Maui Travel Guide 2021 – COVID, Grand Wailea Review and more!

Surprise Hawaii Trip ~ Kristy Wicks

Back at it with a classic Maui Travel Guide Blog post! It feels so good to be traveling again. For those of you who don’t know – it’s Emma here chatting all about how my 5 night trip to Maui went. Spoiler alert: it was pure magic! I will go into all of the details regarding our trip – which airline we used, COVID rules and regulations, where we stayed, where we ate/what we did and our best tips to help you plan your Maui trip. :)

COVID Rules & Regulations

I wrote a blog post before I left on my trip all about what we did to prepare for the COVID rules for traveling to Hawaii and where we were planning on staying. I went into all of the COVID regulations and rules at the time and I said I would report back once I got home. Click here to read some of our best tips and tricks.

Everything we did to prepare for our trip worked perfectly. We followed procedure exactly how they wanted us to and it ran smoothly. Like I mentioned in the planning for Maui blog post, Z and I got tested about 48 hours before we left (with a Rapid NAAT test) at the Oakland Airport. We received the results back around 1 hour after getting it and uploaded everything into the Hawaii Safe Travels portal. We also printed out a copy for the airport. In addition, we printed out the QR code that was e-mailed to us.


We arrived in Maui on April 9th, so this didn’t affect us. Starting May 4, Maui will be requiring all passengers arriving from the mainland to undergo another COVID test at the Maui airport. This is in addition to the negative test you had to take at home.

We flew Southwest and they along with numerous other airlines (Alaska, Hawaiian, United, among others) now allow passengers to get “pre-screened” at your home airports so that once you land in Hawaii you don’t need to wait in any lines. People say that can sometimes take hours. Once we arrived at the Oakland airport the day of the flight, we were able to head straight to the “Hawaii Pre-Check” area right after going through security. They double checked our negative COVID test, scanned the QR code and we were all set! They gave us wrist bands to wear so that once we arrived in Maui we would be able to leave the airport right away. It was SO easy. 100% worth the effort to get everything done before we landed.

Click here to see the current COVID rules & regulations regarding Maui.

Airline & Flight Info

Our Southwest Airlines was an easy direct flight from Oakland to Maui. We booked our tickets on March 1st, so just 5 weeks ahead of our trip. We used airline points to purchase the tickets which was great. For each ticket it was only 17k points each so 34k points in total for our flights. Such a great deal! If you’re not familiar with the Southwest points system we were able to save up a lot of our Southwest points via their credit card over this last year and because we never used any points during 2020 we had a ton to utilize.

I’ve been getting a LOT of questions regarding our travel credit cards/best ways to redeem/and more – I definitely want to write an entire post devoted to this at a later date!

The flights to and from Maui were SO easy. The southwest flight attendants were super nice, they served plenty of soft drinks and snacks throughout the flight, and our bags came out relatively quickly both times! (we checked our luggage) In total, we really enjoyed the experience as we usually do with Southwest. Someone we met while in Hawaii mentioned to us that they flew on Hawaiian & said it was a horrible experience – especially with delays.

Our Condo & Hotel

I mentioned in the previous post that Zach and I were going to stay at a Condo AirBnB for 3 nights & 2 nights at the Grand Wailea Hotel. I’ll share my FULL thoughts and reviews on everything in this post!

Our view for 2 days

Sugar Beach AirBnB

The AirBnB we ended up staying in is absolutely AMAZING. It’s located right on Sugar Beach in Kihei (near Wailea) and we had a fabulous time. The condo is located in a complex called Sugar Beach Resort, which is a condo complex that is mostly full of vacation rentals. It was SO quiet & relaxing – pure bliss. A nice pool & hot tub were on property, plenty of pool chairs and beach chair space plus a grilling area! Our room had a full unobstructed ocean view in a renovated apartment for somewhere around $289 per night. Right now it looks like it’s booked up for the entire year, but if you look at the Sugar Beach Resort website you can see other units for rent.

I shared a mini condo tour in my stories, but for those who missed it… the entire place was renovated recently, the bed was so comfortable, great lanai, and the owners provided every amenity we could ever want! I added a few photos from the Airbnb listing below.

We loved the condo so much! The surrounding area was really beautiful too. The beach was walkable to an ABC Store, delicious bakery & the famous Ululani’s Shave Ice! That being said, I highly recommend having a car rental if you stay in Kihei – especially here. You aren’t close to many restaurants via walking but with a car you’re just a short 5 min drive from the town of Kihei. (I’ll be chatting a bit more about how crazy the car rental situation in Maui is right now a little further down in this post.)

