Hawaii Sailing Trips

102 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
47
52
46
Duration Clear
3
88
16
1
0
Price Clear
$0 $500+
Rating Clear
88
99
100
Specials Clear
102
47
0
12
2
Features Clear
4
79
85
4
87
2
Accessibility Clear
0
34
81
Families Clear
82
25
49

Hawaii Activities

Attractions

Guides

Calendar

Waikiki Friday Night Fireworks Cruise

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring …More

Oahu, USA
4.7 (30)

Waikiki Friday Night Fireworks Cruise

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hour • Free Cancellation
4.7 (30)
from
$60
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 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
4.8 (14)

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 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...

2 hours • Free Cancellation
4.8 (14)
from
$1,150
Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (11)

Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hours • Free Cancellation
5.0 (11)
from
$900
Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA
4.8 (85)

Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours • Free Cancellation
4.8 (85)
from
$112
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
5.0 (2)

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...

3 hours • Free Cancellation
5.0 (2)
from
$1,595
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
5.0 (2)

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...

2 hours • Free Cancellation
5.0 (2)
from
$1,200
Afternoon Sail With the Whales from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (1)

Afternoon Sail With the Whales from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
5.0 (1)
from
$100
Midmorning Whale Watch from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.5 (2)

Midmorning Whale Watch from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
4.5 (2)
from
$100
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

Big Island of Hawaii, USA
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
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
5.0 (3)

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...

2 hours • Free Cancellation
5.0 (3)
from
$1,495
North Shore Catamaran Charters

Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witness the majestic whales and stunning sunsets on the North Shore of Oahu. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (1)

North Shore Catamaran Charters

Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witness the majestic whales and stunning sunsets on the North Shore of Oahu....

1 day 2 hours • Free Cancellation
5.0 (1)
from
$84
Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide …More

Oahu, USA
5.0 (4)

Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide...

2 hours • Free Cancellation
5.0 (4)
from
$65
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while …More

Oahu, USA
5.0 (13)

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutes • Free Cancellation
5.0 (13)
from
$53
BYOB Friday Night Fireworks Cruise

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights …More

Oahu, USA
5.0 (5)

BYOB Friday Night Fireworks Cruise

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights...

2 hours 30 minutes • Free Cancellation
5.0 (5)
from
$139
Sunset Sail Experience by Catamaran in Waikiki

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 …More

Oahu, USA
4.8 (6)

Sunset Sail Experience by Catamaran in Waikiki

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 hours • Free Cancellation
4.8 (6)
from
$92
Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to …More

Oahu, USA
4.6 (10)

Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutes • Free Cancellation
4.6 (10)
from
$77

