were much more expensive using cash and not outstanding value using points. I preferred to keep the points for use on our Maui hotels where we could get the 5th night free.

The hotel had fairly strong reviews even though it didn’t have a beach. It had a lounge where we could get breakfast and snacks and the AAA rate with the ocean view was less than the non-AAA rate garden view room so it was a fairly fantastic deal. The cancelation policy required 30 day notice which was not great but better than a non-refundable rate.

I kept an eye on the rate as the vacation came closer and saw the price stay the same, but the cancelation terms change. About 90 days before the travel it changed to a 48 hour cancelation window so I canceled the original reservation and made a new one for the same price, but with better terms. I like having the flexibility in case anything changes.

Lahaina Hotel

We knew we wanted to spend part of the time on the Lahaina side of Maui. It’s not our favorite side as we really enjoy the Wailea area more, but there’s a bunch of stuff to do there and wanted to split our time as best we could.

Originally we were thinking of splitting it 4 days in Lahaina and 6 days in Wailea. I had originally booked a room in the Westin Maui in Lahaina for 4 days on a cash rate. It was slightly cheaper than a room at the Sheraton Maui just a short distance away (cancelable AAA rates, of course).

As we got closer to the travel dates we decided a better use of our resources would be to use points which would mean using them for 5 nights in Lahaina and another 5 in Wailea, taking advantage of the 5th night free two times. Since we had stayed in the Ritz Carlton in Kapalua, 15 minutes north of Lahaina, during our previous trip to Maui and had a disappointing stay, we were focused on the Sheraton and Westin properties. There were also some Marriott and Westin “vacation club” properties which are timeshare properties that you can stay in on cash rates. Those were much larger rooms/suites with kitchens though they were less appealing for us because they didn’t offer elite benefits like free breakfast or room upgrades. They also weren’t on a part of Kaanapali beach that was as nice as the hotels we were looking at. The beach near those hotels is rather narrow and can get crowded during the day.

I read endless reviews of the Westin and the Sheraton trying to figure out which was best for us. In the end we chose the Sheraton as it was more spread out and we hoped would be more relaxing. The pool wasn’t as nice but the beach was wider and there was a show where someone would jump off the black lava cliff in a nightly ceremony. The boys would certainly love that!

Both hotels were a short walk away from the Whaler’s Village shopping mall which had several places to eat as well. They both shared a shuttle that went into The Lahaina downtown. We could use that if we didn’t feel like driving or dealing with parking, which isn’t free. We figured spending the 200,000 points was better than spending the $1900 cash rate for the room for those 5 days. It wasn’t the best value in my book, but it was solid.

Wailea Hotel

We knew from the start which hotel we wanted to stay at in the Wailea area. On our last trip to Maui we had chosen the Wailea Beach Marriott as an afterthought before we were to end the trip at the Ritz Carlton Kapalua. On that trip we had such a fun time in Wailea Beach and such a disappointing stay at the Ritz Carlton we left The Ritz Carlton early and returned to the Wailea Beach Marriott for the last two days of of our trip!

I barely looked at other properties because the only other Marriott in the area wasn’t on the beach. The cash rates for the Wailea Beach Marriott were north of $500 for the days we were looking or 50,000 points per night. Given the 5th night free we were looking at an excellent value for our 200,000 points to end our stay.

We also hoped my wife’s status and our previous history staying at the hotel might score us an upgrade as well, though we knew a normal room would still be fine for us. The base level rooms came with two queen beds which was awesome. The kids were over the top excited about returning to this property. It is probably one of our favorites of all the places we’ve stayed as there was so much to see and do and it was close to most of the things we like the most in Maui.

We didn’t know what to expect for elite benefits as far as breakfast, though. I had read on some blogs that the breakfast they offered was a bit pathetic. Some reports were that we would get a croissant and a coffee/tea from the on-site store and not breakfast in the restaurant like at other hotels. We knew worst case we could walk up the hill to The Shops at Wailea to eat at one of the restaurants there, but hoped the online reports weren’t accurate.

We had all our hotels booked, now we needed a car to get around.