Every year we like to do a family summer vacation and finally after years of talking about it, we booked Hawaii! Oh man was it a dream! It was truly one of our favorite trips so far… so much so that we are potentially considering heading back next year to visit some other islands. (;
After so many dms and questions about our trip, I knew an itinerary blog post with all the deets was a must. So in today’s blog post, I’m going to give you the nitty gritty, the details we wish knew before going, and everything that is an absolute must to do while you’re on this dream vacay.
For reference, we visited Maui and Oahu so I’m not sure how things are on the other islands, but I’ve got you covered for these two.
Let’s start off with the things we wish we knew while planning this trip — It’s important to note that some of these things are due to the covid restrictions, but either way it’s important to know.
First and foremost and the most important piece of advice I can give…. You are NOT going to conquer all of Hawaii, so take a deep breath and don’t stress it. Just enjoy! This was something I wish I knew before hand. It would have saved a lot of stress on our end. We are 100% that family that loves to take advantage of ever moment on vacation. We love to explore, immerse ourselves in the local towns, do fun activities and seek adventure. So if you’re like us and you want to do it all, then you need to know this lol!
Before we went, we got a few itineraries from some friends for reference and started building ours. When I say we underestimated how much we could actually do in a day, we underestimated big time. We thought we’d be able to get a lot more done than we actually did. Here’s the main reasons why:
- Everything is pretty far from each other. Even though they’re small islands, it takes about 40 minutes to get to each town or location. That time starts to add up quickly, so it’s definitely important to keep that in mind while planning.
- Parking is tough- When I say parking is tough, I really mean it. For one of the main beaches we went to, Lanikai, we had to park 2 miles away and walk to the beach. It’s also packed so get ready to wait for that golden parking spot. But… I promise the wait is always SO worth it!
- Everything closes early and opens at the crack of dawn: I have no clue if this is because of covid or not, but everything in Maui was closed by 8pm… 9pm if we were lucky. In Oahu things stayed open till about 9:30pm. This includes restaurants, which was the biggest shock for us! Also, there’s no such thing as sleeping-in in Hawaii. Everyone is up super early, so if you don’t want to have fomo set your alarms for 6am lol.
- Talking about restaurants… Reservations are nearly impossible to get: Things are booked and busy! Definitely, bittersweet. Sweet, because I LOVE to see Hawaii thriving and back on it’s feet with the year we just had. Bitter because your girl wanted to be booked, busy, and in a food coma at these fabulous restaurants. This was probably the most stressful part, just because we felt like we were in limbo every night. But, we found a trick… put your name down (the wait was usually around an hour and 30) and run back to your hotel to get ready. By the time we were done freshening up, the restaurant was ready to seat us.
Ok, now lets get into the fun part! Below I’ve detailed what we did in both Maui and Oahu. I’m going to star the things that are an absolute MUST. I also answered some of the questions you guys submitted on instagram in a Q&A section below if you want to check that out. Most of the questions submitted were answered within the post, but there were some that definitely needed to be added.
Maui:
- We spent 5 days in Maui and definitely left wanting more!
- We stayed at the Andaz Hotel and we absolutely loved it. This hotel was beautiful and incredibly chic. The whole vibe was exactly what I imagined Hawaii to be like. It was clean, gorgeous, service was incredible, the staff was very kind and the views left me in awe.
What we did:
- Halaekala Sunrise: This famous sunrise was incredible. The view was spectacular but it’s def something you gotta really want to see to make it happen. First you need a reservation in advance. Here’s the link: https://www.recreation.gov/ticket/facility/253731. Tickets sell out in a matter of minutes. Second, the wake up call is 2am in order to arrive to the top of the mountain in time to see the sun in action. It’s also FREEZZZZING! Packing one jacket will not do it. Trust me… we learned the hard way. LAYER, LAYER, LAYER and bring your hotel comforter too! It’s super windy which makes it even worse. As spectacular as the view was, this was definitely a one and done forever type of activity for us. Here’s why, everyone recommends that you do it the first day you arrive because it will help you adjust to the time change, but if anything I thought it made it worse. Ideally I want to be rested and feeling refreshed on my first day so that I can enjoy, but this really slowed us down. We were beyond exhausted. So my recommendation is to actually do it on your last day if Maui is the last island you visit on your trip. This way you go see the sunrise, grab coffee/breakfast at Grandma’s Coffee House (which I’ll talk about below) and then you head to the airport. Catch some sleep on your flight and you’re good to go!
- Black Rock: Loved this beach. It was the first beach we visited besides the one at our hotel. It has something for everyone: cliff jumping for the adventurous type, golden sand and clear water for the ones that just want to sun bathe/swim and turtle watching for those that just want to walk along the beach.
- ⭐️The Road to Hana: We loved this! The scenic drive was a great way to see the lush island of Maui. It’s 3 hours, but only because you’re stopping along the way. You’ll definitely need to get an early start in the am when you do this because it will take up a full day. Some of the stops we did were: Ho’okipa lookout, Ke’anae Peninsula (make sure to stop at Aunty Sandy’s for the BEST banana bread ever!), Waianapanapa State Park—Black Sand Beach (you’ll also need a reservation for this), and Wailua Falls. We used an app called Gypsy Guide that gives you a “personal” tour guide to listen to while you drive through – 10/10 recommend the app, it was great!
