For spring break this year we headed to Hawaii. More specifically, we spent 2 nights in Waikiki on the island of Oahu, followed by 6 nights in Wailea on the island of Maui.
Logistics/Getting There: We left our house on Friday afternoon and used 22,500 total Avios to fly the five of us from DC to LaGuardia on U.S. Airways. We grabbed an Uber at the airport and headed over to the Hampton Inn JFK for the evening (using Hilton points for 2 rooms). Saturday morning, we took the free hotel shuttle to JFK and boarded a Hawaiian Airlines direct flight to Honolulu. This flight was 11 hours, but the time flew by pretty quickly. We booked 11 months in advance and I was able to secure the first three rows of economy plus seating, which were really great seats with lots of legroom. It was 100,000 Hawaiian Airlines miles for the trip, plus some cash for securing the better seats. We arrived in Honolulu at 3:00 local time, which was 9:00pm for us. We quickly got our rental car – a Jeep Wrangler – and headed to the hotel. We had 2 rooms at the Hyatt Place Waikiki booked using Hyatt points (12,000 per room, per night). This hotel was a nice surprise. It was very modern and clean and a short walk to the beach. We weren’t really planning to spend any beach time in Waikikki, we just planned the stopover in Honolulu so we could visit Pearl Harbor. The Hyatt Place includes free breakfast, which turned out to be one of the best free hotel breakfasts we’ve ever had. We had a quick dinner right down the street, and were in bed pretty early.
Day 2, Pearl Harbor: Our ticket time for Pearl Harbor was 8:00 am, which was not a problem at all since we were all up by about 5:30 am, still on East Coast time! We had reserved our tickets in advance through the government website two months in advance. The whole thing is free, although you can pay to tour the USS Missouri nearby, which we did not do. Pearl Harbor itself was very worthwhile. The tour starts with a very informative film, followed by a boat trip out to the memorial, over the sunken ship, and then concludes with some time to browse the exhibits. We spent about 2 hours in total. The 15 year old appreciated it, although the younger two (12 and 10) less so. My husband and I both were very glad to have visited. You are not allowed to bring in any bags, so leave them in the car!
Following Pearl Harbor, we considered how to spend the rest of the day by consulting my Oahu Revealed guidebook, where I had flagged some ideas. I hadn’t made any concrete plans (so unlike me!), but we decided to try renting kayaks and paddling over a sunken island, which seemed like it would be cool. It was about a 30-minute drive to the state park. We got there only to realize the rental place there is closed on Sundays. Or at least this Sunday, which was actually Easter. I had been so surprised to discover in my planning that Pearl Harbor was open on Easter Sunday that I hadn’t thought about other places being closed. Anyway, never fear, I had read in the guidebook that there were 2 other private companies nearby that rented kayaks. I called the first one to make sure they were open. They were, but told me the state does not grant permits to kayak to the sunken island on Sundays, so no one will rent you a kayak there on a Sunday. Ugh! So, we headed back to the hotel and needed a Plan B. The other 2 things we planned for our short time in Waikiki were hiking to Diamond Head and taking surfing lessons. We wanted to save Diamond Head for first thing the next morning when it would be cooler, so surfing lessons it was. We briefly considered driving to the North Shore to the famous Pipeline to see the big waves being surfed, but a quick consult with Google revealed conditions listed only as “fair” and the kids really did not want to drive 2 hours just to watch surfing, they wanted to surf themselves.
Surfing lessons are available on a walk-up basis right down on the beach. It was $40 for a one-hour group lesson, or $60 for a semi-private lesson for an hour, with an additional hour to use the board yourself. We did the $60 option for just the 3 of them. They loved it and caught on right away. Waikiki beach really is the perfect place to try surfing. The waves are very consistent. While the kids surfed, my husband and I hung out on the beach. The beach was beautiful, but not our kind of beach. Pretty much wall-to-wall people. When the hour was over, they were pretty exhausted and not up for another hour. The instructor offered to give my husband and me a lesson the next day, and the kids could use their other hour then. That sounded like a good plan, so we arranged to meet back there the next day at 12:00. The instructor clearly was pushing for it to be later in the day, but we had our flight to Maui in the afternoon and that was as late as we could start.
