Hawaii Holiday & Seasonal Tours

40 Results
Sort by:
Traveler Rating
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

Lanai Snorkel and Dolphin Watch from Maui
Maui, USA
4.6 (220)

Lanai Snorkel and Dolphin Watch from Maui

Snorkel off the island of Lana’i and watch dolphins in the wild all in one trip. You'll discover why Lana’i has been rated one of...

5 hours • Free Cancellation
4.6 (220)
from
$181
Early Bird Whale Watching Cruise from Waikiki
Oahu, USA
4.4 (195)

Early Bird Whale Watching Cruise from Waikiki

See humpback whales during their annual migration in the waters off Oahu on a whale-watching cruise from Waikiki. Enjoy great photo ops of the massive...

2 hours • Free Cancellation
4.4 (195)
from
$85
Kona Haunted Hele Ghost Tour
Big Island of Hawaii, USA
4.4 (98)

Kona Haunted Hele Ghost Tour

One of Kona's most popular nighttime activities and rated excellent on Cool Hawaii! Step into the spooky past and supernatural happenings of Kona on this...

90 to 120 minutes
4.4 (98)
from
$59
Waikiki Glass Bottom Boat Fireworks Tour
Oahu, USA
4.6 (25)

Waikiki Glass Bottom Boat Fireworks Tour

Our Friday Nights Fireworks tour outside of the Waikiki is truly a one of a kind experience. Join us and you’re sure to experience the...

1 hour • Free Cancellation
4.6 (25)
from
$61
Sunset Whale Watching Shared Activity
Big Island of Hawaii, USA
4.7 (7)

Sunset Whale Watching Shared Activity

The Kohala Coast is a whale breeding sanctuary and the best area on the big Island to encounter whale activity. The Namaka is a spacious...

2 hours 15 minutes • Hotel pickup offered • Free Cancellation
4.7 (7)
from
$157
The Lake Effect by Rajiv Joseph
Honolulu, USA
4.0 (1)

The Lake Effect by Rajiv Joseph

Join us at one of Honolulu's finest community theatres providing cutting edge, award winning productions not seen in other theatres on the island. For the...

3 hours • Free Cancellation
4.0 (1)
from
$32
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
Seasonal Small-Group Humpback Whale Watching in Kona
Big Island of Hawaii, USA

Seasonal Small-Group Humpback Whale Watching in Kona

Beat the crowds and enjoy a more personal whale watching experience aboard our comfortable, small-group vessel, designed for up to 10 passengers. With fewer guests...

