Hawaii Cruises, Sailing & Water Tours

472 Results
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

Big Island of Hawaii, USA

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
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours • Free Cancellation
5.0 (2)
from
$1,595
Private Snorkeling Cruise in Waikiki

Embark on an unforgettable adventure with your very own private snorkeling tour to the legendary Turtle Canyon in beautiful Waikiki! Picture yourself diving into the …More

Oahu, USA

Embark on an unforgettable adventure with your very own private snorkeling tour to the legendary Turtle Canyon in beautiful Waikiki! Picture yourself diving into the...

2 hours 30 minutes • Free Cancellation
from
$1,560
Private Kealakekua Bay Captain Cook Snorkeling

There is no better way to explore Hawaii’s #1 snorkel destination than with an affordable private charter from HAWAII MARINE LIFE CHARTERS. Vessel Designed for …More

Big Island of Hawaii, USA

There is no better way to explore Hawaii’s #1 snorkel destination than with an affordable private charter from HAWAII MARINE LIFE CHARTERS. Vessel Designed for...

3 hours 30 minutes • Free Cancellation
5.0 (46)
from
$1,541
Big Island: 4-Hour Private Charter Adventures in Kona Coast

The Kona coastline is an aquatic playground that's filled with possibility, whether it's snorkeling with manta rays, searching for dolphins, or watching whales in winter. …More

Big Island of Hawaii, USA

The Kona coastline is an aquatic playground that's filled with possibility, whether it's snorkeling with manta rays, searching for dolphins, or watching whales in winter....

4 hours
5.0 (9)
from
$1,500
2hr Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours • Free Cancellation
5.0 (3)
from
$1,495
Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people …More

Oahu, USA

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people...

120 to 150 minutes • Free Cancellation
5.0 (55)
from
$1,414
Offshore Fishing Adventures With Ohana Deep Sea Fishing

-Welcome aboard our well-equipped fishing charter boat and set off into the open seas with our expert captain and crew. - Explore prime fishing spots …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

-Welcome aboard our well-equipped fishing charter boat and set off into the open seas with our expert captain and crew. - Explore prime fishing spots...

4 hours • Free Cancellation
5.0 (1)
from
$1,360
Private Boat Charter in Waikiki for Snorkeling and Events

Discover the beauty of Waikiki with a private boat day charter, perfect for snorkeling, coastal cruising, events, and seasonal whale watching from January to March. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Discover the beauty of Waikiki with a private boat day charter, perfect for snorkeling, coastal cruising, events, and seasonal whale watching from January to March....

2 hours • Free Cancellation
5.0 (6)
from
$1,300
Private Luxury Sunset Fireworks Cruise Aboard Limitless

Take your evening on the water to the next level with a private 3-hour Sunset + Fireworks Cruise. This trip combines the serene beauty of …More

Oahu, USA

Take your evening on the water to the next level with a private 3-hour Sunset + Fireworks Cruise. This trip combines the serene beauty of...

3 hours • Free Cancellation
from
$1,299
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
Big Island of Hawaii, USA

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
Kona Hawaii Deep Sea Luxury Fishing Trip on Bite Me 5

In 2024 our vessel underwent a complete retrofit. We offer custom charters to fit all your needs. Experienced and novice alike, you will be guided …More

Big Island of Hawaii, USA

In 2024 our vessel underwent a complete retrofit. We offer custom charters to fit all your needs. Experienced and novice alike, you will be guided...

4 hours • Free Cancellation
4.8 (6)
from
$1,293
Luxury Private Boat Charter in Big Island Hawaii

Please forget about the crammed up tourist boats, and come with us! 6 Guest MAX, Luxurious Snorkel Boat! The most Affordable & Luxurious Snorkel Charter …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

Please forget about the crammed up tourist boats, and come with us! 6 Guest MAX, Luxurious Snorkel Boat! The most Affordable & Luxurious Snorkel Charter...

4 hours • Free Cancellation
5.0 (61)
from
$1,200
Oahu: Private North Shore Boat Charter

Our North Shore adventure tours are perfect for people of all ages. Bring your family or friends and create new memories. Turn the tour into …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Our North Shore adventure tours are perfect for people of all ages. Bring your family or friends and create new memories. Turn the tour into...

2 hours • Free Cancellation
5.0 (7)
from
$1,200
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours • Free Cancellation
5.0 (2)
from
$1,200
Private Luxury Sunset Cruise Aboard Limitless

Set sail with on a private 2-hour sunset cruise, the perfect way to wind down your day in Hawaii. As the sun sinks toward the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Set sail with on a private 2-hour sunset cruise, the perfect way to wind down your day in Hawaii. As the sun sinks toward the...

2 hours • Free Cancellation
from
$1,199

Frequently Asked Questions

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

Recent activity reviews
Activity name

Hawaii Activities
Attractions
Guides
Calendar