My 2-week anniversary trip in Hawaii

After more than a year of working from home, my husband and I took a 2-week trip to Hawaii to celebrate our 2nd anniversary. The trip was like a dream, and we both fell in love with nature and the vibe of Hawaii. In this post, I will share our itinerary and recommendations for traveling in Hawaii. 

Pre-travel planning


Traveling in the COVID era can be stressful. And Hawaii has their ever-changing travel restrictions. We had to get a negative COVID test result within 72 hours of our flight from the mainland to Hawaii. The result was validated when we checked in at JFK, and we got a purple Tyvek wristband before we got on the plane. 

We also had to get another negative COVID test traveling from Oahu to Maui, and paid it out of pocket. It was certainly a hassle, but we were grateful we were able to travel safely. 

Make sure you check the latest travel restrictions on

Credit card

We applied for the Chase Sapphire Reserve credit card before COVID and thought we would take advantage of its travel benefits. We were not able to actually use this card until now. CSR is definitely one of the best credit cards for traveling. 

Hotel or Airbnb

We chose to stay in a hotel in Waikiki when we first got to Oahu because we wanted to have a standardized room and service for better rest after a long flight. We then moved to an Airbnb boat and loved it! It was such a magical experience to stay on a docked boat.

In Maui, accommodations are substantially more expensive than Oahu. Most hotels and resorts are in Kaanapali and Kihei, the so-called sunny side. We chose to stay in Haiku, the so-called rainy side in Maui. As it turns out, it only rained on our first night. Haiku is a quiet small town, and is surrounded by trees, birds, and nature. We loved our Airbnb cottage, and it was nice waking up to chirping birds and the rustling of leaves. It was also a short walk to the ocean cliff from our backyard. 

Car rental

In Oahu, it is easy to get around with Uber since it is more populated and developed. In Maui, car rental is almost a must unless you only join tours that pick you up from your hotels. 

Book early. We booked our cars 5 weeks in advance and was able to get a convertible in Oahu. In Maui, we couldn’t get a convertible and opted for an SUV. Convertibles are such a popular vacation car in Hawaii and you see them everywhere. We enjoyed the fresh air, breeze, and occasional drizzle driving top down in Oahu. For Maui, the roads are narrower and more curvy, and during night time it is difficult to drive due to the complete darkness that envelopes the island. Good thing for star gazing but hi-beam lights for driving is a must almost all the time.

Offline map

In Hawaii, phone signals are spotty, particularly in Maui. Make sure you download offline Google Maps for GPS navigation. 

Playlist and music

We found this Hawaii playlist and enjoyed it a lot while driving on Maui’s curvy roads. Make sure you download music offline on Spotify because you may not have good phone signals. 

Day 1 Arrive in Oahu

The water is so BLUE!

We passed the travel checkpoint with our purple wristbands, and picked up the rental car. The process was much more smooth and faster than I originally thought. We then drove directly to our hotel in Waikiki to check in. 


Parking is notoriously difficult in Oahu, especially in famous beaches, parks, supermarkets, restaurants, etc. 

Most hotels in Waikiki do not offer free parking. While you can certainly risk free street parking, we decided to go with the safe option of paying for the parking lot in the hotel. 

We were able to find street parking for most places we went, probably because there were fewer people during COVID. I always search for the keyword “parking” on Google and Yelp reviews to find out tips on parking. It is a good idea to call restaurants and ask them where you can park. We found that Roy’s Waikiki has complimentary parking in nearby Embassy Suites. 

First dinner

We waited in line for Marugame Udon for about 30 minutes, and it was worth it! The noodles are freshly made and the service is fast. Don’t forget to order tempuras and try a musubi. Udon is a cheap food choice compared to other pricey restaurants in Waikiki. To be honest, many Waikiki restaurants are overpriced, and the quality is not that good. You have a better chance of getting good quality food driving out from Waikiki. 

There is a matcha ice cream store behind Marukame udon. Don’t miss it if you like matcha. 

The shopping malls, food courts, and crowds of Waikiki can be overwhelming at first, but you get used to it pretty quickly. It reminded me of South beach in Miami, and the 5th avenue in New York, combined. It was a nice walk after dinner. 

