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Best Hawaii Itinerary

We started our trip in Maui! Maui is what they call the luxury island. Maui is the most expensive island and home to some of the nicest resorts in all of Hawaii. This island is more relaxed and slower pace. We stayed at an Airbnb on the slower, country side of the Island in a little town called Haiku. We enjoyed this because we enjoyed our drive each day with beautiful mountain views! We rented a Mustang convertible and I promise it was worse the extra cost for the extra views!

Day 1

Woke up early (not yet adjusted to Hawaii time) and went to watch the sunrise at Ho’okipa Beach where the waves are massive and surfing is popular! Grabbed some coffee from the coffee truck, Akamai, while on our way to our whale watching excursion! We booked through Pacific Whale Foundation, which is a nonprofit organization dedicated to helping the whales! All proceeds go towards whale efforts. Whale watching is a MUST in the winter months when they are so active. This was one of our favorite parts of this trip! We spent the afternoon exploring Historic Kaanapali. You can enjoy shopping and restaurants here! We had dinner at the Paia Fish Market. This is a MUST! There are a few locations on the island and this was definitely one of our favorite restaurants (we went back 3 times).

Day 2

We started our day at Wailuku Coffee. They have the BEST coffee shop breakfast and amazing coffee. We also ended up back here on our last day because we loved it so much. And the… the famous Road to Hana! This takes ALL day and you want to start early! The Road to Hana is a long winding road full of waterfalls, cliffs, ocean views and so much more! Make sure you download the GyPSy Guide Maui app! This will tell you everything you need to know while on your Road to Hana trip. He will talk to you through the drive and tell you when to pull over for which attractions. This app is a MUST! We had plans and reservations for Mama’s Fish House, which we hear is a must in Maui but we ended up skipping out. If you’re interested in fancy fish plates, I would still recommend this place! It’s the #1 restaurant in Maui but make sure you call weeks in advance to make a reservation!

Day 3

We spent the day at Ka’anapali Beach! We parked at Whalers Village and walked to the beach. Park here and buy anything (food, a shirt, etc) and use your receipt for parking validation and you won’t have to pay! If you head out to the beach, you can find a great spot to relax. There is also a big cliff you can jump off of down at the north end! We headed back to shower and made a reservation at 5 Palms for dinner! This restaurant is located in a hotel with a beautiful lawn running right into the beach. We headed there for sunset on the lawn and a delicious dinner! One of our most favorite dining experiences while in Hawaii!

Day 4

Our last day in Maui and we had to head back to Wailuku Coffee for breakfast and coffee! We then went to check out Paia Beach Park and grabbed an Acai bowl from Paia Bowls. This was one of the best Acai bowls we had in Hawaii! As we made our way to the airport, we had to grab one last coffee from Akamai which is right by the airport! Flying from island to island can be very cheap and easy! We snagged a flight from Maui to Oahu for $35/person on Hawaiian Airlines.

Day 5

We are in Waikiki, Oahu! Woohooo! We stayed at the Alohilani Resort which was INCREDIBLE! This hotel is right on the Waikiki strip and within walkable distance to almost everything we did on Oahu. Oahu is very different from Maui and we found that out pretty quick! There’s lots going on in Oahu and so much to do! We started our day walking to Barefoot Beach Cafe and fell in love with this place – we ended up back there 3 more times! We spent the day relaxing at our resort pool! In the evening we attended the Ka Moana Lu’au at the Sea Life Park. 100% RECOMMEND THIS! You have to do a Lu’au while in Hawaii and this one was incredible! It was from 5:30-7:30 and it is a buffet style meal with an incredible show.

Day 6

We started this morning back at the Barefoot Beach Cafe! Their breakfast burrito is to die for! Next, we headed to Sandy Beach! This is one of the most unique beaches I have ever been to. The waves are MASSIVE and very short! This place is known for intense buggy boarding and body boarding! It is quite intense and you have to see it once! After a morning at the beach, we headed back to the hotel to drop the car and head to our snorkeling excursion! Of course the harbor was just within walking distance! We grabbed an Acai bowl on the walk there from the Sunrise Shack! We booked our snorkeling excursion through Pink Sails Waikiki and definitely recommend them! We swam with turtles and we will never forget it! We headed back to the hotel to shower and had dinner at Gen Korean BBQ! If you know Korean BBQ, you know it’s hard to find these restaurants anywhere! This place did not disappoint!

Day 7

North Shore day! The north shore is the quiet side of the island where surf is big! Turn on your GyPSy Guide Oahu app for this drive so you don’t miss anything! Stop at the fruit stands, swings alongside the road on the beach, visit the Polynesian Cultural Center if you want and definitely stop at the beaches in the north shore to watch some surf! After the north shore, we headed to the Dole Plantation! Hop on the Pineapple Express for a tour of their farming fields and don’t miss the Dole Whip! Yum!

Day 8

For us, we started the day with a photographer and a sunrise photo shoot! But here’s some free time for you to do something you’d like! I’ll leave some recs at the bottom of the blog of some things that were on our list to do but we ran out of time! For the second half of the day, we took surf lessons! This is HARD but a must do! How many people can say they learned to surf in Hawaii?! We booked through Ampsurf Hawaii. Kai was our instructor and he was amazing! This is the best deal for surf lessons – if you can’t find them for booking, let me know and I will help you! We almost opted out of surf lessons in Hawaii because of the price for just 1 hour but we got the same deal and Kai spent 2 hours with us! We ended the night at the Barefoot Beach Cafe for dinner! They had live music and we enjoyed a beautiful sunset!

Day 9

Our last day! We got up early to start at Diamondhead trail! Right now they are only open Thursday – Sunday and they have limited parking so plan accordingly and try to be there when they open! This trail has an amazing summit. This is a must do and one of those things that you are lucky to do during Covid because usually this trail is PACKED! We had to grab one last breakfast burrito from Barefoot Beach Cafe and we headed to the hotel to shower and pack up. Then we went to Pearl Harbor. This memorial is a beautiful tribute to all the ones who were affected by this tragedy. This was one of the first things on my list to do when we booked this trip. We ended our day with one last Paia Fish Market meal before we headed to the airport!

Hawaii will go down in history as one of our most memorable trips! We feel like we got to enjoy so many beautiful things on these islands and we were FULL by the time we left! Although here are a few things that were on our list that we just simply ran out of time for:

We hope you enjoy as much as we did!

Vince + Courtney

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