Two Weeks in Hawaii
As a travel agent, I’m constantly trying to learn about different destinations and explore them in the flesh. Every year, I make it a goal to visit at least 3 new destinations that I sell a lot of. Typically, I’ll visit Mexico or The Caribbean. I’ve been to Thailand (Southeast Asia is HOT!), Colombia and Peru (South America is also HOT!), and of course Iceland (also hot just not weather wise!). This year, I wanted to switch it up and visit the Hawaiian Islands! As a popular tourist destination, I felt Hawaii would be the next best spot to check out and it did not disappoint. I spent a total of TWO Weeks in Hawaii and wanted to share my itinerary.
Keep in mind that I traveled in July, yet booked everything this past December. So that gave me ample time to make payments along the way, while having the comfort of knowing that my hotels, flights, and rental cars were already locked in and I wouldn’t be disappointed by lack of availability. I also wanted to share that I did travel with my boyfriend (who’s now my fiance but I’ll get to that later!)… and splitting costs most definitely helped with my budget. We were also able to stay 3 of the nights with his aunt and uncle while we were in Oahu which also helped the budget a wee bit.
Perfect for Any Occasion
I’m sure you already know if you’re considering a trip to Hawaii that it is NOT an inexpensive destination. But that is why you call your travel agent… (ME!) and I can assist with getting everything booked and helping you plan and pay off your perfect vacation whether you’re celebrating a new promotion at work, going on a babymoon, enjoying a honeymoon, or going on a girls trip! It’s also perfect for a golf-specific vacation as there are so many beautiful golf courses.
Hawaii is the perfect destination for all occasions and each island offers a little something special. In my case, I was celebrating my big 30th birthday (lovingly known as the “Dirty 30”), celebrating my 1 year anniversary with bae, the first birthday of my fiance’s niece Ava, and my completion of the Hawaii Destination Specialist course. The three islands I visited during my two weeks in Hawaii (in chronological order) are:
- Oahu (7 nights)
- Maui (3 nights)
- The Big Island (3 Nights)
Day 1 – Arrive in Oahu / Waikiki Beach
Day 1 was kind of a blur. Caught a UNITED flight from BWI Airport, with a quick layover in Houston, before the long trek to Honolulu! I went with UNITED Airlines for budget purposes… round-trip flights were $800 which I felt was pretty reasonable. We arrived in Honolulu around 1:30 PM local Hawaiian-Aleutian Standard Time (HST).
First thing we did was pick up our rental car and headed for Waikiki Beach which would serve as home for the next 4 nights. We took it pretty easy this day after all of the traveling. We simply walked around Waikiki Beach people watching before grabbing an early Mexican dinner at Buho de Cocina. I ordered the fish tacos… and they were just as tasty as they were pretty. You can check out their mouthwatering menu here.
Travel tip: Try to make reservations for restaurants ahead of time using OpenTable. I made a reservation here (even though it didn’t appear crowded) as well as pretty much all of the dining because it can get very crowded and the last thing you want after traveling all day is to be denied a table everywhere you go.
Waikiki Beach is not for everyone
It’s been said before, but I’ll say it again. It is crowded, very tourist-y, and expensive even by Hawaii standards. That’s why we chose to only stay here for 4 of the 7 nights in Oahu. But I will say it is like no other place there. It’s this perfect blend of casual surfer vibes mixed with high end shopping like Prada, as shown below. There’s so much to see and do. While visiting Waikiki Beach, don’t forget to snap a photo of the famous former surfer Duke Kahanamoku (shown above on this post).
After some people watching, it was back to the hotel for Netflix + chill. We stayed at the Regency on Beachwalk by Outrigger property. It was a lovely 2-bedroom condo, that we were somehow upgraded to (from a 1-bedroom condo that we actually paid for). I’m personally a huge fan of the Outrigger brand in general for Hawaii. They offer entry level accommodations to more 4-star level accommodations. Great for all budgets. Of course, when working with a travel agent, we can determine the best fit for you (hotel vs. condo with the comforts of home). Here was the view from our room. We were close to shopping, the beach, tons of restaurants. Parking was $35 per night but that’s the going rate for Waikiki. NOT CHEAP! Additionally, you will have a mandatory cleaning checkout fee for each resort you visit. Keep that in mind when budgeting.