- ⭐️Paia Beach: The cutest, smallest, and most colorful surf town. You’ll actually drive past it if you decide to do the Road to Hana. The day we did this, we actually went surfing in the morning and then headed into town. It was a great transition into the afternoon. It’s got a cool atmosphere, fun souvenir shopping, and some yummy lunch spots. Also really recommend Ululani’s for some delish shaved ice.
P.S. This is a great instagram-able town.
- ⭐️Snorkeling: Our absolute favorite activity in Maui! This day out at sea was everyone’s highlight! They took us out to the Lanai reefs and it was beyond gorgeous. The color of the water is unbelievable. After, they took us to another spot where we got to snorkel with sea turtles… being surrounded by them was such a pinch me moment! Loved every moment of it. We booked with the company Sail Maui and I could not recommend them enough! The crew was so kind and friendly. If you decide to do this (which I 1000% recommend you do) you really won’t have to snorkel anywhere else. Nowhere else compared to this.
- ⭐️Lahaina: Our favorite town in Maui! If you decide to do the snorkeling catamaran, you’ll actually leave out of this town. So after we came back from our boat day, we rented a few surfboards, spent a couple hours catching waves, came back in to walk the town, and caught a beautiful sunset. – This was such a perfect day in Maui!
- ⭐️Surfing: Despite what you read online or even in books, the surfing in Maui was actually better than in Oahu in our options. It’s much less crowded and the waves are a pretty decent size. Different beaches are for different levels so just make sure to do a little research or just ask a local when you’re there for the best spot according to your preferences. We personally loved a spot right off of Lahaina Harbor. Just something to keep in mind, in a lot of these surf spot in Maui do not have boards to rent on the fly. Most of the time you need to find a surf shop, rent the board, and then drive it to the location.
Places to Eat and Spots to Snack at:
- MonkeyPod
- Cool Cat Cafe
- Paia Fish Market
- Grandma’s Coffee House
- Mama’s Fish House: We wanted to go here SO bad but couldn’t get reservations. It’s supposed to be the best spot on the island, so definitely try to get in!
- Café Des Amis
- Flatbread Company
- Ululani’s for Shaved ice
Oahu :
- We spent 5 days in Oahu. I think it was a pretty good amount of time. I would have loved one more day though – I think 6 would have been perfect!
- We stayed at the Hyatt Regency which was perfectly located and honestly great! We had a gorgeous view of the incredible tie-dye waters of Waikiki full of surfers and the room was extremely spacious. But we all agreed that when we visit again we’d love to stay at either the Moana Surfrider or the Sheraton Waikiki. We really fell in love with the ambiance at these two spots.
What we did:
- ⭐️Lanikai Beach: Located in the Windward side of Oahu, this beach took our breath away. It felt like we were in Fiji. The water was unreal- The clearest and brightest I’ve ever seen in my life. As I mentioned before, parking for this was a bit of a hassle and is two miles away from the actual beach-but it’s SO worth it! Please, don’t let the walk stop you from going, because this is truly one of the most beautiful beaches on the island!
- ⭐️Haleiwa: Located about 50 mins from Waikiki, this little town in the North Shore is the cutest and a must visit. Weirdly enough it seems to have an adorable western influence. Definitely recommend stopping here in the morning for some shopping (check out Guava for some cute finds) and breakfast at the yummiest spot ever, Haleiwa Bowls. If I could I would live off of their Paniolo bowl. It was delish and one of my favorite snack spots in all of Hawaii lol!
- Sunset Beach: It’s actually one of the most famous beaches in the North Shore. This is where they hold surf competitions in the winter since the Banzai Pipeline surf break is along this stretch of beach. But in the summer, it’s a gorgeous spot to layout and enjoy the water! It was pretty cold though, but if you go on a sunny day, the water sparkles like you’re in a dreaming!
- Horse Back Riding: if you’re looking for a laid back activity to try during sunset, horse back riding was pretty good! It’s a relaxing ride, so if you want something that isn’t so go-go-go this would be it.
- ⭐️Makapu’u Tidepools: This was a spot that I was dying to visit, I had seen the most gorgeous photos of these tide-pools on instagram and really wanted to see it for myself… it did not disappoint! It was truly breathtaking! I will say though, I thought this would take only 10 minutes of our day… and it ended up taking 3 and a half hours lol! Here’s what no-one tells you, in order to get to these pools, you first need to do a 25 minute hike up a mountain and then a VERY steep, rocky, and dangerous hike down (don’t have the time it took us to do this because it felt like forever haha). Was it worth it, YES! But just be prepared for it too take time and pack the proper shoes. It was a mission and a half to do this in flip-flops lol! Definitely recommend sneakers – you are literally rock climbing.
