Top Hawaii Cruises, Sailing & Water 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 Kona Snorkel Tour: Captain Cook Reef Snorkel, Dolphin & Sea Caves Waikiki 2 hour Turtle Canyon Snorkeling Adventure 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 →

Honolulu: Private Whale Watching and Coastal Swimming Tour

Our experienced crew are masters of Hawaii's ocean, ensuring your safety and best possible experience. This tour is on a power catamaran, a boat design …More

Oahu, USA

5.0 (4)

Honolulu: Private Whale Watching and Coastal Swimming Tour

Our experienced crew are masters of Hawaii's ocean, ensuring your safety and best possible experience. This tour is on a power catamaran, a boat design...

2 hours Free Cancellation

5.0 (4)

from
$749

Mauna Kea Deluxe Whale Watch and Boat Cruise

Set sail on the luxurious Olohana powerboat for the Mauna Kea Deluxe Whale Watch, where stunning views and unforgettable wildlife encounters await. This 2-hour cruise …More

Big Island of Hawaii, USA

5.0 (2)

Mauna Kea Deluxe Whale Watch and Boat Cruise

Set sail on the luxurious Olohana powerboat for the Mauna Kea Deluxe Whale Watch, where stunning views and unforgettable wildlife encounters await. This 2-hour cruise...

2 hours Free Cancellation

5.0 (2)

from
$109

Oahu Personalized Private North Shore Highlight Custom Tour

Explore the Seven Mile Miracle known as O`ahuʻs North Shore. Winter brings big waves and world-class surfing, while the summer is calm and perfect for visiting …More

Oahu, USA

5.0 (8)

Oahu Personalized Private North Shore Highlight Custom Tour

Explore the Seven Mile Miracle known as O`ahuʻs North Shore. Winter brings big waves and world-class surfing, while the summer is calm and perfect for visiting...

6 to 12 hours Hotel pickup offered

5.0 (8)

from
$699

Kona Hawaii Deep Sea Fishing experience on the Bite Me 4

Enjoy the day out on the waters off the Kona Coast on this private chartered fishing and boating excursion. Sit back, relax and drink in …More

Big Island of Hawaii, USA

4.6 (25)

Kona Hawaii Deep Sea Fishing experience on the Bite Me 4

Enjoy the day out on the waters off the Kona Coast on this private chartered fishing and boating excursion. Sit back, relax and drink in...

4 to 8 hours Free Cancellation

4.6 (25)

from
$862

Private Group SUP Lessons for 4 by Waikiki Beachboys at the Royal

Learn how to stand up paddle with your own Waikiki Beachboy in the birth place of surfing. We are located in the heart of Waikiki, just …More

Oahu, USA

4.7 (6)

Private Group SUP Lessons for 4 by Waikiki Beachboys at the Royal

Learn how to stand up paddle with your own Waikiki Beachboy in the birth place of surfing. We are located in the heart of Waikiki, just...

1 hour Free Cancellation

4.7 (6)

from
$101

Waikiki to Diamondhead: Sunset BYOB Cruise

Want a spectacular sunset cruise? Our cruise offers multi level viewing of the dramatic Waikiki coastline and spectacular sunset on the water views. We offer …More

Oahu, USA

5.0 (2)

Waikiki to Diamondhead: Sunset BYOB Cruise

Want a spectacular sunset cruise? Our cruise offers multi level viewing of the dramatic Waikiki coastline and spectacular sunset on the water views. We offer...

2 to 190 minutes Free Cancellation

5.0 (2)

from
$139

Our whale watching tours are affordable and are crewed by our local Captains. The best time to see Humpback whales in Hawaii is between the …More

Oahu, USA

4.2 (68)

Waikiki Whale Watching Cruise

Our whale watching tours are affordable and are crewed by our local Captains. The best time to see Humpback whales in Hawaii is between the...

