How to Travel Hawaii With Your BFF: Six Days in Oahu

traveling hawaii

People often think you have to wait to travel Hawaii until you’re older, more established, in love, on a honeymoon, have a lot of money, ect. Well, my BFF and I said “the heck with that!” and we went to Hawaii. We basked in the sun on Waikiki Beach, saw gorgeous sunsets every night, met travelers from around the world and ate lobster on a dinner cruise that circled the harbor. When we first told people that we were going to Hawaii on vacation, a lot people said “that’s too far to go for a week”, “I’m going to wait until I can stay somewhere nice to go”, ect. And if that’s your style, by all means, wait to go! But we had the best week in Oahu and if planning this trip seems a little daunting, keep reading! I’ve outlined the perfect travel Hawaii itinerary anyone can follow.

Day One 

If you’re anything like we were (and if you’re coming from the East Coast like us, you probably will be), you’ll need a day to relax, recover from traveling and take in the scenery. Don’t set your alarm, you’re in Hawaii! Take the first day to soak up some sun on Waikiki Beach, walk along the store fronts and maybe do a little planning for the rest of the week. Heck, I think you should even hit up one of the convenience stores (there’s one on every corner), grab a mini bottle of rum and add it to some OJ. This is vacation for goodness sake!

IMG_1949 IMG_1941

Late Breakfast: Lulu’s Waikiki is situated right across the street from the beach so come prepared to head there after! Lulu’s has an airy feel to it with an open window atmosphere that makes you feel like you’re right on the beach! Try the Loco Moco and the fresh island papaya to get your day started. Ask to sit along the bar facing the water for the best view. When you’re finished, walk across the street and bask in the Hawaiian sun.

Dinner: Rainbow Drive-In was within walking distance from our hostel (not sure what a hostel is?) and fit the bill of trying to find something a bit more local. Our hostel recommended it to us because we wanted something “local, cheap and within walking distance”. I’ll say that we were a little overwhelmed when we arrived. It wasn’t terribly busy and the menu is pretty straight forward but we have no idea what to order. I even Googled “what to order at Rainbow Drive In” while standing in front of the counter. I ended up ordering the Shuyo chicken and my BFF ordered the Loco Moco, a staple in Hawaii.


Between the six hour time difference and spending the day in the sun, we were worn out after dinner. We headed back to the beach to watch the sunset and then we called it a night. Good thing because day two is jam packed! With only five full days in Hawaii, you have to make good use of your time.


Day Two 

For the majority of the time we were in Ohau, we walked or we took the bus to our destinations. Day two was our first go at the bus and it mostly went over without a hitch. You can use the Hawaii Transit App to follow the bus stations and stops and it was extremely helpful the week we were there. You can take a bus from Waikiki to Diamond Head Crater and then a second bus from Diamond Head to Hanauma Bay. I recommend packing a light lunch and snacks to get through the day though there is food for sale at Hanauma.

Breakfast: Eggs ‘n Things is just a short walk down from Lulu’s and there’s a chance you’ll be waiting in a line. Don’t worry though, it goes quick! You can pick out what you want to eat and order at the end of the line. Once you order, a crew member will seat you and in a few minutes you’ll have a wonderful breakfast. We both had omelets since we knew we had some hiking to do and didn’t want to start the day heavy.

Lunch: Head to any of the convenience stores along the strip and grab some provisions for the day. Don’t forget to grab some water and sunscreen, especially if you’re going to head to Diamond Head like we did.

Diamond Head: Ask your hotel/host/hostel what bus you should take to get to Diamond Head. The bus will drop you off a little ways from the entrance so you’ll walk a bit before entering. Since we were walking, it cost us a dollar each. It’s $3 per car if you’re driving. Once you walk in, just follow the crowds. The hike isn’t bad but there’s no shade on the trail. I am afraid of heights though and had to stop a few times once getting closer to the top. You can take an almost vertical staircase without a view or open stairs that show how far you’ve come. The top has wonderful views of Waikiki, Honolulu and the surrounding areas. It can get crowded though so keep that in mind when you pick a time to hike.

travel hawaii
Diamond Head

Hanauma Bay: We decided Hanauma Bay was a must see while in Hawaii and is a famous spot for snorkeling. You pay a seven dollar entrance fee and are required to watch a video on the wildlife you may encounter in the water. You can pay to rent a locker (we did) and also rent snorkeling equipment. I bought mine at one of the convenience stores before leaving Waikiki so I didn’t have to rent and I saved money on the rental. We hung out on the beach and ate our snacks that we packed and then headed into the water to see some beautiful fish swimming about. It was such a beautiful place and I highly recommend the Diamond Head and Hanauma Bay combination. The Bay is a great place to relax after spending the morning hiking. Just a note that the bay is closed on Tuesdays.

travel hawaii
Hanauma Bay

Day Three 

We met a few people in our hostel who arrived in Ohau only for vacation purposes. If it was heavy, they didn’t want any part of it. My BFF and I on the other hand, did not make the trip out to Ohau to skip Pearl Harbor. So day three was dedicated to this. It’s up to you if you want to see it, but it’s a decision we didn’t regret. We took the bus from Waikiki at Kuhio Avenue which took us close to an hour and fifteen minutes. In total, we spent about four hours total at Pearl Harbor and ended up waiting a significant time for a bus back to Waikiki so it ended up being an entire day affair.

