Top Hawaii Cruises, Sailing & Water Tours

Q: What are the best options for Hawaii Cruises, Sailing & Water Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Hawaii Cruises, Sailing & Water Tours are: Maui: Private Ocean Adventure–Luxury Boston Whaler Charter for 6 Maui Intimate Luxury Powerboat Private Charter 2-Tank Dive K2 Power Catamaran featuring the Molokini Crater Certified Diver 2 Tank Shallow Reef Dives Off Wai'anae Kealakekua Bay Captain Cook Snorkel Adventure

Q: What are the best kid-friendly options for Hawaii Cruises, Sailing & Water Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Hawaii Cruises, Sailing & Water Tours are: Waikiki Glass Bottom Boat Cruise Waikiki Beach Glass Bottom Boat Tour Kona Manta Ray Snorkel Tour Guaranteed or come again free Waikiki 2 hour Turtle Canyon Snorkeling Adventure Big Island Manta Ray Night Snorkel View all kid-friendly Tours →

Q: Which Hawaii Cruises, Sailing & Water Tours have Instant Confirmation?

Hawaii Cruises, Sailing & Water Tours with Instant Confirmation include: Waikiki Glass Bottom Boat Cruise Waikiki Beach Glass Bottom Boat Tour Kona Manta Ray Snorkel Tour Guaranteed or come again free Waikiki 2 hour Turtle Canyon Snorkeling Adventure Big Island Manta Ray Night Snorkel View all Tours with Instant Confirmation →

Q: I need a ride! Which Hawaii Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Hawaii Cruises, Sailing & Water Tours include Hotel Pickup: Oahu Dolphin and Snorkel Tour with Waikiki Pickup & Lunch Oahu Circle Island Snorkeling Tour: Dole, Pali Lookout & More Ko Olina Catamaran Sail and Snorkel with Lunch Luxury Snorkel Cruise with Dolphin Watch and Hawaiian Meal Oahu Small-Group Circle Island Tour with Turtle Snorkeling View all Tours with Hotel Pickup →

Q: Got any more Hawaii trip ideas?

We sure do. Check out our curated lists of hand-picked Hawaii Tours. Top 10 Hawaii 2026 Senior-friendly tours Hawaii The best tours and activities for culture lovers in Hawaii Top Day Trips from Hawaii Things to do in Hawaii this summer View all Hawaii Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Hawaii?

Based on our sales data over the past year, the most popular styles of tours and activities in Hawaii are: Hawaii Luxury & Special Occasions Hawaii Luxury Tours Hawaii Outdoor Activities Hawaii Cruises, Sailing & Water Tours Hawaii Tours & Sightseeing View all tour styles in Hawaii →

Maui: Private Ocean Adventure–Luxury Boston Whaler Charter for 6

Welcome to your very own private Maui adventure! Ali’i Nani, roughly translated to “Beautiful Royalty,” evokes elegance, prestige, and the ultimate in luxury. Whether you’re …More

Maui, USA

5.0 (3)

Maui: Private Ocean Adventure–Luxury Boston Whaler Charter for 6

Welcome to your very own private Maui adventure! Ali’i Nani, roughly translated to “Beautiful Royalty,” evokes elegance, prestige, and the ultimate in luxury. Whether you’re...

3 hours Free Cancellation

5.0 (3)

from
$3,295

Maui Intimate Luxury Powerboat Private Charter

Step aboard 'Amore', your private charter and discover Maui’s coastline in comfort and style. Designed for versatility, this premium vessel offers an expansive bow with …More

Maui, USA

5.0 (1)

Maui Intimate Luxury Powerboat Private Charter

Step aboard 'Amore', your private charter and discover Maui’s coastline in comfort and style. Designed for versatility, this premium vessel offers an expansive bow with...

3 hours Free Cancellation

5.0 (1)

from
$1,795

2-Tank Dive K2 Power Catamaran featuring the Molokini Crater

Experience the vibrant underwater world at Molokini Crater, a renowned marine preserve just a short boat ride from Kihei. With over 25 years of expertise, …More

Maui, USA

4.9 (10)

2-Tank Dive K2 Power Catamaran featuring the Molokini Crater

Experience the vibrant underwater world at Molokini Crater, a renowned marine preserve just a short boat ride from Kihei. With over 25 years of expertise,...