The little kitchen was nice to have. One night we ordered a pizza and it was good to have something to eat it on besides the living room couch. The fridge stored cold water for us before we went on excursions.
Day 2 – Hiking / Temple / Luau
Your first full day of your two weeks in Hawaii itinerary should be spent wisely. If you are coming from the U.S. east coast take advantage of your body still being on that time zone. My fiance and I were up BEFORE the crack of dawn because we went to bed so early.
Diamond Head
We left Regency on Beachwalk around 4:30 AM and headed for our first stop, Diamond Head State Monument. It should be noted that early birds will catch the worm here. You’ll have a great parking spot, and get to see the beautiful sunrise while you hike it. But just note that lines start forming EARLY and you will not be allowed in until 6:00 AM. The entry cost is $5.00 per vehicle and small/exact change is appreciated. The hike itself isn’t too long or strenuous, and the views of the city are worth it.
After the hike, you can head back to the bottom and enjoy cold drinks like fresh coconut water still in the shell. You can purchase t-shirts that read “I hiked Diamond Head.” Diamond Head is one of the Quintessential Things to do on Oahu Island. After enjoying refreshments that set us back about $6.00, we headed to the Byodo-In Temple, one of the places on my Oahu bucket list.
Byodo-In Temple
The Byodo-In temple is about a 45 minute drive from Diamond Head. Driving here offered fantastic views. Lush greenery covered in a beautiful coat of fog. The reason I wanted to visit Byodo-In temple so much is because of what it represents. Byodo-in temple represents peace between United States and Japan after Pearl Harbor and Hiroshima attacks. FUN FACT: It is an exact replica of a 900-year old temple at Uji located in Kyoto, Japan. This temple NOT an active Buddhist temple, and all religions are welcome. It offers a place of peace and serenity where you can go to just enjoy the outdoors. There were koi fish to feed and a brass peace bell for you to ring. If you are planning to tour Pearl Harbor, add this to your list. Let this be the happy ending to the movie you will watch there.
Feeling hungry, we asked one of the temple employees where we should head for breakfast. They told us about Cinnamon’s, a popular breakfast spot. Kahlua pork eggs benedict did NOT disappoint. You can read my full blog post on top Hawaiian food HERE. With full bellies, we headed to Waimanalo Beach (my personal fave on the island). Water is calm, unlike the waves encountered at most Hawaiian beaches.
Waimanalo Beach / Hakona Blowhole
After soaking up rays at the beach, we drove a little farther to the Halona Blowhole. We didn’t get close to it because you have to climb down unsteady rocks. I’m way too clumsy to chance it. Here are a few quick pics though of beach + blowhole. Many people also visit Hanauma Bay on this route, a spot we decided to skip.
Travel Tip: There are plenty of tours that will take you around Oahu Island on the “Grand Circle tour.” I highly recommend purchasing a rental car though during your stay. It’ll save you money in the long run by not having to book so many tours. It’s also liberating to be able to pull over on the side of the road and stop whenever you feel like it. The only disadvantage with the car is the $30 – $40 per day parking cost. But not spending $100 + per tour… you’ll still end up ahead.
Paradise Cove Luau
Heading to a luau is one of those quintessential Hawaii experiences. There’s some mixed reviews about how “authentic” they are. But nevertheless, it’s a great way to taste Hawaiian fare and enjoy the beautiful outdoors. Paradise Cove Luau was beautiful and I highly recommend. Check in was at 5:00 PM when the activities began but dinner & show didn’t begin until about 7:00 PM.
The food was plentiful and delicious and the entertainment was great. There are 3 different luau packages and we chose the middle tier “Orchid Luau.” We were in the middle section pretty close to the stage. You can check out my full review of Paradise Cove here. That was pretty much it for Day 2.
Travel tip: If you’re looking for cheesy matching luau sets you can either pre-purchase them or buy them there. I bought ours on Walmart’s website, but the company is called Hawaii Hangover. He was not a fan but I thought we looked pretty luau chic!
Day 3 – North Shore Explore
Day 3 of this two weeks in Hawaii itinerary takes us to North Shore. North Shore quickly became one of my favorite areas on the island. We started with breakfast at Kono’s. Just had a bagel with salmon and capers. Then headed to Waimea Valley. We stopped into the Waimea Falls Park & Botanical Garden. $18 admission. It was an okay place to spend some time. Wouldn’t say it was a highlight of the trip, but it was neat to spend time in nature.