90 to 100 minutes Free Cancellation

4.2 (68)

from
$29

There's no better way to see Hawaii than from the ocean. Breathless views of the island and it's terrain. But the beauty of Hawaii is …More

Big Island of Hawaii, USA

5.0 (10)

3-Hour Luxury Private Custom Charter

There's no better way to see Hawaii than from the ocean. Breathless views of the island and it's terrain. But the beauty of Hawaii is...

3 hours Free Cancellation

5.0 (10)

from
$1,950

Maui: Sunset/Glow Clear Kayak Tour in Olowalu

This is a one of a kind experience. We are the only Clear Kayak Sunset/Glow Tour in Hawaii. Get a unique view of Maui's beautiful …More

Maui, USA

5.0 (5)

Maui: Sunset/Glow Clear Kayak Tour in Olowalu

This is a one of a kind experience. We are the only Clear Kayak Sunset/Glow Tour in Hawaii. Get a unique view of Maui's beautiful...

4 hours Free Cancellation

5.0 (5)

from
$239

Catamaran Private Charter of NaPali Coast on Kauai

We have been operating our tours for over 39 years. We custom-built our vessels to provide you with the ideal sightseeing vessel for our Kauai …More

Kauai, USA

5.0 (1)

Catamaran Private Charter of NaPali Coast on Kauai

We have been operating our tours for over 39 years. We custom-built our vessels to provide you with the ideal sightseeing vessel for our Kauai...

5 hours Free Cancellation

5.0 (1)

from
$3,400

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

Mokulua Islands Self-Guided Kayak Adventure

Explore the Mokolua Islands on this adventurous self-guided tour. The island is a seabird sanctuary and the beach is also a resting spot for monk …More

Oahu, USA

3.9 (7)

Mokulua Islands Self-Guided Kayak Adventure

Explore the Mokolua Islands on this adventurous self-guided tour. The island is a seabird sanctuary and the beach is also a resting spot for monk...

4 hours Free Cancellation

3.9 (7)

from
$82

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

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 Magic Adventure Snorkel: Molokini Crater and Turtle Stop

The unique design of the Maui Magic allows access to destinations that other boats are unable to reach. The Maui Magic explores more of the …More

Maui, USA

4.7 (44)

Maui Magic Adventure Snorkel: Molokini Crater and Turtle Stop

The unique design of the Maui Magic allows access to destinations that other boats are unable to reach. The Maui Magic explores more of the...

5 hours Free Cancellation

4.7 (44)

from
$224

Oahu Customizable Private Community Service Voluntourism Offer

Want to give something back to Hawai`i? So do we! We will each donate 1.5 hours of any tour on the cause of your choice, …More

Oahu, USA

5.0 (4)

Oahu Customizable Private Community Service Voluntourism Offer

Want to give something back to Hawai`i? So do we! We will each donate 1.5 hours of any tour on the cause of your choice,...

6 to 12 hours Hotel pickup offered

5.0 (4)

from
$549

Oahu Private First, Last and Transfer Day Tours with Luggage

Make the first or last day of your vacation the best one, without any hassle or wasted time. We all know the feeling of an early …More

Oahu, USA

5.0 (2)

Oahu Private First, Last and Transfer Day Tours with Luggage

Make the first or last day of your vacation the best one, without any hassle or wasted time. We all know the feeling of an early...

6 to 12 hours

5.0 (2)

from
$799

Custom Private Multi Day Tours on the island of Oahu Hawaii

Your Multi-Day Tours make sure you have the most fun possible, see everything you want, as well as have a driver for things like dinner, golf, …More

Oahu, USA

5.0 (7)

Custom Private Multi Day Tours on the island of Oahu Hawaii

Your Multi-Day Tours make sure you have the most fun possible, see everything you want, as well as have a driver for things like dinner, golf,...

3 days Hotel pickup offered

5.0 (7)

from
$1,998

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

Big Island of Hawaii, USA

5.0 (6)

Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours Free Cancellation

5.0 (6)

from
$276

3 Hour 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

Oahu, USA

5.0 (1)

3 Hour 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...

3 hours Free Cancellation

5.0 (1)

from
$1,995

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

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?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Hawaii Cruises, Sailing & Water Tours are:

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?