3 hours Free Cancellation

4.9 (10)

from
$239

Certified Diver 2 Tank Shallow Reef Dives Off Wai'anae

The best reef diving experience in Hawaiian waters! Join us on a guided tour of two beautiful reefs on the west shore of Oahu. As …More

Oahu, USA

5.0 (3)

Certified Diver 2 Tank Shallow Reef Dives Off Wai'anae

The best reef diving experience in Hawaiian waters! Join us on a guided tour of two beautiful reefs on the west shore of Oahu. As...

3 hours Free Cancellation

5.0 (3)

from
$141

Kealakekua Bay Captain Cook Snorkel Adventure

Captain Cook’s Monument, and the legendary “Place of Refuge” are in one of the most sought-after snorkeling destinations in all the world, Kealakekua Bay. This spot …More

Big Island of Hawaii, USA

5.0 (22)

Kealakekua Bay Captain Cook Snorkel Adventure

Captain Cook’s Monument, and the legendary “Place of Refuge” are in one of the most sought-after snorkeling destinations in all the world, Kealakekua Bay. This spot...

4 hours Free Cancellation

5.0 (22)

from
$286

Personalized Private Pearl Harbor National Memorial Oahu Tours

Visit the World War II Valor in the Pacific National Monument at Pearl Harbor to reflect, remember and understand the tragic events of December 7, …More

Oahu, USA

5.0 (2)

Personalized Private Pearl Harbor National Memorial Oahu Tours

Visit the World War II Valor in the Pacific National Monument at Pearl Harbor to reflect, remember and understand the tragic events of December 7,...

6 to 12 hours Hotel pickup offered

5.0 (2)

from
$699

Kona Hawaii Deep Sea Luxury Fishing Trip on Bite Me 5

In 2024 our vessel underwent a complete retrofit. We offer custom charters to fit all your needs. Experienced and novice alike, you will be guided …More

Big Island of Hawaii, USA

4.9 (7)

Kona Hawaii Deep Sea Luxury Fishing Trip on Bite Me 5

In 2024 our vessel underwent a complete retrofit. We offer custom charters to fit all your needs. Experienced and novice alike, you will be guided...

4 hours Free Cancellation

4.9 (7)

from
$1,293

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

Premium Snorkel Sunset Cruise with Dolphin Watch & Hawaiian Meal

Experience the perfect blend of adventure, relaxation, and natural beauty along Oʻahu’s west coast on this premium snorkel and sunset cruise. Departing from Ko Olina …More

Honolulu, USA

4.7 (50)

Premium Snorkel Sunset Cruise with Dolphin Watch & Hawaiian Meal

Experience the perfect blend of adventure, relaxation, and natural beauty along Oʻahu’s west coast on this premium snorkel and sunset cruise. Departing from Ko Olina...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (50)

from
$154

Two Site Snorkel Adventure featuring the Molokini Crater K2

Experience the vibrant underwater world at Molokini Crater, a renowned marine preserve just a short boat ride from Kihei. With over 25 years of expertise, …More

Maui, USA

5.0 (1)

Two Site Snorkel Adventure featuring the Molokini Crater K2

Experience the vibrant underwater world at Molokini Crater, a renowned marine preserve just a short boat ride from Kihei. With over 25 years of expertise,...

3 hours Free Cancellation

5.0 (1)

from
$176

Join us to observe the behavior of the Humpback Whales while they visit the Hawaiian Islands. Learn more about them from our kind & qualified …More

Big Island of Hawaii, USA

5.0 (20)

Kona: Kohola Whale Watching Excursion

Join us to observe the behavior of the Humpback Whales while they visit the Hawaiian Islands. Learn more about them from our kind & qualified...

3 hours Free Cancellation

5.0 (20)

from
$160

Experience snorkelling with wildlife in exclusive spots, encountering dolphins along the way, sightseeing in small intimate groups with friendly and knowledgeable guides, and enjoy a …More

Maui, USA

5.0 (3)

Maui: Private Luxury Charter Experience

Experience snorkelling with wildlife in exclusive spots, encountering dolphins along the way, sightseeing in small intimate groups with friendly and knowledgeable guides, and enjoy a...

4 hours

5.0 (3)

from
$2,370

Kona Hawaii Fishing/Snorkel Large Group Private Charter on OE

Welcome aboard the Ocean Encounters. This 46' Delta is your pathway to some of the best memories of a lifetime! On this private large group …More

Big Island of Hawaii, USA

4.8 (9)

Kona Hawaii Fishing/Snorkel Large Group Private Charter on OE

Welcome aboard the Ocean Encounters. This 46' Delta is your pathway to some of the best memories of a lifetime! On this private large group...

