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Oahu Outdoor Activities

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Oahu Activities

Attractions

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Oahu friendly hiking experience

SPECIAL DISCOUNT for direct booking in our website: https://www.mshawaiitours.com/ We offer private tours customized to the client. We are flexible for pick up and drop …More

4.7 (14)

Oahu friendly hiking experience

SPECIAL DISCOUNT for direct booking in our website: https://www.mshawaiitours.com/ We offer private tours customized to the client. We are flexible for pick up and drop...

2 to 4 hours • Hotel pickup offered • Free Cancellation
4.7 (14)
from
$300
Semi Private Surfing Lesson 2 hrs

This lesson gives you a more personal surfing experience and allows you to surf at your own pace, Surf by yourself or with a private …More

5.0 (1)

Semi Private Surfing Lesson 2 hrs

This lesson gives you a more personal surfing experience and allows you to surf at your own pace, Surf by yourself or with a private...

2 hours • Free Cancellation
5.0 (1)
from
$156
Private 45 Minute Helicopter Tour with Romantic Landing

Let us whisk you away to an exclusive landing spot at a stunning and private valley on the Windward coast of O'ahu. This beautiful, 4000-acre …More

5.0 (4)

Private 45 Minute Helicopter Tour with Romantic Landing

Let us whisk you away to an exclusive landing spot at a stunning and private valley on the Windward coast of O'ahu. This beautiful, 4000-acre...

1 hour • Free Cancellation
5.0 (4)
from
$3,240
Honolulu Rainforest Self-Guided Audio Tour

See a rarely explored corner of Honolulu! Hawaii's bustling capital may be known for its beaches and high-rise buildings but did you know just a …More

4.3 (7)

Honolulu Rainforest Self-Guided Audio Tour

See a rarely explored corner of Honolulu! Hawaii's bustling capital may be known for its beaches and high-rise buildings but did you know just a...

4 to 5 hours • Free Cancellation
4.3 (7)
from
$20
Diamond Head Shuttle with Malasada

Experience the most popular hiking trails in a short time in the morning Includes a Malasada from Leonard's, where the line is long every day. …More

4.5 (8)

Diamond Head Shuttle with Malasada

Experience the most popular hiking trails in a short time in the morning Includes a Malasada from Leonard's, where the line is long every day....

2 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.5 (8)
from
$69
3 Hour Sightseeing *SPECIALTY Tour

(* A MINIMUM OF 4 PEOPLE IS REQUIRED ON THIS 3 HOUR TOUR) What’s the best way to experience all the diverse beauty of Oahu …More

4.0 (1)

3 Hour Sightseeing *SPECIALTY Tour

(* A MINIMUM OF 4 PEOPLE IS REQUIRED ON THIS 3 HOUR TOUR) What’s the best way to experience all the diverse beauty of Oahu...

3 to 4 hours • Hotel pickup offered • Free Cancellation
4.0 (1)
from
$149
Diamond Head Hike [Starts at 7:00 a.m.]

---Diamond Hike(Sunrise)--- The Diamond Head hike offers some of the best views of Honolulu, Waikiki, Koko Head and Kahala. The early shuttle from Waikiki means …More

5.0 (2)

Diamond Head Hike [Starts at 7:00 a.m.]

---Diamond Hike(Sunrise)--- The Diamond Head hike offers some of the best views of Honolulu, Waikiki, Koko Head and Kahala. The early shuttle from Waikiki means...

2 hours 30 minutes • Hotel pickup offered
5.0 (2)
from
$59
Easy Private Hike in Honolulu (Choose 1 of 2 trails) 2-4hrs

“We enjoyed our tour guide and the privacy of the tour.”

— Tracy_C

“We enjoyed our tour guide and the privacy of the tour.”

— Tracy_C

Choose 1 of 2 hikes, either through the valley to the waterfall, or from the top of mountain with scenic views. This is a private, …More

5.0 (1)

Easy Private Hike in Honolulu (Choose 1 of 2 trails) 2-4hrs

Choose 1 of 2 hikes, either through the valley to the waterfall, or from the top of mountain with scenic views. This is a private,...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$373
Private Flying Dress Photoshoot With A View

Firstly, it's not just a photoshoot, but a journey through the hidden jewels of Oahu, allowing guests to immerse themselves in breathtaking locations while capturing …More

5.0 (2)

Private Flying Dress Photoshoot With A View

Firstly, it's not just a photoshoot, but a journey through the hidden jewels of Oahu, allowing guests to immerse themselves in breathtaking locations while capturing...

