Hawaii Sailing Trips

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Hawaii Activities

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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
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
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
Private South Shore Sail Charter

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, …More

Oahu, USA
5.0 (2)

Private South Shore Sail Charter

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze,...

1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$1,000
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
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
Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them …More

Maui, USA
5.0 (1)

Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them...

2 hours • Free Cancellation
5.0 (1)
from
$164
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and …More

Oahu, USA
4.7 (2,100)

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

2 to 3 hours • Free Cancellation
4.7 (2,100)
from
$99
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
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

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 …More

Honolulu, USA
4.7 (242)

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

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 hours • Free Cancellation
4.7 (242)
from
$79
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
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.6 (81)

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours • Free Cancellation
4.6 (81)
from
$142
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA
4.7 (67)

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (67)
from
$197
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA
4.5 (47)

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes • Free Cancellation
4.5 (47)
from
$110
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.5 (38)

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes • Free Cancellation
4.5 (38)
from
$120

Frequently Asked Questions

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

Recent activity reviews
Staff was great! Not only...
New York City
Ka’anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
Shane_F, Sep 2026
Staff was great! Not only...
Staff was great! Not only did they make sure we had everything we needed they socialized with everyone. Would highly recommend other to go.
Read more
Friendly fun!
New York City
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
David_G, Sep 2026
Friendly fun!
We booked a last minute trip to go see the turtles after a hurricane. The sights weren't awesome because the sea was murkey. But the crew was amazing. They took great care of us. They made sure everybody had something to eat. Something to drink and tried their best to show us turtles. We did see a couple and they assured us that we would normally see more in better weather. We would totally recommend Capt. Anthony and Sophia. And Sofia, again, they were absolutely outstanding.
Read more
Excellent tour and experience
New York City
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
P8063NGpaula, Sep 2026
Excellent tour and experience
Excelllent communication. Our original tour date was cancelled and we were offered a full refund or we could rebook for another day. Glad we rebooked. The experience was perfect. The tour guides were friendly and professional.
Read more
Awesome!
New York City
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
Jennifer_A, Sep 2026
Awesome!
This was incredible! If I could do it again I would but would book for longer! Guides/crew were so nice too! 10 out of 10!
Read more
Such a pretty and...
New York City
Waikiki Sunset Cocktail Cruise – Hilton Hawaiian Village
Jason_W, Sep 2026
Such a pretty and...
Such a pretty and relaxing sunset cruise. The crew was friendly and the views were amazing! Definitely would recommend!
Read more
The Best!
New York City
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Cristina_S, Sep 2026
The Best!
Fantastic crew and captain (captain nick, crewmates nick, and mike?). They quite literally sprang into action when a passenger got injured in the water by a jelly fish. I have never felt more safe, secure, and well taken care of during this excursion. I’d would use this company with this crew anytime time I’m back again on the island. Great experience and fun!
Read more
Beautiful 1st wedding anniversary celebration
New York City
Ka’anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
Eleanor_M, Aug 2026
Beautiful 1st wedding anniversary celebration
We were trying to find a perfect way to celebrate our 1st wedding anniversary and this went above and beyond
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
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
Great experience with awesome crew!
New York City
Waikiki Sunset Cocktail Cruise – Hilton Hawaiian Village
U8414MSdebbiem, Jul 2026
Great experience with awesome crew!
Started off with moving to a different pier due to weather and safety concerns, but they did shuttle us to new location. The Spirit of Aloha was a great boat with awesome crew! Loved the bento box, open bar and the entire experience which included gorgeous rainbows and sunset! Karin, Jackson and Brad were great!!
Read more
100% Recommend
New York City
2 Hour Swim, Snorkel & Sail (Kewalo Harbor)
Candace_W, Jul 2026
100% Recommend
Upon booking, I noticed a disclaimer that said:“Parents/Guardians, please note: while we are an all-ages experience, guests are advised that we are a bar with what can be a party atmosphere. We are not responsible for the actions or expressions of other guests on board.”As a parent traveling with four kids, I was a little concerned at first. However, I decided to go ahead with the booking because of the cost, free drinks snorkeling activities offered, and I’m so glad I did.Our excursion was very relaxed. There were no rowdy guests or inappropriate behavior, and the crew didn’t encourage any kind of party atmosphere. If you’re worried like I was, I’d say it’s simply a general disclaimer rather than a reflection of what you’ll necessarily experience.One thing I was especially glad about was not booking one of the large catamaran cruises with the inflatable water slides and trampoline. Before the trip, I had seriously considered it because it looked like a lot of fun. But while we were out on the ocean, I actually saw one of those boats, and it looked absolutely packed—there had to be close to a hundred people on board.In that moment, I knew I had made the right decision. The smaller catamaran we chose was much more peaceful, with fewer people, plenty of room to relax, and a laid-back atmosphere. Instead of feeling crowded or rushed, we were able to truly enjoy the beautiful Hawaiian scenery, the ocean breeze, and the experience itself. For me, that’s exactly what a vacation should be—relaxing, not hectic—and I’m so thankful we chose the quieter option.My kids all said this was one of their favorite activities of our trip! The snorkeling equipment was clean and sanitized, and the crew did an excellent job making sure everyone felt safe and comfortable. They even gave a thorough demonstration for beginners, which made the experience much less intimidating.We were lucky enough to see sea turtles, big fish, and coral reefs while snorkeling. But surprisingly, my kids’ favorite part wasn’t even the snorkeling—it was relaxing on the catamaran’s netting while the waves splashed up underneath them. They said it felt like an ocean water park ride and couldn’t stop laughing the entire time.This excursion created some of our favorite family memories from Hawaii, and I would absolutely recommend it to other families.
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
Highly recommend
New York City
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
Craig_G, Jun 2026
Highly recommend
Cruise was great. Had a wonderful time. Didn’t see any whales, but it certainly wasn’t for the lack of trying! Highly recommend
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
Great value
New York City
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
O2128WRdianab, May 2026
Great value
This was a great tour. Crew had a lot of knowledge and let us know about rough water ahead of time. We saw so many whales while on tour. Got to see a turtle right next to the boat. Would definitely go out with them again
Read more
Awesome with 3 Tiki!
New York City
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Angela_C, Apr 2026
Awesome with 3 Tiki!
The whale watching was cancelled because there were no whales, which I appreciated that courtesy. We snorkeled with turtles instead as an upgrade offered by the company. The experience was amazing and the crew at 3 Tiki were awesome. Highly recommend.
Read more
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