Premium Oahu Circle Island Tour – Small Group, No Crowds
Overview
Available languages
9 hours 30 minutes
Mobile ticket
During December and January, this tour begins with a sunrise viewing from a beautiful, hand-picked location, timed so you actually get to watch the sun come up over Oahu. It’s a peaceful and memorable start to the day, and a unique seasonal experience you won’t find on most tours.
After sunrise, we explore Oahu’s top highlights with a focus on comfort, culture, and connection. Our groups are intentionally small so you can ask questions, share stories, and get to know your guide and fellow travelers. You’ll feel like a welcomed guest, not part of a crowd.
At The Pineapple EXP, we believe quality matters. We might not be the biggest company on the island, but we work hard to make every guest feel cared for. If you’re visiting in winter and want a Circle Island experience with great views, good company, and genuine hospitality, this is the tour for you.
Additional Info
Service animals allowed
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Suitable for all physical fitness levels
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
Diamond Head State Monument
Have you ever thought you would be driving on the exact same road that Amelia Earhart used as her runway in 1935? Well, that is our FIRST stop! Diamondhead lookout is an amazing location that offers panoramic views of the southern shore of Oahu and Waikiki!
Kahala
Sometimes it is good to dream and day dreaming is what most of us will be doing as we pass by the luxurious neighborhood of Kahala wherein the Sony Open is played every year. The estates here will have most of us rethinking our life choices.
What‘s Included
Waikiki hotel pickup and drop off
Water
Whole Dole pineapple (limit one per party)
Live Commentary
Use of Snorkelling equipment
Air-conditioned vehicle
Pickup points
Select a pickup point
Options
Breathtaking 8-Hour Circle Island Tour from Honolulu
Pickup included
Reviews
1,733 reviews
Total reviews and rating from Viator & Tripadvisor
Great tour
763yipingh,Mar 31, 2026
- Review from Tripadvisor
5.00Great experience with our tour guide Trey. He is informative and engaging. Timely pickup at our hotel. We arrived at each attraction spots earlier than other tour groups, so it was not crowded for us to take pictures. Good restroom breaks in between our stops on the tour. It was a compacted 8-hour tour and we got to see many beautiful sceneries and experience a glimpse of the locals' lives.
Highly recommend this small group tour
Curiosity13535480054,Mar 29, 2026
- Review from Tripadvisor
5.00This was the best thing I did on my first trip to O'ahu. It was a great way to see an overview of the island and get a sense for the place outside of Waikiki. It's a small van tour instead of a large bus which makes a huge difference in how much time you actually get to spend at places rather than having to wrangle guests. Some of the stops were very much tourist traps, but you are going to get than on any tour. The scenic stops were beautiful, the drive was comfortable and pretty, the tour guide (Anna) was incredibly knowledgeable about native flora and fauna, history, legends, and the sites we stopped at. She did a great job of engaging the guests with each other as well. This was definitely the best tour I did on my trip - despite being there during crazy weather and needing to be flexible on some of our stops.
Tyrone & Pinneapple Express Circle Tour is Wroth it!
Mobile611836,Mar 28, 2026
- Review from Tripadvisor
5.00We went on such a fun tour with Pinneapple Express. We loved our tour guide Tyrone. From early in the morning and throughout the day he kept us laughing and gave a lot of good history about Oahu that we were very interested in learning.
Tyrone was great
Brandee S,Mar 28, 2026
- Review from Viator
5.00A must for first timers and I recommend doing this early/first on your trip so if you want to go back to anything you have time. If you can request Tyrone he is an excellent guide and super fun.
Great tour. Tour guide,...
Nisha T,Mar 23, 2026
- Review from Viator
5.00Great tour. Tour guide, Anna, was fun, knowledgeable, and attentive. Good size group of people such that the tour guide could chat with everyone that was interested. The lunch food itself was disappointing tho the spot was clearly setup well for tourists. Overall, great tour and would highly recommend.
Fun circle tour in the rain!
Erica H,Mar 20, 2026
- Review from Viator
5.00It was a very informative & full day traveling with Tyrone & group. We went around the majority of the island for 9 hours.
Honeymoon Starting adventure!
John E,Mar 20, 2026
- Review from Viator
5.00The tour was a good time. Anna was a great guide. Despite the rain we saw some great views and had some good food. Their was a few changes to the tour, no snorkeling cuz of the rain, so more time in town and at Dole. We appreciated the surprise stop at Nanding's Bakery for a Spanish roll while picking up last minute guests. And now we got Mauna Loa chocolate macadamia nuts instead of a pineapple, which I appreciate LOL 🤣. Was a great way to start our honeymoon and get a sense of the island and figure out place we want to go. Well worth it, and I hope you get Anna.
Good venues and great...
Maryann M,Mar 19, 2026
- Review from Viator
5.00Good venues and great tour guide/driver. Anna was very knowledgeable and made the tour very pleasant. Loved the music!!
Circle tour
Curious642815,Mar 18, 2026
- Review from Tripadvisor
5.00Great! Nikki was very informative and interesting. Highly recommend.
A must do on Oahu!!!
Kim T,Mar 12, 2026
- Review from Viator
5.00Anna was the absolute BEST. She was so fun and knowledgable, and made me feel so welcomed as a solo traveler! She texted the night before with all we needed to know, and hotel pickup was right on time at 6:45am. From there I turned my brain off and listened to all her stories/facts/legends/history about the islands, and learned so much! This was an amazing way to see Oahu and stop at so many landmarks, especially if you're not renting a car! Beautiful views, a scenic drive, and little to no crowds. The only thing that would've made it even better is maybe 5-10 extra mins at the Haleiwa stop, but that's if I'm being extra nitpicky. We made it back to Waikiki at around 3/3:30pm. This was probably one of my favorite days of my entire solo trip and I'm so glad I booked this tour bc had I not, I likely wouldn't have been able to see all that I did. I never write reviews lol but I genuinely had an amazing time and Anna deserves HUGE props!!! Would recommend this a million times over
From US$115.00
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Operated by The Pineapple EXP