Hawaii

Day 1 – Arriving in Maui

Our Hawaiian vacation started off in Maui where we had arrived around 4:30 p.m. We got our rental car, (rental cars were quite the obstacle to book in 2021, we lucked out with a really good deal through Costco Travel!) and headed to our AirbnB for the evening. I’m not going to lie, Hawaii is expensive and as much as we wanted an Airbnb closer to the beach, we had to settle for one a little more inland due to price and demand. We stayed in the Waiehu area, not too far from the airport. 

Day 2 – Driving the Road to Hana

This was our Road to Hana day! If you visit Maui, the Road to Hana is a must. We left our Airbnb around 6 am, but the first stop was a local coffee shop called Maui Coffee Attic. I got an iced coffee and we both ordered breakfast burritos, they were delicious! We were talking to the owner and he was actually originally from Kentucky! 

After our quick breakfast stop, we headed to the start of the Road to Hana.

For our day on the Road to Hana, we decided to purchase a tour through an app called Gypsy Guide. We purchased the tour labeled Road to Hana – Maui, it cost us less than $10 and we are so glad we did it! The tour downloaded onto my phone so we didn’t have to worry about when we lost service. It ended up being so informative and helpful along the way to know where the best places were to stop for pictures, trails, and even bathrooms! 

We got back to town from the Road to Hana around 6:00 p.m. and found a Food Truck park right off Haleakala HWY for dinner. After dinner we headed back to our Airbnb to rest up for the night knowing we had a very early morning ahead of us! 

Day 3 – Summit of Maui

Our favorite day on Maui! We started the day leaving our Airbnb around 3 a.m and headed to the summit of Haleakala National Park (37 mile drive going from sea level to 10,023 feet!) When we got to the top around 4 a.m, there weren’t too many people ahead of us so we were able to stay in the car for a few minutes before braving the cold. A little before 4:30, we headed up the steps to the viewing area. It was SO dark and hard to see, but I’m glad we got up there when we did because we got the perfect spot along the ledge to wait for the sunrise! Around 5:30, the sun began to rise and it was magical! Being above the clouds watching the sunrise was amazing and definitely worth the 30º morning.

Before heading back down the mountain, we stopped at a viewing area, but decided not to do any hiking up there due to the wind. 

At the bottom we stopped in a little town called Makawao, where we visited the Komoda Store & Bakery, my sister recommended this bakery and the doughnuts lived up to the hype! It was definitely a popular stop because we had to wait in line for about 30 minutes to get them. 

We headed back to the Airbnb for a nap and to eat lunch, because we were heading to a sunset cruise later on. 

Our sunset cruise left from the Lahaina Harbor in the Lahaina Historic District. Ryan and I first explored the area, going into various shops and I cracked an oyster to get a pearl! The Lahaina Sunset Sail tour was booked through Trilogy and we highly recommend them! We spent the evening on a nice catamaran where we had our own table right in the front of the boat! They served a few different appetizers and unlimited drinks, both which were included in the booking. This was one of our favorite things we did because of the beautiful scenery + the nice boat experience! 

After our sunset sail was over, we headed straight for some gelato before calling it a night. 

Day 4 – Final Day in Maui

We started the day with breakfast at The Gazebo Restaurant, and my sister told me to get there early to avoid a crowd… and well I thought we did but apparently we did not get there early enough! Ryan dropped me off to get in line around 7 a.m. while he went to find a parking spot. To our surprise, the line was MUCH longer than we anticipated and we didn’t get seated until around 10 a.m! Luckily we made friends with the people behind us in line, which made standing in the sun for that long a little more bearable. The food was really good and the view was 100% worth it! Ryan loved the macadamia nut pancakes, which is what they are known for! 

After breakfast, we drove along the coast and Ryan found a place to fly his drone. We got some pretty pictures and videos and continued driving down the coast to Makena State Park/Makena Beach. It was a beautiful day to hang out at the beach for a while, but the waves were a little too rough to swim in! After the beach, we stopped at The Shops at Wailea and then headed to dinner at Coconut’s Fish Cafe. They are known for their fish tacos, which Ryan enjoyed while I got pork tacos! 

That pretty much ended our time in Maui because the next morning we were off to Honolulu! 

Day 5 – Off to O’ahu

We headed out bright and early for our flight from Maui to Honolulu! We flew Hawaiian Airlines because they offer so many affordable flights when island hopping! When we landed at HNL, we made our way to the shuttle we booked through Go Waikiki Shuttle. This shuttle was only $30 round trip per person to our resort, which based on what we had read would be way more affordable than an Uber. 

Once we arrived at the Hilton Hawaiian Village, we were able to check in right away, even though it was 9 a.m.  They ended up offering us a paid upgrade that we took and I AM SO GLAD WE DID! We made our way to our room and I just couldn’t believe our view! After unpacking a bit, we headed to the pool for most of the day and finished the evening off by walking to a nearby mall for dinner and some shopping. 

Day 6 – Morning Hike and Relaxing

Ryan and I woke up around 5 a.m. to get ready for our Diamond Head hike. We took an Uber from the resort to near the entrance of Diamond Head and had to wait until it opened at 6. The hike to the top isn’t too long and we made it up and back down in about an hour! We caught an Uber back to the resort, changed into our swimsuits and headed to the beach. 

On this day we rented chairs and an umbrella and stayed out all day long! I ordered an inner tube from Target through Instacart & it was so relaxing to float out in the ocean and watch sea turtles swim right by. 

Day 7 – Another Pool Day

This day was mostly just hanging out by the pool, but we did rent paddle boards for a little while in the lagoon at our resort. 

That evening we did a little exploring near the Waikiki Beach area with nice shopping and dinner! We made it back to the Hilton just in time to catch the sunset! 

Day 8 – Goodbye Hawaii!

I enjoyed one last cup of coffee on the balcony and then it was time to head home 🙁 It was definitely sad to say goodbye to our view and the resort. We 100% recommend staying at Hilton Hawaiian Village!