We headed back to the hotel to clean up, and then tried to get a reservation for dinner at Duke’s. We couldn’t, and the wait time was 1.5 hours, so we crossed the street to Jimmy Buffet’s were there was no wait. The food was really good and it was a funky atmosphere. By the end we were all exhausted and couldn’t wait to get to bed, so back to the hotel it was. No late-night party scene for us.
Day 3: Monday morning we enjoyed our free breakfast and headed to Diamond Head. We pulled into the parking lot just at 8:00 and already there was a wait for parking spaces. Fortunately it only took a few minutes, but you wouldn’t want to get there much later. We all really enjoyed the hike, and the view was much better than I was expecting. Even though we stayed on the top for some time, taking in the views from different angles, we were back at the car by about 10:00 am.
We headed to an early lunch so we could be on time for our surf lesson. Based on Surfer Dude’s attitude about the 12:00 start, I thought there was a pretty good chance he wouldn’t be there when we got there, and he wasn’t. The nice people in the lesson area offered up another instructor, but we were just happy for the kids to use their other hour while we watched them. Day 2 didn’t go quite as well for them without an instructor pointing out when to get on the wave, but they still had fun. As soon as the hour was up, we high-tailed it back to the Hyatt to get showered and packed for our 2:00 late check-out time. We returned the Jeep, breezed through security, and were on our way to Maui. We booked 5 one-way inter-island flights on Hawaiian air using 25,000 total American Airlines miles.
The flight was a short 35 minutes and soon we were picking up our second rental car, also a Jeep Wrangler. The same identical gray color as the one we had on Oahu! First stop was Costco. I read there was a great Costco right by the airport and it would be worth stocking up on some essentials so we could have breakfast in the room each morning and save some money. This was a really worthwhile stop. It is literally right outside of the airport, not out of the way at all. We bought 3 boogie boards for the kids. These were $25 each and really good quality. In addition, we got a case of water, muffins, croissants, and bagels, 2 pineapples, a bottle of champagne, some chocolate covered macadamia nuts, grapes, strawberries, and sunblock. I knew our rooms had refrigerators and that stuff would be expensive at the resort. After Costco, we were starving, but didn’t really feel like a sit-down restaurant, as we were anxious to check into our hotel. We stumbled upon a place called Maui Tacos in a shopping center just before our hotel. Seriously, some of the best Mexican we have ever had!
Finally, we arrived at the Grand Wailea around 8:00 pm. I cannot say enough about this hotel. Check in was a breeze, we each got a lei and we were assigned 2 adjoining rooms, one king and one with 2 double beds, on the top floor of the Molokini Wing. This resort is sprawling. Our room was at the far end, but other than the long walk from the lobby during which the nice bellman accompanying us gave us a thorough overview of where everything is located, we found our room location excellent. It was a short walk to the beach and pool complex, and very close to a secondary valet station (expensive valet parking only at the Grand Wailea).
I have wanted to stay at the Grand Wailea FOREVER. Rooms were close to $600 per night EACH when we were there, but I was able to redeem just shy of 1,000,000 Hilton points (it is a Waldorf Astoria) for 2 rooms for 6 nights each, for free J And although there is a $40 per night per room resort charge at this hotel, it is waived for points redemptions! I have been stockpiling Hilton points for years for this redemption. So did it live up to expectations? Oh yeah. Exceeded them in every way. I seriously cannot think of one negative thing to say about our stay. The rooms were very nice and spacious. The bathrooms were huge. The lanais were big and it turned out our “garden view” rooms (9101 and 9103) had a nice ocean view. The staff was friendly and helpful. The other guests were pleasant. The grounds were meticulously maintained. The facilities were well taken care of. The pool complex was really fun. The beach was beautiful and not crowded. We had no problem getting complimentary chairs and an umbrella on the beach every day. Towels were plentiful. The restrooms were clean. The location was excellent, very easy to walk to some things and a short drive to everything else.
