Trip Report | Maui, Hawaii

Happy Friday, friends, and cheers to the weekend! I know many of you sent your babes back to school this week… how did that go? Are you enjoying a peaceful house or mourning the end of Summer Break?

We have a few more days until reality kicks back in, and I’m hanging on to it by my fingertips! Our time together as a family of four is fewer and further between these days, which mad our Summer trip to Maui that much more special. It truly was one of the best family vacations we’ve ever had, and we loved every second of it!

So grab your coffee, because this Trip Report is photo overload!

Maui, Hawaii //

aboard the Lani’i Coastal Snorkel Sail on Sail Trilogy

Wailea Beach Path

Maui Tips //

  • Maui is the second largest Hawaiian island, and from what we saw, the most visited! But while all the hot-spots are packed with tourists, you can easily venture out and discover countless peaceful areas. It also 100% lives up to the hype and truly looks like a postcard at every turn.
  • There are five regions of Maui, and all worth exploring, but it does require quite a bit of time in the car (up to an hour-plus depending on where you’re starting and where you’re going). In a perfect world, if we were to go again, I’d spend a week in West Maui and a week in South Maui, with two nights in Hana in the middle! That way you could explore each of the areas more thoroughly with less drive time each day.
  • There are a million and one things to do in Maui, and there’s no way you’ll cover them all in a single trip… so just relax and enjoy what you can. You literally can’t go wrong! And even if you don’t eat at Mama’s Fish House (we didn’t, as they’re booked out six months in advance!), I promise you’ll still have the best time!
  • Maui is expensive. Like absurdly expensive. The only thing to do is make peace with it and understand it costs a lot to import to the middle of the Pacific Ocean! To save in some areas, we ate at mostly small local spots, cooked for ourselves, and packed a lot of picnics. Also, the beaches, parks, and hikes are all free and absolutely stunning, so don’t feel like you need to book all the fancy excursions and activities. Honestly, some of our most magical moments were those we stumbled upon ourselves.
  • You’ll need a rental car, but 4×4 isn’t necessary, and I wouldn’t go any larger than a small SUV (some of the roads are narrow).
  • Rent boogie boards and snorkel gear for the duration of your stay, and just keep them in the car… you never know when you’ll stumble on the perfect spot. We used Auntie Snorkel and had a great experience.
  • Take a cooler with you in the car every day, you never know when you’ll stumble on a Farmers Market or roadside stand that sells yummy snacks and lunches.

Ohai Trail

Road to Hana

snorkeling Lanai’i with Sail Trilogy / They have a photographer on-board for boat and water shots!

What We Did in Maui //

The first thing you want to do is pick up this book… it truly is an incredible guide to everything on the island! I read it on the flight over, making notes of all the things we wanted to do. Once we arrived, I used the island map provided by the rental company and plotted out each of the spots… from there, we just tackled a specific area each day.

So since we stayed in South Maui, that meant a lot of driving on days we explored West Maui… hence why splitting up your stay would be a fun idea for making the most of your time. But fortunately the views are jaw-dropping everywhere you go, so the driving didn’t bother us at all.

We loved every moment we were there, whether it was lounging on our resort’s beach, reading on our patio, hiking trails, or swimming waterfalls… but these are some of the highlights:

