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: 3 Hour Turtle Town Snorkel and Whale Watch Tour in Kihei Lanai Snorkel Safari Experience from Maui Whale Watching Catamaran Sail Beautiful 90 Minute Catamaran Sunset Sail with Drinks! Maui: Whalewatch Sail from Lahaina

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 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 →

Maui: 3 Hour Turtle Town Snorkel and Whale Watch Tour in Kihei

Explore the vibrant underwater world on a 3-hour Turtle Town Tour in Kihei, where you can snorkel with the endangered Hawaiian Green Sea Turtles. Begin …More

Maui, USA

4.8 (16)

Maui: 3 Hour Turtle Town Snorkel and Whale Watch Tour in Kihei

Explore the vibrant underwater world on a 3-hour Turtle Town Tour in Kihei, where you can snorkel with the endangered Hawaiian Green Sea Turtles. Begin...

3 hours Free Cancellation

4.8 (16)

from
$139

Lanai Snorkel Safari Experience from Maui

Explore the stunning marine life and vibrant coral reefs of Lānaʻi on a guided snorkel tour departing from Kā‘anapali Beach. This 4.5-hour adventure includes two …More

Maui, USA

5.0 (18)

Lanai Snorkel Safari Experience from Maui

Explore the stunning marine life and vibrant coral reefs of Lānaʻi on a guided snorkel tour departing from Kā‘anapali Beach. This 4.5-hour adventure includes two...

4 hours 30 minutes Free Cancellation

5.0 (18)

from
$189

2hr whale watching sail aboard the Ho'oNaea Catamaran. Enjoy Oahu's majestic North Shore and encounter the Hawaiian Humpback whales up-close from the of the decks …More

Oahu, USA

4.7 (26)

Whale Watching Catamaran Sail

2hr whale watching sail aboard the Ho'oNaea Catamaran. Enjoy Oahu's majestic North Shore and encounter the Hawaiian Humpback whales up-close from the of the decks...

2 hours Free Cancellation

4.7 (26)

from
$114

Beautiful 90 Minute Catamaran Sunset Sail with Drinks!

The nightly Sunset Sailing trip is a gorgeous 90-minute sail with complimentary drinks. Experience sailing, sightseeing, delicious cocktails, the beautiful Hawaiian Sunset, and perhaps if …More

Oahu, USA

4.9 (19)

Beautiful 90 Minute Catamaran Sunset Sail with Drinks!

The nightly Sunset Sailing trip is a gorgeous 90-minute sail with complimentary drinks. Experience sailing, sightseeing, delicious cocktails, the beautiful Hawaiian Sunset, and perhaps if...

1 hour 30 minutes Free Cancellation

4.9 (19)

from
$56

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

Oahu Custom Private Circle Island and Mini Circle Island Tours

See all O`ahu has to offer and enjoy a ride around the Ko`olau Mountain Range. Visit the South or North Shore on a Mini Circle …More

Oahu, USA

5.0 (20)

Oahu Custom Private Circle Island and Mini Circle Island Tours

See all O`ahu has to offer and enjoy a ride around the Ko`olau Mountain Range. Visit the South or North Shore on a Mini Circle...

6 to 12 hours Hotel pickup offered

5.0 (20)

from
$699

2-HR Gondola cruise in waikiki with cute tour guide & he sings!

Combo deal!! Get this 2 hour gondola cruise and receive an all day hop on hop off waikiki bus voucher after the completion of the …More

Oahu, USA

5.0 (5)

2-HR Gondola cruise in waikiki with cute tour guide & he sings!

Combo deal!! Get this 2 hour gondola cruise and receive an all day hop on hop off waikiki bus voucher after the completion of the...

2 hours Free Cancellation

5.0 (5)

from
$178

We are one of the few companies who offer affordable private charter rates! Our 28 foot boat is big enough to comfortably fit 6 people …More

Kauai, USA

5.0 (14)

Private Na Pali Coast Tour

We are one of the few companies who offer affordable private charter rates! Our 28 foot boat is big enough to comfortably fit 6 people...

5 hours Free Cancellation

5.0 (14)

from
$2,200

Oahu: Whale Watching on "The World Famous North Shore", Hawaii

Our company is uniquely owned by Native-Hawaiian watermen. As the only company of its kind on the island, we hope you'll support local. Our owners, …More

Oahu, USA

4.8 (5)

Oahu: Whale Watching on "The World Famous North Shore", Hawaii

Our company is uniquely owned by Native-Hawaiian watermen. As the only company of its kind on the island, we hope you'll support local. Our owners,...