Turtle Beach
After checking out some time in Waimea Valley, we headed into Hale’iwa town. Hale’iwa is apart of North Shore. There you will find Laniakea Beach (also known as Turtle beach). If you check out the photo below, you’ll see why! Massive turtles all over the beach. It was the coolest thing to witness and a highlight of the day! There are signs up letting you know how much distance you need to keep around them at all times.
After frolicking on the beach and watching turtles living their best life, it was time for lunch! You may have read on hundreds of other blogs about the famous garlic shrimp trucks. CAN CONFIRM… the garlic shrimp trucks in North Shore = Flavortown. Giovanni’s is the most popular truck but that line was WAY too long. Started getting too hangry so had some shrimp from a neighbor truck. Zane’s is the name.
Afterward, we drove to Turtle Bay Resort so I could check it out (#travelagentlife). It’s a beautiful facility, but I’m not sure you really experience “Hawaii” by staying there… You’d certainly get some relaxation in though! The rest of the evening was at leisure. You get exhausted quick in that Hawaii sun.
Day 4 – Pearl Harbor / Waikiki Beach
Day 4 happened to be July 4th! It began with a 7am wake up call. We had a Pearl Harbor/Honolulu City Half day tour. If you are a history buff, you may want to consider a full day tour here where you can actually spend time going on the different memorial sites. When we were there on Independence Day it was closed due to reconstruction. I believe it will be opening up again this fall so get your tickets!
Overall, the museum, movies, artifacts, it was all too real. The video we watched showed actual footage of the Pearl Harbor attack. Then we drove around the city to see the Iolani Palace. Iolani Palace is the only royal palace in this country. We also drove up to Punchbowl Crater, the National Memorial Cemetery.
Afterwards, we spent the rest of the day and night exploring Waikiki Beach some more. I highly recommend grabbing lunch at Duke’s Canoe Club. Don’t leave without trying their hula pie! HERE is their tasty menu. Reservations suggested. Guests of Regency on Beachwalk have pool access at the neighboring Reef Outrigger resort. So we were able to swim in the pool and hot tub as we patiently waited for the fireworks!
Travel Tip: You don’t have to be here on 4th of July to see fireworks. The Hilton Hawaiian Village hotel offers a fireworks display every Friday!
Day 5 – Hotel Site Visits / Stay in Makakilo
So Waikiki Beach and the Pacific Ocean messed my hair UP! So I set up an appointment early on with Drybar. They open super early at 7:00 am so you can get it done before starting your day! Highly recommend.
Afterwards, I had a few hotel site visits lined up. I was able to check out Shoreline Hotel, the most Instagrammable hotel on Oahu! So bright and colorful. Highly recommend for my millennial clients. Checkout that rooftop pool! If only I hadn’t just got my hair done…
After packing up the car, we were headed out of Waikiki Beach and home in Makakilo. Makakilo is where my fiance’s aunt and uncle live so they graciously let us stay with them for the last 3 nights we were in Oahu. This was the night where my fiance’s mom, sister, and cousin arrive in Oahu. So we picked them up from the airport, had dinner and went to sleep early!
Day 6 – Waimanalo Beach / Kualoa Ranch
Day 6 of this two weeks in Hawaii itinerary continues at my favorite beach… Waimanalo! You may have recalled from above about the calm waters. The perfect place for swimming. There’s lot of little shacks set up around here where you can grab a quick picnic lunch and eat it at the beach. After swimming made us hungry we stopped at a casual lunch spot on the side of the road.
Poi Factory offered local fare and I was able to sample ‘lau lau‘ which is kalua pork stuffed in taro leaves. Served with a side of rice and lomi lomi salmon. Delish! The best part was… this “plate lunch” only cost $7.50. So one of the cheapest meals we had. They also had some sweet dishes like coconut ice cream.
Kualoa Ranch
At 3:30p, we had a pre-purchased 90-minute movie tour at Kualoa Ranch. Kualoa Ranch is where MANY t.v. shows and movies were shot. If you are a big movie buff you will enjoy the trivia along the way on the tour! Does that monitor below look familiar to you? Any LOST fans? One of my favorite movies is ’50 First Dates’ so seeing where some of the scenes were filmed was fun!