  • Snorkeling in Honoloa Bay // Go later in the day and you’ll have the place to yourself. It’s a large bay with calm waters and a beautiful reef!
  • Boat Day with Sail Trilogy // If you like getting out on the water, and seeing the island from a new perspective, Sail Trilogy has the nicest boats in the marina! The crews are beyond nice and fun, they serve amazing food and drinks, and snap cool underwater photos while you snorkel!
  • Road to Hana // Yes it’s a long day in the car, and the road is a little narrow and windy, but it was our favorite day of the trip! Several of our top spots were discovered along this drive, so I’ll share a full Road to Hana post soon!
  • Farmers Markets // We caught the Napili and Hana Farmers Markets, and both had the yummiest food and artisan crafts.
  • Nakalele Blowhole // A short, rocky hike with beautiful, cliffside views, and a powerful blowhole.
  • Hike, Hike, Hike! // We like to explore off the beaten path, and had many of the trails all to ourselves! And these shoes were absolutely clutch for everything we did!!
  • Maui Ocean Center // An impressive indoor/outdoor aquarium on the beach, with some really cool exhibits. It’s a great place to burn an hour or so if you’re waiting for your flight or checking in to your condo.
  • Lava Fields // If you’re in the West Maui area, it’s definitely worth driving to the end of the road to see these rolling fields of lava rock! At first glance, it looks like tilled soil, but it’s actually mounds of black lava rock. Follow the road to the end to see La Perouse Bay, a great spot for turtle and dolphin sightings.
  • Wailea Beach Path // Mr. Sugarplum and I loved grabbing an early morning coffee, and walking Wailea Beach and the Wailea Beach Path. The waters and winds are calm in the morning, and it’s fun to watch all the water sports and soak in the views before the resorts come to life.
  • Dragon’s Teeth Point // A breezy path leading out to a cool lava formation, with cliffside views, it’s great for turtle-spotting. DT Fleming Beach is a short path away, and a great spot to swim away from crowds!
  • Iao Valley Monument // An easy, paved trail leads you to the heart of this lush valley… you can also venture off the main trail to swim in the pools, or hike up to the peak.
  • Paia Town // A quirky town with fun shops and food. A great place to explore before a late-afternoon flight, or upon arrival when waiting to check in to your hotel/resort.
  • Kahekili Highway (West Maui’s North Shore Drive) // This one-lane drive from Kapalua to Wailuku is not for the faint of heart, but so fun with incredible views and tiny towns.

Lava Fields

Nakalele Blowhole
on Mr. SP: Long Sleeved Tee | Kore Shorts | Similar Waterproof Shoes
on me: Button Up Shirt | One Piece Swimsuit | Smocked Pull-On Shorts | Teva Sandals

Nakalele Blowhole

Ohai Loop Trail

Road to Hana

snorkeling Lanai’i with Sail Trilogy // They have a photographer on-board for boat and water shots!

Our Favorite Beaches in Maui //

  • Red Sand Beach // Definitely a highlight from our Road to Hana day! The narrow path hike to the beach hugs the edge of the mountain before descending down to a dramatic, hidden cove. The beach is made of soft, tiny red pebbles, with clear, cold water. It’s protected by a line of lava rocks, giving it a lagoon calmness, and fun cliffs for jumping.
  • Po’olenalena Beach // Next door to our resort, we spent more time on this wide, sandy beach than any other. It was calm in the morning, and great waves in the afternoon, with gorgeous sunsets. We set up camp for hours, and rarely saw more than a few people.
  • Slaughterhouse Beach // This beach looks straight out of a movie set! It’s a protected cove fully-surrounded by towering cliffs. The parking lot is small, so you won’t find a lot of people there.
  • Big Beach // A long, wide stretch of beach with a big surf break, there’s plenty of space to spread out. Hike over the cliff to Little Beach, but you might see some boobs!
  • DT Fleming Beach // Follow the trail from Dragon’s Teeth to this wide beach, then hike out via the Ritz Hotel for a little cafe and beautiful amenities.
  • Napili Beach // A gorgeous, white sand beach…but it was shoulder-to-shoulder with people, so we didn’t stay long.
  • Ka’anapali Beach // This beach is huge and wide, and packed with people! But you can walk to the end and jump off the 20-foot black rocks.

Makena Surf Resort / We saw more turtles snorkeling this bay than anywhere else!

Kahekili Highway (West Maui’s North Shore Drive)

Honolulunui Bay

Honolulunui Bay

Lahaina Harbor / Fun spot and town, but super crowded!


Red Sand Beach / My outfit HERE

Makaluapuna Point (Dragon’s Teeth) with DT Fleming Beach in the distance

Turtle-Spotting in Makaluapuna Point

The Ritz Kapalua Hotel / We accessed it from DT Fleming beach, and ate in the ocean-side cafe

Makena Surf Resort

Iao Valley Monument

Iao Valley Monument / Sunrise Crop Tank | Halo Performance Short | Teva Sandals | Aviators

Iao Valley Monument

H.A. Baldwin Beach Park to Paia Secret Beach


Where We Stayed in Maui //

Makena Surf Resort C-102 // We got so lucky finding this spot, and the beautiful rental and resort is a big part of what made our Maui experience so incredible! We didn’t book our July trip until May, so by that time, there were very few options on-island available for our dates! So while this unit is more than we’d budgeted, it was worth every penny!