Breakfast: Pick something up from the convenience stores. We grabbed coffee and some pastries and headed to the bus stop

Lunch: We stayed at Pearl Harbor well into lunch time so luckily they serve food. We grabbed a hot dog near the souvenir shops and it was delicious and cheap.

Pearl Harbor: When you arrive at Pearl Harbor, you’ll need to get in line for tickets to see the U.S.S Arizona. The tickets were free but you have to go at a designated time so we had about 2 hours to kill before we could go. There’s plenty of museums to check out in the mean time and exhibits to look at. Most things are free but we did end up paying extra to go aboard the Blowfin submarine. All I can say about that is I’m glad I don’t have to spend any time on a submarine! When our ticket time arrived, we first watched a movie that explained more of the history of Pearl Harbor. We then took a ferry that took us to the U.S.S Arizona memorial. You can spend as much time as you would like and then can take the ferry back to the base.

travel hawaii
Pearl Harbor

Day Four 

Every day that we spent in Hawaii was magical, but day four was by far my favorite day. Luckily, everything we wanted to do up until this point was easily accessible by foot or bus. Day four was different. We kept hearing that you can’t go to Oahu without visiting the North Shore and who we were to disagree? So, we rented a car through our hostel (and had to pay extra for being under 25) and we were on our way. I’ll admit, we ended up at McDonald’s for breakfast on day four. But before you judge too hard, between the activities and the jet-lag, we were up EARLY in Hawaii. McDonald’s was practically the only place open when we were looking for breakfast on day four. Plus, you can get a side of pineapple and if that’s not my Hawaiian dream, I don’t know what is.

One of the craziest things about Oahu to me was how small it was, which we didn’t quite figure out till we rented a car. You can be on the other side of the island in less than two hours! On day four we went to the Dole Pineapple Plantation, strolled around Haleiwa and stopped at various beaches along our coastal drive back to Waikiki. What a day!

Dole Pineapple Plantation: Forty minutes after leaving Waikiki we pulled up to the Dole Pineapple Plantation. If you want to do only non touristy things while in Hawaii, this shouldn’t be on your list. The plantation is a little cheesy and geared to sell Dole products but I enjoyed going. After making our way through the maze of pineapple themed products (not to be confused with the actual maze), we got in line for Dole Whip which is basically pineapple ice cream heaven. We walked around a “garden” of sorts with different pineapples growing while savoring our ice cream and pretty much decided we were in Hawaii bliss. We paid to take the train through the pineapple plantation which was clearly built as an attraction. It was an entertaining ride and a great end to our Dole plantation visit.

travel hawaii
Dole Whip

Lunch: Giovanni’s Shrimp Truck is a do not miss. My BFF was a little skeptical when we went in search of this SPECIFIC shrimp truck when there were clearly so many food trucks around. But once we bit into the garlicy goodness that coated our shrimp, we knew we had made one of the best decisions of the day. I ordered the Lemon Butter Shrimp but the Scrimp Scampi was the real star.



Waimea Bay: Just up the road from Giovanni’s Shrimp truck is Waimea Bay. This was a nice change of pace from Waikiki as there were only a handful of people around the entire beach. We parked across the street and set up close to the water. The currents at this beach are strong. We went during the summer so the waves were mild but in the winter you shouldn’t swim there. There’s a cliff that many people were jumping off that was really fun to watch. We didn’t partake but maybe next trip! We spent our time here people watching, swimming a little and  reading on the beach.

travel hawaii
Waimea Bay

Shave Ice: Head back towards the shrimp truck. Matsumoto Shave Ice isn’t far away. We waited in a long line but it went quickly. I ordered the Hawaiian (pineapple, coconut, banana) and added ice cream to it. Oh man, there’s a reason this place is famous! It was a nice treat after being in the heat but you really only need a small.


Haleiwa: Once you’re done with your shave ice, there’s a few stores to check out while in Haleiwa. We walked up and down the street and went into a handful of stores before we decided to take the scenic drive home.

We drove 83 back to Waikiki and stopped at some amazing beaches on the way home. On one side of the road you have these towering, lush green mountains looming over you. To your right you have the beautiful ocean till it meets the skyline. A drive I will never forget.


Day 5 and Day 6

You can imagine that after the last few days, we were ready for some extra relaxation. Day five and day six was spent lounging and going on a dinner cruise around the Waikiki beach Harbor.

Breakfast: Duke’s Waikiki might be touristy but you’ll eat right next to the water and the breakfast buffet isn’t half bad.


Lunch: We discovered this amazing food truck next to our hostel on Cartwright Road. I had pesto steak with a salad and the most amazing passion fruit banana bread. For under ten bucks, you can bet we went both day five and day six.


Dinner Day 5: Oahu dinner cruise complete with probably a dozen taro rolls to complement our lobster. The cruise company picked us up from Waikiki and took us to the starting location and brought us back at the end of the evening. It was the perfect last night in Hawaii.


Dinner Day 6: We went back to Lulu’s for one amazing goodbye dinner and a last look at Waikiki beach. It was time to grab our bags and head to the airport for our overnight flight.


The week may be over, but you’ll have wonderful memories and beautiful photos of Hawaii. Make sure to show them to all the people who told you Hawaii is too far away!

You may also like

Leave a Reply

Your email address will not be published. Required fields are marked *