Frequently Asked Questions

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

Recent activity reviews
Love the Majestic
New York City
Waikiki Fireworks Cocktail Cruise
John_C, Aug 2026
Love the Majestic
Fantastic Waikiki Fireworks Cocktail Cruise on the Majestic! What an absolutely wonderful experience! The Waikiki Fireworks Cocktail Cruise aboard the Majestic was one of the highlights of our time in Hawaii. From the moment we stepped onboard, the crew was fantastic—friendly, professional, attentive, and genuinely focused on making sure everyone had a great time. The onboard entertainment was excellent, and the talented lady singing absolutely crushed it! She brought great energy and added so much to the overall atmosphere of the evening. The drinks were also very reasonably priced, and I have to give a special shout-out for the generous pour of wine my wife received—definitely appreciated! The staff truly made this a memorable experience. Cruising along the beautiful Waikiki coastline at night was incredibly scenic, and watching the fireworks from the water was the perfect finishing touch. If you're looking for a fun, relaxing, and memorable evening in Waikiki, I highly recommend the Waikiki Fireworks Cocktail Cruise aboard the Majestic. Great crew, great entertainment, great drinks, and an unforgettable view!
Read more
Amazing!
New York City
Waikiki Friday Night Fireworks Cruise
Buford_A, Aug 2026
Amazing!
That you can bring your own drinks and food on the boat. Enjoy the ride and a create memories with your special someone!
Read more
Awesome experience
New York City
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Climber19817325401, Aug 2026
Awesome experience
The crew took excellent care of us. The small and private experience provided a more intimate setting, allowing for more personalized attention. We had the opportunity to see dolphins and even go snorkeling. The experience was highly customizable, making it an ideal choice for those seeking a private and memorable adventure.
Read more
Must do experience in Hawai’i
New York City
Waikiki Sunset Cruise and Iconic Views with Swimming
Trek786244, Aug 2026
Must do experience in Hawai’i
Excellent experience. I was solo but fun for the whole family. Kids as young as 4/5 were jumping in the ocean and swimming! We saw a few turtles. Great ambiance, watching the sun set in Hawai’i is a once in a lifetime experience!
Read more
Snorkeling Adventure
New York City
North Shore Catamaran Charters
jessicamE4096ZK, Aug 2026
Snorkeling Adventure
Taylor and Dorian were fantastic and very personable! It was a great snorkeling adventure. Saw turtles, dolphins and so much more! Highly recommend, and would do it again!
Read more
Beautiful experience. Book now!
New York City
Waikiki Sunset Cruise and Iconic Views with Swimming
Michelle_F, Aug 2026
Beautiful experience. Book now!
The sunset cruise was a beautiful experience. The employees on the boat were very helpful. Captain was funny.
Read more
Unreal experience
New York City
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
Emma_I, Jul 2026
Unreal experience
It was so much fun!! Amazing crew and we saw beautiful wildlife!! So crazy to see turtles and fish up close. We were also able to jump off the boat into the ocean. Unreal experience! 10/10
Read more
Best experience in the sea
New York City
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
E2422ZTveronicad, Jun 2026
Best experience in the sea
So customized. Great experience. Captain and crew were perfect in the sense that the did theor job and we had quality family time. Pitty we could not snorkel due to climate. But we sailed woth music. Unforgetable
Read more
A wonderful 3 hours with family on the water at Waikiki
New York City
Private Catamaran Sunset Sail in Waikiki
Burleya13, May 2026
A wonderful 3 hours with family on the water at Waikiki
A great day on the water with Tom, Savannah and Bella celebrating Alicia’s 70th birthday with our children and grandchildren. Swimming off the catamaran with dolphins and turtles. We also saw a seal in the harbour before sailing. A great birthday present and memories. Highly recommend the professional expertise of the crew.
Read more
Fireworks in the night!
New York City
Waikiki Fireworks Cocktail Cruise
Susan_M, Apr 2026
Fireworks in the night!
2nd time doing this cruise. Drinks flowing, sparks flying fireworks shooting! Great crowd to share this experience with
Read more
Everything was way better...
New York City
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
Dixan_M, Mar 2026
Everything was way better...
Everything was way better than we expected it, thank you guys for the opportunity, definitely best crew in the city.
Read more
Whale watching
New York City
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
F8473YJernestom, Mar 2026
Whale watching
Great attention by staff. They have everything from sunscreen to drinks so your covered. Great open water views. Saw a few whales. Loved it
Read more
A perfect private catamaran sunset tour
New York City
Private Catamaran Sunset Sail in Waikiki
DebbyL71, Feb 2026
A perfect private catamaran sunset tour
I booked the private catamaran sunset tour for my family and I and we were not disappointed. It was a fantastic tour. The waters were a bit choppy that day, but we all laughed when a couple of the waves got some of us a bit wet!! All fun!! The trip back was so spectacular…..even though it was too overcast for a proper sunset, the suns rays poked through the clouds and made up for it (and the warm blanket for the ride back was the ‘icing on the cake’). Our ‘captain’ and ‘crew member’ were so friendly it made the trip very enjoyable. Thank you so much!!!
Read more
Amazing yacht & views
New York City
2hr Luxury Private Sailing Catamaran for 7-12 People
Voyage42985524840, Jan 2026
Amazing yacht & views
Such a great time, the yacht was perfect & the staff was very friendly. Would definitely book again !
Read more
Epic whale watching!
New York City
Afternoon Sail With the Whales from Lahaina Harbor
vickysJ2938SI, Jan 2026
Epic whale watching!
We had a fantastic time! Only about 12 people on the boat but plenty of room for a lot more comfortably. Served canned drinks, very attentive staff. We saw so many whales breach that we lost count. You won’t regret this one!
Read more
We had a wonderful experience in board. Kids and adults enjoyed our time on the water.
New York City
2hr Luxury Private Sailing Catamaran for 7-12 People
AARON N, Jan 2026
We had a wonderful experience in board. Kids and adults enjoyed our time on the water.
Wonderful time had by all. Staff and management equally kind and professional. Entire experience was great no negatives.
Read more
Hawaii Activities
Attractions
Guides
Calendar
View more
View more