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Hawaii Sailing Trips

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Hawaii Activities

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Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (17)

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours Free Cancellation
5.0 (17)
from
$300
Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (29)

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations...

2 hours Free Cancellation
4.9 (29)
from
$110
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA
4.8 (62)

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour Free Cancellation
4.8 (62)
from
$90
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Maui, USA
4.8 (63)

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes Free Cancellation
4.8 (63)
from
$249
South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have …More

Oahu, USA
4.8 (26)

South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutes Free Cancellation
4.8 (26)
from
$48
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, …More

Oahu, USA
4.8 (37)

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours Free Cancellation
4.8 (37)
from
$250
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 (50)

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 (50)
from
$110
Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner …More

Big Island of Hawaii, USA
4.9 (253)

Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner...

3 hours Free Cancellation
4.9 (253)
from
$136
Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA
5.0 (28)

Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours Free Cancellation
5.0 (28)
from
$170
Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback …More

Oahu, USA
5.0 (21)

Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback...

2 hours Free Cancellation
5.0 (21)
from
$150
Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA
5.0 (18)

Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours Free Cancellation
5.0 (18)
from
$180
Waikiki Friday Night Fireworks Cruise NYE SPECIAL 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 NYE SPECIAL 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
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
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
Maui: 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)

Maui: 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
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

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