It’s a 2-bedroom/2-bath unit with a fully renovated and well-stocked kitchen, comfy beds and couches, and incredible patio view. The resort itself is very quiet and just outside of the busy Wailea hotel zone, with multiple pools, tennis courts, and a short path to the beach. Some of our favorite snorkeling on-island was in the cove by the resort, and we spent more time on the Po’olenalena Beach beach next door than any other.

All of the units are privately owned, with many of them not in a rental pool, so we saw very few people, which was so peaceful to come home to. Parking is steps from the building, which was great for hauling beach gear everyday!

Ali’i Resorts handles the booking, and it was one of the best rental experiences we’ve ever had! They provide all the household necessities (detergent, paper towels, trash bags, etc.), and even refresh your towels every third day and provide full housekeeping every sixth day! Everything is done electronically (including check-in and out), and it was seamless.

Car Rental & Groceries //

We booked our rental car with Wiki Wiki Car Rental through Ali’i Resorts, and the car was waiting for us at the airport upon arrival, and we simply left it in the departure lot when we left! So easy!

Ali’i Resorts also connected us with a local grocery delivery service, and while it was pricey, it was worth it to arrive to a stocked fridge!

Makena Surf Resort / These are the beach-front buildings, which are considerably more expensive

View from Makena Surf C-102 / Short path to the beach

Makena Surf Resort is like a lush garden!

Where We Ate in Maui //

Okay, if you ask anyone where to eat in Maui… they’re all going to say ‘Mama’s Fish House,’ ‘Star Noodle,’ and ‘Monkeypod,’ (to name a few!). The problem is, every tourist on the island is trying to eat there, too… which means unless you snag a reservation months out, or you’re willing to wait for hours, you likely won’t get to see them for yourself!

We don’t really plan our meals or restaurants in advance, so we stuck to local spots and cooking at home. Our favorite thing was actually to pack the cooler with wraps or Farmer’s Market finds, and picnic on the beach, parks, or along the cliffs with a view of the sunset. Here are the places that stood out for us:

  • Paia Fish Market // Fresh fish platters, fish tacos, and steaming bowls of pasta, this popular spot has a fast line and is delicious!
  • a’a Roots Health Cafe // Our top two place on-island for a casual breakfast or lunch. The most beautiful açaí bowls, burritos, and incredible curries and baked goods.
  • Cafe O’Lei Kihei // A nice setting and favorite for locals, they have a big menu of Thai, sushi, and seafood.
  • AE’s Thai Kitchen // A permanent food truck in Hana, it’s heaping portions of delicious Thai food.
  • Paia Bay Coffee // Great stop before starting out for the Road to Hana. Darling setting with top-notch coffee drinks and snacks.
  • Peggy Sue’s Diner // Nothing overly special, but a kitchy spot that’s easy to get in to for old-fashioned burgers and shakes.
  • Hamsa Exotic Kitchen // Catch Eden at Hamsa at either the Napili or Wailea Farmer’s Market, for the best breads, olives, hummus, and more. She’ll suggest the best treats for an incredible picnic! We ate ours at nearby Napili Park.
  • Monkeypod // We happened to be out and hungry one day around 3, and managed to snag a table here. The mai tai was my favorite in Maui, but it’s packed and loud.
  • Pita Paradise // Our last night dinner, it was full of locals and was so yummy! The owner goes out every morning at 5am to fish for that day’s menu!
  • Ululani’s Shave Ice // Several locations around the island, we never drove by without stopping!
  • Coconuts // Yummy fish tacos and sandwiches… go for a late lunch to skip the line.
  • Island Gourmet Market // Near our condo, it has a great selection of pre-made wraps and fruit, perfect for stocking a picnic cooler.
  • Banana Bread & Fresh Pineapple // Pick these up anytime you see them… it may not be ‘the best on the island,’ but I guarantee it’s better than any you’ve had in the States!

Picnic dinner after snorkeling Honoloa Bay

What I Packed & Wore in Maui //

Swimsuits, shorts, and a couple of sundresses was all I needed… and these shoes, of course!