Day 2 Explore

Thanks to the jet lag, we woke up early. Driving in a convertible and listening to our favorite music on Spotify set the tone of our trip for the whole day!

Loco Moco is a must try when you are in Oahu, I recommend to eat it before a big hike because of the high calorie content. We stopped by Highway Inn and ordered take out. I looooove the Smoked Moco with pork belly. 

Shaved ice is another must try. We tried 2 places for shaved ice. Ice Garden and Island Vintage. It is nice having some shaved ice after snorkeling. 

The first time we drove from Honolulu to Kailua was like entering a screensaver filled with lush and vast forest. The mountains were all covered in trees. It was drizzling sometimes on the mountain roads, but the rain was intermittent . 

Kailua beach is our favorite beach in Oahu. It is less crowded and the water is more blue. A lot of kayaking and sailing activities there. 

Water activities

Always, always bring swimwear, towels, water shoes, clothes for change (and snorkeling gears) wherever you go just in case. There were a few times when we wanted to jump in the water, but didn’t have towels or swimwear!!!!! Also apply eco friendly sunscreen generously and often. Hawaii is very protective with the preservation of their island and its occupants. 

On our way back to the hotel, we stopped by Tamashiro Market and bought fresh Poke for snacks. Poke is also a must try when you are in Oahu. My favorite one is spicy tuna. 

After eating poke, we went to Waikiki beach. Waikiki beach is family friendly and relaxing. After a physically demanding activity, it’s a nice walk to cool down. We then had a drink in a restaurant near the beach. Unfortunately, I was not impressed with the drink quality given its high price.

One funny story that night. We went to have a massage because our back hurt as hell after the long flight. We were fortunate to be able to book a late evening couple massage. The skyline night view was stunning from the massage room’s vantage point, and the massage was very relaxing. When we swiped our credit card on the POS machine, the staff accidentally put 2 extra zeros on the keypad which charged for more than $10,000! Luckily they noticed the error before we left, and refunded us immediately. It could have been the largest bill, and the most luxurious massage I’ve ever gotten LMAO

Day 3 First snorkel

Another early day! We went to Joe’s Grill Express for breakfast. It is a low key place near the airport. We had a big breakfast to get ready for our water activities. 

Water wear

Wear a rash guard for water activities. The sun in Hawaii is strong and can be unforgiving. Sunscreen may not provide enough protection when you are soaked under water. 

Kailua sailing

We booked Hawaiian Sailing Canoe Adventure on Airbnb and loved it! It includes sailing near Kailua beach, and a short hike on a small island. 

We got to know other people from the sailing tour, and they kindly lent us their snorkeling gears. My husband was excited to try snorkeling for the first time and couldn’t wait to snorkel at different places in the island.

Our sailing guide recommended that we rent snorkeling gears from Snorkel BobThe best part of Snorkel Bob is that we could rent the gear and travel inter-island. As long as they have a store on the island that you are going to in Hawaii, you could just easily drop off your gears on any of their stores. Snorkel Bob has multiple stores all over Hawaii islands, and this inter-island return is very convenient. 

Hawaii has a large Asian community and many authentic Asian supermarkets. We went to Seafood City, a Filipino supermarket, for dinner. 

Day 4 Surf and snorkel

My first time trying to surf in Haleiwa was not pleasant. Partly because I was still not comfortable with swimming, and partly because our surfing teacher was not good. I later tried to surf again in Maui with a better teacher in a shallower water. But I guess surfing is just not for me. I am more of a snorkel gal. 

I like snorkeling! 

We went to Shark’s Cove for our first snorkeling. Shark’s cove is a great place to get started with snorkeling. The water is shallow and still, and there are a lot of fish! 

We tried to book an appointment for the famous Hanauma bay, but it was almost impossible to secure a spot with their online booking system. 


Wear a rash guard and water shoes for water activities to protect your skin and feet. Also, wear a life jacket or a floating belt if you are not very comfortable with water, like me.


We did some Yelp search and found an Asian fusion restaurant, Lucky Belly, and it was so good!!!! Scallop Cone Sushi and Crispy Duck Tacos are a must try. We got there late at night just before the kitchen was about to close, so it was not as busy as regular dinner time. 

