Hawaii Holiday & Seasonal Tours

40 Results
Sort by:
Price (Low to High)
Filter
Languages Clear
Time of Day Clear
29
24
13
Duration Clear
7
35
7
1
0
Price Clear
$0 $500+
Rating Clear
30
38
39
Specials Clear
39
5
0
12
1
Features Clear
3
20
32
0
28
0
Accessibility Clear
6
21
26
Families Clear
25
16
12

Hawaii Activities

Attractions

Guides

Calendar

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
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
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
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
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
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 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
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

Frequently Asked Questions

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

Recent activity reviews
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
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
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
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
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
Great way to see the island and learned so much!
New York City
5-Hour Private Customized Luxury Convertible Tour of Oahu’s South Shore
Cathy F, Apr 2025
Great way to see the island and learned so much!
This was such a great experience that we booked a 2nd day! Mark was great and so easy to talk to! Loved being able to personalize the experience to the kind of things we liked. HIGHLY RECOMMEND! Learned a lot and had 2 great days!
Read more
Whales!
New York City
Private Whale Watching Adventure
Global442130, Feb 2025
Whales!
Very fun adventure! Boat is great, captain is very nice, whales are breathtaking! Video of our adventure was a cherry on top! Highly recommend!
Read more
Whale-watching at its best!
New York City
Private Whale Watching Adventure
kmberger2018, Jan 2025
Whale-watching at its best!
Five of us had a great adventure on the water with Capt. Chris and Josh in the tiny but mighty RHIB! We were able to move quickly and efficiently to wherever the humpback whales were sighted. Because of this flexibility, we were able to have more encounters with whales than most other boats that took longer to maneuver near the whales. The experience of being closer to the water was exhilarating! We always stayed a respectful distance from the whales, unlike some other tour providers we saw. Chris and Josh were personable and fun to spend the 2 hours with! The best things about this tour is that we did not have to share the railing of a large boat with one hundred other people, and we received an excellent video from Chris of a whale we saw closely as it passed under our boat!
Read more
Wedding
New York City
The Destination Wedding Experience Kauai
Maps66722545893, Jan 2024
Wedding
Was amazing wedding, enjoyed everything place staff's climate everything mesmerizing, especially Mr Navneet, Goutam Sourav Bejoy And Ms Bimit frot office, thanks to all
Read more
Treat Yourself to the Gift of Goddess Empowerment
New York City
Flying Dress Photo Shoot in Maui
L4098OJveroniquer, Mar 2023
Treat Yourself to the Gift of Goddess Empowerment
The flying dress photoshoot was beyond ethereal. I truly felt like a goddess in my silky, hot pink gown as I posed in the magical forests of Maui. I felt so empowered in my femininity, I had to take advantage of these wonderful ladies time here on Maui to shoot again. Both photo shoots left me feeling rejuvenated and absolutely beautiful. The way they captured me in these gowns truly invigorated my own self love and helped me to embrace myself exactly as I am. My inner child was overflowing with joy at the chance to play dress up in these absolutely stunning locations. I will be forever grateful that I did this and for the bright, loving souls behind the scenes. Thank you so much Michelle and Christi for the wonderful work you’re doing in this world.
Read more
Sexy / Unique / Fairytale
New York City
Flying Dress Photo Shoot in Maui
Jonathan T, Feb 2023
Sexy / Unique / Fairytale
I wanted to surprise my wife with something unique and special while we were visiting Maui. I booked the half-hour photo shoot, and she had a blast with our photographer Michelle and the Dress Flyer Christi. My wife absolutely loved the experience. She said it was sexy, exhilarating, and a once in a lifetime experience. When we finished the photo shoot, Michelle showed us a glimpse of some of the pictures she captured. BEAUTIFUL! I highly recommend, can't say enough good things about the whole experience.
Read more
We love Jen Jen
New York City
The Destination Wedding Experience Kauai
chriswU4822RA, Apr 2022
We love Jen Jen
Jen Jen was amazing, she treated us so nice and handled everything for us. There were so many details that we needed assistance with, but Jen came through for us. My wife and I are so grateful we got to spend more time enjoying each others company and loving each other on this beautiful island. We are now married and have wonderful memories thank to Jen and her beautiful voice
Read more
Hawaii Activities
Attractions
Guides
Calendar
View more
View more