2 hours 30 minutes • Free Cancellation
from
$137

Frequently Asked Questions

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

Recent activity reviews
Very nice!
New York City
Lanai Snorkel and Dolphin Watch from Maui
I359ZAkatel, Sep 2026
Very nice!
Very nicely organized tour, sadly we couldn’t see any dolphins, but overall experience was great! Thank you!
Read more
Superb sail
New York City
Lanai Snorkel and Dolphin Watch from Maui
cphoenix2016, Sep 2026
Superb sail
Crew and captain were extremely professional, and the catamaran was beautiful. While we couldn't go to Lanai due to weather conditions(pending hurricane), the captain took us to a safe location to snorkel. As an added bonus, we were "up close and personal" to MANY dolphins going to the sight and returning back. They swam directly under and beside the boat. Incredible!
Read more
Olivia was very...
New York City
Kona Haunted Hele Ghost Tour
Randall_R, Jul 2026
Olivia was very...
Olivia was very knowledgeable about the history of the island. She showed us where some sightings have happened. Those ghosts/spirits didn’t want to talk to us. It was very interesting and she did a great job!
Read more
Memories for a lifetime
New York City
Sunset Whale Watching Shared Activity
Adventure51025397977, Apr 2026
Memories for a lifetime
Some experiences just stay with you, and for us this sunset whale-watching tour was one of them. From the moment we stepped aboard, the crew made us feel less like old friends, not customers. The boat itself was beautiful, but it was the people at the helm that made the day unforgettable. Their knowledge of humpback whales was genuinely impressive: every sighting came with real context and passion, not just a rehearsed script. We got to witness spinner dolphins ride the waves alongside the boat, hear live whale song through the boat’s underwater microphone system, and see a whale calf surface with its mother. Just when we thought it couldn't get any more magical, the crew pulled out a ukulele as the sun started setting. I don't have words for how special it was. If you're debating whether to book, please, just do it. This is an operation that clearly pours their heart into every single tour. Absolutely 5 stars.
Read more
Smooth sailing and beautiful views
New York City
Early Bird Whale Watching Cruise from Waikiki
Navigate794668, Mar 2026
Smooth sailing and beautiful views
My boyfriend and I went on the Early Bird Whale Watching Cruise and we both had a great time. The cruise is ~2 hours long and I wish it could've been longer. It was a beautiful sunny day when we went, but eve if the weather is bad, there is indoor and covered seating and viewing locations. It is a family friendly and accessibility friendly boat making it great for everyone to be on board. The staff were kind and helpful, we enjoyed the onboard Naturalist's informative overview of whales and the other animals of the Hawaiian islands. And even though we didn't see any whales on this trip, you get a voucher to go on another cruise with them during whale season which is a cool gesture
Read more
Family Friendly Friday Night Fireworks
New York City
Waikiki Glass Bottom Boat Fireworks Tour
Nakia_B, Feb 2026
Family Friendly Friday Night Fireworks
We booked this excursion for the kids in our group. The scenery was beautiful and I believe that it was a great idea to watch the fireworks show that happens every Friday night in Oahu from the ocean view. We did not see a lot of fish in the glass bottom but the firework show was amazing the music was great and the staff was very kind. I would definitely recommend this experience to others. This operator offers specific glass bottom boat tours that I believe would have been a great way to view marine life.
Read more
whale watching Star of Honolulu
New York City
Early Bird Whale Watching Cruise from Waikiki
Ambassador9618, Feb 2026
whale watching Star of Honolulu
The Captain and the crew were very helpful and friendly with information and finding whales. Great Time Aloha
Read more
Best Whale Watch Trip Ever
New York City
Sunset Whale Watching Shared Activity
283jefferys, Feb 2026
Best Whale Watch Trip Ever
Crew was great. They don’t crowd the boat. Also, we meet in Kohalo shopping center NOT in downtown Kailua-Kona. It’s very convenient to resorts north of the airport. We saw spinner dolphins, flying fish, and whales! The whale breached 5 times-amazing
Read more
Kona Ghost tour
New York City
Kona Haunted Hele Ghost Tour
David_R, Feb 2026
Kona Ghost tour
More then a ghost tour, lots of history about the Kona area and Hawaii in general, our guide was for informative and knowledgeable, easy to talk to and ask questions of. If your a history buff or a paranormal buff you will enjoy
Read more
The experience was very...
New York City
Waikiki Glass Bottom Boat Fireworks Tour
Danny_T, Jan 2026
The experience was very...
The experience was very fun. It was nice to just cruise and see the city from the ocean at night with a nice night breeze. The captain has a very fun personality and made the ride quite enjoyable. The fireworks we also very nice to see from the ocean view. Regarding the glass bottom; do not expect a full see through bottom. Instead there are 4 large windows attached to the bottom of the boat where you can see the ocean floor and wild life.
Read more
Best encounter with Captain Stefan!!!
New York City
New Year’s Eve Midnight Cruise
_U9584NZ, Jan 2025
Best encounter with Captain Stefan!!!
Captain Stefan guided us around the ship. I was very good at Japanese and liked it. I was so happy to be shown the outside of the 4th floor, to see the stars, and to be treated to juice. He was very kind and funny and had a good time. I was glad that he learned it by attending twice during his trip. The rice was very good, and the dancing, singing and music were wonderful.
Read more
Surfing lessons with dolphins!
New York City
Lanai Snorkel and Dolphin Watch from Maui
jefedh, Aug 2026
Surfing lessons with dolphins!
No time share presentation! LOL Great crew. The education obtained on the outing was outstanding. A great blend of adventure, education, fun and socializing!
Read more
Eco-friendly Lanai
New York City
Lanai Snorkel and Dolphin Watch from Maui
barbaradN100OY, Aug 2026
Eco-friendly Lanai
Qualified, professional staff, attentive to everyone's needs and helpful. The photographer Dana is very good. Very nice tour. Spacious and clean catamaran. Good food and drinks
Read more
Whale of a sunset cruise!
New York City
Sunset Whale Watching Shared Activity
U4448FSmitchh, Dec 2025
Whale of a sunset cruise!
First whale watch tour of season was AWESOME! Lots of spouts, sprays, humps and tails!! Captain Ty showed the way for us, while Mo & Jess’s were the best mates! 5 kids onboard were thoroughly entertained and in awe! Can’t wait for more! Mahalo from the Hess family!!
Read more
Landed in Kona in the...
New York City
Kona Haunted Hele Ghost Tour
Stephanie_B, Nov 2025
Landed in Kona in the...
Landed in Kona in the late afternoon and was looking for a night tour, this was a fun thing to do and thanks Olivia for the awesome tour
Read more
Wonderful historical tour
New York City
Kona Haunted Hele Ghost Tour
Kimberly N, Nov 2025
Wonderful historical tour
Great experience! Our tour guide was friendly and knowledgeable. We ended up being the only family on the tour which added a personal touch. Learned so much about the big island’s culture!
Read more
Hawaii Activities
Attractions
Guides
Calendar
View more
View more