View from our Garden View Room at the Grand Wailea
Day 5: We awoke to a beautiful Maui morning and had some of our Costco breakfast on our lanai. We were surprised to see a lovely view of the ocean from our supposedly non-view, Garden View room.
I had scheduled a complimentary SCUBA lesson at the resort. This is a 30-minute introductory class in a special pool and I thought the kids would enjoy trying SCUBA. We all enjoyed it and ended up signing up for the 2 hour program that includes one hour of pool instruction and about 40 minutes in the ocean. They were already booked for Wednesday, so we signed up for Thursday. After SCUBA, we spent the rest of the day just hanging by the pool/beach. We ate lunch at the Molokini Bistro at the Grand Wailea, overlooking the ocean. Prices weren’t cheap, but not that expensive for a resort, either, and the food was good. You could just go in your swimsuit/cover up, you didn’t have to change, which was really the selling point!
For dinner the first night, I looked on Open Table to see if we could get a reservation somewhere, and was able to at 5 Palms, which was just up the street. The atmosphere was very nice, right on the beach and open air. The food and service, however, were a mixed bag. The restaurant was very pricey. Entrees in the $40-55 range. My kids were very happy with their selections. I had a fish recommended by the waiter that I didn’t really care for. My husband got a steak and the cut of meat was really poor. So bad, he couldn’t really eat it as it was all fat. They took it away, and it never came back. Long after we were all finished, the manager came over to tell us essentially that they were serving a wedding and his steak was long forgotten about. He sort of apologized, and said it would be out soon and no charge. Then about 20 more minutes went by. When it finally came out, the kids were so bored by then I told the waiter I was pretty sure we were entitled to some free desserts at that point. The kids thought this was absolutely hysterical, and now regularly tell me they think they are “entitled to some dessert.” Anyway, we each ordered our own dessert. Desserts were about $15 so we really got our money’s worth here. Of course, it took forever for these to come out. They were delicious, however, and with my husband’s steak and the desserts coming off the bill, the whole meal didn’t seem so expensive after all.
Day 6: Wednesday morning we decided to try driving the Road to Hana. As soon as we got to the starting point, it started to rain so we had to put up the top on the Jeep. We didn’t make many stops due to the rain and having a hard time finding where things are (“wait, I think we just passed a waterfall . . . ). Eventually we came upon Hamoa beach, which my trusty guidebook promised was one of the best bodysurfing beaches. We had brought along the boogie boards, and the kids had a really awesome time for a few hours. Interestingly, a family nearby came over and asked if they could rent our boards for awhile! As it was approaching dinner and everyone was starving, and we still had a long drive back, we got cleaned up and headed out. Because we had a four-wheel drive, we opted to just keep driving around the island, instead of heading back through Hana. I am so glad we did this! The scenery was amazing, so different from the lush side of Hana. Unfortunately, however, there are no restaurants anywhere to be found. We were so hungry as the hours wore on, it was putting the kids in a bad mood. I had brought snacks, but they were long gone by this point. Eventually, we were back near the airport, civilization, and most importantly food. It was a very long day. Driving the road was interesting, and we loved Hamoa, but I’m not sure I would do it again. The kids voted it “worst day in Hawaii!”
Day 7: Thursday morning we had our SCUBA session scheduled for 10:00. After getting suited up with our tanks, we headed into the special pool for instruction and practice. After that, it was done to the beach where we walked into the ocean. The tanks are very heavy and it wasn’t easy for the younger kids, but once we were in the water it was all worth it. We saw a large ray, sea turtles, and a variety of different fish. A really cool activity.
