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Big Island of Hawaii Cruises, Sailing & Water Tours

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Big Island of Hawaii Activities

Attractions

Guides

Calendar

2-Hour Dolphin Watching and Double Reef with Snorkel in Hawaii

Step aboard our 31’ Ocean Craft RHIB, designed for comfort, stability, and an exceptional on-water experience. With overhead shade and forward-facing seats, you’ll enjoy a …More

5.0 (23)

2-Hour Dolphin Watching and Double Reef with Snorkel in Hawaii

Step aboard our 31’ Ocean Craft RHIB, designed for comfort, stability, and an exceptional on-water experience. With overhead shade and forward-facing seats, you’ll enjoy a...

2 hours 30 minutes • Free Cancellation
5.0 (23)
from
$550
Wa'a Rides and Charters - Hawaiian Outrigger Canoe Excursions

Paddling a Hawaiian Outrigger Canoe or Wa'a from the site where King Kamehameha united the Hawaiian Islands and watched over his kingdom is a chance …More

4.9 (25)

Wa'a Rides and Charters - Hawaiian Outrigger Canoe Excursions

Paddling a Hawaiian Outrigger Canoe or Wa'a from the site where King Kamehameha united the Hawaiian Islands and watched over his kingdom is a chance...

1 hour • Free Cancellation
4.9 (25)
from
$69
Afternoon Sail & Snorkel to the Captain Cook Monument

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava …More

4.9 (252)

Afternoon Sail & Snorkel to the Captain Cook Monument

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava...

3 hours • Free Cancellation
4.9 (252)
from
$136
Big Island: Marine Wildlife Excursion

Whale season is never over for Captain Zodiac. Join us for a unique experience of a lifetime where we venture into the unknown! Enjoy a …More

5.0 (27)

Big Island: Marine Wildlife Excursion

Whale season is never over for Captain Zodiac. Join us for a unique experience of a lifetime where we venture into the unknown! Enjoy a...

4 hours • Free Cancellation
5.0 (27)
from
$153
Kona Deluxe Catamaran Whale Watch

Every winter, thousands of humpback whales return to Hawaii's warm waters - and there's no better way to see them than from the deck of …More

4.7 (58)

Kona Deluxe Catamaran Whale Watch

Every winter, thousands of humpback whales return to Hawaii's warm waters - and there's no better way to see them than from the deck of...

1 hour 30 minutes • Free Cancellation
4.7 (58)
from
$109
4-Hour Kona Private Charter

Perfect for all size of couples, families or extended families. Experience Kealakekua Bay, the best place to snorkel on the Big Island or find a …More

5.0 (15)

4-Hour Kona Private Charter

Perfect for all size of couples, families or extended families. Experience Kealakekua Bay, the best place to snorkel on the Big Island or find a...

4 hours • Free Cancellation
5.0 (15)
from
$1,623
Private Charter: Customizable Big Island Boat Adventure

Are you looking to relax with your family or friends? Our modern powered catamaran is designed for open ocean conditions that will allow our passengers …More

5.0 (23)

Private Charter: Customizable Big Island Boat Adventure

Are you looking to relax with your family or friends? Our modern powered catamaran is designed for open ocean conditions that will allow our passengers...

4 hours • Free Cancellation
5.0 (23)
from
$1,882
Kaimana Kealakekua Bay Captain Cook Adventure

Join us for a beautiful ocean tour traveling the Kona coastline to Kealakekua Bay where you will experience a world-renowned reef snorkeling site. This area …More

5.0 (19)

Kaimana Kealakekua Bay Captain Cook Adventure

Join us for a beautiful ocean tour traveling the Kona coastline to Kealakekua Bay where you will experience a world-renowned reef snorkeling site. This area...

3 hours • Free Cancellation
5.0 (19)
from
$160
Royal Humpback Whale Exploration

Humpback whales visit Hawaii from Alaska for a brief time in the winter. this is the time to take in the majestic Humpbacks. Hilo Ocean …More

Likely to Sell Out
Likely to Sell Out
4.8 (12)

Royal Humpback Whale Exploration

Humpback whales visit Hawaii from Alaska for a brief time in the winter. this is the time to take in the majestic Humpbacks. Hilo Ocean...

1 hour 30 minutes • Free Cancellation
4.8 (12)
from
$179
Whale Watching on Big island

Hawaii’s Big Island is home to migrating pods of humpback whales, which often breach as they build up energy for their northward migration. This narrated …More

Likely to Sell Out
Likely to Sell Out
4.7 (23)

Whale Watching on Big island

Hawaii’s Big Island is home to migrating pods of humpback whales, which often breach as they build up energy for their northward migration. This narrated...

