Hawaii Holiday & Seasonal Tours

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Hawaii Activities

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Maui Luxury Boston Whaler Private Charter for up to 6 Passengers
Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (2)

Maui Luxury Boston Whaler Private Charter for up to 6 Passengers

Welcome to your very own private Maui adventure! Ali’i Nani, roughly translated to “Beautiful Royalty,” evokes elegance, prestige, and the ultimate in luxury. Whether you’re...

3 hours • Free Cancellation
5.0 (2)
from
$3,795
Private Whale Watching Adventure
Oahu, USA
4.9 (25)

Private Whale Watching Adventure

**Private boat tour for up to 6 people.** Larger group? Call for options. Escape the crowds and join us on 2-hour private whale watching cruise...

2 hours • Free Cancellation
4.9 (25)
from
$831
5-Hour Private Customized Luxury Convertible Tour of Oahu's South Shore
Likely to Sell Out
Likely to Sell Out
Honolulu, USA
5.0 (8)

5-Hour Private Customized Luxury Convertible Tour of Oahu's South Shore

Price is for car and driver NOT per person. The car can carry 4 passengers plus a driver so the more passengers the better the...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (8)
from
$630
Private Whale Watching Activity: 6 passengers max
Oahu, USA
5.0 (11)

Private Whale Watching Activity: 6 passengers max

Our Captain and mates have travelled all over the polynesian islands to experience other whale-watching tours and have used all the information we've learned from...

2 hours • Free Cancellation
5.0 (11)
from
$524
The Destination Wedding Experience Kauai
Kauai, USA
4.8 (4)

The Destination Wedding Experience Kauai

Want to do something fun and exciting on your destination wedding? Planning a destination wedding and not sure where to go or how much to...

1 day • Free Cancellation
4.8 (4)
from
$500
Flying Dress Photo Shoot in Maui
Maui, USA
5.0 (2)

Flying Dress Photo Shoot in Maui

You are the Emotion…You are the Intrigue…You are the Moment You are cordially invited to the most memorable experience of your life… You may not...

1 hour • Free Cancellation
5.0 (2)
from
$497
4-Hour Light Tackle Bottom Fishing in Lahaina
Maui, USA
4.8 (34)

4-Hour Light Tackle Bottom Fishing in Lahaina

We are a comfortable boat featuring a large shaded area, an onboard restroom, lots of space to move about the open decks and experienced captain...

4 hours • Free Cancellation
4.8 (34)
from
$428
Family Photography session Kauai
Kauai, USA
4.9 (83)

Family Photography session Kauai

This is a personal photographic session for you and our family. We will take pictures of your group which you will be able to cherish...

1 hour • Free Cancellation
4.9 (83)
from
$350
Semi-Private Surf Lesson in Sunny Po'ipu
Likely to Sell Out
Likely to Sell Out
Kauai, USA
5.0 (1)

Semi-Private Surf Lesson in Sunny Po'ipu

Semi-Private Surf Lesson for two or three people max means less people and more waves caught. We are the only Surf School in Po'ipu that...

1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$314
Social influencer and Travel Blogger Adventure on Kauai
Kauai, USA
5.0 (1)

Social influencer and Travel Blogger Adventure on Kauai

This is a unique tour for many reasons because you get to choose the direction we go based on how you want to market your...

1 hour • Free Cancellation
5.0 (1)
from
$300
Private Surf Lessons in Maui
Maui, USA
5.0 (2)

Private Surf Lessons in Maui

The perfect family activity on Maui, surf lessons are one of the best ways to enjoy Maui’s beautiful ocean. Unlike most large “surf schools,” our...

1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$288
New Year’s Eve Midnight Cruise
Oahu, USA
3.0 (4)

New Year’s Eve Midnight Cruise

Cruise in comfort aboard Hawaii's largest dinner cruise, taking in the breathtaking Waikiki skyline and the vibrant Honolulu city lights. Savor a gourmet dinner accompanied...