My Teva Sandals | Men’s Teva Sandals

Racerback Tank | Floral Skirt | Cut-Out Sandals (Also HERE) | Aviators

Paradise Smocked Waist Dress (code SUGARPLUM10 to save 10%) | Cut-Out Sandals (Also HERE) | Rattan Circle Bag | Woven Headband | Aviators

Button Romper | Oversized Straw HatAviators

Ribbed Swimsuit | Tie-Waist Skirt (code SUGARPLUM10 to save 10%) | Oversized Straw Hat | Straw Tote Bag | Removable TasselAviators

Halo Performance Crop | Halo Performance Short | Teva Sandals | Baseball Cap

Cabana Dress (code SUGARPLUM10 to save 10%) | Cut-Out Sandals (Also HERE) | Straw Hat (A01: Beige) | All-Weather Bangles | Gold Hoop Earrings | Aviators

Boca Chica Halter Bodysuit (code SUGARPLUM10 to save 10%) | Jean Shorts | Cut-Out Sandals (Also HERE) | Rattan Circle Bag | All-Weather Bangles

Tie One-Piece Swimsuit | Oversized Straw Hat | All-Weather Bangles | Gold Hoop Earrings | Aviators


Oh Maui, we loved you!! I hope this Trip Report is helpful for your future trips, or at least brightened your Friday! Feel free to leave any other questions in the comments, and I’d love to hear what we need to add to our list for next time! Happy weekend, lovebugs!



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Leave a Comment


  1. Lisa wrote:

    What an amazing trip you had! Great pictures!
    Thank you so much for posting this! I received the Maui book this week and have been planning our October trip. Yesterday I booked the same Trilogy tour-makes me feel good that you liked it, as there are so many to choose from.
    I’ll be planning our hiking days today and will be using your list. I’m going to order those shoes too!
    Mahalo 🏝

    Posted 8.12.22 Reply
    • Cassie wrote:

      Mahalo, Lisa! I’m so thrilled that my trip report was helpful for you!! Enjoy your trip in October! xo, C

      Posted 8.12.22 Reply
  2. Sandy wrote:

    SP’s- Thank you for this. Easily one of your most awesome/helpful posts.
    So, is a box of cereal up to $10 now?? Heard on the radio, absolutely everything on the island is shipped in, everything.
    Glad the tourism is back for the island and it’s people. You cannot go wrong w/a trip to Maui.
    Agree on the “need two weeks”, it’s true! One time, the airlines could not get us back home until 5 days later, and we said…..Okay!!!! So hard to leave that magical place. Thanks again!! xo.

    Posted 8.12.22 Reply
    • Cassie wrote:

      5 extra days in Maui… sign me up, ha! Xoxo, C

      Posted 8.12.22 Reply
  3. Sandy wrote:

    Ps-Sorry. But every moment is fun on Maui. Even watching how bad the golfers were @ Kapalua, ha,ha! That’s ok, they were at there dream course! : )

    Posted 8.12.22 Reply
  4. Annie wrote:

    Maui is my happy place, nothing beats it!

    Posted 8.12.22 Reply
    • Cassie wrote:

      It just might been mine now, too!! xo, C

      Posted 8.12.22 Reply
  5. Cheri wrote:

    We were just on Maui at the end of July too! Loved it! We had gotten married there 20 years ago and went back with our daughter for an early anniversary trip (Sept). We stayed at the Sheraton Maui on Ka’anapali beach where the Black Rock is and absolutely loved it! We got to do a luau at the exact location we got married at 20 years ago!

    I agree with all you said, it is truly a memorable experience wherever you go on Maui, and just driving and experiencing the views everywhere is what makes the trip. Every local we encountered was so friendly and just really brought that spirit of Aloha that you hear about. Maui truly lives up to the hype and will always be a special place for me.

    Posted 8.12.22 Reply
    • Cassie wrote:

      This is all so so true, Cheri! Maui was magical, and we loved every second of it. Happy 20th anniversary! xo, C

      Posted 8.12.22 Reply
  6. Lisa wrote:

    Love your trip report – it brings back so many great memories! We haven’t been to Maui in a few years and I miss it. Add Mala Ocean Tavern to your restaurant list for the next time you go – best tuna and salmon burgers ever. Those catamaran pics make me want a morning mai tai haha.

