Maui Thanksgiving 2019
Maui WOW- you really impressed me. I thought Kauai was pretty amazing, but man, Maui, you, were, incredible. Perfect weather (IMO- 80 degrees and sunny with zero humidity, low 70's at night), beautiful beaches and beautiful mountains, tons of dining options, a warm and swimmable ocean, a national park, other islands for day trips a quick sail away- how does it get better??? Joe and I traveled with another couple for a week to Maui for Thanksgiving week this year and it was the absolute right decision. We heard it was the busiest week of the year for the island, but honestly I didn't feel like it was crowded at all. We were still able to do everything we wanted to do, eat at amazing restaurants, get bar seats- so the crowds really didn't effect us. Here's a summary of our daily activities:
Saturday night in Wailea: Arrived into OGG around 6pm from our layover in Seattle. Our friends had already gotten in earlier and had picked up the rental car from Hertz, as well as went grocery shopping for our Airbnb, so we got a free ride straight to our condo in Wailea at the Palms complex. Our Airbnb was really nice- 2br/2ba with a large lanai we used every day for breakfast, big kitchen and living room, tons of space and perfect for 2 couples. After showering off we grabbed dinner at Matteo's Osteria- which was a nice italian spot close to the shops at Wailea. Decent italian, great customer service, a good option for a last minute Saturday night reservation after a long day of travel.
Sunday in Wailea: Started off the morning with a run around Wailea. There is a great path along the beaches which we ended up doing a few times that week. Then time for the beaches! I really loved the beaches in Wailea, the ocean was super calm and pretty warm, great for swimming. Not crowded at all, and most of the beaches had shady spots to move too when you needed a minute out of the sun. Pick any beach in Wailea, they were all awesome with facility options all over, most had parking, and a few were just right down the street from us. However, we did end up driving most of the time b/c the condo had beach chairs, snorkel gear, beach towels, so we didn't want to walk all that gear all over the place. We beached it up most of the day and had a quick drink at the Grand Wailea hotel, also snuck in a quick waterslide. After a great beach day we checked out the condo pool and hot tub, and then did dinner at Monkeypod. Known for their Mai-tai's and had really good food and not overpriced (which alot of places are in Maui). We walked from our condo which took about a half hour, and then stopped on the way home by the shops at Wailea for gelato.
Monday in Wailea: Everyone is going to tell you about the Road to Hana the minute you mention Maui, and now I know there is a good reason. Because it's amazing. It's an extremely long day, but it's worth it. You will see countless waterfalls, you can do some rock jumping, check out beautiful beach parks most notably the black sand beach, you will reach Hana and be like why?, but it's about the journey on this trip, absolutely not the destination. We downloaded the Chaka guide app- which gave us extremely accurate directions on where to stop on the Road to Hana. It was 100% the right move renting a car and doing it ourselves. We did the full loop, and with a million stops it took us about 13 hours round trip. You don't go far, but you go slow, and you stop so much that is where the time ends up ticking. Since the sun sets in November around 5:30pm- go as early as possible. Once you get past Hana when doing the loop the road gets windy, goes down to one lane at times, you will go extremely slow, but it is beautiful and worth it. Just do it- take the day (I would recommend our timing of doing it the 2nd day of our trip was pretty spot on), go early (like wake up and try to leave before 7am), pack snacks (however if you like banana bread you are in luck there are a ton of stands), stop in Hana for a sec (we ate at the Hana cafe which was whatever but needed), and enjoy the beautiful scenery. When we got back to Wailea we ordered Fabiani's on Grubhub and picked it up since it was a long day and we were exhausted (delivery services are not a thing in Maui- so weird. Not even alot of take out options. They want you out in their restaurants!)
Tuesday in Wailea: Morning run on the beach path, then drove 15min down the road to Makena beach. Spent the day at the Makena beach park- and then drove to Kihei for some shopping and happy hour. There is a cute outdoor local shopping mall with bars right in the town where we did some souvenir shopping and had a few drinks and snacks at South Shore Tiki Lounge. We also made a stop for a couple at Lava Rock - looks like it turns into the club at night. After Kihei and showers, drove about 30 minutes to Momma's Fish House- another place everyone will tell you to go to in Maui and they would be right. The best meal of the trip in my opinion, and the most expensive. Mostly fresh fish dishes, the restaurant is beautiful- if you can go early for the view do it. Lunch is also a good option there. Make reservations now, we made them months in advance and it was booked solid when we were there. It's pretty close to a small hippy town called Paia which had some cute stores and restaurants (like one main street), so again this could be a day trip since it is far from most places.
