The Definitive Guide to the Perfect Maui Vacation - Finding The Strongest Mai Tais + More of Maui's Best Kept Secrets
Aloha, HENRYs! In 2019, both K + I traveled - separately - to Maui for our first times - crazy, right!? With all of the destinations we’ve been to, it’s hard to believe that we waited so long to visit this relaxing, beautiful island, but we’re so glad that we finally did! This post is kind of a long one, so we’ll jump right into it! As always, we’ve highlighted all of our Maui recs on the ‘gram. Make sure to follow us to get even more details on all of our travels!
When To Visit + The 411 On Our Flights
K traveled to Maui in September of 2019 with a few of her fellow teacher friends for a little over 48 hours. (Side note - for those who think she’s crazy to go for just a weekend, as a teacher, she doesn’t have a ton of flexibility when it comes to taking time off during the school year). These spontaneous Hawaii trips are becoming an annual tradition as last September, they spent a weekend in Kauai as well. Click HERE to read her travel guide on her Kauai trip. They scored a great flight deal by tracking prices on Hopper + Google Flights. As soon as they received an alert for a great deal, they elected to use their Alaska companion fares to make it even more affordable and booked the trip for $300! More information on how we score the best flight deals can be found HERE.
I traveled to Maui for the week of Christmas in 2019, one of the most popular (aka expensive) times to visit the island. Even with deal hunting, you would be hard pressed to find a “cheap” flight deal to the island during this time, but our trip was generously gifted to us by Zach (my fiance’s) grandma + we could not be more grateful to her. It was the most wonderful experience.
From what we’ve heard, there is never a bad time to visit the island weather-wise, but avoiding Spring Break, Thanksgiving + Christmas are the best ways to save money on flights + hotels, as well as avoid mass amounts of tourists.
I mean…how is this view NOT worth it for 48 hours!? Also, view from Mama’s Fish House, so if you’re here for the food recs, scroll on down.
Where to Stay
View from the balcony of our condo on Kaanapali Beach. How could you not be happy here!?
Maui is a small enough island that no matter where you stay, you will be able to get to any point of interest during your trip - however, some spots may be a few hour drive. No matter where you are traveling to, we always recommend using Google Maps to plot all of the activities + restaurants that you plan on visiting + selecting to stay in the area where most of the “pins” are concentrated - pending that the area is within your budget of course.
When visiting Maui, the primary parts of the island for tourists, as well as the most recommended restaurants, are Wailea, Ka’anapali and Kapalua.
K stayed in this Airbnb in Kihei. Because she was visiting the island for such a short time, she chose Kihei for its proximity to the airport, as well as its central location to get to most of the spots on her Maui bucket list. Had she been staying for a longer trip, she would have picked a different neighborhood, but loved the property.
I stayed in Kaanaapali in a condo building called Aston at The Whaler. Rooms are bookable through VRBO, Expedia + all of the typical home sharing websites. I loved the prime location on Kaanapali Beach - one of the most beautiful beaches I saw on the trip, the spacious rooms + the close proximity to downtown Lahaina + Whaler’s Village, all with lots of great shops, bars + restaurants. Because it is a condo building, there aren’t restaurants on the property or pool bars, but we were able to bring our own drinks + snacks to the beach.
If we were both to return to Maui, I would absolutely return to Kaanapali, but would stay somewhere new. On a beach vacation, I prefer somewhere with restaurants on site, poolside service, etc. vs a condo or rental property. I would also be interested to stay in Wailea or Kapalua. Keep these spots in mind when searching for hotels for your Maui trip! While we haven’t stayed at any of these, a few of the top recs we’ve received have been Andaz Maui at Wailea, Montage Kapalua Bay and Grand Wailea.
Where to Eat + Drink
Maui Brewing Company - This was where K went as soon as she landed + had great food + drinks. It’s an awesome spot to stop in for a casual drink + if you’re not a beer drinker (@kelda) they also have cider.