- Pearl Harbor: A staple! If you’re in Hawaii you’ve gotta do it, even if you’re not a history buff. You do need tickets to get on the ships, but like most tickets in Hawaii they sell out in minutes. Unfortunately, we weren’t able to snag them, but went anyways. If you decide to forgo the ships this will only take you about an 1 to 2 hours to do. My dad was really stoked about visiting this memorial and we all left happy that we did it.
- ⭐️Surfing: As I mentioned before, Maui’s surfing was better because it’s much less packed, but that doesn’t mean I didn’t loveeee surfing in Waikiki! Surfing in general is a blast and even though I’m nowhere near being a pro lol, I could do it all day long! Renting boards is pretty easy here. There’s actually a little surf shop right by the Hyatt Regency called Moku that rents boards for $5! It’s the best deal you’re going to find!!
- ⭐️Waimea Bay: So this bay has a story. We actually passed by this bay our first day visiting the North Shore and decided to keep on driving to Sunset beach instead because it was packed and there was no parking. After talking to a local, they mentioned this bay and insisted it was a must… “And if you’re lucky, you’ll get to swim with dolphins” she said . That’s all we needed to hear to head back to Waimea on our last day! And oh my gosh did it not disappoint. As we start walking to the beach I see the dolphins jumping and spinning out of the water (no, I’m not exaggerating! It was as if they were putting on a show for the people on shore). We grabbed our snorkels, franticly jumped into the water, and swam WAYYYY out… nothing! The dolphins were nowhere to be found. We waited it out for a few minutes and right as I was about to start swimming back, my brother taps me on the shoulder and screams “OMG OMG LOOK DOWN!!!” I kid you not, there were 40 to 50 dolphins swimming under us. To say I freaked out is an understatement. We were both screaming with excitement. It was such an unbelievable and overwhelming experience! I felt like I was going to explode with excitement, disbelief, joy, adrenaline and a little tiny bit of fear (they are wild animals after all). Not even 10 minutes later another pod comes swimming up to us! With the dolphins just 4 feet away, I was able to really enjoy the moment this time and just bask in the trill. It was the most unforgettable experience and definitely a highlight of my life lol. Like I said on IG, I know that sounds cheesy or whatever, but seriously I never thought I’d have the chance to do something like that… swim with the dolphins..in the wild, like how crazy is that! But it happened and it was incredible. So yes this is a MUST MUST MUST do if you visit Oahu! Some things to note: Like I mentioned parking is tough here, but there’s a lot across the street that you can park at that’s $20. Also get there early. We hear the dolphins are there in the mornings. We arrived at 11:30am-12pm- somewhere around that time.
Places to Eat and Spots to Snack at:
- Honolulu Coffee: Get the Hawaiian Latte and an almond Croissant. You’ll thank me later, I promise! This is the coffee shop that made me say “Okay, I can officially move to Hawaii, I’ve found the perfect coffee.” – Priorities am I right!
- Haleiwa Bowls: The best bowls in all of Hawaii!
- Moani – Absolutely delish! It’s a new spot and we loved it.
- Ruth Chris
- Moana Surfrider Poolside Cafe
Q & A
Surfing was a blast! Just like riding a bike, once you get it down, you’ll always have it. That’s not to say you won’t be wobbly lol! But slowly and surly you start gaining more confidence and it becomes a smooth ride. It’s one of my favorite activities to do! 100% recommend you try. As for food, it was delish. My favorite spots were: MonkeyPod: Got this amazing macadamia nut crusted fresh fish in a maui pineapple relish, organic brown rice, lemon beurre blanc. – It melted in my mouth and I’m literally drooling thinking about it. Cool Cat Cafe: split half and half with my mom. We ordered the fresh fish tacos and this incredible Burger called the Don Ho that comes with with bacon, Jack cheese, pineapple and their famous sweet Hawaiian sauce. Haleiwa Bowls was also such a food highlight for me. We actually went back twice lol. And of course Honolulu Coffee!
A Car is 1000% needed! I don’t think there is any other way to get around the island honestly. Prices are through the roof, but here’s something that helped us get somewhat of a deal… sign up for any and everything you can when it comes to subscription lists and membership lists. A lot of times they’ll give you better deals just for signing up with your email.
Everything starred is a must! For a Honeymoon specifically, I think the snorkeling catamaran is great! Such a fun activity to experience together. Lanikai is also a great beach. Would be so romantic to pack a picnic or grab pizza on the way to spend the day there and have a beach day/ lunch. Of course catch a sunset- I thought the sunsets in Waikiki beach were out of this world!
The hotels were expensive, but it’s also because everything is booked and full because of covid. So the moment something becomes available, people jump on it no matter what the price- there really isn’t another option. Are they worth it? I mean, yes because Hawaii is worth it! Hehe hope that answers your question.
I’m the queen of over packing! We packed as if we were walking in a fashion show lol…I didn’t use half of it haha! But that always happens with us… especially me lol! Definitely pack some cute dinner outfits but no need to over due it like I did. For the most part what you really need is, bathing suits, coverups, denim shorts, airy tops that you can throw over a bikini top, causal fresh summer dresses, and that’s pretty much it. When it comes to shoes, one pair of heels, one pair of sneakers you can hike in and flip-flops!
Ok, now I really want to go!