Hawaii Cruises, Sailing & Water Tours

Beautiful 90 Minute Catamaran Sunset Sail with Drinks!
Oahu, USA

The nightly Sunset Sailing trip is a gorgeous 90-minute sail with complimentary drinks. Experience sailing, sightseeing, delicious cocktails, the beautiful Hawaiian Sunset, and perhaps if...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (9)
from
$56.36
Lanai Snorkeling Half Day with Sea Scooter
Likely to Sell Out
Likely to Sell Out
Maui, USA

Winner of 2018 Travel & Hospitality Award Winner & Certificate of Excellence Cool Hawaii Award for 9 years in a row. Our 50 ft Sanity...

4 hours 15 minutesFree Cancellation
4 hours 15 minutesFree Cancellation
4 hours 15 minutes • Free Cancellation
5.0 (8)
from
$192.80
Waikiki's Premier Small Group Sunset Yacht + Tasting
Oahu, USA

Get the ultimate all-inclusive experience on a 43-foot world renown yacht while enjoying the Waikiki Sunset on this 2 hour experience. There’s more than enough...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (8)
from
$245.30
Oahu Personalized Private North Shore Highlight Custom Tour
Likely to Sell Out
Likely to Sell Out
Oahu, USA

Explore the Seven Mile Miracle known as O`ahuʻs North Shore.  Winter brings big waves and world-class surfing, while the summer is calm and perfect for visiting...

6 to 12 hoursHotel pickup offered
6 to 12 hoursHotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (7)
from
$699
Guided E-Bike and Kayak Tour to Mokulua Islands in Kailua, Oahu
Oahu, USA

Embark on an exhilarating 5-hour journey to the Mokulua Islands, led by our experienced guides! Say goodbye to car hassles—your transportation to Kailua Beach is...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
5.0 (7)
from
$285
Waikiki Beach Catamaran Friday Night Fireworks Tour
Oahu, USA

This sail only happens once a week and there’s no better way to take in the fireworks than from the waters aboard our catamaran, where...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (7)
from
$63
Big Island: 5-Hour Kona Private Boat Charter
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...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.9 (7)
from
$1,740
Guided Kayak Tour to Kailua’s Twin Islands
Oahu, USA

Embark on an exhilarating guided kayak tour to the Mokulua Islands, led by our experienced guides! As we paddle towards Moku Nui, a designated bird...

3 to 5 hoursFree Cancellation
3 to 5 hoursFree Cancellation
3 to 5 hours • Free Cancellation
5.0 (6)
from
$219
Oahu: Private North Shore Boat Charter
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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (6)
from
$1,200
Private Boat Charter in Waikiki for Snorkeling and Events
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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (6)
from
$1,300
Afternoon Ali'i Adventure
Big Island of Hawaii, USA

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 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (6)
from
$276
Kona Hawaii Deep Sea Luxury Fishing Trip on Bite Me 5
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 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.8 (6)
from
$1,392.18
Sunset Sail Experience by Catamaran in Waikiki
Oahu, USA

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (6)
from
$92.31
Hawaii Volcanoes National Park Experience from Maui
Big Island of Hawaii, USA

Here is your chance to visit Hawaii’s only active volcano and see the youngest of the Hawaiian Islands. On this inter-island excursion, you’ll visit the...

8 to 10 hoursFree Cancellation
8 to 10 hoursFree Cancellation
8 to 10 hours • Free Cancellation
5.0 (6)
from
$589.99
Private Charter Custom Kealakekua Bay Snorkeling
Big Island of Hawaii, USA

We are a local Hawaiian family operation. Providing that family friendly vibe, with an authentic Hawaiian style touch adding native culture and traditions to help...

4 hours 30 minutesFree Cancellation
4 hours 30 minutesFree Cancellation
4 hours 30 minutes • Free Cancellation
5.0 (6)
from
$799
Whale Watching in Kona
Big Island of Hawaii, USA

We are a small Hawaiian ʻohana-owned and operated business. A family of five—Kaleo, Leila, and their three sons Kaeo, Hauʻoli, and Makana—shares their love for...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (6)
from
$125

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

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