Travel Tip: If you’re planning on visiting Kualoa Ranch, you need to make sure you have your tickets purchased. I saw SO many tourists getting turned away because they didn’t plan ahead. It could’ve been because I was there in July during peak summertime but better safe than sorry!
Day 7 – Aloha Swap Meet / Dole Plantation
Don’t waste your money in the overpriced ABC Stores scattered around town. These ABC Stores do not serve liquor… they sell souvenirs. Save your money and make it out to the swap meet where you can mingle with locals and support them directly. Cheaper prices too! Currently, the Aloha Swap Meet is open every Wednesday, Saturday, and Sunday. Takes place at the Aloha Stadium. I went on a Sunday and it wasn’t crowded at all.
Grab a cold shave ice or a coconut as you walk through the stalls. After you drink the coconut water, they hammer out the coconut meat for you.
Dole Pineapple Plantation
After shopping and grabbing souvenirs, we headed to Dole Pineapple Plantation. It’s very tourist-y but it’s still a good time. There, you will find the world’s largest maze. Took us 43 minutes and some change to complete it. Of course we rewarded ourselves with Dole Whip afterwards! Add some extra crushed pineapples in there for good measure.
There’s a large onsite gift shop if you wanted to bring some pineapple flavored goodies back in your carry on bag.
Our last night in Makakilo (and Oahu Island) ended with delicious grilled dinner and some tasty margaritas! Mahalo to Aunt Leslie and Uncle Andrew for their hospitality!
Day 8 – Arrive in Maui / Upcountry
Corey and I left Oahu pretty early… around 8:00 AM. There are SO many Hawaiian Airlines flights each day. I do, however, recommend pre-purchasing all of your flights ahead of time just to guarantee your spot. Hawaiian Airlines was efficient, QUICK, and offered great service. They even offered us juice/coffee for a little 45 minute flight! When you’re in an expensive area like Hawaii you accept ANYTHING free. “I’ll take a juice please!!”
We landed around 9:00 AM. Scooped up our Jeep rental car and headed towards Upcountry. Upcountry is about 35 minutes away from the OGG Airport and offers you peace and serenity after all of the overcrowded Oahu experience.
Ali’i Kula Lavender Farm
There are quite a few popular venues located in Upcountry. You could easily make a full day out of touring that area alone. There’s the Surfing Goat Dairy Farm and Maui Pineapple Farm. Upcountry is also where the Ocean Vodka distillery is located. And the O’o Farm offering farm to table lunches daily. Price tag was a bit too steep for us though. Instead, we chose to purchase the $26 picnic lunch at Ali’i Kula Lavender Farm.
We enjoyed walking around the lavender fields as they were in full bloom (apparently peak bloom season is June – Aug). After the clock hit 10:30 AM we were able to ask for our boxed lunch. They had different items but chose the bacon club ranch sandwich. It came with purple sweet potato chips and a lavender brownie for dessert. We also enjoyed lavender infused lemonade. Very tasty for $26! Plus… it came with a reusable bag.
Don’t sleep on the gift shop either! Lots of lavender infused goodies and soaps/perfumes. Need help falling asleep, let the lavender help!
Kaanapali Maui at the Eldorado by Outrigger
As you know now, I’m a huge fan of the Outrigger Resort. Decided to stay at the Kaanapali Maui while on this island. So after we relaxed in Upcountry, we headed to Lahaina to check in. Enjoyed the rest of the day at the pool and ordered a pizza from RoundTable. Took it easy with Netflix + Chill.
Travel Tip: Unless you want heart burn I suggest NOT getting their buffalo hot wings.
Day 9 – Road To Hana
The Road to Hana was the whole reason for renting the Jeep. My short self prefers a Hyundai but nah, not this trip. You can read more about the Road to Hana here. It’s a lot to type…
After the exhausting Road To Hana, we had dinner back in Lahaina at Paia Fish Market. It’s a community-table style restaurant so we were able to meet two wonderful people from Maine who we kept in contact with. 10/10 recommend that restaurant. The original Paia Fish Market is actually in Paia Town.
Day 10 – Lahaina / Wailea
Today we took it pretty easy. 10 days in… you don’t want to overdo it. ESPECIALLY after The Road to Hana which is long and treacherous. In the morning we grabbed a quick breakfast at Belle Surf Cafe then walked around Front Street. If you’re staying in Lahaina, you can’t really miss Front Street. That’s where a lot of the restaurants are.
