Hawaii Sailing Trips

104 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
48
52
46
Duration Clear
3
91
16
0
0
Price Clear
$0 $500+
Rating Clear
90
100
102
Specials Clear
104
43
0
17
2
Features Clear
5
79
88
4
90
2
Accessibility Clear
0
31
80
Families Clear
79
26
48

Hawaii Activities

Attractions

Guides

Calendar

Waikiki Turtle Snorkeling Tour with Free Pickup
Honolulu, USA
4.9 (277)

Waikiki Turtle Snorkeling Tour 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
3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
4.9 (277)
from
$89
Deluxe Sail & Snorkel to the Captain Cook Monument
Big Island of Hawaii, USA
4.9 (476)

Deluxe Sail & Snorkel to the Captain Cook Monument

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument"...

4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4.9 (476)
from
$178.72
Maui Sunset Sail
Maui, USA
4.8 (209)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (209)
from
$137.82
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
Oahu, USA
4.9 (255)

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (255)
from
$49.99
Molokini Snorkel and Performance Sail: Mā’alaea Harbor
Maui, USA
4.9 (218)

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.9 (218)
from
$200
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
Maui, USA
4.9 (111)

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.9 (111)
from
$163.20
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
Maui, USA
5.0 (66)

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (66)
from
$216.22
Afternoon Sail & Snorkel to the Captain Cook Monument
Big Island of Hawaii, USA
4.9 (251)

Afternoon Sail & Snorkel to the Captain Cook Monument

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.9 (251)
from
$135.64
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
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (59)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (59)
from
$289
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (18)

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (18)
from
$251.10
Luxury Catamaran Whale Watch
Maui, USA
4.9 (90)

Luxury Catamaran Whale Watch

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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (90)
from
$119
Private Catamaran Charter in Waikiki (1-6 Guests)
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (25)

Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (25)
from
$900
Snorkel Sail Adventure off Ka'anapali Beach in Maui
Lahaina, USA
5.0 (45)

Snorkel Sail Adventure off Ka'anapali Beach in Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (45)
from
$192.17
Morning Whale Watch: Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (29)

Morning Whale Watch: Lahaina Harbor

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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (29)
from
$100.22
Maui Turtle Snorkel & Sail with Lunch & Open Bar
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (40)

Maui Turtle Snorkel & Sail with Lunch & Open Bar

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (40)
from
$122.40

Frequently Asked Questions

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

Hawaii Activities
Attractions
Guides
Calendar
View more
View more
Language
Currency

Site Settings

Activity name

Currency

Activity name

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

Activity name

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.

Cool Support

Ask us anything!

Activity name

Cool Robot