cool hawaii
Top Oahu activities
Cruise ship visitors
Oahu trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by time
  • Tours by the numbers
  • Shore excursions
  • Cruise ships
  • Cruise lines
  • Oahu travel guides
  • Oahu travel calendar
  • Oahu attractions
Top Maui activities
Cruise ship visitors
Maui trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by time
  • Tours by the numbers
  • Shore excursions
  • Cruise ships
  • Cruise lines
  • Maui travel guides
  • Maui travel calendar
  • Maui attractions
Top Big Island activities
Cruise ship visitors
Big Island trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by time
  • Tours by the numbers
  • Shore excursions
  • Cruise ships
  • Cruise lines
  • Big Island of Hawaii travel guides
  • Big Island of Hawaii travel calendar
  • Big Island of Hawaii attractions
Top Kauai activities
Kauai trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by time
  • Tours by the numbers
  • Kauai travel guides
  • Kauai travel calendar
  • Kauai attractions
Language $Currency
Login / Sign up
Bookings
Bookings
Wallet
$0.00
Wishlists
Wishlists
Cool Rewards Rewards
Gift cards
Profile
Help Center
Language
Log out
Gift Cards Gift Cards Rewards Rewards Specials Specials Group Travel Group Travel Contact Contact
Tours by category
Top 10 Tours Top 10 Tours
Pearl Harbor Tours Pearl Harbor Tours
Sightseeing Tours Sightseeing Tours
Helicopter Tours Helicopter Tours
Snorkeling Tours Snorkeling Tours
Luxury Tours Luxury Tours
View all tours View all tours
See more
Tours by accessibility
Wheelchair accessible Wheelchair accessible
Service animals allowed Service animals allowed
All fitness levels All fitness levels
Stroller accessible Stroller accessible
Kid-friendly tours Kid-friendly tours
Infants go free Infants go free
See more
Tours by feature
Free cancellation Free cancellation
Badge of Excellence Badge of Excellence
Likely to sell out Likely to sell out
Instant confirmation Instant confirmation
Hotel pickup Hotel pickup
Private tours Private tours
See more
Tours by time
Morning tours Morning tours
Afternoon tours Afternoon tours
Evening & night tours Evening & night tours
Overnight tours Overnight tours
Up to 1 hour Up to 1 hour
1 to 4 hours 1 to 4 hours
See more
Tours by the numbers
Under $50 Under $50
From $50 - $100 From $50 - $100
From $100 - $250 From $100 - $250
From $250 - $500 From $250 - $500
Over $500 Over $500
100+ reviews 100+ reviews
See more
Shore excursions
Honolulu shore excursions Honolulu shore excursions
Honolulu cruise port schedule Honolulu cruise port schedule
Cruise ships
Ruby Princess Ruby Princess
Carnival Legend Carnival Legend
Emerald Princess Emerald Princess
ms Koningsdam ms Koningsdam
Crown Princess Crown Princess
Carnival Radiance Carnival Radiance
See more
Cruise lines
Princess Cruises Princess Cruises
Carnival Cruise Line Carnival Cruise Line
Holland America Holland America
Silversea Cruises Silversea Cruises
Oceania Cruises Oceania Cruises
Cunard Cunard
See more
Oahu travel guides
Senior-friendly tours Oahu Senior-friendly tours Oahu
The best tours and activities for culture lovers in Oahu The best tours and activities for culture lovers in Oahu
Top Day Trips from Oahu Top Day Trips from Oahu
Things to do in Oahu this summer Things to do in Oahu this summer
Rainy day activities Rainy day activities
Oahu Foodie Tours Oahu Foodie Tours
View all recommendations View all recommendations
See more
Oahu travel calendar
Thanksgiving Thanksgiving
Veteran's Day Veteran's Day
New Year’s Day long weekend New Year’s Day long weekend
Christmas Eve Christmas Eve
New Year’s Eve New Year’s Eve
Hanukkah Hanukkah
View calendar View calendar
See more
Oahu attractions
Waikiki Beach tours Waikiki Beach tours
Diamond Head tours Diamond Head tours
Hanauma Bay tours Hanauma Bay tours
Halona Blowhole tours Halona Blowhole tours
Kewalo Basin tours Kewalo Basin tours
Sandy Beach Park tours Sandy Beach Park tours
View all View all
See more
Tours by category
Top 10 Tours Top 10 Tours
Sightseeing Tours Sightseeing Tours
Helicopter Tours Helicopter Tours
Road To Hana Tours Road To Hana Tours
Haleakala Tours Haleakala Tours
Snorkeling Tours Snorkeling Tours
View all tours View all tours
See more
Tours by accessibility
Wheelchair accessible Wheelchair accessible
Service animals allowed Service animals allowed
All fitness levels All fitness levels
Stroller accessible Stroller accessible
Kid-friendly tours Kid-friendly tours
Infants go free Infants go free
See more
Tours by feature
Free cancellation Free cancellation
Badge of Excellence Badge of Excellence
Likely to sell out Likely to sell out
Instant confirmation Instant confirmation
Hotel pickup Hotel pickup
Private tours Private tours
See more
Tours by time
Morning tours Morning tours
Afternoon tours Afternoon tours
Evening & night tours Evening & night tours
Overnight tours Overnight tours
Up to 1 hour Up to 1 hour
1 to 4 hours 1 to 4 hours
See more
Tours by the numbers
Under $50 Under $50
From $50 - $100 From $50 - $100
From $100 - $250 From $100 - $250
From $250 - $500 From $250 - $500
Over $500 Over $500
100+ reviews 100+ reviews
See more
Shore excursions
Kahului shore excursions Kahului shore excursions
Lahaina shore excursions Lahaina shore excursions
Cruise ships
Pride of America Pride of America
Safari Explorer Safari Explorer
Wilderness Explorer Wilderness Explorer
Ruby Princess Ruby Princess
Carnival Legend Carnival Legend
ms Koningsdam ms Koningsdam
See more
Cruise lines
UnCruise Adventures UnCruise Adventures
Norwegian Cruise Line Norwegian Cruise Line
Princess Cruises Princess Cruises
Carnival Cruise Line Carnival Cruise Line
Holland America Holland America
Silversea Cruises Silversea Cruises
See more
Maui travel guides
Senior-friendly tours Maui Senior-friendly tours Maui
The best tours and activities for culture lovers The best tours and activities for culture lovers