We saw fishermen who just returned to shore with their fresh morning catch. There were also travelers hearing instruction near the boats and wearing a wet suit. My guess is they are going to be diving or surfing… One of the most popular tourist attractions here is snorkeling in Molokini. We decided it’d be too much to pack in after The Road to Hana wore us out so we skipped it.
Four Seasons at Wailea
After exploring Lahaina, we explored the other resort haven… Wailea. Wailea is where you will find your more upscale resorts like the Andaz, Grand Wailea, and The Four Seasons. I was fortunate to be able to set up an appointment and peep the inside. At $1,000 per night, it’s certainly not the right property for everyone. But for my luxury clients, it would be a perfect fit.
This property is wonderful for families and couples alike. The water is calm during some parts of the day.
Day 11 – Arrive on The Big Island
We made it to Maikai Lani Malasadas right at 7:30 AM when they opened. I was dying to try malasadas for the first time. Yum! Worth the wait. Because I was NOT about to wait in that long line at Leonard’s Bakery in Oahu… These malasadas were fresh, local, and delicious. Nothing fancy. Just a little dough of bliss topped with some powdered sugar.
LAST CHANCE: If you haven’t checked out my post on Top Foods to Eat in Hawaii check it out.
Then we headed to the airport to catch our flight to The Big Island. The OGG Airport didn’t have many food stalls so just ate Burger King until it was time to fly Hawaiian Airlines!
Landed on the Big Island in the afternoon. Picked up the rental car (was so GLAD to be out of the huge Jeep!) and went to dinner. Got my hair done at a salon there called Naked Roots Salon. Shout out to Cameon, the owner, who fixed me right up! Also she recommended Umeke’s which is where we went for dinner. Sampled poke for the first time (not a fan!). Enjoyed some boneless Kalbi short ribs. I was entertained that our receipt came in an empty SPAM can. I highly recommend this restaurant in Kona. There’s also a quick take out location if you’re on the go.
Day 12 – Volcanoes National Park / Punalu’u Black Sand Beach
You can’t visit The Big Island and not see Volcanoes National Park. At $25 fee per car, it was the most expensive park we visited in Hawaii but it was neat. Admittedly, I was hoping to see some lava or something. Just an empty crater. we walked by sulphur springs though (smelly!) We also saw the steam vents shooting up.
On the way to Volcanoes National Park, you’ll pass by the Punalu’u Black Sand Beach which is worth a stop. It’s also where my fiance and I decided to share with our loved ones that we are engaged (yay!)
Travel tip: Don’t walk this black sand barefoot (OUCH!). I was hobbling all the way until I felt water on my feet. It’s a scorcher.
Day 13 – Family Time in Hilo
Our last full day in Hawaii (tears)… for those heading to the Big Island you could drive to Hilo if you wanted to see some different terrain. You’ll pass by farms and cattle, desert landscape, trees… It’s insane. The Big Island is apparently home to 11 different climates.
Hilo is where Corey’s brother lives, so we got to see him for a day as well as his wife Sam and daughter Ava! If you haven’t had your fix of Shave Ice yet grab it here! So many shave ice stands… I tried the mango, passion fruit, and coconut flavors. It was at a little stand on the side of the street.
All in all, it was a great time with family and really enjoyed the company. As we were leaving Hilo and heading back to Kona, we saw this beautiful rainbow. Considering it was our last night there, I’m taking that as a proper goodbye!
Travel Tip: The most popular shave ice company is Matsumoto in the North Shore of Oahu. Apparently it’s Obama’s favorite so… naturally… But that line was out the door. In all honesty, you can’t really go wrong buying the shave ice from another stop.
Day 14 – Kona Coffee Farm and Museum / Back to the Mainland
Enjoyed some coffee at the Kona Coffee Farm and Museum. UNLIMITED FREE SAMPLES. Remember further up I wrote that you do not turn down anything free here. This is no exception! I did buy some souvenirs in their gift shop so I guess I didn’t freeload too much.
The museum is small but the staff makes this place. Very friendly! They were patient enough to go over the different flavors. My favorite was the toasted coconut!
Overall, this trip was one for the books! If you’re looking to plan your trip to Hawaii and need some additional suggestions please feel free to reach out to me: cassandra@accent-on-travel.net. My service is complimentary and I’d be happy to get you a quote.
