Hawaii Cruises, Sailing & Water Tours

Effortless Luxury Sailing Cruises
Oahu, USA

Discover Oahu’s breathtaking coastline aboard the luxurious Makani Catamaran, one of Waikiki’s largest and most elegant 65-foot sailing vessels. Departing from convenient Kewalo Basin Harbor...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.6 (664)
from
$89
Waikiki 2 Hours Friday Night Fireworks Catamaran Cruise
Oahu, USA

Enjoy the spectacular FRIDAY NIGHT FIREWORKS show along the beautiful coastline of Waikiki while we get up close and personal with the explosiveness and the...

1 hour 45 minutesFree Cancellation
1 hour 45 minutesFree Cancellation
1 hour 45 minutes • Free Cancellation
4.7 (649)
from
$84.72
Maui Ma'alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
Maui, USA

Come enjoy Prime Rib, Baby Back Ribs, Kiawe Smoked Chicken Leg and Thigh combo, Fresh Island Fish, or Penne Pasta with Thai Basil Marinara. A...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.6 (638)
from
$149.95
Waikiki Deluxe Catamaran Whale Watch
Honolulu, USA

Experience the wonder of Hawaii's humpback whales on a smooth, scenic sail along the Waikiki coastline. From December through April, these majestic creatures migrate to...

2 hoursHotel pickup offeredFree Cancellation
2 hoursHotel pickup offeredFree Cancellation
2 hours • Hotel pickup offered • Free Cancellation
4.6 (621)
from
$119
Glass-Bottom Boat Reef Tour
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

Our tours depart from the Kailua-Kona pier on the Big Island of Hawaii. Discover the beauty of Kona's underwater world aboard Marian, a 36-foot (10-meter), custom-designed glass-bottom boat....

50 minutesFree Cancellation
50 minutesFree Cancellation
50 minutes • Free Cancellation
4.7 (524)
from
$72
Maui Sunset Dinner Cruise & Whale Watch
Maui, USA

Experience Maui's top-rated whale watch with the experts in conservation and Marine Naturalists departing from the historic Ma'alaea Harbor. Enjoy a premium dinner cruise with...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.7 (503)
from
$189.36
Award-winning Dinner Cruise: Four Course Dining Experience
Maui, USA

For a uniquely Maui dining experience, join the sunset dinner cruise, where you'll enjoy exquisite dining while surrounded by spell-binding views of the Pacific and...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.4 (377)
from
$170.18
Waikiki Beach Glass Bottom Boat Cruise
Oahu, USA

Enjoy the beauty of Oahu’s South Shore as we cruise from the Kewalo Basin Harbor toward Lē’ahi (Diamond Head). Enjoy the clear view of the...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.7 (330)
from
$46
West Oahu Dolphin Watch and Snorkel Sail with Lunch
Oahu, USA

Discover the beauty of West O‘ahu’s coastline on a 3-hour sailing adventure from Wai‘anae Small Boat Harbor. Cruise along the scenic coast as our crew...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.6 (317)
from
$125.96
Voted Best First Time Diving Experience in Hawaii
Likely to Sell Out
Likely to Sell Out
Oahu, USA

Japanese, Chinese, Spanish, and Korean speaking instructors available upon request. Personal Underwater photographer available to capture and record your diving experience at an additional cost....

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.7 (305)
from
$239
Oahu 5-in-1 Deluxe Cruise: Turtle Snorkeling & Ocean Activities
Oahu, USA

In addition to the amazing turtle snorkeling in the beautiful waters of Waikiki, our 135-passenger boat offers a unique selection of activities that set us...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.7 (290)
from
$49
Glass-Bottom Boat Cruise from Waikoloa
Big Island of Hawaii, USA

Discover the Big Island’s vibrant underwater world on this glass-bottom boat cruise on Anaeho’omalu Bay. From Waikoloa, near Kona, board a comfortable 26-foot (7.9-meter) boat...

30 minutesFree Cancellation
30 minutesFree Cancellation
30 minutes • Free Cancellation
4.7 (278)
from
$50
Waikiki Sunset Cocktail Cruise aboard the Majestic by Atlantis
Oahu, USA

See spectacular sunset and city lights views aboard Majestic by Atlantis Cruises, Hawaii's newest yacht cruise featuring Waikiki's only full-service bar and lounge on the...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.6 (258)
from
$76.58
Whale Watch Excursion from the Big Island
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA

This two-and-a-half hour whale watch tour with a certified naturalist departs from the Kailua-Kona pier during whale season (December to April). Hear singing males on...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.5 (250)
from
$151.34
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Honolulu, USA

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (242)
from
$79
Lanai Snorkel and Dolphin Watch from Maui
Maui, USA

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 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.6 (216)
from
$180.92

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

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Cool Hawaii wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

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If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.