2 hours 30 minutes • Free Cancellation
4.7 (23)
from
$80
Historic Hilo Bay and Coconut Island Guided Kayak Adventure

Experience the history and natural beauty of old Hawaii, unlike anywhere else in the islands, as you will soon discover Hilo Bay captures the feeling …More

Likely to Sell Out
Likely to Sell Out
4.5 (30)

Historic Hilo Bay and Coconut Island Guided Kayak Adventure

Experience the history and natural beauty of old Hawaii, unlike anywhere else in the islands, as you will soon discover Hilo Bay captures the feeling...

2 hours • Free Cancellation
4.5 (30)
from
$160
2.5-Hour Whale Watching On A 41' Super-Raft

A Whale of a Time in Hawaii! Step aboard our luxurious 41ft Super-Raft for a fun filled adventure on the water. Enjoy the thrill of …More

Likely to Sell Out
Likely to Sell Out
4.8 (14)

2.5-Hour Whale Watching On A 41' Super-Raft

A Whale of a Time in Hawaii! Step aboard our luxurious 41ft Super-Raft for a fun filled adventure on the water. Enjoy the thrill of...

2 hours 30 minutes • Free Cancellation
4.8 (14)
from
$135
Kona - 8 Hour Private Fishing Charter in Kailua-Kona, Hawaii

If there is anything you would specifically like us to accommodate, please let us know in advance and we will do everything possible to meet …More

Likely to Sell Out
Likely to Sell Out
4.6 (9)

Kona - 8 Hour Private Fishing Charter in Kailua-Kona, Hawaii

If there is anything you would specifically like us to accommodate, please let us know in advance and we will do everything possible to meet...

8 hours • Free Cancellation
4.6 (9)
from
$1,295
Mauna Kea Signature Coastline Cruise Day & Sunset Options

Unwind in true island style on our Mauna Kea Coastline Cruise, departing from Kawaihae Harbor aboard Olohana — a 41-foot luxury powerboat designed for comfort …More

Likely to Sell Out
Likely to Sell Out
4.6 (8)

Mauna Kea Signature Coastline Cruise Day & Sunset Options

Unwind in true island style on our Mauna Kea Coastline Cruise, departing from Kawaihae Harbor aboard Olohana — a 41-foot luxury powerboat designed for comfort...

90 to 120 minutes • Free Cancellation
4.6 (8)
from
$99
Kona Hawaii Deep Sea Fishing experience on the Bite Me 4

Enjoy the day out on the waters off the Kona Coast on this private chartered fishing and boating excursion. Sit back, relax and drink in …More

4.6 (25)

Kona Hawaii Deep Sea Fishing experience on the Bite Me 4

Enjoy the day out on the waters off the Kona Coast on this private chartered fishing and boating excursion. Sit back, relax and drink in...

4 to 8 hours • Free Cancellation
4.6 (25)
from
$862
Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

5.0 (6)

Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours • Free Cancellation
5.0 (6)
from
$276