2 hours Free Cancellation

4.8 (5)

from
$135

Private Charter 12 Passenger X-Treme Vessel 3 Hours

Travel & Hospitality Award Winner, BBB A+ Rated, Winner of and 2018 Certificate of Excellence Cool Shore Excursions Award. …More

Maui, USA

4.7 (11)

Private Charter 12 Passenger X-Treme Vessel 3 Hours

Travel & Hospitality Award Winner, BBB A+ Rated, Winner of and 2018 Certificate of Excellence Cool Shore Excursions Award....

3 days 4 hours Free Cancellation

4.7 (11)

from
$2,300

Maui Private Paddleboard (SUP) Whale Watch: All Skill Levels

Our Private Tours are always Private and Customized to suit everyone's abilities in your family/group. Whale Watching on a Paddleboard is the BEST and most …More

Maui, USA

4.9 (9)

Maui Private Paddleboard (SUP) Whale Watch: All Skill Levels

Our Private Tours are always Private and Customized to suit everyone's abilities in your family/group. Whale Watching on a Paddleboard is the BEST and most...

2 hours Free Cancellation

4.9 (9)

from
$189

Private Oahu Pearl Harbor and Island Sightseeing Combination Tour

Combine any route or tour into one incredible, unforgettable day. Visit Pearl Harbor, then head up to the North Shore, or even cruise around the …More

Oahu, USA

5.0 (15)

Private Oahu Pearl Harbor and Island Sightseeing Combination Tour

Combine any route or tour into one incredible, unforgettable day. Visit Pearl Harbor, then head up to the North Shore, or even cruise around the...

6 to 12 hours Hotel pickup offered

5.0 (15)

from
$699

Enjoy a relaxing cruise along the North Shore of Oahu. Take in the breathtaking views of Oahu from the water where you can see Mt. …More

Oahu, USA

5.0 (4)

Private Sunset Luxury Cruise of Oahu

Enjoy a relaxing cruise along the North Shore of Oahu. Take in the breathtaking views of Oahu from the water where you can see Mt....

2 hours Free Cancellation

5.0 (4)

from
$400

Kona - 8 Hour Private Fishing Charter in Kailua-Kona, Hawaii

If there is anything you would specifically like us to accommodate, please let us know in advance and we will do everything possible to meet …More

Big Island of Hawaii, USA

4.6 (9)

Kona - 8 Hour Private Fishing Charter in Kailua-Kona, Hawaii

If there is anything you would specifically like us to accommodate, please let us know in advance and we will do everything possible to meet...

8 hours Free Cancellation

4.6 (9)

from
$1,295

Aloha Gondola Cruise with Drinks & Pastries

Impress your family with the very Best Waikiki has to offer. This is the only commercial cruise experience that tours within the tranquil waters of …More

Oahu, USA

5.0 (4)

Aloha Gondola Cruise with Drinks & Pastries

Impress your family with the very Best Waikiki has to offer. This is the only commercial cruise experience that tours within the tranquil waters of...

1 hour Free Cancellation

5.0 (4)

from
$250

Private cruise Gondola waikiki with cute tour guide & he sings!

Drift and relax under the starlight as you glide effortlessly on the tranquil waters of Waikiki. Gaze in awe under romantic moonlight while interacting with …More

Oahu, USA

5.0 (2)

Private cruise Gondola waikiki with cute tour guide & he sings!

Drift and relax under the starlight as you glide effortlessly on the tranquil waters of Waikiki. Gaze in awe under romantic moonlight while interacting with...

1 hour Free Cancellation

5.0 (2)

from
$670

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

Oahu, USA

5.0 (4)

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 (4)

from
$1,495

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

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

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

Mauna Kea Signature Coastline Cruise Day & Sunset Options

Unwind in true island style on our Mauna Kea Coastline Cruise, departing from Kawaihae Harbor aboard Olohana — a 41-foot luxury powerboat designed for comfort …More

Big Island of Hawaii, USA

4.6 (8)

Mauna Kea Signature Coastline Cruise Day & Sunset Options

Unwind in true island style on our Mauna Kea Coastline Cruise, departing from Kawaihae Harbor aboard Olohana — a 41-foot luxury powerboat designed for comfort...

90 to 120 minutes Free Cancellation

4.6 (8)

from
$99

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?