Mama’s Fish House - OH. MY. GOD. There’s a reason that Mama’s Fish House is so well known. It’s for sure way pricier than either of us would normally spend + you need to make a reservation weeks in advance, but it’s so so good. The menu changes daily based on what fish is caught fresh that morning. We were greeted with a cup of the most delicious soup + a warm lemon poppy seed bread with fresh whipped butter. We would recommend splitting an entree with whoever you’re dining with + then ordering a few different appetizers. I split an entree with a friend (fish stuffed with crab + lobster) along with the crab cakes. All of the food was so, so good. Neither of us were super impressed with the drinks, however, + if you’re looking for a way to save money we’d probably skip them + go for a drink elsewhere afterward.
Mai Tai Time! Highly recommend stopping in for Happy Hour for $5 off the signature cocktails + great appetizer deals!
Monkeypod Kitchen - They’re known for their Mai Tai + it was so, so good. The food was also delicious. Have to recommend the raw platter app because we were both craving some poke almost immediately upon landing. They had live music + the service was also top-notch (they even gave us a free dessert). You’ll also want to make reservations here to avoid a wait. Monkeypod has locations throughout the Hawaiian Islands, so should be easy to add your agenda no matter where you’re staying! The only downside was the location. We can’t speak to all of them, but we both went to separate Monkeypod locations in Maui + the setting is essentially in a mall - not what we’d expect for the ambience of such a quality restaurant.
Paia Bowls - K stopped here for breakfast before her Road to Hana + enjoyed acai bowls + some avo toast. It was the perfect refuel stop before her drive. The acai + avo was fresh + delicious!
Fleetwood’s On Front Street - The rooftop at Fleetwood’s, along with the absolutely amazing food + deal on champagne, made it my favorite restaurant of the entire Maui trip. I would recommend visiting during their Happy Hour - when all bottles of champagne, even the $400 Dom, are half off. The food was SO good too - even better than Mama’s Fish House in my opinion, although a much more low key atmosphere. This would be at the top of my list to visit for my next return.
Down The Hatch - Great spot for fish tacos in downtown Maui. Fairly affordable + kind of a hole in the wall where you go up to a counter to order. We dined here after we completed the Road To Hana as it didn’t require dressing up. We were tired + wanted something casual, but still delicious! Down The Hatch fit the bill.
Places We Wouldn’t Return: We had heard rave reviews about both The Gazebo + Slappy Cakes for breakfast spots + I was honestly unimpressed with both - maybe I just ordered the wrong things! The Gazebo routinely has a wait time of over an hour for breakfast - no reservations accepted - and with such a wait, I would have expected more.
Other Recs: We didn’t have time on our trips to visit the following spots, but have heard amazing things + would love to visit next time. We can’t attest to their quality, but have heard great feedback if you need more!
What to Do
Road to Hana - The Road to Hana is probably the #1 thing that will pop up when you Google what to do in Maui. I’m not going to lie - it is a LONG road, but the scenery is beautiful. There’s a north road + a south road . From what the locals told us, the north road can take a little longer but is better paved. We were told the south road has more gravel portions + it can be easy to get a flat tire, so rental companies prohibit you from driving it. We can’t speak to whether or not that was actually true as we both did the north road. Along the road you’ll find a ton of hikes, swimming holes + small local food stands.
Pro Tip #1: If you’re only in Maui for a short time, like K was, pick one hike that you want to go on or one part of the road that you really want to see + make that your destination. You’ll be able to get through the road in about 8 hours doing this (vs. 12+ if you continue to stop) + then you’ll still have time to do something in the evening!
Pro Tip #2: Start early! The Road To Hana is, oftentimes, a one lane road with almost 60 bridges that can handle just one car at a time. If you leave too late in the day, you will be stuck in so much traffic + it will make the journey that much longer. We were both on the road at 6 AM + had no issues with traffic, but did notice that the road was very backed up on our return!