Frequently Asked Questions

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

Recent activity reviews
Spinning dolphins
New York City
2-Hour Dolphin Watching and Double Reef with Snorkel in Hawaii
A2154WKrebeccao, Sep 2026
Spinning dolphins
We first did the Manta Ray night snorkel with this charter and loved it so much we booked a Dolphin Watching and 2 reef snorkel. It was just us 5 so we had a great time and Brian was very knowledgeable. We would have had a great time even if the boat was full which held 10 guests. The 2 reefs were excellent. The boating community is very close and help each other out. We were next to a scuba charter and they told Brian which reefs were good that day. Brian told us about the different types of dolphins and we saw a large group of dolphins with babies! They were jumping and spinning. It was amazing.
Read more
Eric is the best guide...
New York City
Historic Hilo Bay and Coconut Island Guided Kayak Adventure
Melinda_M, Sep 2026
Eric is the best guide...
Eric is the best guide and we had a great time. We saw three sea turtles. We learned a lot and made great memories.
Read more
Friendly captain and crew
New York City
4-Hour Kona Private Charter
Johannah_B, Aug 2026
Friendly captain and crew
We are a family ranging from 4 to 73 y/o. We enjoyed the boat ride although sitting for awhile in a bumpy ride is not so comfortable still we had fun. Captain and crew were very friendly and informative. We saw a lot if dolphins and fishes while snorkeling at captain cook. We wish we even had more time snorkeling. My niece 6 y/o and nephew 4 y/o was their first time snorkeling and they were experts right away. I was kinda scared for them going into the water but they actually had the most fun. There was enough lunch and snacks and drinks for our family. We even brought home the leftovers. It’s also easy to find the location and once you book, you just show up and they were really nice. They even gave us sun screen to use. Also everything is provided for the snorkeling.
Read more
Amazing
New York City
Afternoon Sail & Snorkel to the Captain Cook Monument
Makayla_T, Aug 2026
Amazing
Super fun and a beautiful place to snorkel! Everyone was super friendly and inviting. Had a fun and relaxing boat ride.
Read more
Great experience! Highly recommend
New York City
Afternoon Sail & Snorkel to the Captain Cook Monument
Wendy_S, Aug 2026
Great experience! Highly recommend
Great Experience!! Boat was clean, lots of shade if you wanted it and lots of deck space if you didn’t. Crew was amazing and knowledgable! Saw dolphins on the way to and from the bay and lots of beautiful fish while snorkeling. Complimentary snacks, soda, water and juice were plentiful! Cocktails for purchase after snorkeling were super yummy! Would definitely recommend!
Read more
Book the sunset cruise! 100%
New York City
Mauna Kea Signature Coastline Cruise Day & Sunset Options
MariaFloat, Jul 2026
Book the sunset cruise! 100%
Awesome experience from start to finish; beautiful sunset, awesome service, the host is beautiful, and some very cool flying fish! The crew was totally professional, and made the evening special. Thank you, Captain Keith, Nicole and Hunter, y’all are pros and we can’t wait to sail again. Dinner was great and drinks were flowing. You guys are the best!
Read more
Fishing around in Kona!!
New York City
Private Charter: Customizable Big Island Boat Adventure
dougrF5108OJ, Jul 2026
Fishing around in Kona!!
This was a very fun family event with snorkeling and having dolphins swim next to us and behind us. The snacks were tasty. Highly recommend!!
Read more
Kona Trip, May 2026
New York City
Wa’a Rides and Charters – Hawaiian Outrigger Canoe Excursions
chrisrP8672FQ, May 2026
Kona Trip, May 2026
Awesome experience, learning some outrigger basics and paddling out on the bay. Grant was a pleasure to speak with just in general (especially about my Ironman experience). My wife sat in front, controlling the pace, and even jumped in the water briefly at our turn around spot. I'd recommend Kona Boys as your Go-to for the paddling experience.
Read more
Relaxing and Educational
New York City
Wa’a Rides and Charters – Hawaiian Outrigger Canoe Excursions
Hillary_W, May 2026
Relaxing and Educational
What a relaxing and educational way to start the day! Grant was an awesome guide. We couldn't have asked for a better morning on the water. Thank you!
Read more
Whales and Waterfalls
New York City
Royal Humpback Whale Exploration
R3917CHdennisl, Mar 2026
Whales and Waterfalls
My wife and I took the whale watching tour. We saw a bunch of whales and got some great pictures. Then they took us to see some amazing waterfalls and told us about the beautiful beach areas. The old sugar plantation, fallen arch, surf areas and the water break. Very entertaining guild and boat captain.
Read more
Glorious whale sightings
New York City
Royal Humpback Whale Exploration
billkQ8206JK, Mar 2026
Glorious whale sightings
The captain and crew were obviously very experienced at finding and following the humpbacks. Also, whitecaps appeared suddenly, and I was impressed with the way he followed the whales and yet sliced through the waves at an optimum angle to minimize rocking.
Read more
Fun experience even in rain
New York City
Whale Watching on Big island
ThrRubner, Mar 2026
Fun experience even in rain
Even with the bad weather, Jeremiah and Ula made sure to make the best of it. We did get to see five whales which was so cool. And towards the end of our tour, we spotted two more and instead of rushing us back to the harbor, they let us stay and watch them. Thus is the perfect lengrh of time for a tour like this.
Read more
Great marine animals
New York City
Whale Watching on Big island
142kristid, Mar 2026
Great marine animals
Crew was very helpful and friendly. Very knowledgeable. They tried to find as many animals for us as they could. We saw a whale, spinner dolphins and bottlenose dolphins.
Read more
Awesome kayak tour
New York City
Historic Hilo Bay and Coconut Island Guided Kayak Adventure
MonicaT274, Mar 2026
Awesome kayak tour
Great tour. It was just the two of us with our guide. He was informative and made our tour extremely memorable snd personal.
Read more
Great experience
New York City
Kona Deluxe Catamaran Whale Watch
davidwU8742WA, Feb 2026
Great experience
Great Service and had Blast with the wife. Thanks guys
Read more
Afternoon Fun!
New York City
Kona Deluxe Catamaran Whale Watch
jennifercQ3130HB, Feb 2026
Afternoon Fun!
I had a wonderful experience on why Nautical’s afternoon whale watch! Friendly crew, room, and shade & and my favorite…. a hydrophone to hear the whales! They swam in incredibly close to us and we had an incredible view! I highly recommend! 🐋
Read more
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