Home » Travel » five days in maui || travel guide

five days in maui || travel guide

Ajeet and I recently went to Hawaii with my parents to celebrate my mom’s birthday and it was one of the best trips we’ve taken so far! I was lucky that my sister had already been to Maui before so she helped me find cute restaurants and good family-friendly activities. I wanted to share everything we got to do + some of the recommendations that y’all sent over that we’re going to have to tackle next time! 🙂

PS— make sure and decide whether you think it’s worth it for you to rent a car. We decided to rent a car in advance because we knew we’d be driving back and forth a lot and wanted that convenience of having our own car but if you plan to stay in the resort or near it you won’t need a car and can just uber places.



I spent a lot of time researching this and wanted to break the area down for you a little bit. We ended up staying at Grand Wailea which is on the south side of Maui (Kihei & Wailea are both on the south side). We were about 20-30 minutes from the airport and closer to Hana if you wanted to do that during your trip. I will say that the resort did feel a little more for kids (especially with the outdoor pool area and such) but we honestly didn’t mind it one bit! The property itself was beautiful and a bit cheaper than Four Seasons which was our first option, hehe. Overall, I do think that both Kihei and Wailea are great for families because you’re surrounded by beaches and everything is very much kid friendly. There’s tons to do and you can’t go wrong in either location here.

maui travel guide

If you’re looking for more of a secluded and more romantic feel, head up west to Lahaina or Ka’anapali for sure. It’s a little less crowded there but you’re still surrounded by great food options and tons of things to do. The hotel I initially wanted to book was Hyatt Regency Maui Resort and Spa (west side) but it sold out before I grabbed a room. I’d look into that if it’s available because the area is nice and you’re close to tons of cute boutique shopping spots.


  • Whale watching is a must!!
    • We actually got lucky and got to see whales during our sunset sail ride and knocked out both the ride + whale watching in one go. You have to make sure you’re in the right season though. We were right at the tail end of whale watching season when we went (March 22) but still got to see a few luckily! Peak season is mid January to end of February.

  • Sunset Sailing
    • Speaking of sailing, I highly recommend doing this one evening! We booked the Alii Nui Sailing Charters that left out of Ma’alaea Harbor and I was so impressed by the food options + customer service the entire trip. It was roughly 2.5 hours long and you get dinner + drinks throughout the evening. This is when we saw the whales!!

  • Watch the sunrise at Haleakala
    • Oh my gosh y’all! I’m so bummed we didn’t get to do this!! You HAVE to make reservations for sunrise (you can go at sunset no problem) but I was told it’s the best during sunrise. It’s about 1.5-2 hours away from Wailea but we were told it’s 100% worth the drive (you’re going about 10,000 ft up). You’ll have to leave the hotel in the wee hours of the night to get there before sunrise but we were told you get to literally drive through the clouds and once you get up there, you’re aligned with the clouds + the sun and it’s an incredible experience.
    • If you do decide to go, be sure to dress warm!! It gets super cold up there.
    • Don’t forget to make reservations—you pay per car.
  • Road to Hana
    • This is another thing we didn’t do but it’s honestly because Ajeet and I just went on our big California road trip up the coast and didn’t want to rush into another one. You’ll definitely need an entire day set for this drive. There are winding roads but tons of stopping points along the way that are supposedly breathtaking!
  • Lu’au
    • We booked the Lu’au at Grand Wailea and it was wonderful! You have the option to choose from premium seating or regular/standard and we just got regular. The only real difference was you get better seats (the first two rows) and drinks 30 minutes prior to start time. We sat in the third row and saw everything because the performers were elevated on stage so I personally don’t think paying for premium is worth it. I actually was a few minutes late (naturally) and skipped the pig roasting portion which I’m glad because my heart wouldn’t be able to take that! Other than that, the experience was amazing. Definitely something that you should do once.
    • If you’re not staying in the Wailea area then check out Old Lahaina Luau and it’s the most authentic.

  • Ali’I Kula Lavender Farm
    • My mom loves flowers and botanical gardens so we actually took her here on her birthday! The views from here are incredible and definitely worth the drive up. It’s actually on the way to Haleakala if you wanted to plan those two on the same day.

  • Drive to Banyan Tree Lahaina.
    • You can spend half a day here just exploring Lahaina and shopping around. A great place to get souvenirs and such too!
  • Farmers market (Swap Meet)
    • There are a few farmers markets in Maui but the one we went to is called “Swap Meet” or also known as Maui Exposition. It’s the biggest one in Maui and is only open on Saturday’s from 7am-1pm. It’s 50 cents per person to get in and they have pretty unique stuff!


  • Kihei Caffe: Holy moly SO GOOD. This place serves breakfast all day and it’s in a very cute shopping area so you can stroll through that maze once you’re finished eating! Very affordable compared to other places.

Maui Travel guide

  • Mama’s Fish House: We got lucky and I booked the reservation the night before—I’m assuming someone cancelled! This place gets booked fast so if you know you’re visiting Maui, plan to call and reserve your table in advance. This was definitely one of the top 10 restaurants I’ve ever been to. SO GOOD! It’s also closer to the airport fyi (30-40 min from Grand Wailea).

  • Ululani’s Shaved Ice: I wish we go this every single day!! There was a location in Lahaina and Kihei—both are yum!
  • Monkeypod: The great thing about this restaurant is that there is one on each side of the island so you should be able to easily get to one if you’re craving a good lunch spot.

  • Lappert’s: You know me, I always have to find a delicious dessert spot no matter where I go!! There’s usually about a 15-30 minute wait at this ice cream shop just fyi!! It’s worth it 100%.

  • Island Gourmet Market (grocery store but has good food). This is right by Grand Wailea so we went there a couple of times!


Other recommendations that you all sent me:



  • Rent a car and do the Road to Hana (very popular)
  • Iao State Park and Maui Twin Falls (twin falls should be part of road to Hana)
  • Helicopter Tour through the mountains to see the cliffs and waterfalls
  • Horseback Trail Ride
  • Swim with turtles at Napili Beach
  • Snorkeling to Molokini
  • Zip lining through Ka’anapali Rainforest

I hope this guide was helpful!! I wanted to share everything we did + some of the recs you guys sent over to me as well. Let me know if you have any questions at all. I respond to comments on Instagram the fastest so if you comment there with any questions I’ll get back to you asap! Otherwise, comment down below or DM me if that’s easier. Chat soon! Xo


1 Comment

  1. Alice Rivera
    April 4, 2019 / 4:47 PM

    This was Amazing!!

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