Hawaii Sailing Trips

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Hawaii Activities

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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
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (316)

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutes • Free Cancellation
4.9 (316)
from
$73
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.9 (215)

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique...

2 hours • Free Cancellation
4.9 (215)
from
$71
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from …More

Oahu, USA
4.9 (18)

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from...

2 hours • Free Cancellation
4.9 (18)
from
$70
2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and …More

Oahu, USA
5.0 (3)

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and...

2 hours • Free Cancellation
5.0 (3)
from
$70
Friday Night Firework Cruise in Waikiki

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, …More

Oahu, USA
4.8 (35)

Friday Night Firework Cruise in Waikiki

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline,...

1 hour • Free Cancellation
4.8 (35)
from
$70
Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA
4.6 (87)

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours • Free Cancellation
4.6 (87)
from
$68
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
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic …More

Oahu, USA
4.9 (210)

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes • Free Cancellation
4.9 (210)
from
$62
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
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
3.5 (4)

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take...

2 hours • Free Cancellation
3.5 (4)
from
$60
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the …More

Oahu, USA
4.8 (595)

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...

2 hours • Free Cancellation
4.8 (595)
from
$56
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Hawaii TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a …More

Oahu, USA
4.9 (988)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Hawaii TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a...

2 hours • Free Cancellation
4.9 (988)
from
$55
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, …More

Oahu, USA
4.9 (255)

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes • Free Cancellation
4.9 (255)
from
$53
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
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never …More

Oahu, USA
4.7 (1,265)

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours • Free Cancellation
4.7 (1,265)
from
$53

Frequently Asked Questions

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

Recent activity reviews
Amazing sail & sunset cruise!
New York City
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
Dama_M, Sep 2026
Amazing sail & sunset cruise!
Great sunset cruise! The crew was very helpful & friendly-Alex, Alejandro & Jandy❤️ I would definitely go again🌊😊
Read more
Dream Sailing!
New York City
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
Colleen_E, Sep 2026
Dream Sailing!
Phenomenal experience. Capt Mo, John, & Kai were wonderful & entertaining. We felt so confident with their seamanship and safe with thier knowledge of the area and Swim precautions at the same time they made it a fun and humorous adventure. Little Dog stole the show though! Mahalo for a wonderful time!
Read more
Amazing company
New York City
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Meander19015932008, Sep 2026
Amazing company
That was such a breath taking experience. The crew was so kind & good company!
Read more
Perfect evening activity
New York City
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
172addisont, Sep 2026
Perfect evening activity
Very friendly staff and the perfect ride time to enjoy the water and sunset!
Read more
Great day out
New York City
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Anna_B, Sep 2026
Great day out
Kurt = ⭐️⭐️⭐️⭐️⭐️ Great way to see the island when visiting just for a few days. Loved all the scenic location stops, especially sunrise. Photography tips were great too!
Read more
Last minute booking!
New York City
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
AB19110, Sep 2026
Last minute booking!
Fun trip with the all girl Tuesday crew! Booked last minute and had a great time, beautiful sunset and saw dolphins 😍
Read more
Fantastic Evening On the Water
New York City
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Raewyn_B, Sep 2026
Fantastic Evening On the Water
We had a wonderful time out on the water! The music was great- plenty of drinks & the crew made sure we were all looked after🍹The sunset was amazing - a fabulous memory to take home from Honolulu🌅
Read more
Waikīkī afternoon sailing
New York City
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu – Best Value
karenwbrisbane, Sep 2026
Waikīkī afternoon sailing
10/10 all the way. Such an unforgettable experience. Pre wedding celebration afternoon sail went out from the beach to the deep blue waters off Waikiki where we enjoyed drinks and took in the stunning views. The crew were all welcoming and ensured we had a great time.
Read more
Awesome Laid-back sunset cruise
New York City
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
Kim_U, Sep 2026
Awesome Laid-back sunset cruise
Wonderful relaxing experience at great price! Excellent crew! Very helpful and pleasant! Surprise charcuterie snackboard! Highly recommend if your laid back.
Read more
It made us feel happy
New York City
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
163JaneS, Sep 2026
It made us feel happy
We took this amazing catamaran ride on our last day on Oahu, and what a highlight of the trip it was! Of course, the perfect weather contributed to the fun. But the crew, the views, the music and the drinks were outstanding. We enjoyed every minute of it. Do it by all means, and you won’t regret it.
Read more
Awesome Friday Nt Firework Experience
New York City
Friday Night Firework Cruise in Waikiki
jocelynd939, Sep 2026
Awesome Friday Nt Firework Experience
Awesome Firework Cruise experience! We are locals that bought our family to enjoy a Friday Nt in Waikiki. The crew was really fun and had very nice conversations with them! Would totally go again and recommend the Moana! Mahalo!
Read more
Fun Trip! Great for photo taking!
New York City
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
laneowyang, Sep 2026
Fun Trip! Great for photo taking!
very helpful crew! I was having a foot problem and the crew made sure i got on and off safely. Wish there were benches to sit on while wating for the ship.
Read more
Good times
New York City
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu – Best Value
T9716AEwendyb, Sep 2026
Good times
Met a great friend there, love my experiences with Holokai 🤗🤗🤗🤗
Read more
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
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
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