1 hour • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$450
Honolulu's Waikiki Self-Guided Walking Audio Tour

The surf’s always up with this self-guided walking tour of the Waikiki neighborhood of Honolulu! Stroll along the shimmering sand of Waikiki Beach and take …More

4.8 (4)

Honolulu's Waikiki Self-Guided Walking Audio Tour

The surf’s always up with this self-guided walking tour of the Waikiki neighborhood of Honolulu! Stroll along the shimmering sand of Waikiki Beach and take...

1 to 2 hours • Free Cancellation
4.8 (4)
from
$10
Discover Popoia Island and Kailua Bay by Kayak Guided Tour

Kayak in the crystal clear waters of Kailua Bay with one of our guides and visit one of Oahu's smallest offshore islands. It's only a …More

5.0 (4)

Discover Popoia Island and Kailua Bay by Kayak Guided Tour

Kayak in the crystal clear waters of Kailua Bay with one of our guides and visit one of Oahu's smallest offshore islands. It's only a...

3 hours • Free Cancellation
5.0 (4)
from
$169
Oahu East Coast to Mountain Slingshot Tour

Embark on an unforgettable journey through Oahu's breathtaking east coast and majestic mountains with our exclusive Oahu East Coast to Mountain Tour. Setting out from …More

5.0 (4)

Oahu East Coast to Mountain Slingshot Tour

Embark on an unforgettable journey through Oahu's breathtaking east coast and majestic mountains with our exclusive Oahu East Coast to Mountain Tour. Setting out from...

8 hours • Free Cancellation
5.0 (4)
from
$298
Waikiki Surf Lesson (Hawaiian Boy Surf School)

Escape to paradise and ride the turquoise waves with Hawaiian Boy Surf School. Born and raised on the sun-kissed shores of Hawaii, our passionate Native …More

3.8 (10)

Waikiki Surf Lesson (Hawaiian Boy Surf School)

Escape to paradise and ride the turquoise waves with Hawaiian Boy Surf School. Born and raised on the sun-kissed shores of Hawaii, our passionate Native...

1 hour • Free Cancellation
3.8 (10)
from
$75
Hawaii's Magnificent Cliffs Photography

This Adventure photo session takes you to a stunning location. At the photo location, you have marvelous views of the ocean and cliffside views with …More

5.0 (4)

Hawaii's Magnificent Cliffs Photography

This Adventure photo session takes you to a stunning location. At the photo location, you have marvelous views of the ocean and cliffside views with...

30 minutes
5.0 (4)
from
$350
Private Off Road Explorer's Tour

Experience Oahu's North Shore like never before with a private off-road tour at Gunstock Ranch! Explore scenic mountain trails, historic WWII sites, and a hidden …More

4.7 (6)

Private Off Road Explorer's Tour

Experience Oahu's North Shore like never before with a private off-road tour at Gunstock Ranch! Explore scenic mountain trails, historic WWII sites, and a hidden...

1 hour • Free Cancellation
4.7 (6)
from
$128
Surf Lesson In Waikiki- Female Instructor

Get a 90-minute personalized surfing lesson, with a friendly, easygoing instructor, catering to your skill level. As long as you can swim, there is no …More

5.0 (1)

Surf Lesson In Waikiki- Female Instructor

Get a 90-minute personalized surfing lesson, with a friendly, easygoing instructor, catering to your skill level. As long as you can swim, there is no...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$135

Frequently Asked Questions

These answers are based on answers previously given to Cool Hawaii customers' questions.