Day 5 Hawaiian cooking class and Airbnb boat

Another early morning with Hawaiian style cooking class. This is my Top 1 favorite Airbnb experience of all time. Linda, our chef, was very cool and knowledgeable. She not only taught us to make poke, musubis, and mochi, but also shared her inspiring life stories. If you do get to book her experience, ask her about her life. It’s like a movie. We got to know her cute dogs and a pig appropriately named…. Bacon. I highly recommend it!

After the cooking class, we decided to go for a short hike at Pillbox. The view was mesmerizing.

A friend recommends a Japanese supermarket called Don Quijote with a wide selection of Japanese food, deli, cosmetics, and tools. It is a great place to buy grocery and sake. For dinner, we entered a random restaurant in Ala Moana. Ala Moana is a popular shopping center in Oahu. Both of us are not big fans of shopping. So for us, Ala Moana is a place with food options and free parking. 

We checked in our Airbnb boat for the night. The first night we slept on the boat felt like a gentle cradle from the sea, swinging you into a lullaby. You could hear water splash outside and feel the fresh breeze brushing your face.

Day 6 Sandbar

We booked a half day kayak rental for the famous sandbar. Unfortunately, the sandbar was not exposed on the day of our visit and the water was waist high. The kayaking was still fun, and we were playing music while we were kayaking and enjoying the view. We were also able to snorkel a bit nearby. Make sure you bring water, snacks, and sunscreen. 

After kayaking and resting on our Airbnb boat, we went for dinner at Roy’s Waikiki. It is a must try when you are in Oahu. Misoyaki Butterfish is my favorite. Make sure you reserve a table weeks in advance!!! 

Day 7 Arrive in Maui

Most roads in Maui are right by the coastline, making it such a majestic experience simply driving. Getting spoiled by the coastline view in Maui, driving felt lackluster when we came back to New York. 

The Airbnb cottage we stayed is in Haiku, and the nearest grocery store is 20 min drive away. Our Airbnb host told us to do some grocery shopping on our way from the airport to her place. Although we gave up the quick access to shopping, we got to enjoy the serene sound of nature. 

We absolutely loved our cottage. It is $$$ but worth every penny. Compared to hotels, we think Airbnb is a better choice to stay in Maui and it feels just like home when you can cook your own meals. Living in a remote area surrounded by trees is such a opposite contrast to living in resorts, surrounded by buildings. Every morning, we woke up with an array of chirping birds, crickets, and sometimes roosters. 

There is a public pool and a private jacuzzi. It became my routine to jump in the jacuzzi after a long day of outdoor activities. 

Day 8 Snorkel

We booked a last minute tour to Molokini on Airbnb. Snorkeling was a new interest we developed during this trip. The boat tour took off from Kihei, and was a short ride to Molokini. The water in Molokini is crystal clear! The spectrum of aquatic life that you get to swim with is breathtaking. It is the best place I’ve snorkeled and I can’t wait to come back. 

Oh make sure you don’t sit in the back of the raft if you don’t want strong waves splash on your face for 20 minutes.  

After the snorkeling, we randomly entered a vintage store Rainbow attic in Kihei and bought a few discounted vintage clothes. We asked the staff for food recommendations and he recommended Nutcharee’s Authentic Thai Food. It is the best Thai food I’ve ever had, having lived in New York for a decade. The serving size is large, and we ended up eating the food for both lunch and dinner. 

Day 9 Road to Hana

Road to Hana is a must do when you are in Maui. A nice lady whom we met during the Molokini snorkeling tour recommended us an audio app for Road to Hana: Shaka Guide. We were very happy with this App. It tells you where is a good place to stop, the history, and most importantly, where to go for the restroom. 

Road to Hana is more of a journey than a destination. A few tips before you start the journey:

  1. make a reservation in advance for the black sand beach at 
  2. download Google Maps offline 
  3. download your favorite playlists / songs / podcasts offline on Spotify
  4. bring swimwear, towels, water shoes, hiking shoes, water, snacks, cash, sunscreen, etc
  5. leave early to get the full experience

The final stop for our Road to Hana trip is the Haleakala National Park seven sacred pools. The admission ticket is $30, and you can enter the park multiple times with the ticket in 3 days. So if you also plan to go to the Haleakala Crater, better go within 3 days of Road to Hana. 