2 hours 15 minutes • Free Cancellation
3.0 (4)
from
$258
Ultimate Na Pali Coast Zodiac Boat Snorkeling and Sea Cave Tour
Kauai, USA
4.8 (96)

Ultimate Na Pali Coast Zodiac Boat Snorkeling and Sea Cave Tour

Unique and personal zodiac snorkeling adventure on Kauai’s stunning NaPali Coast. Guided snorkeling, coastline and sea cave touring (when conditions are right) with spectacular views,...

5 hours • Free Cancellation
4.8 (96)
from
$257
6 Dual-Zipline Mountain Adventure in Maui
Maui, USA
5.0 (910)

6 Dual-Zipline Mountain Adventure in Maui

Maui's ONLY all dual-line zipline adventure offers the longest ziplines, breathtaking views, a thrilling ATV ride-a-long and a spectacular 360 foot suspension bridge trek. Come...

3 hours 30 minutes • Free Cancellation
5.0 (910)
from
$250
The Secret Waterfall Private tour with photos
Kauai, USA
4.8 (59)

The Secret Waterfall Private tour with photos

This is an amazing photographic waterfalls tour. This guided 3-hour tour is a PRIVATE small-group tour that will take you to some of the most...

3 hours • Free Cancellation
4.8 (59)
from
$250
Maui: Lahaina Cacao Farm Tour and Feast
Maui, USA
5.0 (3)

Maui: Lahaina Cacao Farm Tour and Feast

Come Explore Maui’s Ku’ia Estate Cacao Farm! Your journey begins at the Ku’ia Estates Chocolate Factory in Lahaina, the largest chocolate factory in the state...