Recent activity reviews
1000/10 Explorers Tour with Devin
New York City
Private Off Road Explorer’s Tour
jadehY937DE, Sep 2026
1000/10 Explorers Tour with Devin
Super cool one of a kind experience! Devin was an amazing driver and tour guide. She was a lot of fun (request her if you can!). All the sights we saw were so beautiful and we were able to grab some guava right off the tree! Highly recommend doing this.
Read more
Kayaking
New York City
Discover Popoia Island and Kailua Bay by Kayak Guided Tour
Erik_W, Aug 2026
Kayaking
Mario was very knowledgeable and friendly. Getting to ocean was fun on electric bikes. Kayaking was great. It was a beautiful day.
Read more
Great island tour
New York City
Oahu East Coast to Mountain Slingshot Tour
littry65, Jul 2026
Great island tour
This was an awesome trip, the slingshot GPS is a bit tricky to follow but when we switched to my phone we were fine. We visited several beautiful sites, some listed, and some we added. Well worth the rental fee.
Read more
Funnnn
New York City
Oahu East Coast to Mountain Slingshot Tour
Jeese b, May 2026
Funnnn
The staff was awesome the slingshot was soo much fund
Read more
Start anywhere
New York City
Honolulu’s Waikiki Self-Guided Walking Audio Tour
Ed_B, May 2026
Start anywhere
Download and install was simple. Can start anywhere along the tour which is great. Short audio stories are informational
Read more
It was an activity in English, but easy to understand phrases...
New York City
Waikiki Surf Lesson (Hawaiian Boy Surf School)
Celia_H, Apr 2026
It was an activity in English, but easy to understand phrases...
It was an activity in English, but he explained it in an easy-to-understand way! It was a lot of fun and a great lecture and I was able to stand on the surfboard from the first shot! I'm going to ask you the next time!
Read more
Family Self Guided Tour
New York City
Honolulu Rainforest Self-Guided Audio Tour
Noria V, Mar 2026
Family Self Guided Tour
The self guided tour gave us many great places to visit.
Read more
BEST THING TO DO IN O'AHU
New York City
Private Off Road Explorer’s Tour
Phylicia330, Feb 2026
BEST THING TO DO IN O'AHU
This was one of the best experiences I have ever had traveling with my kids around the world! We planted a tree, and that was such a special experience for just my family and our friends who joined us. A very intimate group.
Read more
Ali is great.
New York City
Surf Lesson In Waikiki- Female Instructor
harthanj, Jan 2026
Ali is great.
Ali is great. I was super nervous about looking stupid doing my first surf lesson as a 37yo guy from the Midwest that had never thought about surfing until I booked my trip to Hawaii. Ali reached out before my lesson and made me feel like even if I couldn't catch a few waves during my lesson that it wasn't a big deal... which made it so much easier to actually do well. Once I got to my lesson she was direct and to the point on what I should do, even to the point that she told me "no, do it again like I told you" on the shore and after about 10 minutes on land she said "okay lets get in the water". I would have never believed i would catch my first two waves(forget the third and forth that I messed up because I wasn't doing what Ali said I should) even when I had poor technique Ali was kind,direct, and positive. Out of 12 waves I attempt in my lesson I am pretty sure I caught 8 of them. Ali is amazing. Btw apparently she also does hiking/rock climbing tours and after my experience with my surf lesson, I would go anywhere with Ali... because I know she has my back!!!
Read more
Perfect afternoon.
New York City
Discover Popoia Island and Kailua Bay by Kayak Guided Tour
Mark C, Jan 2026
Perfect afternoon.
Excellent experience. Kyle was our guide. He was very sensitive to our needs. He seemed knowledgeable on local history, culture species of fish, birds,etc. We really enjoyed the experience and would recommend it to anyone. We did the half day excursion.
Read more
Great instruction!
New York City
Waikiki Surf Lesson (Hawaiian Boy Surf School)
Eldon_O, Jan 2026
Great instruction!
Preston was awesome! My son and I both got up on our first try after his class. He asked about our history and went with smaller boards for us. The whole experience was fantastic. You meet at the famous Duke statue.
Read more
Diamond head hike review
New York City
Oahu friendly hiking experience
Tim M, Dec 2025
Diamond head hike review
Pietra was the best tour guide! Her knowledge of the island and infectious positivity was a highlight of our trip! She helped us get wonderful photo opportunities at the site and took photos for us as well. She shared wonderful insights of the island and told of of the rich history here. 10/10 I recommend Massimo tours!
Read more
Great Experience!
New York City
Oahu friendly hiking experience
jeffmJ8077IA, Dec 2025
Great Experience!
This was the highlight of our trip to Hawaii. We had several activities, but this one was the best one and most informative. Would definitely recommend to anyone!
Read more
It was amazing! Our...
New York City
Diamond Head Hike [Starts at 7:00 a.m.]
Jessica_G, Jul 2025
It was amazing! Our...
It was amazing! Our driver got us there early and we were able to start the hike! We had enough time to hike and get pictures!
Read more
We enjoyed our tour guide...
New York City
Easy Private Hike in Honolulu (Choose 1 of 2 trails) 2-4hrs
Tracy_C, May 2025
We enjoyed our tour guide...
We enjoyed our tour guide and the privacy of the tour. It was just me and my son and we took an incredibly awesome hike and took the most amazing pictures!
Read more
Great hike but frustrating drive to and from.
New York City
Diamond Head Hike [Starts at 7:00 a.m.]
tobyc693, Apr 2025
Great hike but frustrating drive to and from.
The hike itself was strenuous (for an 80 year old) but exhilarating. The drive to and from the starting point, however, was VERY annoying. We were in a van with about eight others, all of whom were from Japan. Although our driver spoke English, he was Japanese and spoke Japanese 90% of the time to our other passengers. The driver was a lively 70+ man but I would have felt he should have given us equal time as we learned nothing from the info and tips he was giving to our Japanese friends.
Read more
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