Day 10 Mama’s fish house and more snorkel

We booked Mama’s fish house weeks in advance to celebrate our anniversary. We got seated by the window and the view didn’t disappoint. My favorite dish was the Macadamia crusted Mahi Mahi stuff with crab. The serving size is big, and we had our leftover to go for dinner (but we left it in the car and forgot to eat it). 


Book online early and book for the earliest spot to get seated by the window.

After lunch, we drove to Honolua bay for snorkeling. It was a bit tricky to find the entrance, and there was a sign saying it is a private property. We ran into the owners (I guess) who were driving through the gate, and told us we could just walk in. It turns out there were a few people already snorkeling there. The water was muddy near the rocks, and we needed to swim a bit further for better visibility. It is a very good snorkeling spot with a lot of live reefs and fish. Further out you could see the true beauty of the bay. With a height of 15 to 20 feet of coral reefs or maybe even more (not really sure how big because they were humungous!) combined with the vast area of the bay. The snorkeling experience is definitely a must try. This area was also Instagram-ready with a lot of trees. We saw a few wedding photo shootings there. 

We stopped by Kaanapali beach on our way back to Haiku. There are a lot of resorts and luxury hotels in Kaanapali beach. Watching sunset on Kaanapali beach is an appropriate way to wind down and ease into the night. 

After returning our snorkel gears to Snorkel bob, we had tacos at Coconut’s Fish Cafe for dinner. The fish taco was pretty good. 

Day 11 Scuba diving and sunset at Haleakala 

First time scuba diving! We booked this private session on Airbnb and experienced it we sure did! Our guides Jake and Joe was pivotal to the unfamiliar experience we were about to partake. With their patience and knowledgeable expertise, we were able to immerse ourselves with our mini adventure. Knowing what it feels like and the fundamentals that you need to know while scuba diving is fascinating to go through. We saw schools of fish, swam underneath and beside turtles and sharks!

As I mentioned early, the Haleakala park admission is valid for 3 days. We heard both sunrise and sunset at Haleakala is magnificent to see. We chose to go for the sunset view.  As we started to drive up to the mountain, it was very cloudy and we were worried we might not be able to see the sunset. However, as we kept driving and the elevation got higher, we realized that the vantage point only got better. The sun was shining so brightly above the cloud that one would feel as if they were floating with the clouds.

Watching the sunset above the ocean of cloud was such an awe. 

After the sunset, we kept on driving to the summit observatory. Standing on the summit, we could see the shorelines of Maui, and the starry sky. 

Driving downhill in pitch black darkness was not easy, so be prepared.  


Bring a thick jacket and long pants because the summit will be chilly. Also bring water and some food. 

Day 12 Kula

Another last minute booking for goat yoga! It was so much fun hanging out with the mini goats outdoor. 

In the afternoon, we booked a private dinner party on Airbnb with a local chef. Their venue was on the mountain and the view was majestic. We had fresh ono fish, octopus, and wagyu beef. We talked with other people at the dinner party about traveling and food, and it was a great experience for people who consider themselves a foodie! 

Day 13 Last snorkel and surf

The last time we snorkeled, we saw a lot of turtles!!! They were not afraid of human, and slowly swam right next to you. It was great to have some nice photos and videos shooting during snorkel with this Airbnb experience. I recommend this to anyone who likes snorkeling and turtles.

In the afternoon, I tried surfing for a second time, and still didn’t enjoy it. I guess surfing is just not for me. 

After surfing, we went to 808 Deli for sandwich. Our snorkeling guide recommended this place to us, and it was great and not expensive! We ordered by phone, picked up, and then ate across the street near the beach. Life in Maui is so good. 

When we got back to our Airbnb at night, the sky was clear and the moon was nowhere to be found. We laid down on the deck outside the cottage and star gazed. I miss Maui already. 

Day 14 Leave Hawaii

See you next time, blue water!

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