Wednesday in Wailea: National Park time! Another early morning start, we drove 1.5hrs up to Hakelakula National Park- 10,000ft in elevation. There is a popular option that tours offer where you can get up before sunrise, bus it up to the top, and ride bikes down the volcano, but we were interested in hiking and sleeping so we did not do that- however a couple friends' of mine have and loved it- so you have options how you want to enjoy this National Park. We did the Lelewi overlook (1 mile round trip to a lookout point), and then the sliding sands trail to split rock- which was about a 45min hike down, and 1hr 15 min hike back up. The craziest views of the volcano- so eerie. This is a very exposed hike, nowhere to hide from the sun, but since you are up so high it's actually pretty chilly at the start, but by the time you are heading back you will warm up quick so layers are key for this excursion. The elevation and the down then up of this hike made it not the easiest, but worth doing. Very unique. After spending time in the park we stopped in Paia town for lunch at the Flatbread lunch company (organic pizzas, pretty good and affordable), some shopping at some really cute surf boutique stores, and then back to Wailea to clean up. After a quick break- we were back in the car for another half hour trek to the Mill house for dinner. This is another place I wish I could have seen in the daytime. It's on an old plantation, and is huge with cool grounds, so again if you have the option to go for lunch or a sunset happy hour I would do that. Great place, really good food and cocktails. That drive though! Ubering is an option- Maui does have Uber and Lyft, but since we had a rental car we were going to use it- and use it we did!
Thursday - the move to Kaanapali: We said goodbye to Wailea in the morning, drove 30mins to the airport to drop off the rental car, then Ubered over to Kaanapali to check at the Westin Resort for the second half of our trip. What a different feeling. Wailea is referred to as the Beverly Hills of Maui, whereas Kaanapali is where everyone else is hanging. In other words, resort life to the fullest. But this is not necessarily a bad thing. Kaanapali still has beautiful beaches and scenery - and a different set of mountains in the background. Our first day we hung at the Westin pool and the beach, and got in the lava rock jump at the end of the beach (love love love a good jump spot). For dining and shopping, this area is way more convenient. The Whaler's Village complex was right next door to the Westin- so we ended up eating there every day except our first night where we had booked the Luau at the hotel. It was not my fave- shows are not really my thing. It was expensive, all you can eat but the food was hotel buffet so not the best, all you can drink but the wine was cheap, a little too long (3 hours) just not for me. But if you want to see hula girls and fire dancers- that's what you will get.
Friday in Kaanapali: Our last excursion day. I had booked Sail Maui a couple weeks in advance. They provided everything, a light breakfast in the morning, packed sandwiches for lunch, snacks on the way back. Plus free drinks, coffee, water, etc. We sailed off from the Lahaina harbor for a 7+hour day of sailing and sightseeing. About 15mins into our boat ride, we saw a bunch of Humpback whales. Ah-ma-zing. We were super close! Apparently the big season for their migration is Dec-Feb, when you are guaranteed so see one, so book that boat! We stopped a couple more times at some snorkel spots (the best snorkeling I have done to date, the boat was super good with defogging your masks, fitting your equipment, and pointing us in the right direction). Next stop was Lanai, where we docked for a few hours- checked out their almost private beach, did a quick hike to Sweetheart rock and hung out in some tide pools. On the sail back, we did something super cool. We parked in a super deep channel, where the water was this crazy bright blue, and you were able to open your eyes underwater without them stinging. It was nuts. Super cool. I highly recommend booking this trip with this sailing company. Back at the Lahaina harbor we did some shopping (same shops that are in Whalers village basically- also has Mick Fleetwood's bar/restaurant Fleetwood's on Front which was recommended to me but we didn't go). We caught the Westin shuttle back to the hotel- then had dinner at Hula Grill in Whaler's Village. Another amazing dinner outdoors- does not get any better.
Saturday in Kaanapali: Last day, so sad. We started with yoga by the ocean (actually was a really good class- $15 through the Westin) and a run on the beach path. Then one last pool day, complete with one last water slide. We ended how we started, with dinner at the Monkeypod (this location in Whaler's Village)- and if you go do the happy hour- it saved us a ton of money. Gelato's to end the night, a beach stroll, and then off to the airport.
Beaches in Wailea-Makena
Road to Hana- full loop: definitely stop at the black sand beach and a few waterfalls with swimming holes. Download the Chaka app, rent a car and do it yourself!
Dinner at Mamma's Fish House, Mill House and MonkeyPod. Book Mamma's way in advance and go when the sun is out to both Mamma's and Mill House
Shopping in Paia
Halekalua National Park
Sail Maui day trip to Lanai Island