By the time we were done with SCUBA it was around 1:00, so we headed to Molokini Bistro, conveniently located right above the SCUBA area, for lunch. After that, it turned into a really windy day. Too windy for the beach/pool, so we decided to go for a drive. We headed to West Maui to check out the Kaanapali area. We parked at Whaler’s Village (pay parking only) and walked through the shopping area and along the beach for awhile. We checked out Black Rock. We were going to eat dinner there, but no one was all that hungry and the kids were dying to play Mini Golf at a course we had passed, so we headed out. Well, I knew we were in trouble when we pulled in the parking lot at Mini Golf and there were several school buses. There was a tour group there and the nice girl behind the counter warned me that there was a group of 200 kids playing! No thank you. So, we decided to head back to Maui Taco, followed by a stop next door at Cold Stone Creamery, then back to the hotel.
Day 8: Another resort day spent enjoying the beach and the pools. The pools at the Grand Wailea are really amazing, all interconnected by water slides. We had reservations for the Te Au Moana luau next door at the Marriott that evening, with check in at 4:30, so we had an early lunch at Molokini Bistro.
Te Au Moana luau: I wasn’t 100% sold on booking a luau as I didn’t think the kids would enjoy it all that much, and it is an expensive activity for a party of 5. But it seemed so quintessentially Hawaiian that we had to do it. I had read that the luau and the Marriott was better than the one at the Grand Wailea, and for variety we decided to go next door. The luau turned out to be very nice. The food was good and there were interesting demonstrations, including a ceremony with the pig. I think the kids enjoyed it. We were able to walk back to the Grand Wailea along the ocean path, since it is right next door.
Day 9: Saturday morning we had reservations for a snorkel cruise to Molokini Crater on the Four Winds II. It was about a 30-minute drive from the hotel to the dock. Breakfast was included while we headed out to the Crater. We were given some basic instruction and soon we were there. Wow, this was really fun! There were so many fish to watch. You were free to get back on the boat at any time, and get back in at any time. We stayed out for awhile, then came on board to warm up, and then back in the water. The boat has a water slide which I thought would be a huge hit with the kids, but for some reason none of them even tried it. After everyone was done, lunch was served. The crew grilled up burgers, chicken, etc. and it was all pretty good. On the way back, we had more sea turtle sightings, and some whales!
The boat dock happened to be right next to the Mini Golf place from earlier in the week, so we stopped for a game. Extremely overpriced and crowded, and but it made the kids happy. Later that evening, we went to the shopping complex next door to the Grand Wailea for dinner at Island Style Cheeseburger, which was very good. After the kids were settled into their room for the night, my husband and I headed out for a nice farewall walk around the resort. Did I mention the Grand Wailea is gorgeous?
Day 10: We awoke to that sad “vacation is over” feeling, but we were still facing quite a long 2-day journey home. We finished up most of our Costco food purchases on the lanai before packing up. We attempted to give away the boogie boards to several groups we passed, but we had no takers! Finally we just left them near the pool with a little sign that said “free!” To get home using miles, I booked Maui to San Francisco on Hawaiian Airlines (via Honolulu), but I couldn’t get the connection to Dulles. So I booked that separately, San Francisco to Dulles on Virgin America, also using miles. We were going to be arriving in San Francisco late Saturday night, with the Virgin America departing Sunday morning, so I booked 2 rooms at the Hyatt Regency San Francisco Airport (free airport shuttle) for the night. The hotel was nice, but we barely saw any of it we were in so late and out so early. The Virgin America flight was more than half full of middle school students on a spring-break trip to see the Cherry Blossoms in Washington.
Final Thoughts: Hawaii was really fun as a family. It was a nice combination of beach/pool relaxation and activities to keep everyone happy. The kids don’t love just hanging by a pool, but the waterslides kept them busy at the Grand Wailea. The flights were long, but everyone did really well and I think it was worth it. As for the Grand Wailea, it is rare that I think I will go back to a destination, but I really hope to go back one day. Maybe when the kids are older and it is just the two of us and we only need one room! I’ve already started replenishing my supply of Hilton points!