4 to 8 hours Free Cancellation

4.8 (9)

from
$2,624

Private Stand Up Paddling Lesson in Makena

Makena Bay is one of the most popular launching points for so many water activities as it offers such a great experience. Calm waters over …More

Maui, USA

5.0 (2)

Private Stand Up Paddling Lesson in Makena

Makena Bay is one of the most popular launching points for so many water activities as it offers such a great experience. Calm waters over...

2 hours Free Cancellation

5.0 (2)

from
$183

Hawaii Volcanoes National Park Experience from Maui

Here is your chance to visit Hawaii’s only active volcano and see the youngest of the Hawaiian Islands. On this inter-island excursion, you’ll visit the …More

Big Island of Hawaii, USA

5.0 (6)

Hawaii Volcanoes National Park Experience from Maui

Here is your chance to visit Hawaii’s only active volcano and see the youngest of the Hawaiian Islands. On this inter-island excursion, you’ll visit the...

8 to 10 hours Free Cancellation

5.0 (6)

from
$590

Big Island: 5-Hour Kona Private Boat Charter

Perfect for all size of couples, families or extended families. Experience Kealakekua Bay, the best place to snorkel on the Big Island or find a …More

Big Island of Hawaii, USA

4.9 (7)

Big Island: 5-Hour Kona Private Boat Charter

Perfect for all size of couples, families or extended families. Experience Kealakekua Bay, the best place to snorkel on the Big Island or find a...

5 hours Free Cancellation

4.9 (7)

from
$1,243

Kona: 2.5-Hour Whale Watching On A 41' Super-Raft

A Whale of a Time in Hawaii! Step aboard our luxurious 41ft Super-Raft for a fun filled adventure on the water. Enjoy the thrill of …More

Big Island of Hawaii, USA

4.8 (14)

Kona: 2.5-Hour Whale Watching On A 41' Super-Raft

A Whale of a Time in Hawaii! Step aboard our luxurious 41ft Super-Raft for a fun filled adventure on the water. Enjoy the thrill of...

2 hours 30 minutes Free Cancellation

4.8 (14)

from
$135

Embark on an unforgettable journey aboard our intimate sunset cruise, where the Hawaiian sky transforms into a stunning canvas of gold, pink, and violet hues. …More

Oahu, USA

5.0 (13)

Sunset Cruise along Waikiki Coastline

Embark on an unforgettable journey aboard our intimate sunset cruise, where the Hawaiian sky transforms into a stunning canvas of gold, pink, and violet hues....

1 hour 30 minutes Free Cancellation

5.0 (13)

from
$125

Private Waikiki 5 Hour Charter on board Ocean Therapy

Snorkel or SCUBA Dive Along the Waikiki Coast Up to 6 Guests | 5+ Hours | Certified Divers & Snorkelers Welcome Escape the crowds and …More

Oahu, USA

5.0 (1)

Private Waikiki 5 Hour Charter on board Ocean Therapy

Snorkel or SCUBA Dive Along the Waikiki Coast Up to 6 Guests | 5+ Hours | Certified Divers & Snorkelers Welcome Escape the crowds and...

5 hours Free Cancellation

5.0 (1)

from
$2,800

10 Passenger Max Customizable Private Charter

• Vessel Designed for Exploration: HAWAII MARINE LIFE CHARTERS uses a 31’ Ocean Craft RHIB—the same "super-raft" used by military and law enforcement. This design …More

Big Island of Hawaii, USA

5.0 (14)

10 Passenger Max Customizable Private Charter

• Vessel Designed for Exploration: HAWAII MARINE LIFE CHARTERS uses a 31’ Ocean Craft RHIB—the same "super-raft" used by military and law enforcement. This design...

4 hours Free Cancellation

5.0 (14)

from
$1,740

Frequently Asked Questions

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

What are the best options for Hawaii Cruises, Sailing & Water Tours?

What are the best kid-friendly options for Hawaii Cruises, Sailing & Water Tours Tours?

Which Hawaii Cruises, Sailing & Water Tours have Instant Confirmation?

Which Hawaii Cruises, Sailing & Water Tours have Free Cancellation?

Hawaii Cruises, Sailing & Water Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Hawaii Cruises, Sailing & Water Tours have Hotel Pickup?

Got any more Hawaii trip ideas?

What are the most popular styles of Tours and Activities in Hawaii?