3 hours 30 minutes • Free Cancellation
5.0 (3)
from
$236

Frequently Asked Questions

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

Recent activity reviews
Exceptional in every way!!
New York City
6 Dual-Zipline Mountain Adventure in Maui
DayTrip06627975964, Sep 2026
Exceptional in every way!!
The highlight of trip to Maui. Our guides Justin and Dan were exceptional and calmed by wife's nerves with their focus on you can be safe and still have fun. The tour included so much mire than 6 great zip line runs. Starting with the 4 whellndrive van and them at off road run up the mountain the strip was great from start to finish and included an walk across a suspension bridge with beautiful views. 2 out of the 6 runs are extremely long and speeds are great. By the 2nd run all.of my wife's fears were gone and she had that need for speed. Overall highly recommend!!!!
Read more
Zipline
New York City
6 Dual-Zipline Mountain Adventure in Maui
Odyssey67524697213, Sep 2026
Zipline
Danny, Just and Wyatt. Great guides, super cool people. Awesome hospitality with an exhilarating experience!
Read more
Amazing adventure
New York City
Ultimate Na Pali Coast Zodiac Boat Snorkeling and Sea Cave Tour
Michelle_F, Sep 2026
Amazing adventure
Amazing experience! So much fun & so much adrenaline! I would do it again! Get ready to hold on tight!
Read more
Best photography!!!!
New York City
Family Photography session Kauai
Myranda_J, Aug 2026
Best photography!!!!
Zane was amazing to work with. He gave us some great insight to the island and mad us feel so comfortable! Hands down an amazing experience! ❤️
Read more
Fun, fabulous and great meal in the treehouse
New York City
Maui: Lahaina Cacao Farm Tour and Feast
bogeymom, Aug 2026
Fun, fabulous and great meal in the treehouse
Fabulous, fun and educational….the chocolate was divine!!! Gabriel, our guide, was the best!
Read more
The Captain found fish...
New York City
4-Hour Light Tackle Bottom Fishing in Lahaina
Teddy_H, Aug 2026
The Captain found fish...
The Captain found fish right away. Everyone on the boat caught something. The crew were friendly and helpful the entire trip. Boat ride was also fun.
Read more
Fast and fun!!!
New York City
Ultimate Na Pali Coast Zodiac Boat Snorkeling and Sea Cave Tour
MargySansone, Aug 2026
Fast and fun!!!
A fast ride through the water to see beautiful waterfalls, beaches and caves. Snorkeling was ok. We saw many dolphins and a seal. Captain Nick and Ona were wonderful guides. Very knowledgeable and A+ in boat handling! An awesome trip for my family of 10 from 16 to 70s!!! Highly recommended!!!
Read more
Kauai photo session
New York City
Family Photography session Kauai
David_C, Aug 2026
Kauai photo session
This was a great experience! Our photographer was very talented and had an eye for setting up and capturing great shots. He made us feel very comfortable through the whole shoot. This is a fantastic way to remember your time on Kauai. My wife and I are very glad we booked and would do it again!
Read more
Don’t pass on a great tour!
New York City
Maui: Lahaina Cacao Farm Tour and Feast
T36KTjonathanm, Jul 2026
Don’t pass on a great tour!
Our visit was easily one of the highlights of our trip to Maui! My wife and I had an incredible lunch in the Treehouse as part of an amazing tour and the entire experience exceeded our expectations.Our guide, Sean, was outstanding. He was incredibly knowledgeable, friendly, and passionate about what he does. We learned so much about chocolate farming, production, and processing—things we had never even considered before. Sean answered all of our questions and made the tour both informative and engaging.The chocolate tasting was phenomenal. Every sample was delicious, and it was clear how much care goes into every step of the process. We were also really impressed by the farm’s commitment to sustainability and giving back to the local community. It’s refreshing to see a business so dedicated to making a positive impact while producing such exceptional chocolate.If you’re visiting Maui, don’t miss this experience. The Treehouse lunch, the tour, and the chocolate are all fantastic—and if you have the chance, ask for Sean. He made an already amazing experience even better!
Read more
5 ⭐️ Fantastic fishing trip
New York City
4-Hour Light Tackle Bottom Fishing in Lahaina
NorthStar721851, Jun 2026
5 ⭐️ Fantastic fishing trip
Our family went fishing with this company and had a FANTASTIC time. Highly recommend! Guides were great and very helpful. The boat is top notch- clean, large, and had a great awning to help in the heat of the day. 5⭐️
Read more
The best!
New York City
Maui Luxury Boston Whaler Private Charter for up to 6 Passengers
annabK7253FY, May 2026
The best!
We booked a private snorkeling afternoon for our family and had an amazing time!! Travis & Dustin are truly the best! Can’t recommend enough.
Read more
Had a great time.
New York City
5-Hour Private Customized Luxury Convertible Tour of Oahu’s South Shore
W4421GGdavidh, May 2026
Had a great time.
Really enjoyed this trip. Mark was extremely flexible and very knowledgable, as well as friendly. Would definately recomend him to anyone..
Read more
Great whale watching tour
New York City
Private Whale Watching Activity: 6 passengers max
483arnolda, Feb 2026
Great whale watching tour
Great experience. Crew was amazing
Read more
10/10 loved the private whale watching
New York City
Private Whale Watching Activity: 6 passengers max
677kristens, Jan 2026
10/10 loved the private whale watching
Philip was excellent. The boat was so nice and comfortable. We saw some great wildlife. Would definitely recommend.
Read more
Photos of a Lifetime
New York City
Social influencer and Travel Blogger Adventure on Kauai
G3504VPmichelleh, Dec 2025
Photos of a Lifetime
I had an amazing time shooting in different locations. I always get a little nervous in front of the camera, but Zane was incredible to work with. If you’re solo traveling and was wondering how to get photos of a lifetime, this is it. The photos look incredible, but the memories were definitely an added bonus. Thanks again!!
Read more
Awesome day
New York City
Maui Luxury Boston Whaler Private Charter for up to 6 Passengers
Njf0618, Dec 2025
Awesome day
We had such an awesome day - got to pick where we went and what we did. We added an extra hour to the 3 hour tour and besides cruising the coast we went out to Molokini and I snorkeled - didn’t have to go back to the boat the boat stayed by me. Captain Bree and her mate Alex were very helpful and we enjoyed the day. Got to see some whale tails and a slap as well as them blowing. It’s early so there weren’t many to see yet but they found a pic of males. I couldn’t recommend them more if you want to treat yourself to a wonderful morning or afternoon.
Read more
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