The location of our AirBnb was a huge plus for us because it was SO. QUIET. Every night we sat out on our lanai for hours while reading or chatting – all we ever heard was the crashing of waves.

gorgeous 6am light from our Lanai

aerial view via Hawaii.House

Grand Wailea Review

Surprise Hawaii Trip ~ Kristy Wicks

After we checked out of our Airbnb Zach and I drove to the car rental place in Kihei to drop off our car. After catching a cab to the Grand Wailea, we were able to check-in. We actually booked the 2-night stay for free through our Hilton Amex Aspire Credit Card (once again, I’ll chat about all of this in a different post.). When you book the “free nights” on the credit card, you have to book the least expensive room in the entire hotel, no matter which hotel you end up booking with. We ended up booking the “Terrace View” room, which we would have been perfectly happy with.

Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Our room view
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Thanks Mom!

When we checked into the Grand Wailea, to our surprise they upgraded us to one of the highest room levels. We were SHOCKED. This isn’t usually the norm. They put us up in the Napua Club Ocean View room, which comes with the Napua club access where we can have breakfast and cocktails & appetizers every day. We were so excited! Plus, due to Zach’s Diamond level status – they gave us a $20 credit for breakfast to eat at the real restaurant per person, daily. We had so many options!

Something to note: the week we visited the Grand Wailea it was DEAD. Apparently they were only 1/4 full compared to full capacity a week before. Luckily we missed the Spring Break and Easter time periods.

The room we were given was a little tired (as are many of the rooms at the Grand Wailea we’ve heard) but we had a great view of the ocean from our lanai. This room typically goes from $1100-1300 per night. WOW. I could not imagine paying full price for this room. Truly, could not fathom it. Because Even though the pools, grounds, and beach is wonderful.. the room itself is lackluster. The Napua tower is in dire need of an upgrade, for sure.

Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip

Now, I think it’s important to know that Zach and I typically aren’t “resort” people. Usually when we travel, we backpack or stay in an AirBnB/Homestay option and do every activity possible. However, in this case – we knew our room was FREE and we also had a $250 Hilton credit to use on anything while on property – food/drinks, spa so it was too hard to resist. We enjoyed relaxing.

Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
View from the restaurant in the AM

It’s important to note that the Napua club breakfast & appetizer/cocktail hour has also been changed due to COVID. I added a photo below of what it used to look like – your typical breakfast buffet. Now, everything is individually wrapped in small portions with fewer options. For us, we liked it because we hadn’t paid for it.. but if I had, I probably would have been really disappointed.

photo via My Points Life
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
It’s hard to beat this view from the Napua club though.

Of course, the grounds of the Grand Wailea are spectacular. Zach and I just walked around admiring the gorgeous landscaping, the fresh florals everywhere, and the different waterfalls and ponds located throughout the property. We also couldn’t help but admire the stunning chapel. ;) Maybe we will have to renew our vows in 100 years there?

Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip

For the two days we were at the hotel we headed to the adult pool and reserved chairs. It is such a relaxing area with a gorgeous pool & two hot tubs on either side. Zach and I would jump in the cool pool, swim for a while then head straight to the hot tub. Normally, The Grand Wailea has an online reservation system for people to reserve the pool and beach chairs. Apparently two weeks before we came, Spring break was CRAZY and crashed the entire system so they reverted back to a system of waiting in line at 7am and reserving chairs with the pool attendant. (Apparently this also changed after we left – now it’s first come first serve.)

Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Our pool chairs on two of the days faced the adult pool, which was nice.
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Another view we had

Renting a Car

This part should have been hard considering all of the nightmare stories we heard from everyone renting cars… but it was surprisingly easy for us. We rented our car from Kihei Rent-a-Car about a month before we arrived! Such a great company, and an easy process.

I heard horror stories a few days before we landed that apparently due to COVID, there were car shortages on the island.. many of the rent-a-car places sent their cars back to the mainland to be used when Hawaii shut down last year. Now there is a HUGE car shortage on the island and we heard that people were paying upwards of $600 per day with the larger car rental companies. (AVIS, Hertz, etc.) INSANE. Read this article about tourists renting U-Hauls.

With Kihei Rent-a-Car, we paid $80 total for 2 days. It was an older heavily used Nissan Sentra. We knew we didn’t need anything fancy – all we were doing was driving around a little, no road to Hana vibes or anything so we were very satisfied with this car. They told us in advance what we were paying for. They will pick you up from the airport depending on your arrival time as well – I would highly suggest planning a flight that arrives earlier if you’re not renting a car at the airport. They also have nicer cars and jeeps if that suits you better.