Top Day Trips from Maui Top Day Trips from Maui
Things to do in Maui this summer Things to do in Maui this summer
Rainy day activities Rainy day activities
Maui Foodie Tours Maui Foodie Tours
View all recommendations View all recommendations
See more
Maui travel calendar
Thanksgiving Thanksgiving
Veteran's Day Veteran's Day
New Year’s Day long weekend New Year’s Day long weekend
New Year’s Eve New Year’s Eve
Hanukkah Hanukkah
MLK Day MLK Day
View calendar View calendar
See more
Maui attractions
Molokini Crater tours Molokini Crater tours
Paia tours Paia tours
Hoʻokipa Beach Park tours Hoʻokipa Beach Park tours
Road to Hana tours Road to Hana tours
Waianapanapa State Park tours Waianapanapa State Park tours
Hana tours Hana tours
View all View all
See more
Tours by category
Top 10 Tours Top 10 Tours
Sightseeing Tours Sightseeing Tours
Helicopter Tours Helicopter Tours
Snorkeling Tours Snorkeling Tours
Adventure Tours Adventure Tours
Volcano Tours Volcano Tours
View all tours View all tours
See more
Tours by accessibility
Wheelchair accessible Wheelchair accessible
Service animals allowed Service animals allowed
All fitness levels All fitness levels
Stroller accessible Stroller accessible
Kid-friendly tours Kid-friendly tours
Infants go free Infants go free
See more
Tours by feature
Free cancellation Free cancellation
Badge of Excellence Badge of Excellence
Likely to sell out Likely to sell out
Instant confirmation Instant confirmation
Hotel pickup Hotel pickup
Private tours Private tours
See more
Tours by time
Morning tours Morning tours
Afternoon tours Afternoon tours
Evening & night tours Evening & night tours
Overnight tours Overnight tours
Up to 1 hour Up to 1 hour
1 to 4 hours 1 to 4 hours
See more
Tours by the numbers
Under $50 Under $50
From $50 - $100 From $50 - $100
From $100 - $250 From $100 - $250
From $250 - $500 From $250 - $500
Over $500 Over $500
100+ reviews 100+ reviews
See more
Shore excursions
Hilo shore excursions Hilo shore excursions
Hilo cruise port schedule Hilo cruise port schedule
Cruise ships
Pride of America Pride of America
Ruby Princess Ruby Princess
Carnival Legend Carnival Legend
Emerald Princess Emerald Princess
ms Koningsdam ms Koningsdam
Norwegian Spirit Norwegian Spirit
See more
Cruise lines
Norwegian Cruise Line Norwegian Cruise Line
Princess Cruises Princess Cruises
Carnival Cruise Line Carnival Cruise Line
Holland America Holland America
Silversea Cruises Silversea Cruises
Oceania Cruises Oceania Cruises
See more
Big Island of Hawaii travel guides
Senior-friendly tours Big Island of Hawaii Senior-friendly tours Big Island of Hawaii
The best tours and activities for culture lovers The best tours and activities for culture lovers
Top Day Trips from Big Island of Hawaii Top Day Trips from Big Island of Hawaii
Things to do on the Big Island this summer Things to do on the Big Island this summer
Rainy day activities on the Big Island Rainy day activities on the Big Island
Big Island of Hawaii Foodie Tours Big Island of Hawaii Foodie Tours
View all recommendations View all recommendations
See more
Big Island of Hawaii travel calendar
Thanksgiving Thanksgiving
Veteran's Day Veteran's Day
New Year’s Day long weekend New Year’s Day long weekend
New Year’s Eve New Year’s Eve
Hanukkah Hanukkah
MLK Day MLK Day
View calendar View calendar
See more
Big Island of Hawaii attractions
Kona tours Kona tours
Anaeho'omalu Bay tours Anaeho'omalu Bay tours
Keauhou Bay tours Keauhou Bay tours
Captain Cook Monument tours Captain Cook Monument tours
Kealakekua Bay tours Kealakekua Bay tours
Honokohau Harbor tours Honokohau Harbor tours
View all View all
See more
Tours by category
Top 10 Tours Top 10 Tours
Sightseeing Tours Sightseeing Tours
Helicopter Tours Helicopter Tours
Snorkeling Tours Snorkeling Tours
Adventure Tours Adventure Tours
Dinner Cruises Dinner Cruises
View all tours View all tours
See more
Tours by accessibility
Wheelchair accessible Wheelchair accessible
Service animals allowed Service animals allowed
All fitness levels All fitness levels
Stroller accessible Stroller accessible
Kid-friendly tours Kid-friendly tours
Infants go free Infants go free
See more
Tours by feature
Free cancellation Free cancellation
Badge of Excellence Badge of Excellence
Likely to sell out Likely to sell out
Instant confirmation Instant confirmation
Hotel pickup Hotel pickup
Private tours Private tours
See more
Tours by time
Morning tours Morning tours
Afternoon tours Afternoon tours
Evening & night tours Evening & night tours
Overnight tours Overnight tours
Up to 1 hour Up to 1 hour
1 to 4 hours 1 to 4 hours
See more
Tours by the numbers
Under $50 Under $50
From $50 - $100 From $50 - $100
From $100 - $250 From $100 - $250
From $250 - $500 From $250 - $500
Over $500 Over $500
100+ reviews 100+ reviews
See more
Kauai travel guides
Senior-friendly tours Kauai Senior-friendly tours Kauai
The best tours and activities for culture lovers in Kauai The best tours and activities for culture lovers in Kauai
Top Day Trips from Kauai Top Day Trips from Kauai
Things to do in Kauai this summer Things to do in Kauai this summer
Rainy day activities Rainy day activities
Kauai Foodie Tours Kauai Foodie Tours
View all recommendations View all recommendations
See more
Kauai travel calendar
Thanksgiving Thanksgiving
Veteran's Day Veteran's Day
New Year’s Day long weekend New Year’s Day long weekend
New Year’s Eve New Year’s Eve
Hanukkah Hanukkah
MLK Day MLK Day
View calendar View calendar
See more
Kauai attractions
Waimea Canyon tours Waimea Canyon tours
Na Pali Coast tours Na Pali Coast tours
Kauai Coffee Company tours Kauai Coffee Company tours
Hanalei Bay tours Hanalei Bay tours
Spouting Horn tours Spouting Horn tours
Kalalau Lookout tours Kalalau Lookout tours
View all View all
See more
Start your search
Change your search
Place or activity
Select Dates