    Posted 8.12.22 Reply
    • Cassie wrote:

      Oh yummy, thank you for that rec!! xo, C

      Posted 8.12.22 Reply
  7. Rhonda wrote:

    Wow! This was like reliving our trip in May…I second your sentiments exactly. What a memorable trip. I discovered ‘Maui Revealed’ on the first day there but it was the best discovery because I referred to it daily!! Highly recommend it to anyone taking the trip. Also, my tip for Mama’s Fish House…just go there early in your trip and see if they have a reservation for later in the week. That’s what we did and it was probably our favorite meal of the trip (besides the mai tais at Monkeypod!). 🙂 Your pictures are fantastic!

    Posted 8.12.22 Reply
    • Cassie wrote:

      Ohh thank you, very good tip about Mama’s Fish House!! xo, C

      Posted 8.12.22 Reply
  8. andrea in mn wrote:

    My family went to Maui when I was a senior in high school, with my cousins. We had a FANTASTIC time, and you mentioning these spots was a little trip down memory lane. Love your reference to Big Beach, as I recall that too. At 18, I didn’t venture over, but others in our group did! Ha Ha!

    Take care and enjoy your last days of break. Here in MN, we don’t go back until September. We have to have our State Fair first!!!

    Posted 8.12.22 Reply
    • Cassie wrote:

      HOW FUN! And woo hoo, the State Fair, enjoy! xo, C

      Posted 8.12.22 Reply
  9. MelanieL wrote:

    What a fun trip report! I love your casual approach to vacations, it’s so inspiring! I can’t wait to take my family to Hawaii some day! 🙂

    Posted 8.12.22 Reply
    • Cassie wrote:

      Oh gosh well thank you!!! Travel is my love language! xo, C

      Posted 8.12.22 Reply
  10. Suzy Fine wrote:

    We were there the same time as you – if your readers are looking for other restaurants I highly suggest Ka’ana Kitchen at the Andaz, Spago, and Merriman’s (MonkeyPods sister, more formal restaurant). We absolutely love Monkeypod for the reasons you didn’t – we love the atmosphere it is super loud – but that is what makes it so much fun! And the Mai Tais are top notch!! Can’t wait to get back in a few months!!

    Posted 8.12.22 Reply
    • Cassie wrote:

      Ahh thank you for these recs!!! Hopefully the Sugarplums can make it back to Maui one day and try them out! xo, C

      Posted 8.12.22 Reply
  11. Tania wrote:

    We are going to Maui in 2 weeks and this post is very helpful for planning and packing purposes. Thank you! Such great timing.

    Posted 8.12.22 Reply
    • Cassie wrote:

      That’s great, Tania!!! I’m so glad my post was helpful and hope y’all have an absolutely incredible trip! xo, C

      Posted 8.14.22 Reply
  12. Kim wrote:

    I love Maui! We used to take my son every thanksgiving and stay at the Four Seasons in Wailea. It’s a beautiful resort with lots of amenities. Most of which are included in the room rate. When we didn’t go with my son, we also went in November. It’s a nice time to go because the weather is still perfect but you don’t get the summer crowds to compete with. You can get into Mama’s Fish House! The last time my husband and I went was in 2018. We decided to book the same condo complex where we honeymooned. It’s called the Sugar Beach Resort in Kihei. It is such a lovely place, right on the beach & pretty centrally located. We spent time trying new things in central Maui. We did the Ocean Vodka tour, Maui Brewing Company tour (also has a great restaurant) and hiked the Waihee Ridge trail a couple of times which is amazing. We really liked the condo and would probably book it again. Different experience than a resort but had it’s pluses.

    Posted 8.12.22 Reply
    • Cassie wrote:

      Wow Kim, that sounds fantastic!!! I hope you have an upcoming trip planned soon! xo, C

      Posted 8.14.22 Reply
  13. Raelynn Miller wrote:

    Having lived on Maui for 10 years I can tell you; you missed one of the most spectacular parts of Maui… sunrise at the top of Haleakala..

    Posted 8.13.22 Reply
    • Cassie wrote:

      Well darnit, Raelynn!!! All the more reason for us to go back in the future, we loved it there! xo, C

      Posted 8.14.22 Reply
  14. Kevin wrote:

    We just went to Oahu this summer and the prices did not seem bad at all. Of course we live in California, but it was a surprise to see that even gasoline was cheaper. And it seemed like eating out was more affordable too. I wonder if the lower minimum wage came into play?