Something to note – THERE ARE LITTLE TO NO UBERS/LYFTS AVAILABLE RIGHT NOW. Make sure if you want to plan on getting around and traveling to different places to rent a car in advance. The little taxi services that are available today are running on fumes and SO busy. When you arrive, make sure to pre-book your return airport transportation through your hotel (if you don’t have a car). We did it the day before through the Grand Wailea and it was very easy.

Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip

Where We Ate

Zach and I ate a good amount of food for only being there 5 nights! We tried all the places below and I gave my full honest reviews. We highly recommend everything we tried.


  • Tamura’s Fine Wine & Liquors – Has AMAZING Poke bowls in Kihei and is very close to the beach to sit and have a picnic. Zach and I did this on the first official day we were there for lunch and we loved it. Very fresh! (Has other locations also)
  • South Maui Fish Company – Super popular place in Kihei (food truck in the middle of an outdoor shopping area) that has great poke and grilled fish tacos. Delicious!
  • Akamai Coffee – Our favorite local coffee shop. They have multiple locations on the island.
  • Sugar Beach Bake Shop – Best fresh malasadas (filled sugar donuts) and other pastries/quiches. Takeaway bakery that sells out so go early.
  • Maui Bread Company – Another bakery we loved.. delicious local sweet breads and products.
  • Foodland – The local grocery store has great Poke and takeaway dinner options if you don’t want to go out.
  • Ululani’s Shave Ice – Extremely popular shave ice spot near our Condo. We waited in line for an hour around 1pm. We had no idea how popular this place was until we got there and tried it – best shave ice ever!
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Down the Hatch

Lahaina Area

  • Leoda’s Kitchen and Pie Shop – Halfway in between Kihei and Lahaina right off of the main road sits a delicious pie shop. They also serve food that’s supposed to be great (My Dad’s favorite place) but we only tried their pies. We personally LOVED the Key Lime & Banana Cream.
  • Down the Hatch – Right in the heart of Historic Lahaina on front street. We came here for dinner and drinks one night (about 40 minutes away from Kihei) and loved their seafood and atmosphere. Our favorite dish was the Lava Shrimp Tacos.
  • Fish Market Maui – A bit north of Lahaina, we ate here after driving around during the day. Delicious meat plates, poke, and more!
  • The Coffee Store in Napili – Amazing coconut coffee, busy place near Napili Bay.
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Fish Market Maui


  • Monkeypod Kitchen – I feel like this place is on every single list, but it’s for good reason. The Mai Tai’s and drinks are excellent and the food is always delicious! Expect a long wait (they aren’t currently taking reservations) but it’s worth it.
  • Ferraro’s at the Four Seasons – The views from this restaurant were spectacular. We went here as a special dinner for my birthday! Basically an unobstructed view of the ocean – make sure to get seated a little before sunset. We weren’t blown away by the food but the drinks and dessert were great.

Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip

What We Did

Honestly… we didn’t go crazy and take the road to Hana or go on any big hikes while we were on Maui. This was our first official time traveling since March 2020 and we really just wanted to relax. We did a few fun things the first couple of days we were there but besides that, we just relaxed by the pool, ocean, etc.

  • I did get a relaxing massage in our condo by Na Alii Massage. Zach booked this for me as my birthday gift and it was SO nice not worrying about heading to a spa – all I had to do was wait for them to come to me! Wonderful experience, highly recommend.
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip
  • Zach and I drove from Kihei up through Lahaina to Napili Bay for a day of swimming and lounging. It truly is a gorgeous beach and bay, the ocean is this bright shade of blue that we loved. (I personally wouldn’t want to stay at one of these resorts because the beach was SO crowded.. Kihei is a little less stressful for me, but visiting was a ton of fun.)
  • Visit Nakalele Blowhole – Just a 20-30 drive past Lahaina sits a gorgeous little hike to a huge blow hole. We took tons of videos and it was a really fun experience!
  • Drive around and EAT! Z and I did this a good amount, just exploring different little towns and trying lunch options.
  • Walk through all of the resorts in the Wailea area – we loved walking from the four seasons through all of the local hotels. They are gorgeous and it was interesting comparing them to the Grand Wailea!
Maui Travel Guide 2021 - Where to stay, eat and play.. plus planning for COVID regulations and restrictions. How to book your maui trip

Overall, GO TO MAUI RIGHT NOW. It’s 100% worth it! Yes, there are mask requirements (at least in California, we still have them too so it’s not a crazy shock for me) for the beach and even just walking around, but it did not take away anything from our trip. We had such a blast.

Let me know, are you planning on traveling to Maui anytime soon? Have you recently visited? If so, what are your plans? Let me know in the comments below! Hopefully this Maui Travel Guide helped you!


