A Fun and Romantic Trip to Oahu and Kauai

Recently, Jennifer and her husband returned from a trip to Oahu and Kauai.

When Jennifer first approached me, she initially thought she wanted to take an 8 night vacation to Oahu. After I asked her several questions on her vision for her trip, I realized four nights on Oahu and four nights on Kauai would be a great mix of city, adventure, and enjoying Hawaii's beautiful landscapes.

Jennifer and her husband started their trip in Oahu. When arriving at the Honolulu airport, most people have a vision of being greeted with a flower lei and welcomed to the islands. Most people don’t know this is an extra charge and must arranged in advance. It’s called lei service and most transfer companies offer it. A transfer is a better way to go than taking a taxi. A shared shuttle to your hotel is usually a significant savings over a taxi. A private transfer is not significantly more.

After chatting about all the hotel options in Waikiki, we narrowed down to the
Outrigger Reef Waikiki Beach because of the resort's great location. You are beachfront on Waikiki Beach with lots of dining options nearby. The resort usually has good promotions that help lower the rate. Since most flights from Honolulu back to mainland USA are overnight flights, the hotel will hold your bags on your check out day and let you use a room shower – a great perk.

One note about most resorts in Honolulu – they have resort fees. These fees can range from $15 - $50 per day plus tax. I always make sure my clients know what the fees will be when comparing resorts.

One tour I recommend is Arizona Memorial, USS Missouri and City Tour

The Pearl Harbor tours have very early start times. Hotel pick up is between 5:30 am – 6:00 am. The reason for this is that the tour companies want to get to the Pearl Harbor sites right when they open versus later in the afternoon when the crowds will be larger. I recommend taking the early tour on your first or second day in Honolulu because you will still be on your local time. For instance, if you are traveling from the Midwest, 5:30 m Hawaii time is 9:30 am Central time. My personal experience is that it takes me a few days to adjust to the new time zone so it’s nice to know when you wake up at 4:00 am Hawaii time, you only have an hour or so until your tour starts.

For a more unusual activity, Diamond Head Trikke Guided Tour is a fun option. Trikkes are three wheeled scooter like device. Click here for a picture.  Here’s what she thought:

“The trikke tour did not really include diamond head (just an fyi) but did a great city tour...it lasted about 2 to 2 and a half hours. The tour guide was super easy going and silly.”

One must do activity in Oahu is snorkel Hanauma Bay Snorkeling – I think Jennifer describes it best:


“Snorkeling...was amazing. I recommend not booking this ahead of time. I would tell people that is the day to rent a car. That way you can arrive and leave when you want. It was a 30 minute drive to Hanauma Bay. It cost 1 dollar to park. We got there before they opened which was a great idea. We waited about 30 minutes in line before they opened. It was 7.50 to get in (no matter what). We got our tickets and watched a 10 minutes video about the bay and rules. Everyone must. They have food and rentals of everything right there. It was super cheap. We spent about 2 or 3 hours but you could stay all day if you wanted. You could pack food of your own too. It would have stunk of we ended up using the transportation provided because we would have had to leave earlier.”


One note on Jennifer’s advice not to book Hanauma Bay in advance – this may not work on your trip. Hanauma Bay has a limit on the number of people who can snorkel per day so they can sell out. We can talk about what the best option for you may be depending on the time of year you are visiting.


Depending on how much of Oahu you’d like to see, most people spend 3 – 4 nights in Oahu and then move on to another island. One day is usually a Pearl Harbor tour. The next day is some type of land exploration like the Trikke tour, climbing Diamond Head, or visiting the Dole Plantation. The third day is a water experience like snorkeling Hanauma Bay or surfing the North Shore.

After four nights in Oahu, Jennifer and her husband moved on to Kauai.

Kauai  has many beautiful resorts. The Sheraton Kauai Resort was a good fit for Jennifer's trip because the hotel is in a great location and often offers promotions that include breakfast. It also has a great luau on site. We originally booked Jennifer for the Smith's luau, but that was 45 minutes from the hotel so she worked with the representatives on site to rebook for the Sheraton's luau. It worked out great!

Here’s Jennifer’s review of the luau:

“Our hotel luau started at 530. It ended around 845. The food was great and there was tons. Open bar was awesome and nobody had to drive or leave an hour early. The entertainment was top notch. It had about 275 people so it was a bit crowded but our table mates were fun and we made it work. It was buffet style appetizers, then dinner then dessert. It worked well. We were both able to drink then walk back to our room. That was perfect.”

One must do activity is to see the Napali coast. Since much of the coastline is inaccessible, you can do this by helicopter or boat. Jennifer and her husband took the Napali Sunset Dinner Cruise.


Here’s her review:

“Sunset cruise was perfect. Our crew was great. Friendly, out going, silly, and super easy going. Our caption knew his stuff and made us feel right at home. The weather had been bad for the last week so the surf on the napali coast was having 30 foot swells so we had to go to the other side of the island...unlucky. But we still got to see seals, turtles, dolphins and two whales. We had snacks, drinks and dinner. We ended up not seeing a sunset because it was so cloudy but it was just unlucky again. It was totally worth it. The worst part was it was 11 miles away (24 minutes) so we took a cab and it cost 38.70 without tip...one way. So we spent 85 round trip on cab fare. There really was no other way to do it if you want to drink on the cruise.”

Many people try surfing on Oahu, but Kauai also offers the chance to surf without having to compete with the pro surfers. Jennifer and her husband booked a Semi-Private Surf Lesson.


“Surfing was totally worth the semi private price. We ended up having our own instructors...so it was one to one. But two to one would have been ok. 4 to 1 would have stunk! I was able to stand up for several waves. We spent every minute of our time in the water. Maybe even a few extra. We forgot towels...definitely something to remind people of.”

Have you been to Oahu or Kauai? What tips do you have? Please leave them in the comments below.

If you are thinking about a trip to Hawaii, email me so we can evaluate your options.

Aloha!