Small-Group Oahu Circle Island Tour with Professional Photography
See more
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.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 9.5 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Waikiki hotel pickup and drop off
- Water
- Live Commentary
- Use of Snorkelling equipment
- Air-conditioned vehicle
Itinerary
-
Stop 1
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!
-
Stop 2
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.
-
Stop 3
Halona Blowhole. Halona means “Of Happy Fortune” this amazing sight is one of just three in the world! And what happy fortune we have to be able to show it to YOU!
-
Stop 4
Cruzen over to Makapu’u Lookout we will be passing by the most sought out bodysurfing beach on the island-even by presidents; Sandy Beach! Don’t let the smaller waves fool you, that water is ruff!
-
Stop 5
Some call this place “The Dragon” These cliffs whereupon The Dragon lay will loosen the jaw in awe! I’m sure your tour guide will be more than happy to explain way! Well, SHOW you why! It’s an amazing site! Unfortunately this place is closed to commercial vehicles. However, you can still see The Dragon!
-
Stop 6
Experience Hawaiʻi’s natural “wind bath” at Nuʻuanu Pali Lookout, where powerful trade winds, towering cliffs, and panoramic Windward Coast views create one of Oʻahu’s most unforgettable stops.
-
Stop 7
Are you hungry yet? Well, you will be. And what better place to get lunch than the North Shores’ Fumis shrimp truck! These generously sized shrimp has taste you will call home about. If you are not a shrimp eater it’s completely okay; there are other options. Including a very inviting Vegetarian noodle plate that might have you driving to the north shore for more the next day!
-
Stop 8
Now, let us get those swimsuits on! If you don’t want to swim or snorkel it is completely fine; there is plenty enough shade to stretch, relax and read that favorite book! Don’t forget; the snorkel gear is FREE to rent!
-
Stop 9
Cliff walking anyone? of course it is completely up to you; you can always stay on the safe side of the railing and still get to see an amazing view. Makapu’u Lookouts’ amazing cliffs make a feast for your eyes. Not only because it means “bulging eye” in Hawaiian, either.
-
Stop 10
The very first place a foreigner landed in Hawaii was here in the 1700's! That was Capitan Cook and his crew. Waimea Bay is beyond majestic. From the beautiful, rainforest kissed cliffs that surround it to the proud protruding rock in the center. You will see nothing but beauty.
-
Stop 11
The original Hawaiian name for this place is Paumalū. Sunset Beach is known for big wave surfing during the winter season and I mean BIG. Keep your eyes open, you may see some surfers on the tops of the waves!
-
Stop 12
Let us time travel back to the 1800’s. Back to a little place now called Historic Haleiwa Town. Matsumoto’s Shave Ice isn’t the only thing cool about this place! Just wait and see!
-
Stop 13
Our last location is sweet to say the least; The Dole Plantation. Home of the world famous, oh yes, DOLE WHIP. Ask your Guide how you can win a FREE one!
-
Stop 14
Food and beach usually equates to a long nap but not yet! We are headed to the North Shore Macadamia Nut Farm! And yes, there are FREE samples of both macadamia nuts AND coffee!
Meeting point & pickup
Hotel pickup included for all travelers
Aloha!
Please be advised that we only do pickups in Waikiki and Ala Moana Area. Also, your pickup time may be subject to change and is at your drivers discretion (we do sunrise pickups during winter months). We DO NOT do pickups outside of Waikiki / Ala Moana area. We DO NOT pickup from Airport hotel, or Ko'olina area. Correctly input your location and, as long as your hotel is in Waikiki / Ala Moana area, we will be able to pick you up. If you purchase tickets and your location is outside of Waikiki / Ala Moana area, you must find a way to a Waikiki hotel. Pickups start at 7am. If you are driving to Waikiki, please email us so that we can guide you to a place where you can park for free. Please be advised that snorkeling / swimming time will be allotted at North Shore beach stop. See you soon!
How to get there
Pickup is available from 79 listed hotels. Exact pickup time is confirmed after booking.
Cancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day(s) before
- 0% refund if cancelled 0–1 day(s) before
- May be cancelled for bad weather
- May be cancelled if there are not enough travelers
Instant confirmation
Your booking is confirmed immediately after checkout.
From $99.00 per person
- Free cancellation
- Secure checkout with our booking partner