Hawaii Sailing Trips

103 Results
Sort by:
Price (Low to High)
Filter
Languages Clear
Time of Day Clear
50
52
46
Duration Clear
4
91
14
0
0
Price Clear
$0 $500+
Rating Clear
90
101
101
Specials Clear
102
42
0
13
2
Features Clear
4
75
86
4
89
1
Accessibility Clear
0
31
83
Families Clear
82
22
47

Hawaii Activities

Attractions

Guides

Calendar

Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (2,417)

Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with...

2 hours Free Cancellation
4.9 (2,417)
from
$90
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), …More

Honolulu, USA
4.9 (670)

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hours Hotel pickup offered Free Cancellation
4.9 (670)
from
$90
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
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 small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (109)

Waikiki small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

2 hours Free Cancellation
5.0 (109)
from
$99
Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (121)

Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come...

2 hours Free Cancellation
4.9 (121)
from
$99
Waikiki Turtle Snorkeling Adventure(8am)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.9 (139)

Waikiki Turtle Snorkeling Adventure(8am)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the...

3 hours Hotel pickup offered Free Cancellation
4.9 (139)
from
$100
Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

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

Maui, USA
5.0 (1)

Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

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
$102
Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (382)

Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes Free Cancellation
4.8 (382)
from
$109
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
Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

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
4.9 (103)

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

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
4.9 (103)
from
$110
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
Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

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)

Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

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
$110
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
Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way …More

Maui, USA
4.9 (90)

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours Free Cancellation
4.9 (90)
from
$119
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 (44)

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 (44)
from
$120

Frequently Asked Questions

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

Recent activity reviews
View traveler photos & reviews
Activity name

Hawaii Activities
Attractions
Cruise Ports
Guides
Calendar
View more
View more