    Posted 8.13.22 Reply
    • Cassie wrote:

      Oh wow, that is so interesting!!!!

      Posted 8.14.22 Reply
  15. Kim wrote:

    What a great family trip! Thank you for the detailed recommendations!

    Posted 8.13.22 Reply
    • Cassie wrote:

      Thank you so much, Kim!! We had such a blast as a family! xo, C

      Posted 8.14.22 Reply
  16. Melissa wrote:

    My husband is looking for water shoes like Mr. SP is wearing, but the link says “unable to locate.” Could you provide any other details if you have a chance?

    Posted 8.13.22 Reply
    • Cassie wrote:

      Oh shoot, Melissa! Let me fix that wonky link in the post! And I’m sorry – I don’t have any more details on Mr. SP’s shoes other than they are Merrell brand and he loves them! xo, C

      Link to similar:

      Posted 8.14.22 Reply
  17. Denise wrote:

    Maui is truly my happy place. We are headed back in September and I’m adding some of your tips to my list. Did I see on IG that you had family photos made? Would you mind sharing who you used if you were happy with them? Aloha! Denise

    Posted 8.15.22 Reply
    • Cassie wrote:

      hi Denise! We found her on IG as ‘indigo child’….she did a wonderful job!

      Posted 10.13.22 Reply
  18. Jennifer wrote:

    I’m heading to Maui in January, and cannot wait! I’ve been to Oahu and the big island already, so it will be fun to compare. Purchasing the book in a moment. Thank you for the recap!!

    Posted 8.15.22 Reply
    • Cassie wrote:

      You’re very welcome, so glad the post was helpful for you!!! xo, C

      Posted 8.16.22 Reply
  19. Denise wrote:

    We are going to Maui in September. Would you mind sharing the photographer you used for your family photos. Loved your recap. We’ve been several times and you did things we’ve never done. Look forward to seeing new things.

    Posted 8.19.22 Reply
    • Cassie wrote:

      Hi Denise! We used a sweet girl I found on IG…but it’s been almost a month and we don’t yet have our photos back, so I’m not sure I can recommend her just yet! 😉 Fingers crossed they arrive soon!

      Posted 8.23.22 Reply
  20. Heather wrote:

    This is so helpful! We have our trip planned for right after Christmas into January (since our kids in TX go back to school so late!). So funny as I made a reservation at Mama’s Fish house two months ago and when I looked again, it is totally booked for the whole week! It looks like no matter what you do or where you go in Maui, you can’t go wrong! Thanks for all the tips – we will use them!

    Posted 8.23.22 Reply
    • Cassie wrote:

      That is certainly true, Heather!!! You cannot go wrong when you’re in Maui!! Have an amazing trip! xo, C

      Posted 8.23.22 Reply
  21. Betty wrote:

    Hi Cassie. Love your travel reports. It’s given me so many ideas for future vacays. Our family is headed to Mauro in I toner and I am looking for a photographer for family pics. Would you share the photographer you used? Thanks!

    Posted 9.23.22 Reply
    • Cassie wrote:

      Hi Betty! We used a girl I found on IG, Child Indigo. Asia did a beautiful job and was so nice! have a great trip!

      Posted 9.23.22 Reply
  22. Angie V wrote:

    Thank you so much for all of this! My husband and I are planning our first trip for the beginning of April. Red Sand Beach question – looks amazing, but I have read several articles/reports about how dangerous it is and people sharing their injuries from falling down the side. Thoughts on your comfort level/worth it as a stop on the Road to Hana? Thanks much!

    Posted 11.2.22 Reply
    • Cassie wrote:

      Hi Angie! I’m so excited for your trip, and am thrilled my post was helpful in planning. The walk from the parking lot to Red Sand Beach is maybe 10 mins, and completely walkable in regular shoes. We saw people of all ages walking both ways. The trail is a little gravely in spots, and you do have to pause and let people pass, but nothing that concerned me as long as you’re being aware. xo. C

      Posted 11.8.22 Reply
      • Angie V wrote:

        Thank you so much! Now to decide if I can deal with my motion sickness to handle the drive 🙂

        Posted 12.8.22 Reply
        • Cassie wrote:

          Ugh! I’m sure you’ve tried all the remedies under the sun, but the prescription patch is supposed to be magic! xo, C

          Posted 12.8.22 Reply