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21 thoughts on “Maui Travel Guide 2021 – COVID, Grand Wailea Review and more!

  1. What a fantastic trip. We are headed to Maui next week. Thank you for all your helpful tips. We are flying out of SJC and staying for 2 weeks. Looking forward to relaxing and taking in the beautiful views.

  2. My boyfriend and I just booked a trip to Maui and the Big Island for July!!! We still have a lot of planning to do but this blog post was super helpful ☺️☺️

  3. Thank you so much for your great tips! My whole family is going to Maui in July(12 of us). We rented a house and have our rented already! We have reservations at a luau and Mama’s Fish House. Things are booking up fast!!

    1. That sounds like so much fun! Yes definitely book ahead for everything in the summer, it gets crazy. I’m so happy you’re able to go as a family. Hot tip: a lot of the COVID restrictions require large groups to not go places together (no more than 5 or 6) and same with restaurants.. so just be careful of that! We have heard of people being ticketed, etc.

  4. Heading to the GW at the end of August. 6 nights free using points! Score! Plus used 24k points each to fly from Long Beach. Another score! Rental car, I have two reserved with two companies to be safe, $600.

    Concerned with how tired the resort is though. Your blog confirmed what I have been reading.

    Did you hear any buzz as to 100% vaccination to enter the state? I heard that is coming. If I need find a new destination fast!

    1. Hi Jamie, I didn’t hear that it will be a major requirement. Right now the big island is allowing vaccinated visitors to avoid the COVID test (I believe) and I think that might be what Maui will do eventually. I would be surprised if Hawaii only allowed vaccinated visitors, seems highly unlikely.

      The rooms at the resort are definitely tired (at least in the Napua Tower.) The rest of the grounds and everything else is wonderful.

  5. Wow! So informative & detailed… thank you so much for thinking of us while on your Maui vacation.. Truly enjoyed all
    Your advice, almost felt like I was there too ..

  6. Going to Maui end of May as my daughter is graduating from college. Its her grad gift. I am in process of booking stuff now. Any recs on hotels in the Wailea area would be so helpful. Your blog post was great. Did you happen to go through the Fairmont or any others in Wailea besides the Four Seasons and Grand wailea that you would suggest

    1. Hi Stacey,

      How fun!! We also walked through the Marriott that is next door to the Grand Wailea. We didn’t walk through the Andaz, but we have had many friends stay there and love it. Same with the Fairmont, we didn’t go through but we’ve heard great things.

      I think it just depends on budget but I do love the Grand Wailea/Four Seasons location. The only negative with the marriott is that there isn’t a beach right in front of the hotel, you have to walk from the resort to the Grand Wailea beach area. Not sure if the Fairmont/Andaz have a huge beach area but if you’re more pool people anyways, that wouldn’t matter.

  7. We are going to Maui next Wednesday for a week. Leaving our 3 kids at home in Seattle!!! We plan to do hikes, rent a plane and sight see from the sky, trilogy excursion to snorkel, pool, beach, lots of shave ice, pictures galore, and road to Hana. We made restaurant reservations to a couple of places too, Dukes Cafe and the Fish Company.

  8. My daughter and I leave for Maui next Sunday, may 2nd. I can’t wait! And thank you for all the info. Super excited!

  9. We are here right now. We always stay in Kihei and love it! We rented a cabana at the Fairmont for the day-such a fun experience. We love Coconuts-best fish and pork tacos ever! Feels so good to be back!!

    1. That sounds wonderful – we wanted to try Coconuts but when we found out that there is a Coconuts right near us in the bay area we decided to skip and try it while we are home, haha. Love renting a cabana!!

  10. Emma!!!! THANK YOU SO MUCH!! This information is invaluable. We are leaving on June 3. Your information regarding the Covid test was awesome because my son lives in San Francisco so we were able to book him an appointment at the Oakland airport. Same place you went. The rental car is our big issue because they are so expensive. I emailed Kihei rental car company and I’m waiting to hear back from them. We used to go to Hawaii every year but we haven’t been back in quite a few years so we are so looking forward to it. Again, thank you so much.

  11. Thank you for all the great tips! We are booked to go at the end of August for our 30th anniversary, so I’m hoping by then the mask mandate for outdoors has been dropped. I will not wear a mask outside. I have until July 16th to decide, but that is my deal breaker. I hope it’s not an issue by then! The second test is also concerning, I wonder if some will have their vacation completely ruined by a false positive, after testing negative just a couple of days previous. That’s kind of risky, especially if your trip is only for 7 nights! Ugh!

  12. We are currently in Maui at the Kei Lani and your post was soooo helpful, especially about all the requirements. I referred to it many times as we were planning. Thank you Emma!