Hawaii Sailing Trips

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Hawaii Activities

Attractions

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Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.8 (327)

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (327)
from
$84.15
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (1,445)

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard our either...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (1,445)
from
$80.71
Kona Tradewind Catamaran Day Sail
Big Island of Hawaii, USA
4.8 (49)

Kona Tradewind Catamaran Day Sail

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (49)
from
$80.10
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.9 (210)

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (210)
from
$79
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Honolulu, USA
4.7 (242)

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (242)
from
$79
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (306)

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (306)
from
$72.96
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (18)
from
$70
2 Hour Swim, Snorkel & Sail (Kewalo Harbor)
Oahu, USA
5.0 (3)

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$70
Friday Night Firework Cruise in Waikiki
Oahu, USA
4.8 (34)

Friday Night Firework Cruise in Waikiki

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline,...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.8 (34)
from
$69.99
Waikiki Sunset Cruise and Iconic Views with Swimming
Oahu, USA
5.0 (2)

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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (2)
from
$65
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Oahu, USA
4.9 (202)

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (202)
from
$61.50
Waikiki Friday Night Fireworks Cruise
Oahu, USA
4.7 (29)

Waikiki Friday Night Fireworks 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
1 hour • Free Cancellation
1 hour • Free Cancellation
4.7 (29)
from
$60
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Oahu, USA
4.9 (1,706)

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Hawaii's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (1,706)
from
$59.99
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
Maui, USA
3.5 (4)

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
3.5 (4)
from
$59.95
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
Oahu, USA
4.8 (583)

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (583)
from
$56
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
Oahu, USA
4.9 (960)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Hawaii TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (960)
from
$54.98

Frequently Asked Questions

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

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Lowest Price Guarantee

Activity name

We guarantee the lowest price on all the activities available to book on our site. We'll refund the difference if you find the exact activity cheaper online until 48 hours before your activity starts.

We Make It Easy!

Gather your information

Locate your Cool Hawaii Booking Number and the proof of the lower price you found.

Send it to us

Email [email protected] with the documents, your name, and your home address.

We'll review

We'll review your materials and get in touch as soon as possible.

Receive your refund

If everything checks out, we'll refund you the price difference.

Refund Terms & Conditions

The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Cool Hawaii promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same activity, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Hawaii and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased activity into one or more parts sold separately.
  • Cool Hawaii reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Hawaii.

Sorting, ranking, and search results

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Cool Hawaii wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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