Pro Tip #3: Download GyPSy Guides! For less than $10, we had a fully guided tour of the entire Road To Hana. The app tracks the GPS location of your car so that it can accurately narrate where you are, what you’re seeing, the historical significance + all of the fun facts along the way. Much of the road is without any kind of cell service, so this is a super helpful way to be sure that you don’t miss any of the important stops or turn offs too!
Fun Fact: Banana Bread “hunting” is a thing + we highly recommend partaking! All of the little stalls + shops along the road will sell banana bread. K + her friends bought a loaf of banana bread at multiple stands to try them + compare. Her favorite? The chocolate chip banana bread from Hana Farms - we both stopped there + it was the cutest! Also, a great pit stop to pick up some souvenirs if you’re into that!
Hana Farms - Our favorite roadside restaurant along the way!
Haleakala National Park - This was K’s pick for their destination on the Road to Hana, but a stop that I made also. Haleakala National Park is home to a bamboo forest, the Seven Sacred Pools + the Pipiwai Trail. It cost us $25 to enter the park +, even though K went in September + I went in December, unfortunately, the water levels were too high at both times for us to swim in the Seven Sacred Pools. The bamboo forest made it still worth the drive for us. I’d highly recommend this stop on the Road to Hana + the trail is only 4 miles round trip which makes it a pretty quick stop if you’re crunched for time. My other (personal favorite) stop along the road was Wai’anapanapa State Park.
Watch the Sea Turtles - The only other time I had seen sea turtles was in Curacao + they were underwater so I didn’t really get to see them. We went to Ho’okipa Beach at sunset on our last night to watch the surfers + see the sea turtles come out of the water + onto the beach for the evening. They were totally majestic + seeing them with the surfers behind them was a perfect end to our trip.
Nuage Blue in Paia.
Shop in Paia - Paia is such an adorable town with the cutest boutiques - great if you’re looking to pick up some new clothes or gifts to take back home! There are also plenty of good eats here (if you’re here for the food, scroll down for the best recs). If you’re planning to dine at Mama’s Fish House, plan to arrive in Paia a few hours before dinner to shop + watch the sunset at Ho’okipa Beach - mentioned above.
Lounge on the Beach - Obviously, if you’re in Maui, you should 100% spend some time on the beach. K went to Baldwin State Park to spend the afternoon + it was a great beach with plenty of space to spread out + the water was swimmable. We also read a lot about Makena Beach + would have liked to visit if we had more time.
MauiWine - We love wine tasting+ MauiWine was one place that we both really wanted to visit, but we opted for more beach time instead. If you’re into wine tasting, the reviews are all great + we’d love to know what you think.
And there you have it! Some of our top recommendations for this beautiful + relaxing island. Just writing it makes us want to go back - like tomorrow. As a reminder, we write travel guides for all of the cities that we visit which can be found HERE. If you need help planning your Maui trip - or any trip - email us, slide into our DMs or book a consultation service!
Other Helpful Travel Resources. Nothing Sponsored Here. Sharing Only What We Actually Use!
Chase Sapphire Card - This is the primary credit card that both of us use + are able to cover at least half of our trips a year with just Chase points alone. Click HERE to sign up. With our unique referral code, you’ll get 80,000 points (equivalent to $750 in airfare) when you sign up.
Delta American Express Card - This is both of our secondary travel credit cards. Perfect for those who live in a Delta hub like we do. The benefits more than pay for themselves. Free checked bags for you + up to 6 companions, discounted CLEAR membership, priority boarding, the list goes on. Click HERE to sign up + get 50,000 miles - more than enough for a round trip international flight, sometimes even in business!
AirBnB - Especially when traveling with friends or a large group, AirBnB is our preferred form of accommodation. If you haven’t booked an AirBnB before, click HERE for $55 off your first stay!
Mobile Passport - Our (totally free!) secret to getting through customs even faster than those with Global Entry!
