Oahu Sunrise Tour: Winter Island Highlights

Join our Oahu 10 Stop Circle Island Tour and experience personalized attention, small tour groups, and a personable atmosphere. Enjoy a free Dole Pineapple and don’t miss the locally grown Kahuku Shrimp!

Duration: 9 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • Diamond Head State Monument - Imagine driving on the very road that Amelia Earhart used as her runway in 1935. That’s our first stop! Diamond Head lookout offers breathtaking views of Oahu’s southern shore and Waikiki.
  • Kahala - Dreaming is encouraged as we pass through the luxurious Kahala neighborhood, home to the annual Sony Open. The…
What's Included
  • Waikiki hotel pickup and drop off
  • Water
  • Live Commentary
  • Use of snorkeling equipment
  • In-vehicle air conditioning
Additional Information

In December and January, this tour kicks off with a breathtaking sunrise viewing from a specially selected spot, perfectly timed to witness the sun rising over Oahu. It’s a serene and unforgettable way to start the day, offering a distinctive seasonal experience not commonly found on other tours.
Following the sunrise, the tour continues with an…

Location
Diamond Head State Monument
18th Ave., Waikiki
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(1814 Ratings)
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76ajd
Sep 11, 2026
Make it your first tour in Oahu - Where to start? When Leonani first showed up for pickup, my wife and I chuckled at how young she was. To be honest we were a bit concerned. SHAME ON US! This young lady was incredible! While talking about the culture and lore of the island, she drove like a pro, would interrupt her own storytelling to point out various points of interest, and then without missing a beat… would start right back into the storytelling! She was knowledgeable about not just the history and culture but also current events. She never lost her smile, joy, or enthusiasm. Just an incredible guide! As a reference, the next day we did a tour to Pearl Harbor and Honolulu. The guide, with a different company, was our age, 50-60, and mentioned similar things that Leonani had mentioned. The difference was clear. He did not sound confident and the information he gave lacked the lore/ culture we had just experienced. In fact, due to what we had learned the previous day, we helped our group learn even more. MAHALO to Pineapple Express and especially to Leonani for destroying our preconceived expectations! STRONGLY recommend this tour!!
Review provided by Tripadvisor
Leopoldo_v
Sep 9, 2026
Circle Island Tour September 2026 - Diffently must do. Plan and schedule early on your vacation. We planned our the day after our arrival on Oaho.
Review provided by Viator
Marsha_w
Sep 8, 2026
Must Do! - I have to say this was one of the best tours I've ever done! From the moment we were picked up until we were dropped off, we saw so many places and had a blast with the driver/owner, Tyrone. Tyrone was fun, entertaining and very knowledgeable of the island. The small group also made this tour amazing. Our group was friendly and we enjoyed ourselves as if we were all family. Highly recommend this tour !
Review provided by Viator
Ana_m
Sep 5, 2026
Waikiki island tour - Best experience ever,Piilani was so kind and she had everything on point, we had so much fun !!! I recommend everyone to have a tour with Piilani,she's Awesome!
Review provided by Viator
524adrianner
Sep 3, 2026
Pineapple Express Oahu circle tour - My husband and I had a wonderful day with PE our tour guide. She was very informative and friendly. Well worth doing this day tour
Review provided by Tripadvisor
Paul_l
Aug 19, 2026
We had Leo as our guide,... - We had Leo as our guide, and she made the experience memorable, with interesting stories and fun commentary. There was so much beauty to see throughout the trip. Thanks again, Leo! Mahalo!
Review provided by Viator
Michele_h
Aug 18, 2026
A Great Island Tour! - We had an absolutely wonderful experience on this island tour! Ryan was an exceptional tour guide. He was friendly, engaging, and incredibly knowledgeable about Hawaiian history, culture, and the island. His insight and stories added so much to every stop and made the entire experience feel much more meaningful than simply sightseeing. I especially loved the small-group format. It made the tour feel relaxed and personal. We were able to really enjoy the scenery, ask questions, and learn so much along the way. This was a fantastic way to experience the island and was definitely one of the highlights of our trip. Ryan made an already beautiful tour even better. I would highly recommend this tour and if you’re lucky enough to have Ryan as your guide, you’re in for a great day!
Review provided by Viator
Anita_g
Aug 17, 2026
Great Circle Tour! - Nikki was a great tour guide! We had a lot of fun and great unexpected stops! Even with the rain and winds at times, we still had a great time! This was the day before Hurricane Lala! But still a lot of fun!
Review provided by Viator
622baileyf
Aug 11, 2026
Great for seeing the whole island! - Had a great time all around the island with PE as our lovely driver! She is very knowledgeable and great at trying to avoid crowds and knows all the back roads. Tour is around 8 hours and would recommend doing it at the very beginning of your stay on O’ahu. Great for seeing where you want to spend more time on the island.
Review provided by Tripadvisor
Yash_k
Sep 7, 2026
Awesome Guide, but mid Tour - The Pros: Our guide Leio was awesome. She was energetic, friendly and fun. Pineapple Express should give her a raise. The Cons: The tour only passes by the most exciting stops and stops at stores. They want you to buy stuff from stores they have tie ups with. The tour stops at the macadamia nut store for 30 minutes, where there is literally nothing to do. Then we stopped at Dole plantation for only 20 minutes. There was so much to do there, but 20 minute stop is too short to do anything. Our intent of booking this tour was to see tourist attractions on Ohau that we couldn’t see without a driving license. But the tour guide only kept saying “You should go here, it’s really good” at all the actual exciting places that are on the “pass by” list.
Review provided by Viator
From $99
up to 14 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).